N,O-Bis(trimethylsilyl)acetamide Chemical 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

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

Sensitive 

Moisture Sensitive

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 Information

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

F 

10-21

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29310095

Toxicity

LD50 orally in Rabbit: 1580 mg/kg

MSDS

• Language:English Provider:Trimethylsilyl N-trimethylsilylacetamidate
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N,O-Bis(trimethylsilyl)acetamide Usage And Synthesis

Description

Clear to yellowish clear liquid liquid which is soluble in many nonpolar and polar aprotic solvents.
The trimethylsilyl group is a frequently utilized monofunctional blocking group for protic organic and inorganic materials. As it eliminated during the silylation is neutral acetamide, N,O-Bis(trimethylsilyl)acetamide can be preferably used for substrates which are acid- or base-sensitive.
N,O-bis(trimethylsilyl)-acetamide is an effective silylating agent. It is used in the pharmaceutical and in the chemical industry. Typically the silylating reaction with BSA results in neutral by-products only.

Uses

1. Used for blocking and protection of hydroxyl groups in natural products, e.g. amino acids, carbohydrates;
2. Used for blocking and protection of functional groups in organic intermediates;
3. Used for formation of derivatives of H-acid compounds for analysis;

The silylated derivatives are volatile and can therefore be determined by gas chromatography. Deblocking is preferably carried out by means of hydrolysis, giving high yields. In some cases, thermal elimination of the trimethylsilyl group is possible.

Physical properties

bp 71–73°C/35 mmHg.

Uses

Powerful silylation reagent for a wide range of functional groups under mild conditions

Uses

N,O-bis(trimethylsilyl)-acetamide (BSA) is frequently used with TMCS as a catalyst to modify a variety of functional groups including carboxyl groups. In one novel application, BSA was used to measure carboxypeptidase activity by forming derivatives which could be determined by gas chromatography.BSA has been used to prepare derivatives of steroids and glucocorticoids.

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.

N,O-Bis(trimethylsilyl)acetamide(10416-59-8)Related Product Information

• Thioacetamide
• Acetaminophen
• N,N-Dimethylacetamide
• 2-Cyanoacetamide
• Acetamide
• N-(Trimethylsilyl)acetamide
• 2,2,2-TRIFLUORO-N,O-BIS(TRIMETHYLSILYL)-ACETAMIDE,Trifluoro-N,O-bis(trimethylsilyl)acetamide,N,O-bis(trimethylsilyl)acetamide,*with 10%
• tert-Butyldimethylsilyl chloride
• N,N'-Methylenebisacrylamide
• N,N'-Dimethyl-1,2-ethanediamine
• N,N-Bis(2-cyanoethyl)formamide
• TERT-BUTYL N-(TERT-BUTOXYCARBONYLOXY)CARBAMATE
• N,N'-BIS(3-AMINOPROPYL)ETHYLENEDIAMINE
• 2,2-Bis(trimethylsilyl)acetamide
• 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-Acetamid
• TRIMETHYLSILANE
• Bovine albumin
• N,O-BIS(TERT-BUTYLDIMETHYLSILYL)ACETAMIDE