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10416-59-8

Basic Information
CAS No.: 10416-59-8
Name: N,O-Bis(trimethylsilyl)acetamide
Molecular Structure:
Molecular Structure of 10416-59-8 (N,O-Bis(trimethylsilyl)acetamide)
Formula: C8H21NOSi2
Molecular Weight: 203.43
Synonyms: Ethanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester;N-trimethylsilyl-1-trimethylsilyloxy-ethanimine;N-(Trimethylsilyl)acetimidic acid, trimethylsilyl ester;Trimethylsilyl N-trimethylsilylacetamidate;N,O-Bis(trimethylsilyl);N,O-Bis(trimethylsily)acetamide;N, O-Bis(trimethylsilyl)acetamide;N,O-Bis (Trimethylsilyl)acetamide;N.O-Bis(trimethylsilyl)acetamide;N,O-Bis-(trimethylsilyl)-acetamide;N,O-Bisltrimethylsilyl;N, O-Bis (Trimethylsilyl) Acetamide;N,O-Bis (Trimethylsilyl) Acetamide;N,O-bis-(Trimethylsilyl)acetamide;N,O-Bis-(trimethylsilyl)-acetamide(BSA);Bis trimethyl silyl acetamide;
EINECS: 233-892-7
Density: 0.83 g/cm3
Melting Point: 24 °C
Boiling Point: 162.1 °C at 760 mmHg
Flash Point: 65.5 °C
Solubility:
Appearance: Clear to yellowish clear liquid
Hazard Symbols: CorrosiveC
Risk Codes: 10-14-22-34-40-20/21/22-11
Safety: 26-36/37/39-45-7/8-43A-36-30-23-16-7/9
Transport Information: UN 2920 8/PG 2
PSA: 21.59000
LogP: 3.09120
Synthetic route
18156-74-6

1-(Trimethylsilyl)imidazole

13435-12-6

N-Trimethylsilylacetamide

10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

Conditions
ConditionsYield
at 175℃; under 75.0075 - 146.265 Torr; 30-theoretical-plates distillation column of Old-ershaw type;79.3%
at 150 - 180℃; under 78.7579 - 150.015 Torr; 20-theoretical-plates distillation column of Old-ershaw type;198.6 g
at 100 - 121℃; under 11.2511 Torr; 30-theoretical-plates distillation column of Old-ershaw type;118.9 g
at 130 - 162℃; under 75.0075 Torr; 20-theoretical-plates distillation column of Old-ershaw type;154.2 g
at 175℃; under 71.2571 - 150.015 Torr; 20-theoretical-plates distillation column of Old-ershaw type;
60-35-5

acetamide

75-77-4

chloro-trimethyl-silane

10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

18306-95-1

O,O-diethyl S-(trimethylsilyl) phosphorodithioate

16767-75-2

N-sulphinylacetamide

A

2901-90-8

bis(diethoxyphosphoryl)disulphide

B

10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

C

6926-73-4

bis(diethoxyphosphinothioyl)trisulfide

D

107-46-0

Hexamethyldisiloxane

Conditions
ConditionsYield
for 24h; Ambient temperature; sealed tube;A 2.3 g
B 1.1 g
C 2.1 g
D 1.4 g
18306-95-1

O,O-diethyl S-(trimethylsilyl) phosphorodithioate

16767-75-2

N-sulphinylacetamide

A

2901-90-8

bis(diethoxyphosphoryl)disulphide

B

10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

C

107-46-0

Hexamethyldisiloxane

D

4147-89-1

1,1,1-trimethyl-N-phenyl-N-(trimethylsilyl)-silanamine

Conditions
ConditionsYield
for 24h; Ambient temperature; sealed tube;A 2.3 g
B 1.1 g
C 1.4 g
D 2.1 g
16767-75-2

N-sulphinylacetamide

4551-15-9

phenylthiotrimethylsilane

A

10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

B

107-46-0

Hexamethyldisiloxane

C

882-33-7

diphenyldisulfane

Conditions
ConditionsYield
for 24h; Ambient temperature;A 1.6 g
B 1.3 g
C 1.7 g
60-35-5

acetamide

18156-74-6

1-(Trimethylsilyl)imidazole

10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

Conditions
ConditionsYield
at 165℃; under 112.511 - 150.015 Torr; 20-theoretical-plates distillation column of Old-ershaw type;155.7 g
at 140 - 166℃; under 75.0075 Torr; 20-theoretical-plates distillation column of Old-ershaw type;
at 163 - 180℃; under 75.0075 - 150.015 Torr; 20-theoretical-plates distillation column of Old-ershaw type;167.6 g
at 175℃; under 78.7579 - 150.015 Torr; 20-theoretical-plates distillation column of Old-ershaw type;199.5 g
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

(3R,4R)-2-Amino-4-(5-benzyloxy-pyridin-2-yl)-4-hydroxy-3-methyl-butyric acid

(3R,4R)-2-Amino-4-(5-benzyloxy-pyridin-2-yl)-3-methyl-4-trimethylsilanyloxy-butyric acid

Conditions
ConditionsYield
In methanol for 18h; Ambient temperature;100%
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

172405-14-0

N4-Boc-cytosine

528584-48-7

2-(trimethylsilyl)-N4-Boc-cytosine

Conditions
ConditionsYield
In acetonitrile at 20℃; for 2h;100%
1017684-56-8

3-cinnamyloxy-3-(3,4-methylenedioxyphenyl)-2-nitro-1-propanol

10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

(1R*,4S*,5R*,8R*)-8-(3,4-methylenedioxyphenyl)-4-phenyl-2-(trimethylsilyloxy)-1-(trimethylsilyloxy)methyl-2-aza-3,7-dioxabicyclo[3.3.0]octane

Conditions
ConditionsYield
With triethylamine In toluene; acetonitrile at 85℃; for 24h;100%
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

triethylammonium α-L-2',3'-dideoxy-3'-thiacytadin-5'-yl phosphonate

C14H28N3O5PSSi2

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 0.166667h;100%
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

28192-98-5

1-cyclohexyl-1-hydroxy-1-phenylpropan-2-one

119497-46-0

1-cyclohexyl-1-phenyl-1-(trimethylsiloxy)propan-2-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 130℃; for 12h;98.1%
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

559-74-0

friedelin

161739-59-9

3-trimethylsiloxyfriedel-2-ene

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium at 20℃; for 1h;98.1%
99-20-7

TREHALOSE

10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

42390-78-3

2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;98%
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 15 - 20℃; for 0.75h;
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 0℃; for 2h; Inert atmosphere;
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Chemistry

Molecular Formula: C8H21NOSi2
Molecular Weight: 203.43
Index of Refraction: 1.411
Molar Refractivity: 60.83 cm3
Molar Volume: 244.7 cm3
Surface Tension: 17 dyne/cm
Density: 0.83 g/cm3
Flash Point: 65.5 °C
Enthalpy of Vaporization: 38.23 kJ/mol
Boiling Point: 162.1 °C at 760 mmHg
Vapour Pressure: 2.88 mmHg at 25 °C
Melting point: 24 °C
Storage tempreture: 0-6 °C
Sensitive: Moisture sensitive
Appearance: Clear to yellowish clear liquid
Structure of N-(Trimethylsilyl)acetimidic acid, trimethylsilyl ester (CAS NO.10416-59-8):
                              
IUPAC Name: Trimethylsilyl (1E)-N-trimethylsilylethanimidate
Canonical SMILES: CC(=N[Si](C)(C)C)O[Si](C)(C)C
Isomeric SMILES: C/C(=N\[Si](C)(C)C)/O[Si](C)(C)C
InChI: InChI=1S/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3/b9-8+
InChIKey: SIOVKLKJSOKLIF-CMDGGOBGSA-N
Product Category of N-(Trimethylsilyl)acetimidic acid, trimethylsilyl ester (CAS NO.10416-59-8): API intermediates;Trimethylsilylation (GC Derivatizing Reagents);Analytical Chemistry;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents;Synthetic Organic Chemistry

Uses

 N-(Trimethylsilyl)acetimidic acid, trimethylsilyl ester (CAS NO.10416-59-8) is available for the preparation of protective solute of cephalosporins drugs. As a pharmaceutical intermediate, it can be used to produce cephalo-type antibiotics.

Toxicity Data With Reference

1.    

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 .

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by intraperitoneal route. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits toxic fumes of NOx. 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

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.