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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 25248Generated: October 23, 2026

trimethylsilyl N-trimethylsilylethanimidate

BSA · BIS(TRIMETHYLSILYL)ACETAMIDE · TMS-BA · TriMethylsilyl N-(triMethylsilyl)acetiMidate · trimethylsilyl N-trimethylsilylethanimidate · trimethylsilyl (E)-N-(trimethylsilyl)acetimidate · CB2500 · dynasylan bsa

https://huagongshe.com/en/chemical/25248

trimethylsilyl N-trimethylsilylethanimidate molecular structure

Identifiers & Physical Properties

CAS No.10416-59-8
Molecular formulaC8H21NOSi2
Average molar mass203.43 g/mol
Monoisotopic mass203.11616735 g/mol
SMILESCC(=N[Si](C)(C)C)O[Si](C)(C)C
InChIKeySIOVKLKJSOKLIF-UHFFFAOYSA-N
PubChem CID25248
DTXSIDDTXSID5051525

Chemical & Physical Properties

Topological polar surface area21.6
Hydrogen bond donors0
Hydrogen bond acceptors2
Rotatable bonds3
Heavy atoms12
Formal charge0
Complexity176
SpringerMaterials Properties29Si nuclear magnetic resonance spectrum
Melting point24 °C
Boiling point71-73 °C35 mm Hg(lit.)
Density0.832 g/mL at 20 °C(lit.)
Vapor pressure10 hPa (50 °C)
Refractive indexn20/D 1.417(lit.)
Flash point53 °F
Storage conditionsStore below +30°C.
SolubilityMiscible with many nonpolar and polar aprotic solvents.
Physical stateCrystalline Powder, Crystals and/or Chunks
pKa (acidity coefficient)5.82±0.50(Predicted)
Specific gravity0.832
ColorLight yellow or beige to brown
Hydrolytic Sensitivity7: reacts slowly with moisture/water
SensitivityMoisture Sensitive
BRN1306669
InChI1S/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3/b9-8+
InChIKeySIOVKLKJSOKLIF-CMDGGOBGSA-N
SMILESC\C(O[Si](C)(C)C)=N/[Si](C)(C)C
CAS DataBase Reference10416-59-8(CAS DataBase Reference)
EWG's Food Scores1
FDA UNIIR14N49I64O
NIST Chemistry ReferenceEthanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester(10416-59-8)
EPA Substance Registry SystemEthanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester (10416-59-8)
UNSPSC Code41116105
NACRESNA.22
GHS pictogramGHS02,GHS05,GHS07
Signal wordDanger
GHS hazard statementsH226-H302-H314
GHS precautionary statementsP210-P233-P280-P301+P312-P303+P361+P353-P305+P351+P338
Personal protective equipment (PPE)Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard symbolsC,Xn,F
Risk statements (R)10-14-22-34-40-20/21/22-11
Safety statements (S)26-36/37/39-45-7/8-43A-36-30-23-16-7/9
UN transport numberUN 2920 8/PG 2
Water hazard class (WGK)3
RTECS numberAK3000000
F10-21
TSCA inventory statusTSCA listed
Hazard class8Acute Tox. 4 OralFlam. Liq. 3Skin Corr. 1B
Packing groupII
Customs code29310095
Storage class3 - Flammable liquids
ToxicityLD50 orally in Rabbit: 1580 mg/kg
REACH registrationsActive
Limited quantities1.0 L (0.3 gallon) (liquid)
Excepted quantitiesMax Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & Regulations

F10-21
Personal protective equipment (PPE)Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Water hazard class (WGK)3
TSCA inventory statusTSCA listed
RTECS numberAK3000000
UN transport numberUN 2920 8/PG 2
Customs code29310095
ToxicityLD50 orally in Rabbit: 1580 mg/kg
Risk statements (R)10-14-22-34-40-20/21/22-11
Signal wordDanger
GHS pictogramGHS02,GHS05,GHS07
Hazard symbolsC,Xn,F
Safety statements (S)26-36/37/39-45-7/8-43A-36-30-23-16-7/9
Hazard class8Acute Tox. 4 OralFlam. Liq. 3Skin Corr. 1B
Storage class3 - Flammable liquids
Packing groupII
GHS hazard statementsH226-H302-H314
Limited quantities1.0 L (0.3 gallon) (liquid)
Excepted quantitiesMax Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH registrationsActive
GHS precautionary statementsP210-P233-P280-P301+P312-P303+P361+P353-P305+P351+P338

Applications & Uses

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

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.

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.

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.

Preparation & Synthesis

Preparation

N,O-Bis(trimethylsilyl)acetamide is made by the reaction of acetamide with a large excess of chlorotrimethylsilane in the presence of triethylamine.