Meta tags:

Headings (most frequently used words):

from, bromide, organobromine, chemistry, contents, general, properties, synthetic, methods, applications, in, nature, safety, see, also, references, bromine, hydrogen, salts, fire, retardants, fumigants, and, biocides, dyes, pharmaceuticals, designer, drugs,

Text of the page (most frequently used words):
the (71), and (38), compounds (37), are (27), organobromine (26), #bromide (25), #bromine (22), edit (19), from (17), for (16), organic (11), carbon (11), chemistry (10), with (10), this (9), use (9), doi (9), also (9), fire (8), wikipedia (7), retardants (7), such (7), used (7), bond (6), chemical (6), other (6), 1021 (6), bromoform (6), synthesis (6), but (6), hydrogen (6), under (5), page (5), was (5), organobromides (5), naturally (5), brominated (5), produced (5), most (5), reaction (5), salts (5), synthetic (5), applications (5), hbr (5), toggle (4), contents (4), search (4), bonds (4), occurring (4), john (4), marine (4), some (4), mammals (4), main (4), alkyl (4), aromatic (4), derivatives (4), ethylene (4), addition (4), include (4), bromides (4), have (4), nature (4), commercially (4), free (4), hide (4), move (4), sidebar (4), table (3), view (3), safety (3), articles (3), many (3), cells (3), asparagopsis (3), production (3), halogenated (3), products (3), journal (3), bromoxynil (3), encyclopedia (3), wiley (3), sons (3), found (3), example (3), organoiodine (3), organochlorine (3), see (3), agents (3), that (3), their (3), one (3), algae (3), several (3), designer (3), drugs (3), pharmaceuticals (3), dyes (3), contain (3), fumigant (3), biocides (3), like (3), conditions (3), can (3), prominent (3), tetrabromobisphenol (3), acid (3), radical (3), substitution (3), reactions (3), methods (3), reactivity (3), general (3), properties (3), tools (3), add (2), languages (2), contact (2), about (2), privacy (2), policy (2), available (2), terms (2), using (2), wikimedia (2), commons (2), unsourced (2), statements (2), short (2), description (2), wikidata (2), retrieved (2), https (2), uses (2), gordon (2), gribble (2), organohalogen (2), acc (2), chem (2), res (2), toxic (2), 2005 (2), url (2), vesicle (2), red (2), 2003 (2), society (2), reviews (2), volume (2), pages (2), vanadium (2), bromoperoxidase (2), natural (2), dehalogenation (2), dibromo (2), hydroxybenzonitrile (2), 1002 (2), catalysis (2), alpha (2), ketones (2), bromination (2), copper (2), sodium (2), dissociation (2), energies (2), pmid (2), 2016 (2), bromo (2), because (2), seaweed (2), even (2), references (2), organofluorine (2), alkylating (2), commonly (2), both (2), highly (2), variety (2), been (2), persistent (2), pollutants (2), structure (2), left (2), bisphenol (2), dibromoindigo (2), tyrian (2), purple (2), employed (2), form (2), ion (2), chloride (2), human (2), though (2), water (2), more (2), organisms (2), than (2), tons (2), bromomethane (2), edible (2), which (2), not (2), drug (2), needed (2), significance (2), dye (2), popular (2), environmental (2), growing (2), reductive (2), methyl (2), fumigants (2), precursors (2), covalent (2), ethers (2), they (2), significant (2), bromoacetic (2), cubr (2), displacement (2), generated (2), brch (2), industrial (2), rch (2), rchbrch (2), give (2), following (2), containing (2), application (2), catalysts (2), chlorine (2), could (2), electrophilic (2), bonded (2), appearance (2), upload (2), file (2), changes (2), links (2), history (2), read (2), article (2), subsection (2), log (2), create (2), account (2), donate (2), menu (2), topic, mobile, cookie, statement, statistics, developers, code, conduct, legal, contacts, disclaimers, text, additional, may, apply, site, you, agree, registered, trademark, non, profit, organization, foundation, inc, creative, attribution, sharealike, license, rendered, parsoid, last, edited, september, 2026, utc, hidden, categories, october, 2015, all, matches, category, org, index, php, title, organobromine_chemistry, oldid, 1374268441, unknown, academic, research, widespread, core, legend, ces, ccf, cbk, ccm, cam, cpu, cnp, cpa, cth, cac, cyb, ctm, cer, cho, cdy, ctb, cgd, ceu, csm, cpm, cnd, cpr, cce, cla, csg, cra, cat, cpo, cbi, cpb, ctl, chg, cau, cpt, cir, cos, cre, cta, chf, clu, cba, ccs, cxe, cte, csb, csn, cin, ccd, cag, cpd, crh, cru, ctc, cmo, cnb, czr, csr, crb, ckr, cbr, cse, cas, cge, cga, czn, ccu, cni, cco, cfe, cmn, ccr, cti, csc, cca, car, ccl, csi, cal, cmg, cna, cne, cbe, cli, che, elements, periodic, 1998, 152, ar9701777, 141, agency, substances, disease, registry, dibromochloromethane, aug, wwwn, cdc, gov, tsp, phs, phslanding, aspx, 711, tid, 128, rhoda, marshall, hamilton, dring, harper, alga, falkenbergia, stage, play, role, bromocarbon, chemosphere, 471, 475, diversity, 1999, 335, 346, 1039, a900201d, jayme, carter, franklin, alison, butler, catalyzed, biosynthesis, american, 2004, 126, 15060, 15066, ja047925p, cupples, sanford, sims, ioxynil, diiodino, appl, env, micro, 3741, 3746, desulfitobacterium, chlororespirans, david, ioffe, arieh, kampf, kirk, othmer, technology, 2002, 0471238961, 0218151325150606, a01, dennis, bauer, roger, macomber, 1975, iodide, oxidations, dimethyl, sulfoxide, convenient, two, step, diketones, methylene, 1992, jo00901a027, 1990, carroll, king, kenneth, ostrum, 1964, selective, 3461, jo01035a003, 3459, james, nowick, guido, lutterbach, reagents, 2001, 047084289x, rs054, blanksby, ellison, april, molecules, 12693923, ar020230d, 255, saikia, indranirekha, borah, arun, jyoti, phukan, prodeep, 7042, 27199233, acs, chemrev, 5b00400, 6837, 116, matson, michael, orbaek, alvin, 2013, seawater, animals, developed, techniques, converting, forms, made, sponges, corals, november, 978, 118, 22882, isbn, inorganic, dummies, chapter, groups, active, singles, group, halogens, briny, often, implicated, hormone, disruptors, dibromide, greatest, concern, carcinogenic, conventional, result, biodegradation, metabolites, methoxylated, hydroxylated, aryl, well, dioxin, considered, antifeedant, tambjamine, these, interspecies, warfare, important, defense, against, multicellular, parasites, preference, bromouracil, tyrosine, identified, white, blood, induced, halogenation, invading, pathogens, myeloperoxidase, eosinophil, peroxidase, common, organohalides, concentration, only, sea, prevalent, abundance, reflects, easy, oxidation, equivalent, potent, electrophile, enzyme, larger, family, catalyzes, environment, oceans, estimated, release, million, 000, annually, eaten, hawaii, limu, kohu, concentrate, essential, volatile, oil, prepared, drying, vacuum, condensing, dry, ice, comprises, weight, known, toxin, small, amounts, present, appear, pose, harm, taxiformis, bromoperoxidases, appeared, market, alongside, attempt, circumvent, existing, laws, citation, cathinones, amphetamines, bromomethcathinone, vasodilator, sedative, anticancer, agent, antiseptic, otherwise, rarely, pharmaceutically, useful, contrast, situation, equivalents, hydrobromide, cases, serves, innocuous, counterion, biological, merbromin, pipobroman, brotizolam, nicergoline, valued, before, development, industry, late, 19th, century, indicator, analytical, bromothymol, blue, anthroquinone, obtained, once, commercial, component, agriculture, displacing, dbcp, declining, owing, health, considerations, effective, its, controlled, treatment, representative, dbdmh, herbicides, moieties, subject, debrominated, originally, isolated, ability, reductively, dechlorinate, phenolic, anaerobic, pesticides, dibromodimethylhydantoin, montreal, protocol, chloropropane, leaded, gasoline, widely, member, methylethylidene, bis, bromophenol, figure, tetrabromophthalic, anhydride, polymers, wherein, backbone, features, hexabromocyclododecane, bromodiphenyl, additives, chemically, attached, material, protect, controversial, three, industrially, chbr, salt, mediated, ions, provided, function, nucleophiles, formation, another, methanol, hoch, convert, alcohols, must, done, low, temperature, allyl, direction, reversed, bromoalkanes, tertiary, amines, quaternary, ammonium, via, route, styrene, phenethyl, adds, across, double, markovnikov, rule, converts, bromotrifluoromethane, fluoroform, prepare, carbonyl, benzylic, allylic, substrates, especially, prone, directly, acetic, presence, catalyst, phosphorus, tribromide, undergo, simultaneously, evolution, albr3, febr3, happen, rings, based, fecl3, alcl3, yield, would, drop, slightly, dihalogens, brcl, details, usual, patterns, alkenes, reliably, without, dibromides, vicinal, resembles, intermediate, between, represent, compromise, cost, principal, nucleophilic, coupling, grignard, dehydrobromination, strengths, 115, kcal, mol, iodine, respectively, fluorine, halogen, relatively, consequently, electronegative, nonpolar, organohalide, minor, none, biosynthesized, required, fallen, increased, scrutiny, impact, fact, retardant, manufacture, currently, major, element, polybrominated, diphenyl, study, called, pervasive, compound, least, item, projects, printable, version, download, pdf, print, export, switch, legacy, parser, get, shortened, cite, information, permanent, link, related, what, here, actions, english, talk, русский, português, nederlands, 한국어, 日本語, italiano, français, euskara, español, deutsch, čeština, català, العربية, top, personal, special, recent, community, portal, learn, help, contribute, random, current, events, navigation, jump, content,

Text of the page (random words):
organobromine chemistry wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 general properties 2 synthetic methods toggle synthetic methods subsection 2 1 from bromine 2 2 from hydrogen bromide 2 3 from bromide salts 3 applications toggle applications subsection 3 1 fire retardants 3 2 fumigants and biocides 3 3 dyes 3 4 pharmaceuticals 3 5 designer drugs 4 in nature 5 safety 6 see also 7 references toggle the table of contents organobromine chemistry 14 languages العربية català čeština deutsch español euskara français italiano 日本語 한국어 nederlands português русский 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia organic compound containing at least one covalent carbon bromine bond organobromine chemistry is the study of the synthesis and properties of organobromine compounds also called organobromides 1 which are organic compounds that contain carbon bonded to bromine the most pervasive is the naturally produced bromomethane one prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire retardants and in fact fire retardant manufacture is currently the major industrial use of the element bromine a variety of minor organobromine compounds are found in nature but none are biosynthesized or required by mammals organobromine compounds have fallen under increased scrutiny for their environmental impact general properties edit most organobromine compounds like most organohalide compounds are relatively nonpolar bromine is more electronegative than carbon 2 9 vs 2 5 consequently the carbon in a carbon bromine bond is electrophilic i e alkyl bromides are alkylating agents 2 carbon halogen bond strengths or bond dissociation energies are of 115 83 7 72 1 and 57 6 kcal mol for bonded to fluorine chlorine bromine or iodine respectively 3 the reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds for many applications organobromides represent a compromise of reactivity and cost the principal reactions for organobromides include dehydrobromination grignard reactions reductive coupling and nucleophilic substitution synthetic methods edit from bromine edit alkenes reliably add bromine without catalysis to give the vicinal dibromides rch ch 2 br 2 rchbrch 2 br aromatic compounds undergo bromination simultaneously with evolution of hydrogen bromide catalysts such as albr3 or febr3 are needed for the reaction to happen on aromatic rings chlorine based catalysts fecl3 alcl3 could be used but yield would drop slightly as dihalogens brcl could form the reaction details following the usual patterns of electrophilic aromatic substitution rc 6 h 5 br 2 rc 6 h 4 br hbr a prominent application of this reaction is the production of tetrabromobisphenol a from bisphenol a free radical substitution with bromine is commonly used to prepare organobromine compounds carbonyl containing benzylic allylic substrates are especially prone to this reactions for example the commercially significant bromoacetic acid is generated directly from acetic acid and bromine in the presence of phosphorus tribromide catalyst ch 3 co 2 h br 2 brch 2 co 2 h hbr bromine also converts fluoroform to bromotrifluoromethane from hydrogen bromide edit hydrogen bromide adds across double bonds to give alkyl bromides following the markovnikov rule rch ch 2 hbr rchbrch 3 under free radical conditions the direction of the addition can be reversed free radical addition is used commercially for the synthesis of 1 bromoalkanes precursors to tertiary amines and quaternary ammonium salts 2 phenethyl bromide c 6 h 5 ch 2 ch 2 br is produced via this route from styrene hydrogen bromide can also be used to convert alcohols to alkyl bromides this reaction that must be done under low temperature conditions is employed in the industrial synthesis of allyl bromide hoch 2 ch ch 2 hbr brch 2 ch ch 2 h 2 o methyl bromide another fumigant is generated from methanol and hydrogen bromide from bromide salts edit bromide ions as provided by salts like sodium bromide function as a nucleophiles in the formation of organobromine compounds by displacement 4 an example of this salt mediated bromide displacement is the use of copper ii bromide on ketones 5 6 r co ch 2 r 2 cubr 2 r co chbr r 2 cubr hbr applications edit structure of three industrially significant organobromine compounds from left ethylene bromide bromoacetic acid and tetrabromobisphenol a fire retardants edit organobromine compounds are widely used as fire retardants 7 the most prominent member is tetrabromobisphenol a 4 4 1 methylethylidene bis 2 6 di bromophenol see figure it and tetrabromophthalic anhydride are precursors to polymers wherein the backbone features covalent carbon bromine bonds other fire retardants such as hexabromocyclododecane and the bromodiphenyl ethers are additives and are not chemically attached to the material they protect the use of organobromine fire retardants is growing but is also controversial because they are persistent pollutants fumigants and biocides edit ethylene bromide obtained by addition of bromine to ethylene was once of commercial significance as a component of leaded gasoline it was also a popular fumigant in agriculture displacing 1 2 dibromo 3 chloropropane dbcp both applications are declining owing to environmental and health considerations methyl bromide is also an effective fumigant but its production and use are controlled by the montreal protocol growing in use are organobromine biocides used in water treatment representative agents include bromoform and dibromodimethylhydantoin dbdmh 7 some herbicides such as bromoxynil contain also bromine moieties like other halogenated pesticides bromoxynil is subject to reductive dehalogenation under anaerobic conditions and can be debrominated by organisms originally isolated for their ability to reductively dechlorinate phenolic compounds 8 dyes edit many dyes contain carbon bromine bonds the naturally occurring tyrian purple 6 6 dibromoindigo was a valued dye before the development of the synthetic dye industry in the late 19th century several brominated anthroquinone derivatives are used commercially bromothymol blue is a popular indicator in analytical chemistry pharmaceuticals edit commercially available organobromine pharmaceuticals include the vasodilator nicergoline the sedative brotizolam the anticancer agent pipobroman and the antiseptic merbromin otherwise organobromine compounds are rarely pharmaceutically useful in contrast to the situation for organofluorine compounds several drugs are produced as the bromide or equivalents hydrobromide salts but in such cases bromide serves as an innocuous counterion of no biological significance 7 designer drugs edit organobromine compounds such as 4 bromomethcathinone have appeared on the designer drug market alongside other halogenated amphetamines and cathinones in an attempt to circumvent existing drug laws citation needed in nature edit organobromine compounds are the most common organohalides in nature even though the concentration of bromide is only 0 3 of that for chloride in sea water organobromine compounds are more prevalent in marine organisms than organochlorine derivatives their abundance reflects the easy oxidation of bromide to the equivalent of br a potent electrophile the enzyme vanadium bromoperoxidase one of a larger family of bromoperoxidases catalyzes this reaction in the marine environment 9 the oceans are estimated to release 1 2 million tons of bromoform and 56 000 tons of bromomethane annually 10 red algae such as the edible asparagopsis taxiformis eaten in hawaii as limu kohu concentrate organobromine and organoiodine compounds in vesicle cells 95 of the essential volatile oil of asparagopsis prepared by drying the seaweed in a vacuum and condensing using dry ice is organohalogen compounds of which bromoform comprises 80 by weight 11 bromoform produced by several algae is a known toxin though the small amounts present in edible algae do not appear to pose human harm 12 some of these organobromine compounds are employed in a form of interspecies chemical warfare in mammals eosinophil peroxidase important for defense against multicellular parasites uses bromide ion in preference to chloride ion 5 bromouracil and 3 bromo tyrosine have been identified in human white blood cells as products of myeloperoxidase induced halogenation on invading pathogens 13 structure of some naturally occurring organobromine compounds from left bromoform a brominated bisphenol dibromoindigo tyrian purple and the antifeedant tambjamine b in addition to conventional brominated natural products a variety of organobromine compounds result from the biodegradation of fire retardants metabolites include methoxylated and hydroxylated aryl bromides as well as brominated dioxin derivatives such compounds are considered persistent organic pollutants and have been found in mammals safety edit alkyl bromine compounds are often alkylating agents and the brominated aromatic derivatives are implicated as hormone disruptors of the commonly produced compounds ethylene dibromide is of greatest concern as it is both highly toxic and highly carcinogenic see also edit organofluorine compounds organochlorine compounds organoiodine compounds references edit matson michael orbaek alvin w 2013 06 04 chapter 12 the main groups re active singles the group 17 halogens briny bromine inorganic chemistry for dummies john wiley sons isbn 978 1 118 22882 1 retrieved 12 november 2016 because bromine is found in seawater marine animals developed techniques for converting it to other forms for example organobromides compounds with carbon and bromine are made by sponges corals seaweed and even some mammals saikia indranirekha borah arun jyoti phukan prodeep 2016 use of bromine and bromo organic compounds in organic synthesis chemical reviews 116 12 6837 7042 doi 10 1021 acs chemrev 5b00400 pmid 27199233 blanksby sj ellison gb april 2003 bond dissociation energies of organic molecules acc chem res 36 4 255 63 doi 10 1021 ar020230d pmid 12693923 james s nowick guido lutterbach sodium bromide in encyclopedia of reagents for organic synthesis john wiley sons 2001 doi 10 1002 047084289x rs054 l carroll king g kenneth ostrum 1964 selective bromination with copper ii bromide the journal of organic chemistry 29 12 3459 3461 doi 10 1021 jo01035a003 dennis p bauer roger s macomber 1975 iodide catalysis of oxidations with dimethyl sulfoxide convenient two step synthesis of alpha diketones from alpha methylene ketones the journal of organic chemistry 40 13 1990 1992 doi 10 1021 jo00901a027 1 2 3 david ioffe arieh kampf bromine organic compounds in kirk othmer encyclopedia of chemical technology 2002 by john wiley sons doi 10 1002 0471238961 0218151325150606 a01 cupples a m r a sanford and g k sims 2005 dehalogenation of bromoxynil 3 5 dibromo 4 hydroxybenzonitrile and ioxynil 3 5 diiodino 4 hydroxybenzonitrile by desulfitobacterium chlororespirans appl env micro 71 7 3741 3746 jayme n carter franklin alison butler vanadium bromoperoxidase catalyzed biosynthesis of halogenated marine natural products journal of the american chemical society 2004 volume 126 15060 15066 doi 10 1021 ja047925p gordon w gribble the diversity of naturally occurring organobromine compounds chemical society reviews 1999 volume 28 pages 335 346 doi 10 1039 a900201d rhoda a marshall john t g hamilton m j dring d b harper do vesicle cells of the red alga asparagopsis falkenbergia stage play a role in bromocarbon production chemosphere 52 2003 471 475 agency for toxic substances and disease registry bromoform and dibromochloromethane aug 2005 url https wwwn cdc gov tsp phs phslanding aspx id 711 tid 128 gordon w gribble 1998 naturally occurring organohalogen compounds acc chem res 31 3 141 152 doi 10 1021 ar9701777 v t e compounds of carbon with other elements in the periodic table ch che cli cbe cb cc cn co cf cne cna cmg cal csi cp cs ccl car ck cca csc cti cv ccr cmn cfe cco cni ccu czn cga cge cas cse cbr ckr crb csr cy czr cnb cmo ctc cru crh cpd cag ccd cin csn csb cte ci cxe ccs cba clu chf cta cw cre cos cir cpt cau chg ctl cpb cbi cpo cat rn fr cra lr rf db csg bh hs mt ds rg cn nh fl mc lv ts og cla cce cpr cnd cpm csm ceu cgd ctb cdy cho cer ctm cyb cac cth cpa cu cnp cpu cam ccm cbk ccf ces fm md no legend chemical bonds to carbon core organic chemistry many uses in chemistry academic research no widespread use bond unknown retrieved from https en wikipedia org w index php title organobromine_chemistry oldid 1374268441 category organobromides hidden categories articles with short description short description matches wikidata all articles with unsourced statements articles with unsourced statements from october 2015 this page was last edited on 10 september 2026 at 23 07 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents organobromine chemistry 14 languages add topic