trimethylarsine

AsMe₃ is a pyramidal molecule. The As-C distances average 1.519 Å, and the C-As-C angles are 91.83°{{cite book | author=Wells, A.F. | title=Structural Inorganic Chemistry, fifth edition | publisher=Oxford University Press |year=1984 |isbn= 978-0-19-855370-0}}

Trimethylarsine can be prepared by treatment of arsenic oxide with trimethylaluminium: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.

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

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.{{cite journal | author=Cullen, W.R., Reimer, K.J. | title=Arsenic speciation in the environment |journal=Chem. Rev. |volume = 89 | pages = 713–764|year=1989 | doi=10.1021/cr00094a002 | issue=4| hdl=10214/2162 | hdl-access=free }} 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.{{cite journal | author=Feldmann, J., Cullen, W.R. | title=Occurrence of Volatile Transition Metal Compounds in Landfill Gas: Synthesis of Molybdenum and Tungsten Carbonyls in the |journal=Environ. Sci. Technol.| volume=31 | pages = 2125–2129 |year=1997 | doi=10.1021/es960952y | issue=7}}{{cite journal

| author= Pinel-Raffaitin, P., LeHecho, I., Amouroux, D., Potin-Gautier, M.

| title = Distribution and Fate of Inorganic and Organic Arsenic Species in Landfill Leachates and Biogases

| journal = Environ. Sci. Technol.

| year = 2007

| volume = 41

| issue = 13

| pages = 4536–4541

| doi = 10.1021/es0628506

| pmid= 17695893| bibcode = 2007EnST...41.4536P

}}{{cite conference

| author= Khoury, J.T.| title = Analysis of Volatile Arsenic Compounds in Landfill Gas

| book-title = Odors & Air Emissions 2008

| location = Phoenix, Arizona

| date = April 7, 2008

| publisher = Water Environment Federation|display-authors=etal}}

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

:AsMe₃ + 1/2 O₂ → OAsMe₃ (TMAO)

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.{{cite journal

| author= Frederick Challenger

| title = Biological methylation

| journal = Q. Rev. Chem. Soc.

| year = 1955

| volume = 9

| issue =3

| pages = 255–286

| doi = 10.1039/QR9550900255}}

Under wet conditions, the mold Microascus brevicaulis produces significant amounts of methyl arsines via methylation{{cite journal

|author1=Ronald Bentley |author2=Thomas G. Chasteen

|name-list-style=amp | title = Microbial Methylation of Metalloids: Arsenic, Antimony, and Bismuth

| journal = Microbiology and Molecular Biology Reviews

| year = 2002

| volume = 66

| issue = 2

| pages = 250–271

| doi = 10.1128/MMBR.66.2.250-271.2002

| pmid= 12040126

| pmc= 120786}}

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.{{cite journal

|author1=William R. Cullen |author2=Ronald Bentley | title = The toxicity of trimethylarsine: an urban myth

| journal = J. Environ. Monit.

| year = 2005

| volume = 7

| issue =1

| pages = 11–15

| doi = 10.1039/b413752n

| pmid= 15693178}}{{cite journal

|author1=Frederick Challenger |author2=Constance Higginbottom |author3=Louis Ellis | title = The formation of organo-metalloidal compounds by microorganisms. Part I. Trimethylarsine and dimethylethylarsine

| journal = J. Chem. Soc.

| year = 1933

| pages = 95–101

| doi = 10.1039/JR9330000095}}

Trimethylarsine is potentially hazardous,{{cite journal | author=Andrewes, Paul| title=Dimethylarsine and Trimethylarsine Are Potent Genotoxins In Vitro |journal=Chem. Res. Toxicol. |year=2003|volume=16|issue=8|pages=994–1003 |doi=10.1021/tx034063h| pmid=12924927 |display-authors=etal}}{{cite journal | author=Irvin, T.Rick| title=In-vitro Prenatal Toxicity of Trimethylarsine, Trimethylarsine Oxide and Trimethylarsine Sulfide |journal=Applied Organometallic Chemistry| volume=9| issue=4 |pages=315–321 |year=1995 | doi=10.1002/aoc.590090404|display-authors=etal}}{{cite journal

|author1=Hiroshi Yamauchi |author2=Toshikazu Kaise |author3=Keiko Takahashi |author4=Yukio Yamamura | title = Toxicity and metabolism of trimethylarsine in mice and hamsters

| journal = Fundamental and Applied Toxicology

| year = 1990

| volume = 14

| issue = 2

| pages = 399–407

| doi = 10.1016/0272-0590(90)90219-A

| pmid= 2318361}} although its toxicity is often overstated.

{{Reflist|30em}}

• [https://web.archive.org/web/20070625210143/http://lb.chemie.uni-hamburg.de/static/data/48_3vr6vtls.html Index by Molecular Formula]
• [https://web.archive.org/web/20070927222100/http://people.clarkson.edu/orgs/indhygie/manual/chemhyg.htm Information on Hazardous Chemicals by Class]
• [http://mmbr.asm.org/cgi/content/full/66/2/250?maxtoshow=&HITS=10&...ls.asm.org%2Fcgi%2Fsearch#Gosio%20Gas%20Is%20Trimethylarsine Microbial Methylation of Metalloids: Arsenic, Antimony, and Bismuth]
• [https://web.archive.org/web/20070715111141/http://chemeducator.org/sbibs/s0007002/spapers/720051rb.htm Arsenic Curiosa and Humanity]

Category:Organoarsenic compounds

Category:Foul-smelling chemicals

Category:Methyl compounds