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methyllithium 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 synthesis 2 reactivity 3 structure toggle structure subsection 3 1 bonding 4 references toggle the table of contents methyllithium 21 languages العربية تۆرکجه čeština deutsch ελληνικά español فارسی suomi français magyar italiano 日本語 한국어 nederlands português русский srpskohrvatski српскохрватски српски srpski தமிழ் اردو 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 methyllithium skeletal formula of tetrameric methyllithium with all implicit hydrogens shown names iupac name methyllithium other names lithium methanide identifiers cas number 917 54 4 y 3d model jsmol interactive image abbreviations meli beilstein reference 3587162 chebi chebi 51486 y chemspider 10254338 y echa infocard 100 011 843 ec number 213 026 4 gmelin reference 288 pubchem cid 2724049 comptox dashboard epa dtxsid7061273 inchi inchi 1s ch3 li h1h3 y key dvsdbmfjeqpwno uhfffaoysa n y smiles li c properties chemical formula c h 3 li molar mass 21 98 g mol 1 solubility in water reacts hazards occupational safety and health ohs osh main hazards pyrophoric nfpa 704 fire diamond 3 4 2 w except where otherwise noted data are given for materials in their standard state at 25 c 77 f 100 kpa y verify what is y n infobox references chemical compound methyllithium is the simplest organolithium reagent with the empirical formula lich 3 this s block organometallic compound adopts an oligomeric structure both in solution and in the solid state this highly reactive compound invariably used in solution with an ether as the solvent is a reagent in organic synthesis as well as organometallic chemistry operations involving methyllithium require anhydrous conditions because the compound is highly reactive towards water oxygen and carbon dioxide are also incompatible with meli methyllithium is usually not prepared but purchased as a solution in various ethers synthesis edit in the direct synthesis methyl bromide is treated with a suspension of lithium in diethyl ether 2 li mebr lime libr the lithium bromide forms a complex with the methyllithium most commercially available methyllithium consists of this complex low halide methyllithium is prepared from methyl chloride 1 lithium chloride precipitates from the diethyl ether since it does not form a strong complex with methyllithium the filtrate consists of fairly pure methyllithium alternatively commercial methyllithium can be treated with dioxane to precipitate libr dioxane which can be removed by filtration 2 the use of halide free vs libr meli has a decisive effect on some syntheses 3 reactivity edit methyllithium is both strongly basic and highly nucleophilic due to the partial negative charge on carbon and is therefore particularly reactive towards electron acceptors and proton donors in contrast to n buli meli reacts only very slowly with thf at room temperature and solutions in ether are indefinitely stable water and alcohols react violently most reactions involving methyllithium are conducted below room temperature although meli can be used for deprotonations n butyllithium is more commonly employed since it is less expensive and more reactive methyllithium is mainly used as the synthetic equivalent of the methyl anion synthon for example ketones react to give tertiary alcohols in a two step process ph 2 co meli ph 2 c me oli ph 2 c me oli h ph 2 c me oh li nonmetal halides are converted to methyl compounds with methyllithium pcl 3 3 meli pme 3 3 licl such reactions more commonly employ the grignard reagents methylmagnesium halides which are often equally effective and less expensive or more easily prepared in situ it also reacts with carbon dioxide to give lithium acetate ch 3 li co 2 ch 3 co 2 li transition metal methyl compounds can be prepared by reaction of meli with metal halides especially important are the formation of organocopper compounds gilman reagents of which the most useful is lithium dimethylcuprate this reagent is widely used for nucleophilic substitutions of epoxides alkyl halides and alkyl sulfonates as well as for conjugate additions to α β unsaturated carbonyl compounds by methyl anion 4 many other transition metal methyl compounds have been prepared 5 zrcl 4 6 meli li 2 zrme 6 4 licl structure edit two structures have been verified by single crystal x ray crystallography as well as by 6 li 7 li and 13 c nmr spectroscopy the tetrameric structure is a distorted cubane type cluster with carbon and lithium atoms at alternate corners the li li distances are 2 68 å almost identical with the li li bond in gaseous dilithium the c li distances are 2 31 å carbon is bonded to three hydrogen atoms and three li atoms the nonvolatility of meli 4 and its insolubility in alkanes results from the fact that the clusters interact via further inter cluster agostic interactions in contrast the bulkier cluster tertiary butylli 4 where intercluster interactions are precluded by steric effects is volatile as well as soluble in alkanes 6 colour code li purple c black h white the hexameric form features hexagonal prisms with li and c atoms again at alternate corners colour code li purple c black h white the degree of aggregation n for meli n depends upon the solvent and the presence of additives such as lithium bromide hydrocarbon solvents such as benzene 7 favour formation of the hexamer whereas ethereal solvents favour the tetramer bonding edit these clusters are considered electron deficient that is they do not follow the octet rule because the molecules lack sufficient electrons to form four 2 centered 2 electron bonds around each carbon atom in contrast to most organic compounds the hexamer is a 30 electron compound 30 valence electrons if one allocates 18 electrons for the strong c h bonds 12 electrons remain for li c and li li bonding there are six electrons for six metal metal bonds and one electron per methyl η 3 lithium interaction the strength of the c li bond has been estimated at around 57 kcal mol from ir spectroscopic measurements 7 references edit lusch m j phillips w v sieloff r f nomura g s house h o 1984 preparation of low halide methyllithium organic syntheses 62 101 collected volumes vol 7 p 346 holland patrick l smith michael e andersen richard a bergman robert g 1997 x ray crystal structures of cp ni pet 3 x x br o p c 6 h 4 me nh p c 6 h 4 me s p c 6 h 4 me och 3 ch 2 c 6 h 5 me h pet3 understanding distortions and trans influences in cyclopentadienyl complexes journal of the american chemical society 119 52 12815 12823 doi 10 1021 ja971830o göttker schnetmann inigo mecking stefan 2020 a practical synthesis of tmeda ni ch 3 2 isotopically labeled tmeda ni 13 ch 3 2 and neutral chelated nickel methyl complexes organometallics 39 18 3433 3440 doi 10 1021 acs organomet 0c00500 s2cid 224930545 lipshutz b h sengupta s 1992 organocopper reagents substitution carbo metallocupration and other reactions organic reactions vol 41 pp 135 631 doi 10 1002 0471264180 or041 02 isbn 9780471264187 morse p m girolami g s 1989 are d 0 ml 6 complexes always octahedral the x ray structure of trigonal prismatic li tmed 2 zrme 6 journal of the american chemical society 111 11 4114 4116 doi 10 1021 ja00193a061 elschenbroich c 2006 organometallics weinheim wiley vch isbn 978 3 527 29390 2 1 2 brown t l rogers m t 1957 the preparation and properties of crystalline lithium alkyls journal of the american chemical society 79 8 1859 1861 doi 10 1021 ja01565a024 v t e lithium compounds list compounds with noble gases lihe hlihe hypothetical lifheo hypothetical lihe 2 hypothetical heo lif 2 hypothetical la 2 3 x li 3x tio 3 he hypothetical compounds with halogens flibe flinak liat hypothetical libr libro libro 2 libro 3 libro 4 licl liclo liclo 2 liclo 3 liclo 4 lif li 2 f lifo lii liio liio 2 liio 3 liio 4 oxides and hydroxides lio lio 2 lio 3 li 2 o li 2 o 2 lioh compounds with chalcogens licf 3 so 3 lihso 3 lihso 4 li 2 po li 2 s li 2 se li 2 seo 3 li 2 seo 4 li 2 te lite 3 li 2 teo 3 li 2 teo 4 compounds with pnictogens li 1 x al x ge 2 x po 4 3 lial 1 x ti 2 x po 4 3 li 3 sb lias liasf 6 li 3 aso 4 lifepo 4 lige 2 po 4 3 lih 2 aso 4 li 2 haso 4 li 2 hpo 3 li 2 hpo 4 li 3 po 3 li 3 po 4 lih 2 po 3 lih 2 po 4 lin 3 li 3 n linh 2 li 2 nh lino 2 lino 3 li 2 n 2 o 2 li 2 napo 3 linano 2 li 3 p lipf 6 li 3 po 4 li sbf 6 liti 2 po 4 3 lizr 2 po 4 3 compounds with group 14 elements li 2 c 2 li 2 co 3 li 2 gef 6 li 2 geo 3 lihco 3 li 3 h co 3 2 lisi li 2 sif 6 li 2 sio 3 li 2 si 2 o 5 li 4 sio 4 li 2 snf 6 compounds with group 13 elements cslib 6 o 10 lialcl 4 lialf 4 li 3 alf 6 lialh 4 lialo 2 lib c 2 o 4 2 lib c 6 f 5 4 libf 4 libh 4 libo 2 lib 3 o 5 li 2 b 4 o 7 libsi 2 ligah 4 compounds with transition metals li aucl 4 licoo 2 li 2 cro 4 li 2 cr 2 o 7 li 2 iro 3 li 7 la 3 zr 2 o 12 limn 2 o 4 li 2 moo 4 li 0 9 mo 6 o 17 linbo 3 li 2 nbo 3 li 2 pto 3 li 2 ruo 3 litao 3 li 2 tif 6 li 2 tio 3 li 4 ti 5 o 12 livo 3 li 3 v 2 po 4 3 liwf 6 li 2 wo 4 li 2 zrf 6 li 2 zro 3 organic soaps hemolithin extraterrestrial protein organolithium reagents gilman reagent ch 3 cooli c 4 h 6 lino 4 lic 2 f 6 no 4 s 2 lin sime 3 2 li 3 c 6 h 5 o 7 c 5 h 5 li lin c 3 h 7 2 c 6 h 5 2 pli c 18 h 35 lio 3 c 6 h 13 li c 4 h 9 li ch 3 chlich 2 ch 3 ch 3 3 cli c 12 h 28 bli ch 3 li li c 10 h 8 c 5 h 11 li c 5 h 3 lin 2 o 4 c 6 h 5 li lic 2 ch 3 c 7 h 5 lio 3 lio 2 c ch 2 16 ch 3 c 4 h 5 lio 4 liet 3 bh lioc ch 3 3 c 9 h 18 lin lic 2 h 3 lic 11 h 23 coo ch 3 ch oh cooli lic 2 h 2 clo 2 lic 2 h 3 io 2 li ch 3 2 n licho 2 lich 3 o lic 2 h 5 o li 2 c 2 o 4 other compounds li 2 li x be y hypothetical licn li 2 cn 2 licno lih lina liscn liyf 4 neodymium doped minerals amblygonite berezanskite brannockite cryolithionite darapiosite darrellhenryite elbaite fluorine elbaite fluor liddicoatite emeleusite eucryptite faizievite hectorite hsianghualite jadarite kunzite lavinskyite lepidolite lithiophilite lithiophosphate manandonite manganoneptunite nambulite neptunite olympite petalite pezzottaite rossmanite saliotite sogdianite spodumene sugilite tiptopite tourmaline triphylite zabuyelite zektzerite zinnwaldite other li related aluminium lithium alloys heteroatom promoted lateral lithiation lb buffer lithium atom lithium medication lithium cocrystal lini x co y al z o 2 lini x mn y co z o 2 lithium soap lithium triangle lucifer yellow magnesium lithium alloys nasicon environmentally friendly red light flare retrieved from https en wikipedia org w index php title methyllithium oldid 1372033472 categories organolithium compounds methylating agents methyl complexes pyrophoric materials organic compounds with 1 carbon atom cubane type clusters hidden categories articles without inchi source articles without kegg source articles without unii source echa infocard id from wikidata articles containing unverified chemical infoboxes chembox image size set articles with short description short description matches wikidata this page was last edited on 29 august 2026 at 23 23 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 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