Bis(trimethylsilyl)acetamide

Bis(trimethylsilyl)acetamide
Names
	Preferred IUPAC name N-Trimethylsilyl-1-trimethylsilyloxyethanimine
	Systematic IUPAC name Trimethylsilyl N-(trimethylsilyl)ethanecarboximidate
	Other names N,O-Bis(trimethylsilyl)acetamide
Identifiers
CAS Number	10416-59-8 ;
3D model (JSmol)	Interactive image; Interactive image;
Abbreviations	BSA
Beilstein Reference	1306669
ChemSpider	23581 ; 4523073 (E) ; 10516629 (Z) ;
ECHA InfoCard	100.030.799
EC Number	233-892-7;
MeSH	N,O-bis(trimethylsilyl)acetamide
PubChem CID	25248; 6913588 (E); 5372922 (Z);
RTECS number	AK3000000;
UNII	R14N49I64O ;
UN number	2920
CompTox Dashboard (EPA)	DTXSID5051525 ;
	InChI InChI=1S/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3 Key: SIOVKLKJSOKLIF-UHFFFAOYSA-N; InChI=1/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3/b9-8+;
	SMILES CC(=N[Si](C)(C)C)O[Si](C)(C)C; CC(O[Si](C)(C)C)=N[Si](C)(C)C;
Properties
Chemical formula	C8H21NOSi2
Molar mass	203.432 g·mol−1
Appearance	Liquid
Density	0.832 g cm−3
Melting point	24 °C (75 °F; 297 K)
Boiling point	71 to 73 °C (160 to 163 °F; 344 to 346 K) at 35mmHg
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H302, H314
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+312, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P330, P363, P370+378, P403+235, P405, P501
Related compounds
Related Amides	Dimethylacetamide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Bis(trimethylsilyl)acetamide (BSA) is an organosilicon compound with the formula Me₃SiNC(OSiMe₃)Me (Me = CH₃). It is a colorless liquid that is soluble in diverse organic solvents, but reacts rapidly with compounds, including solvents and moisture, containing OH and NH functional groups. It is used in analytical chemistry for the derivatisation of compounds in analysis to increase their volatility, e.g. for gas chromatography.[1] It is also used to introduce the trimethylsilyl protecting group in organic synthesis.[2] A related reagent is N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA).

Synthesis and reactions

BSA is prepared by treating acetamide with trimethylsilyl chloride in the presence of a base:[2]

2 Me₃SiCl + H₂NC(O)Me + 2 Et₃N → Me₃SiNC(OSiMe₃)Me + 2 Et₃NHCl

The reaction of BSA with alcohols gives the corresponding trimethylsilyl ether, together with N-(trimethylsilyl)acetamide as a byproduct:

ROH + Me₃SiNC(OSiMe₃)Me → Me₃SiN(H)C(O)Me + ROSiMe₃

References

Blau, Karl; J. M. Halket (1993). Handbook of Derivatives for Chromatography (2nd ed.). John Wiley & Sons. ISBN 0-471-92699-X.

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[1] Blau, Karl; J. M. Halket (1993). Handbook of Derivatives for Chromatography (2nd ed.). John Wiley & Sons. ISBN 0-471-92699-X.

[eEROS-2] Harry Heaney, Jian Cui, “N,O-Bis(trimethylsilyl)acetamide” Encyclopedia of Reagents for Organic Synthesis Copyright © 2007 John Wiley & Sons. doi:10.1002/047084289X.rb208.pub2.