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Trimethylarsine

August 24, 2023

Trimethylarsine (abbreviated TMA or TMAs) is the chemical compound with the formula (CH3)3As, commonly abbreviated AsMe3 or TMAs. This organic derivative of arsine has been used as a source of arsenic in microelectronics industry,[1] a building block to other organoarsenic compounds, and serves as a ligand in coordination chemistry. It has distinct "garlic"-like smell. Trimethylarsine had been discovered as early as 1854.

Trimethylarsine
Structural formula of trimethylarsine with an implicit electron pair
Ball and stick model of trimethylarsine
Names
Preferred IUPAC name
Trimethylarsane
Other names
  • Gosio gas
  • Trimethanidoarsenic
Identifiers
  • 593-88-4 Y
3D model (JSmol)
  • Interactive image
  • Interactive image
1730780
ChEBI
  • CHEBI:27130 Y
ChemSpider
  • 62200 Y
ECHA InfoCard 100.008.925
EC Number
  • 209-815-8
141657
MeSH Trimethylarsine
  • 68978
RTECS number
  • CH8800000
UNII
  • MQ83UQ8A1Q Y
  • DTXSID4073203
  • InChI=1S/C3H9As/c1-4(2)3/h1-3H3 Y
    Key: HTDIUWINAKAPER-UHFFFAOYSA-N Y
  • InChI=1/C3H9As/c1-4(2)3/h1-3H3
    Key: HTDIUWINAKAPER-UHFFFAOYAT
  • [As](C)(C)C
  • C[As](C)C
Properties
C3H9As
Molar mass 120.027 g·mol−1
Appearance Colourless liquid
Density 1.124 g cm−3
Melting point −87.3 °C (−125.1 °F; 185.8 K)
Boiling point 56 °C (133 °F; 329 K)
Slightly soluble
Solubility in other solvents organic solvents
Structure
Trigonal pyramidal
0.86 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable
GHS labelling:
Danger
H301, H331, H410
Flash point −25 °C (−13 °F; 248 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
 Cacodylic acid
Triphenylarsine
Pentamethylarsenic
Trimethylphosphine
Trimethylamine
Supplementary data page
Trimethylarsine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Structure and preparation

AsMe3 is a pyramidal molecule. The As-C distances average 1.519 Å, and the C-As-C angles are 91.83°[2]

Trimethylarsine can be prepared by treatment of arsenic oxide with trimethylaluminium:[3]

As2O3 + 1.5 [AlMe3]2 → 2 AsMe3 + 3/n (MeAl-O)n

Occurrence and reactions

Trimethylarsine is the volatile byproduct of microbial action on inorganic forms of arsenic which are naturally occurring in rocks and soils at the parts-per-million level.[4] Trimethylarsine has been reported only at trace levels (parts per billion) in landfill gas from Germany, Canada, and the U.S.A., and is the major arsenic-containing compound in the gas.[5][6][7]

Trimethylarsine is pyrophoric due to the exothermic nature of the following reaction, which initiates combustion:

AsMe3 + 1/2 O2 → OAsMe3 (TMAO)

History

Poisoning events due to a gas produced by certain microbes was assumed to be associated with the arsenic in paint. In 1893 the Italian physician Bartolomeo Gosio published his results on "Gosio gas" that was subsequently shown to contain trimethylarsine.[8] Under wet conditions, the mold Microascus brevicaulis produces significant amounts of methyl arsines via methylation[9] of arsenic-containing inorganic pigments, especially Paris green and Scheele's Green, which were once used in indoor wallpapers. Newer studies show that trimethylarsine has a low toxicity and could therefore not account for the death and the severe health problems observed in the 19th century.[10][11]

Safety

Trimethylarsine is potentially hazardous,[12][13][14] although its toxicity is often overstated.[10]

References

  1. ^ Hoshino, Masataka (1991). "A mass spectrometric study of the decomposition of trimethylarsine (TMAs) with triethylgallium (TEGa)". Journal of Crystal Growth. 110 (4): 704–712. Bibcode:1991JCrGr.110..704H. doi:10.1016/0022-0248(91)90627-H.
  2. ^ Wells, A.F. (1984). Structural Inorganic Chemistry, fifth edition. Oxford University Press. ISBN 978-0-19-855370-0.
  3. ^ V. V. Gavrilenko, L. A. Chekulaeva, and I. V. Pisareva, "Highly efficient synthesis of trimethylarsine" Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 2122–2123, 1996.
  4. ^ Cullen, W.R., Reimer, K.J. (1989). "Arsenic speciation in the environment". Chem. Rev. 89 (4): 713–764. doi:10.1021/cr00094a002. hdl:10214/2162.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ Feldmann, J., Cullen, W.R. (1997). "Occurrence of Volatile Transition Metal Compounds in Landfill Gas: Synthesis of Molybdenum and Tungsten Carbonyls in the". Environ. Sci. Technol. 31 (7): 2125–2129. doi:10.1021/es960952y.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ^ Pinel-Raffaitin, P., LeHecho, I., Amouroux, D., Potin-Gautier, M. (2007). "Distribution and Fate of Inorganic and Organic Arsenic Species in Landfill Leachates and Biogases". Environ. Sci. Technol. 41 (13): 4536–4541. Bibcode:2007EnST...41.4536P. doi:10.1021/es0628506. PMID 17695893.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Khoury, J.T.; et al. (April 7, 2008). "Analysis of Volatile Arsenic Compounds in Landfill Gas". Odors & Air Emissions 2008. Phoenix, Arizona: Water Environment Federation.
  8. ^ Frederick Challenger (1955). "Biological methylation". Q. Rev. Chem. Soc. 9 (3): 255–286. doi:10.1039/QR9550900255.
  9. ^ Ronald Bentley & Thomas G. Chasteen (2002). "Microbial Methylation of Metalloids: Arsenic, Antimony, and Bismuth". Microbiology and Molecular Biology Reviews. 66 (2): 250–271. doi:10.1128/MMBR.66.2.250-271.2002. PMC 120786. PMID 12040126.
  10. ^ a b William R. Cullen; Ronald Bentley (2005). "The toxicity of trimethylarsine: an urban myth". J. Environ. Monit. 7 (1): 11–15. doi:10.1039/b413752n. PMID 15693178.
  11. ^ Frederick Challenger; Constance Higginbottom; Louis Ellis (1933). "The formation of organo-metalloidal compounds by microorganisms. Part I. Trimethylarsine and dimethylethylarsine". J. Chem. Soc.: 95–101. doi:10.1039/JR9330000095.
  12. ^ Andrewes, Paul; et al. (2003). "Dimethylarsine and Trimethylarsine Are Potent Genotoxins In Vitro". Chem. Res. Toxicol. 16 (8): 994–1003. doi:10.1021/tx034063h. PMID 12924927.
  13. ^ Irvin, T.Rick; et al. (1995). "In-vitro Prenatal Toxicity of Trimethylarsine, Trimethylarsine Oxide and Trimethylarsine Sulfide". Applied Organometallic Chemistry. 9 (4): 315–321. doi:10.1002/aoc.590090404.
  14. ^ Hiroshi Yamauchi; Toshikazu Kaise; Keiko Takahashi; Yukio Yamamura (1990). "Toxicity and metabolism of trimethylarsine in mice and hamsters". Fundamental and Applied Toxicology. 14 (2): 399–407. doi:10.1016/0272-0590(90)90219-A. PMID 2318361.

External links

  • Microbial Methylation of Metalloids: Arsenic, Antimony, and Bismuth

August 24, 2023
trimethylarsine, abbreviated, tmas, chemical, compound, with, formula, commonly, abbreviated, asme3, tmas, this, organic, derivative, arsine, been, used, source, arsenic, microelectronics, industry, building, block, other, organoarsenic, compounds, serves, lig. Trimethylarsine abbreviated TMA or TMAs is the chemical compound with the formula CH3 3As commonly abbreviated AsMe3 or TMAs This organic derivative of arsine has been used as a source of arsenic in microelectronics industry 1 a building block to other organoarsenic compounds and serves as a ligand in coordination chemistry It has distinct garlic like smell Trimethylarsine had been discovered as early as 1854 Trimethylarsine Structural formula of trimethylarsine with an implicit electron pair Ball and stick model of trimethylarsineNamesPreferred IUPAC name TrimethylarsaneOther names Gosio gasTrimethanidoarsenicIdentifiersCAS Number 593 88 4 Y3D model JSmol Interactive imageInteractive imageBeilstein Reference 1730780ChEBI CHEBI 27130 YChemSpider 62200 YECHA InfoCard 100 008 925EC Number 209 815 8Gmelin Reference 141657MeSH TrimethylarsinePubChem CID 68978RTECS number CH8800000UNII MQ83UQ8A1Q YCompTox Dashboard EPA DTXSID4073203InChI InChI 1S C3H9As c1 4 2 3 h1 3H3 YKey HTDIUWINAKAPER UHFFFAOYSA N YInChI 1 C3H9As c1 4 2 3 h1 3H3Key HTDIUWINAKAPER UHFFFAOYATSMILES As C C CC As C CPropertiesChemical formula C 3H 9AsMolar mass 120 027 g mol 1Appearance Colourless liquidDensity 1 124 g cm 3Melting point 87 3 C 125 1 F 185 8 K Boiling point 56 C 133 F 329 K Solubility in water Slightly solubleSolubility in other solvents organic solventsStructureCoordination geometry Trigonal pyramidalDipole moment 0 86 DHazardsOccupational safety and health OHS OSH Main hazards FlammableGHS labelling PictogramsSignal word DangerHazard statements H301 H331 H410Flash point 25 C 13 F 248 K Safety data sheet SDS External MSDSRelated compoundsRelated compounds Cacodylic acidTriphenylarsinePentamethylarsenicTrimethylphosphineTrimethylamineSupplementary data pageTrimethylarsine data page 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 Contents 1 Structure and preparation 2 Occurrence and reactions 3 History 4 Safety 5 References 6 External linksStructure and preparation EditAsMe3 is a pyramidal molecule The As C distances average 1 519 A and the C As C angles are 91 83 2 Trimethylarsine can be prepared by treatment of arsenic oxide with trimethylaluminium 3 As2O3 1 5 AlMe3 2 2 AsMe3 3 n MeAl O nOccurrence and reactions EditTrimethylarsine is the volatile byproduct of microbial action on inorganic forms of arsenic which are naturally occurring in rocks and soils at the parts per million level 4 Trimethylarsine has been reported only at trace levels parts per billion in landfill gas from Germany Canada and the U S A and is the major arsenic containing compound in the gas 5 6 7 Trimethylarsine is pyrophoric due to the exothermic nature of the following reaction which initiates combustion AsMe3 1 2 O2 OAsMe3 TMAO History EditPoisoning events due to a gas produced by certain microbes was assumed to be associated with the arsenic in paint In 1893 the Italian physician Bartolomeo Gosio published his results on Gosio gas that was subsequently shown to contain trimethylarsine 8 Under wet conditions the mold Microascus brevicaulis produces significant amounts of methyl arsines via methylation 9 of arsenic containing inorganic pigments especially Paris green and Scheele s Green which were once used in indoor wallpapers Newer studies show that trimethylarsine has a low toxicity and could therefore not account for the death and the severe health problems observed in the 19th century 10 11 Safety EditTrimethylarsine is potentially hazardous 12 13 14 although its toxicity is often overstated 10 References Edit Hoshino Masataka 1991 A mass spectrometric study of the decomposition of trimethylarsine TMAs with triethylgallium TEGa Journal of Crystal Growth 110 4 704 712 Bibcode 1991JCrGr 110 704H doi 10 1016 0022 0248 91 90627 H Wells A F 1984 Structural Inorganic Chemistry fifth edition Oxford University Press ISBN 978 0 19 855370 0 V V Gavrilenko L A Chekulaeva and I V Pisareva Highly efficient synthesis of trimethylarsine Izvestiya Akademii Nauk Seriya Khimicheskaya No 8 pp 2122 2123 1996 Cullen W R Reimer K J 1989 Arsenic speciation in the environment Chem Rev 89 4 713 764 doi 10 1021 cr00094a002 hdl 10214 2162 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Feldmann J Cullen W R 1997 Occurrence of Volatile Transition Metal Compounds in Landfill Gas Synthesis of Molybdenum and Tungsten Carbonyls in the Environ Sci Technol 31 7 2125 2129 doi 10 1021 es960952y a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Pinel Raffaitin P LeHecho I Amouroux D Potin Gautier M 2007 Distribution and Fate of Inorganic and Organic Arsenic Species in Landfill Leachates and Biogases Environ Sci Technol 41 13 4536 4541 Bibcode 2007EnST 41 4536P doi 10 1021 es0628506 PMID 17695893 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Khoury J T et al April 7 2008 Analysis of Volatile Arsenic Compounds in Landfill Gas Odors amp Air Emissions 2008 Phoenix Arizona Water Environment Federation Frederick Challenger 1955 Biological methylation Q Rev Chem Soc 9 3 255 286 doi 10 1039 QR9550900255 Ronald Bentley amp Thomas G Chasteen 2002 Microbial Methylation of Metalloids Arsenic Antimony and Bismuth Microbiology and Molecular Biology Reviews 66 2 250 271 doi 10 1128 MMBR 66 2 250 271 2002 PMC 120786 PMID 12040126 a b William R Cullen Ronald Bentley 2005 The toxicity of trimethylarsine an urban myth J Environ Monit 7 1 11 15 doi 10 1039 b413752n PMID 15693178 Frederick Challenger Constance Higginbottom Louis Ellis 1933 The formation of organo metalloidal compounds by microorganisms Part I Trimethylarsine and dimethylethylarsine J Chem Soc 95 101 doi 10 1039 JR9330000095 Andrewes Paul et al 2003 Dimethylarsine and Trimethylarsine Are Potent Genotoxins In Vitro Chem Res Toxicol 16 8 994 1003 doi 10 1021 tx034063h PMID 12924927 Irvin T Rick et al 1995 In vitro Prenatal Toxicity of Trimethylarsine Trimethylarsine Oxide and Trimethylarsine Sulfide Applied Organometallic Chemistry 9 4 315 321 doi 10 1002 aoc 590090404 Hiroshi Yamauchi Toshikazu Kaise Keiko Takahashi Yukio Yamamura 1990 Toxicity and metabolism of trimethylarsine in mice and hamsters Fundamental and Applied Toxicology 14 2 399 407 doi 10 1016 0272 0590 90 90219 A PMID 2318361 External links EditIndex by Molecular Formula Information on Hazardous Chemicals by Class Microbial Methylation of Metalloids Arsenic Antimony and Bismuth Arsenic Curiosa and Humanity Retrieved from https en wikipedia org w index php title Trimethylarsine amp oldid 1086538413, wikipedia, wiki, book, books, library,

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