Pharmaceutical Intermediates N,O-Bis(trimethylsilyl)acetamide 10416-59-8 In Medicine

Product Details

Quick Details

CasNo： 10416-59-8
Molecular Formula： C₈H₂₁NOSi₂
Appearance： Clear to yellowish clear liquid
Purity： 99%

Pharmaceutical Intermediates N,O-Bis(trimethylsilyl)acetamide 10416-59-8 In Medicine

10416-59-8 Name
Name	N,O-Bis(trimethylsilyl)acetamide
Synonym	dynasylan bsa;Co-Formula CFS-598;trimethylsilyl N-trimethylsilylethanimidate;BIS(TRIMETHYLSILYL)ACETAMIDE;Acetimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester;bis(trimethylsllyl)acetamide;CB2500;Ethanimidicacid,N-(trimethylsilyl)-,trimethylsilylester

10416-59-8 Chemical & Physical Properties
Melting point	24 °C
Boiling point	162.1±0.0 °C at 760 mmHg
Density	0.8±0.1 g/cm3
Molecular Formula	C8H21NOSi2
Molecular Weight	203.429
Flash Point	65.5±22.6 °C
PSA	21.59000
LogP	3.16
Exact Mass	203.116165
Vapour Pressure	2.9±0.3 mmHg at 25°C
Index of Refraction	1.411
Storage condition	0-6°C

10416-59-8 Usage

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, 10416-59-8 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

Used for blocking and protection of hydroxyl groups in natural products, e.g. amino acids, carbohydrates; Used for blocking and protection of functional groups in organic intermediates; 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

10416-59-8 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

10416-59-8 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.

InChI:InChI:1S/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3/b9-8+

10416-59-8 Relevant articles

A at the same time improve the N, O — double (three a silicon-based) acetamide purity and yield of production method

-

Paragraph 0046-0057; 0073-0085; 0099-0111; 0125-0137, (2018/05/24)

The invention provides a production method for improving the purity and yield of N,O-bis(trimethyl silyl) acetamide simultaneously. The production method comprises the steps of trimethylchlorosilane preparation, charging, synthetic reaction and distillation. In the step of distillation, front cut fraction is obtained through distillation, and a finished product is obtained through distillation; in the step of trimethylchlorosilane preparation, according to the mole ratio of the trimethylchlorosilane to acetamide being 2.11-2.22:1, the trimethylchlorosilane is sucked into a trimethylchlorosilane overhead tank, and the vacuum degree of the trimethylchlorosilane overhead tank is kept 0.001-0.005 MPa before charging. According to the prepared product BSA, the product purity reaches 99.58-99.66%, the impurity number and content are reduced, and the amine content is 0.20-0.25%; the BSA once through yield reaches 93.42-93.7%, and the raw material conversion rate is high and is improved by more than 3% compared with the prior art.

Semi-continuous process for preparing bis-silyl carboxamides

-

Example 3, (2008/06/13)

For preparing bis-silyl carboxamides in a semi-continuous, reacting an amide or the N-trimethylsilyl derivative thereof with a silylating agent and, at the same time, extracting the bis-silyl carboxamide formed by distillation under reduced pressure.

Carbacephalosporin compound, their preparation and use

-

, (2008/06/13)

Carbacephalosporin compounds of formula (I), STR1 salts thereof, processes for their synthesis and uses thereof, wherein: R1 is hydrogen, methoxy or formamido; R2 is an acyl group; CO2 R3 is a carboxy group or a carboxylate anion, or R3 is a carboxy protecting group or a pharmaceutically acceptable salt-forming group or in vivo hydrolysable ester group; R4, R5, R6 and R7 represent hydrogen or a substituent; R4 and R7 may be replaced by a chemical bond between the two carbon atoms shown; R5 and R6 may be linked together into a cyclic system. The compounds (I) have antibacterial properties.

BIS (TRIMETHYLSILYL) AMIDE AS NITRILE PRECURSOR

Rigo, Benoit,Lespagnol, Charles,Pauly, Marc

, p. 347 - 348 (2007/10/02)

Bis (trimethylsilyl) amides are converted into nitriles with high yields when they are treated with a catalyst (tetrabutylammonium fluoride, Lewis acids or iron phthalocyanine).