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ks 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 chemical compound osmium tetroxide stick model osmium tetroxide ball and stick model of osmium tetroxide names preferred iupac name osmium tetraoxide systematic iupac name tetraoxoosmium other names osmium viii oxide identifiers cas number 20816 12 0 y 3d model jsmol interactive image chebi chebi 88215 y chemspider 28158 y echa infocard 100 040 038 ec number 244 058 7 mesh osmium tetroxide pubchem cid 30318 rtecs number rn1140000 unii p40w033bgm y un number un 2471 comptox dashboard epa dtxsid5042245 inchi inchi 1s 4o os y key vuvgyhudaiclfk uhfffaoysa n y inchi 1s 4o os key vuvgyhudaiclfk uhfffaoysa n inchi 1 4o os ro4os c1 5 2 3 4 key vuvgyhudaiclfk tyhkrqciae smiles o os o o o properties chemical formula oso 4 molar mass 254 23 g mol appearance white volatile solid odor acrid chlorine like density 4 9 g cm 3 1 melting point 40 25 c 104 45 f 313 40 k boiling point 129 7 2 c 265 5 f 402 8 k solubility in water 5 70 g 100 ml 10 c 6 23 g 100 ml 25 c solubility soluble in most organic solvents ammonium hydroxide phosphorus oxychloride solubility in ccl 4 375 g 100 ml vapor pressure 7 mmhg 20 c 3 structure 4 crystal structure monoclinic ms20 space group c2 c lattice constant a 9 379 å b 4 515 å c 8 630 å α 90 β 116 58 γ 90 lattice volume v 326 8 å 3 formula units z 4 molecular shape tetrahedral hazards ghs labelling pictograms signal word danger hazard statements h300 h310 h314 h330 precautionary statements p260 p262 p264 p270 p271 p280 p284 p301 p310 p301 p330 p331 p302 p350 p303 p361 p353 p304 p340 p305 p351 p338 p310 p320 p321 p330 p361 p363 p403 p233 p405 p501 nfpa 704 fire diamond 3 0 1 ox lethal dose or concentration ld lc lc lo lowest published 1316 mg m 3 rabbit 30 min 423 mg m 3 rat 4 hr 423 mg m 3 mouse 4 hr 5 niosh us health exposure limits pel permissible twa 0 002 mg m 3 3 rel recommended twa 0 002 mg m 3 0 0002 ppm st 0 006 mg m 3 0 0006 ppm 3 idlh immediate danger 1 mg m 3 3 safety data sheet sds icsc 0528 related compounds other cations ruthenium tetroxide hassium tetroxide related osmium oxides osmium iv oxide except where otherwise noted data are given for materials in their standard state at 25 c 77 f 100 kpa n verify what is y n infobox references chemical compound osmium tetroxide also osmium viii oxide is the chemical compound with the formula oso 4 the compound is noteworthy for its many uses despite its toxicity and the rarity of osmium it also has a number of unusual properties one being that the solid is volatile the compound is colourless but most samples appear yellow 6 this is most likely due to the presence of the impurity osmium dioxide oso 2 which is yellow brown in colour 7 in biology its property of binding to lipids has made it a widely used stain in electron microscopy physical properties edit crystal structure of oso 4 4 osmium viii oxide forms monoclinic crystals 4 8 it has a characteristic acrid chlorine like odor the element name osmium is derived from osme greek for odor oso 4 is volatile it sublimes at room temperature it is soluble in a wide range of organic solvents it is moderately soluble in water with which it reacts reversibly to form osmic acid see below 9 pure osmium viii oxide is probably colourless 10 it has been suggested that its yellow hue is attributable due to osmium dioxide oso 2 impurities 11 the osmium tetroxide molecule is tetrahedral and therefore nonpolar this nonpolarity helps oso 4 penetrate charged cell membranes melting and crystallization of osmium tetroxide structure and electron configuration edit the osmium of oso 4 has an oxidation number of viii however the metal does not possess a corresponding 8 charge as the bonding in the compound is largely covalent in character the ionization energy required to produce a formal 8 charge also far exceeds the energies available in normal chemical reactions the osmium atom exhibits double bonds to the four oxide ligands resulting in a 16 electron complex oso 4 is isoelectronic with permanganate and chromate ions synthesis edit oso 4 is formed slowly when osmium powder reacts with o 2 at ambient temperature reaction of bulk solid requires heating to 400 c 12 os 2 o 2 oso 4 reactions edit oxidation of alkenes edit alkenes add to oso 4 to give diolate species that hydrolyze to cis diols the net process is called dihydroxylation this proceeds via a 3 2 cycloaddition reaction between the oso 4 and alkene to form an intermediate osmate ester that rapidly hydrolyses to yield the vicinal diol as the oxygen atoms are added in a concerted step the resulting stereochemistry is cis idealized depiction of the cis dihydroxylation of alkenes oso 4 is expensive and highly toxic making it an unappealing reagent to use in stoichiometric amounts however its reactions are made catalytic by adding reoxidants to reoxidise the os vi by product back to os viii typical reagents include h 2 o 2 milas hydroxylation n methylmorpholine n oxide upjohn dihydroxylation and k 3 fe cn 6 water these reoxidants do not react with the alkenes on their own other osmium compounds can be used as catalysts including osmate vi salts oso 2 oh 4 2 and osmium trichloride hydrate oscl 3 x h 2 o these species oxidise to osmium viii in the presence of such oxidants 13 lewis bases such as tertiary amines and pyridines increase the rate of dihydroxylation this ligand acceleration arises via the formation of adduct oso 4 l which adds more rapidly to the alkene if the amine is chiral then the dihydroxylation can proceed with enantioselectivity see sharpless asymmetric dihydroxylation 14 oso 4 does not react with most carbohydrates 15 the process can be extended to give two aldehydes in the lemieux johnson oxidation which uses periodate to achieve diol cleavage and to regenerate the catalytic loading of oso 4 this process is equivalent to that of ozonolysis coordination chemistry edit structure of oso 3 n t bu multiple bonds are not drawn explicitly illustrating the type of osmium viii oxo imide that adds alkenes en route to the amino alcohol 16 oso 4 is a lewis acid and a mild oxidant it reacts with alkaline aqueous solution to give the perosmate anion oso 4 oh 2 2 17 this species is easily reduced to osmate anion oso 2 oh 2 4 when the lewis base is an amine adducts are also formed thus oso 4 can be stored in the form of osmeth in which oso 4 is complexed with hexamine osmeth can be dissolved in tetrahydrofuran thf and diluted in an aqueous buffer solution to make a dilute 0 25 working solution of oso 4 18 with tert bunh 2 the imido derivative is produced oso 4 me 3 cnh 2 oso 3 ncme 3 h 2 o similarly with nh 3 one obtains the nitrido complex oso 4 nh 3 koh k oso 3 n 2 h 2 o the oso 3 n anion is isoelectronic and isostructural with oso 4 oso 4 is very soluble in tert butyl alcohol in solution it is readily reduced by hydrogen to osmium metal the suspended osmium metal can be used to catalytically hydrogenate a wide variety of organic chemicals containing double or triple bonds oso 4 4 h 2 os 4 h 2 o oso 4 undergoes reductive carbonylation with carbon monoxide in methanol at 400 k and 200 bar to produce the triangular cluster os 3 co 12 3 oso 4 24 co os 3 co 12 12 co 2 12 oxofluorides edit osmium forms several oxofluorides all of which are very sensitive to moisture purple cis oso 2 f 4 forms at 77 k in an anhydrous hf solution 19 oso 4 2 krf 2 cis oso 2 f 4 2 kr o 2 oso 4 also reacts with f 2 to form yellow oso 3 f 2 20 2 oso 4 2 f 2 2 oso 3 f 2 o 2 oso 4 reacts with one equivalent of me 4 n f at 298 k and 2 equivalents at 253 k 12 oso 4 me 4 n f me 4 n oso 4 f oso 4 2 me 4 n f me 4 n 2 cis oso 4 f 2 uses edit organic synthesis edit in organic synthesis oso 4 is widely used to oxidize alkenes to the vicinal diols adding two hydroxyl groups at the same side syn addition see reaction and mechanism above this reaction has been made both catalytic upjohn dihydroxylation and asymmetric sharpless asymmetric dihydroxylation osmium viii oxide is also used in catalytic amounts in the sharpless oxyamination to give vicinal amino alcohols in combination with sodium periodate oso 4 is used for the oxidative cleavage of alkenes lemieux johnson oxidation when the periodate serves both to cleave the diol formed by dihydroxylation and to regenerate oso 4 the net transformation is identical to that produced by ozonolysis below an example from the total synthesis of isosteviol 21 biological staining edit oso 4 is a widely used staining agent used in transmission electron microscopy tem to provide contrast to the image 22 this staining method may also be known in the literature as the oto 23 24 osmium thiocarbohydrazide osmium method or osmium impregnation 25 technique or simply as osmium staining as a lipid stain it is also useful in scanning electron microscopy sem as an alternative to sputter coating it embeds a heavy metal directly into cell membranes creating a high electron scattering rate without the need for coating the membrane with a layer of metal which can obscure details of the cell membrane in the staining of the plasma membrane osmium viii oxide binds phospholipid head regions thus creating contrast with the neighbouring protoplasm cytoplasm additionally osmium viii oxide is also used for fixing biological samples in conjunction with hgcl 2 its rapid killing abilities are used to quickly kill live specimens such as protozoa oso 4 stabilizes many proteins by transforming them into gels without destroying structural features tissue proteins that are stabilized by oso 4 are not coagulated by alcohols during dehydration 15 osmium viii oxide is also used as a stain for lipids in optical microscopy 26 oso 4 also stains the human cornea see safety considerations a sample of cells fixed stained with osmium tetroxide black embedded in epoxy resin amber the cells are black as a result of the effects of osmium tetroxide polymer staining edit it is also used to stain copolymers preferentially the best known example being block copolymers where one phase can be stained so as to show the microstructure of the material for example styrene butadiene block copolymers have a central polybutadiene chain with polystyrene end caps when treated with oso 4 the butadiene matrix reacts preferentially and so absorbs the oxide the presence of a heavy metal is sufficient to block the electron beam so the polystyrene domains are seen clearly in thin films in tem osmium ore refining edit oso 4 is an intermediate in the extraction of osmium from its ores osmium containing residues are treated with sodium peroxide na 2 o 2 forming na 2 oso 4 oh 2 which is soluble when exposed to chlorine this salt gives oso 4 in the final stages of refining crude oso 4 is dissolved in alcoholic naoh forming na 2 oso 2 oh 4 which when treated with nh 4 cl to give oso 2 nh 4 3 cl 2 this salt is reduced under hydrogen to give osmium 9 buckminsterfullerene adduct edit oso 4 allowed for the confirmation of the soccer ball model of buckminsterfullerene a 60 atom carbon allotrope the adduct formed from a derivative of oso 4 was c 60 oso 4 4 tert butyl pyridine 2 the adduct broke the fullerene s symmetry allowing for crystallization and confirmation of the structure of c 60 by x ray crystallography 27 medicine edit the only known clinical use of osmium tetroxide is for the treatment of arthritis 28 the lack of reports of long term side effects from the local administration of osmium tetroxide oso 4 suggest that osmium itself can be biocompatible though this depends on the osmium compound administered safety considerations edit label with poison warning oso 4 will irreversibly stain the human cornea which can lead to blindness the permissible exposure limit for osmium viii oxide 8 hour time weighted average is 2 μg m 3 8 osmium viii oxide can penetrate plastics and food packaging and therefore must be stored in glass under refrigeration 15 references edit osmium tetroxide icsc 0528 inchem koda yoshio 1986 boiling points and ideal solutions of ruthenium and osmium tetraoxides journal of the chemical society chemical communications 1986 17 1347 1348 doi 10 1039 c39860001347 1 2 3 4 niosh pocket guide to chemical hazards 0473 national institute for occupational safety and health niosh 1 2 3 krebs b hasse k d 1976 refinements of the crystal structures of ktco 4 kreo 4 and oso 4 the bond lengths in tetrahedral oxo anions and oxides of d 0 transition metals acta crystallographica b 32 5 1334 1337 bibcode 1976accrb 32 1334k doi 10 1107 s056774087600530x osmium tetroxide as os immediately dangerous to life or health concentrations national institute for occupational safety and health girolami gregory 2012 osmium weighs nature chemistry 4 11 954 bibcode 2012natch 4 954g doi 10 1038 nchem 1479 pmid 23089872 cotton and wilkinson advanced inorganic chemistry p 1002 1 2 osmium tetroxide as os documentation for immediately dangerous to life or health concentrations idlhs centers for disease control 2 november 2018 1 2 thompson m osmium tetroxide oso 4 bristol university retrieved 2012 04 07 butler i s harrod j f 1989 inorganic chemistry principles and applications benjamin cummings p 343 isbn 978 0 8053 0247 9 retrieved 2012 04 07 cotton f a 2007 advanced inorganic chemistry 6th ed new delhi india j wiley p 1002 isbn 978 81 265 1338 3 1 2 3 housecroft c e sharpe a g 2004 inorganic chemistry 2nd ed prentice hall pp 671 673 710 isbn 978 0 13 039913 7 ogino y chen h kwong h l sharpless k b 1991 on the timing of hydrolysis reoxidation in the osmium catalyzed asymmetric dihydroxylation of olefins using potassium ferricyanide as the reoxidant tetrahedron letters 32 32 3965 3968 doi 10 1016 0040 4039 91 80601 2 berrisford d j bolm c sharpless k b 1995 ligand accelerated catalysis angewandte chemie international edition 34 10 1059 1070 doi 10 1002 anie 199510591 1 2 3 hayat m a 2000 principles and techniques of electron microscopy biological applications cambridge university press pp 45 61 isbn 0 521 63287 0 brian s mcgilligan john arnold geoffrey wilkinson bilquis hussain bates michael b hursthouse 1990 reactions of dimesityldioxo osmium vi with donor ligands reactions of mo 2 2 4 6 me 3 c 6 h 2 2 m os or re with nitrogen oxides x ray crystal structures of 2 4 6 me 3 c 6 h 2 n 2 oso 2 ono 2 2 2 4 6 me 3 c 6 h 2 oso nbu t 2 4 6 me 3 c 6 h 2 2 oso 3 nbu t and reo 3 n 2 4 6 me 3 c 6 h 2 2 j chem soc dalton trans 8 2465 2475 doi 10 1039 dt9900002465 greenwood norman n earnshaw alan 1997 chemistry of the elements 2nd ed butterworth heinemann doi 10 1016 c2009 0 30414 6 isbn 978 0 08 037941 8 kiernan j a re disposal of osmium tetroxide waste department of anatomy cell biology the university of western ontario archived from the original on 2011 07 11 retrieved 2...