N,O-Bis(trimethylsilyl)acetamide structure

3D Mol Similar

N,O-Bis(trimethylsilyl)acetamide

: Iupac Name：trimethylsilyl (1Z)-N-trimethylsilylethanimidate; CAS No.: 10416-59-8; Molecular Weight：203.432; Modify Date.: 2022-10-31 06:29; Introduction: 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. View more+

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1. Names and Identifiers

: 1.1 Name; N,O-Bis(trimethylsilyl)acetamide; 1.2 Synonyms; (E)-Trimethylsilyl N-(trimethylsilyl)acetimidate Acetimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester bis(trimethylsllyl)acetamide bis-TMS-acetamide bsa kit CB2500 Co-Formula CFS-598 dynasylan bsa EINECS 233-892-7 Ethanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester, (1E)- Ethanimidicacid,N-(trimethylsilyl)-,trimethylsilylester MFCD00008270 TMS-BA tms-ba kit TMS-BA KitBSA Kit TMS-BABSA Trimethylsilyl (1E)-N-(trimethylsilyl)ethanimidate Trimethylsilyl (1E)-N-(trimethylsilyl)ethanimidoate Trimethylsilyl N-(trime Trimethylsilyl N-(trimethylsilyl)acetimidate trimethylsilyl N-trimethylsilylethanimidate; View all

1.3 CAS No.: 10416-59-8

1.4 CID: 5372922

1.5 EINECS(EC#): 233-892-7

1.6 Molecular Formula: C8H21NOSi2 (isomer)

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

1.8 InChIkey: SIOVKLKJSOKLIF-HJWRWDBZSA-N

1.9 Canonical Smiles: CC(=N[Si](C)(C)C)O[Si](C)(C)C

1.10 Isomers Smiles: C/C(=N/[Si](C)(C)C)/O[Si](C)(C)C

2. Properties

2.1 Density: 0.823

2.1 Melting point: 24℃

2.1 Boiling point: 71-73℃ (35 torr)

2.1 Refractive index: 1.4165-1.4185

2.1 Flash Point: 42℃

2.1 Precise Quality: 203.11600

2.1 PSA: 21.59000

2.1 logP: 3.09120

2.1 Solubility: Miscible with many nonpolar and polar aprotic solvents.

2.2 Appearance: Clear to yellowish clear liquid

2.3 Storage: Keep Cold. Moisture Sensitive.

2.4 Color/Form: Light yellow or beige to brown

2.5 pKa: 5.82±0.50(Predicted)

2.6 Water Solubility: Insoluble

2.7 Stability: Stable under normal temperatures and pressures.

2.8 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 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 Preparation Products And Raw materials Raw materials

3.2 Usage: 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.

4. Safety and Handling

4.1 Symbol: GHS02, GHS05, GHS07

4.1 Hazard Codes: C

4.1 Signal Word: Danger

4.1 Risk Statements: R10;R14;R22;R34

4.1 Safety Statements: S26;S30;S36;S43;S7/8

4.1 Packing Group: II

4.1 Hazard Class: 8

4.1 Hazard Declaration: H226-H302-H314

4.1 RIDADR: UN 2920

4.1 Caution Statement: P280-P305 + P351 + P338-P310

4.1 WGK Germany: 3

4.1 RTECS: AK3000000

4.1 Report: Reported in EPA TSCA Inventory.

4.2 Safety: Moderately toxic by intraperitoneal route. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits toxic fumes of NO_x. See also ESTERS.
Hazard Codes: C,Xn,F
Risk Statements: 10-14-22-34-40-20/21/22-11
10: Flammable?
14: Reacts violently with water?
22: Harmful if swallowed?
34: Causes burns?
40: Limited evidence of a carcinogenic effect?
20/21/22: Harmful by inhalation, in contact with skin and if swallowed?
11: Highly Flammable?
Safety Statements: 26-36/37/39-45-7/8-43A-36-30-23-16-7/9
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36/37/39: Wear suitable protective clothing, gloves and eye/face protection?
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)?
7/8: Keep container tightly closed and dry?
43: In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water)?
36: Wear suitable protective clothing?
30: Never add water to this product?
23: Toxic by inhalation?
16: Explosive when mixed with oxidizing substances?
7/9: Keep container tightly closed and in a well-ventilated place?
RIDADR: UN 2920 8/PG 2
WGK Germany: 3
RTECS:? AK3000000
F: 10-21
F10: Keep under argon
F21: Sensitive to humidity
TSCA: Yes
HazardClass: 8
PackingGroup: II
HS Code: 29310095; View all

4.3 Sensitive: Moisture Sensitive

4.4 Specification: ?N-(Trimethylsilyl)acetimidic acid, trimethylsilyl ester , its cas register number is 10416-59-8. It also can be called N,O-Bis(trimethylsilyl)acetamide ; BSA ; Dynasylan BSA ; and Trimethylsilyl N-trimethylsilylacetamidate . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product:?Do not induce vomiting. Get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, N-(Trimethylsilyl)acetimidic acid, trimethylsilyl ester (CAS NO.10416-59-8) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials, ignition sources, exposure to moist air or water. And also prevent it to broken down into hazardous decomposition products:?Nitrogen oxides, carbon monoxide, carbon dioxide, nitrogen, silicon dioxide.; View all

4.5 Toxicity

???

ipr-mus LDLo:750?mg/kg

???

StoGD# ?? Personal Communication to NIOSH from Fr. Gary D. Stoner, Dept. of Community Medicine, School of Medicine, University of California, La Jolla, CA 92037, May 25, 1975 27May75 .

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 3

Acute toxicity - Oral, Category 4

Skin corrosion, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H226 Flammable liquid and vapour H302 Harmful if swallowed H314 Causes severe skin burns and eye damage
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 Keep container tightly closed. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P242 Use non-sparking tools. P243 Take action to prevent static discharges. P280 Wear protective gloves/protective clothing/eye protection/face protection. P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P260 Do not breathe dust/fume/gas/mist/vapours/spray.
Response	P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P370+P378 In case of fire: Use ... to extinguish. P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
Storage	P403+P235 Store in a well-ventilated place. Keep cool. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

IR : liquid film

7. Synthesis Route

10416-59-8Total: 5 Synthesis Route

60-35-5 240 Suppliers

75-77-4 202 Suppliers

10416-59-8 367 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 88, p. 3390 - 3395
Yield: null

60-35-5 240 Suppliers

18156-74-6 155 Suppliers

10416-59-8 367 Suppliers

Literatures:
Atofina Patent: US6335456 B1, 2002 ; Location in patent: Example 6 ;
Yield: null

16767-75-2 1 Suppliers

4551-15-9 16 Suppliers

10416-59-8 367 Suppliers

107-46-0 182 Suppliers

Literatures:
J. Gen. Chem. USSR (Engl. Transl.), , vol. 53, # 5 p. 1009 - 1013,891 - 894
Yield: null

View all

8. Precursor and Product

precursor:

16767-75-2

18306-95-1

60-35-5

18156-74-6

75-77-4

4551-15-9

13435-12-6

product :

17242-85-2

67014-25-9

58138-78-6

33282-64-3

10497-05-9

2641-79-4

18037-10-0

32865-86-4

3444-09-5

13435-12-6

30148-50-6

2078-13-9

10437-02-2

1833-53-0

55030-41-6

6651-34-9

43183-36-4

7288-28-0

79314-27-5

6689-37-8

3442-82-8

7057-43-4

4387-16-0

5269-44-3

View all

9. Other Information

9.0 Physical properties: bp 71–73°C/35 mmHg.

9.1 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.

9.2 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.

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

9.4 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.

9.5 Usage: N,O-Bis(trimethylsilyl)acetamide is used as a regioselective desulfation reagent as well as a preparatory agent for carbohydrate and alcohol trimethylsilyl ethers. It is also used for the derivatization of polar functional groups such as carboxylic acids, phenols, steroids, amines, alcohols, alkaloids and amides. It is employed in the formation of stable trimethylsilyl derivatives. Further, it is used in analytical chemistry for the derivatization of compounds in analysis to increase their volatility and to introduce the trimethylsilyl protecting group in organic synthesis. In addition to this, it is used in the protection of hydroxyl groups in natural products, functional groups in organic intermediates and derivatization reagent for gas chromatography-Mass spectral analysis of phenolic acids in fruits.

9.6 BRN: 1306669

9.7 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.

9.8 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.

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

9.10 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.

10. Computational chemical data

Molecular Weight: 203.432g/mol
Molecular Formula: C₈H₂₁NOSi₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 203.11616736
Monoisotopic Mass: 203.11616736
Complexity: 177
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 21.6
Heavy Atom Count: 12
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceByIAwAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHhABAEAAAACBgABCAAAAAAEgAAAgAAAAAAAAAAAAAAAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

How to Improve Drug Yield and Purity in Synthesis? Jun 19 2023
Currently, in the synthesis of drugs such as penicillin, cephalosporin, and prostaglandin in China, most of them use trimethylchlorosilane as a protecting agent. However, the use of such substances as..
Why is N, O-Bis(trimethylsilyl)trifluoroacetamide (BSTFA) a Perfect Substitute for N, O-bis(trimethylsilyl)acetamide (BSA)? Nov 25 2019
N, O-bis(trimethylsilyl)acetamide (BSA) is a neutral silane protective agent commonly used for protecting amino acids, carboxylic acids, alcohols, and amides. It is also utilized in passivating chrom..

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