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N,O-Bis(trimethylsilyl)acetamide

N,O-Bis(trimethylsilyl)acetamide Structure
CAS No.
10416-59-8
Chemical Name:
N,O-Bis(trimethylsilyl)acetamide
Synonyms
BSA;BIS(TRIMETHYLSILYL)ACETAMIDE;TriMethylsilyl N-(triMethylsilyl)acetiMidate;TMS-BA;dynasylan bsa;bis(trimethylsllyl)acetamide;N.O-Bis(trimethylsilyl)acetamide (BSA);(E)-TriMethylsilyl N-(triMethylsilyl)acetiMidate;trimethylsilyl (1E)-N-trimethylsilylethanimidate;BSiA
CBNumber:
CB7366985
Molecular Formula:
C8H21NOSi2
Molecular Weight:
203.43
MOL File:
10416-59-8.mol
MSDS File:
SDS
Modify Date:
2024/7/1 19:01:27

N,O-Bis(trimethylsilyl)acetamide Properties

Melting point 24 °C
Boiling point 71-73 °C35 mm Hg(lit.)
Density 0.832 g/mL at 20 °C(lit.)
vapor pressure 10 hPa (50 °C)
refractive index n20/D 1.417(lit.)
Flash point 53 °F
storage temp. Store below +30°C.
solubility Miscible with many nonpolar and polar aprotic solvents.
form Crystalline Powder, Crystals and/or Chunks
pka 5.82±0.50(Predicted)
Specific Gravity 0.832
color Light yellow or beige to brown
Sensitive Moisture Sensitive
Hydrolytic Sensitivity 7: reacts slowly with moisture/water
BRN 1306669
CAS DataBase Reference 10416-59-8(CAS DataBase Reference)
NIST Chemistry Reference Ethanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester(10416-59-8)
EPA Substance Registry System Ethanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester (10416-59-8)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS02,GHS05,GHS07
Signal word  Danger
Hazard statements  H226-H302-H314
Precautionary statements  P210-P233-P280-P301+P312-P303+P361+P353-P305+P351+P338
Hazard Codes  C,Xn,F
Risk Statements  10-14-22-34-40-20/21/22-11
Safety Statements  26-36/37/39-45-7/8-43A-36-30-23-16-7/9
RIDADR  UN 2920 8/PG 2
WGK Germany  3
RTECS  AK3000000
10-21
TSCA  Yes
HazardClass  8
PackingGroup  II
HS Code  29310095
Toxicity LD50 orally in Rabbit: 1580 mg/kg
NFPA 704
3
3 0
W

N,O-Bis(trimethylsilyl)acetamide price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 8.18727 N,O-Bis(trimethylsilyl)acetamide for synthesis 10416-59-8 25ML ₹8720.01 2022-06-14 Buy
Sigma-Aldrich(India) 8.18727 N,O-Bis(trimethylsilyl)acetamide for synthesis 10416-59-8 100ML ₹16720 2022-06-14 Buy
Sigma-Aldrich(India) 15269 N,O-Bis(trimethylsilyl)acetamide for GC derivatization, LiChropur?, ≥98.5% (GC) 10416-59-8 5ML ₹4297.53 2022-06-14 Buy
Sigma-Aldrich(India) 15269 N,O-Bis(trimethylsilyl)acetamide for GC derivatization, LiChropur?, ≥98.5% (GC) 10416-59-8 10X1ML ₹15209.13 2022-06-14 Buy
Sigma-Aldrich(India) 15269 N,O-Bis(trimethylsilyl)acetamide for GC derivatization, LiChropur?, ≥98.5% (GC) 10416-59-8 25ML ₹16583.9 2022-06-14 Buy
Product number Packaging Price Buy
8.18727 25ML ₹8720.01 Buy
8.18727 100ML ₹16720 Buy
15269 5ML ₹4297.53 Buy
15269 10X1ML ₹15209.13 Buy
15269 25ML ₹16583.9 Buy

N,O-Bis(trimethylsilyl)acetamide Chemical Properties,Uses,Production

Physical properties

bp 71–73°C/35 mmHg.

Uses

N,O-Bis(trimethylsilyl)acetamide is a powerful silylating agent; reacts with a wide range of functional groups.
BSA was used to trimethylsilylate the hydroxyl group of 12 selectively to form in almost quantitative yield (eq 32).The presence of catalytic amounts (~0.02 equiv) of tetrabutylammonium fluoride (TBAF) significantly promoted the silylation of alcohols under mild conditions with high chemoselectivity, i.e., TBAF plays a role as a smooth silyl transfer catalyst from nitrogen to the hydroxyl group.

Preparation

made by the reaction of acetamide with a large excess of chlorotrimethylsilane in the presence of triethylamine.

General Description

N,O-Bis(trimethylsilyl)acetamide is an excellent silylation reagent. For some sterically hindered primary or secondary nitro compounds, N,O-bis(trimethylsilyl)acetamide and BSTFA achieve better results than normal silylation conditions.

Purification Methods

Fractionate it through a spinning band column and collect liquid b 71-73o/35mm, and not higher because the main impurity MeCONHSiMe3 distils at b 105-107o/35mm. It is used for derivatising alcohols and sugars [Klebe et al. J Am Chem Soc 88 3390 1966, see Matsuo et al. Carbohydr Res 241 209 1993, Johnson Carbohydr Res 237 313 1992]. Itis FLAMMABLE and TOXIC.

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