Basic information
- CAS
10416-59-8- Standard SMILES
C/C(=N\[Si](C)(C)C)O[Si](C)(C)C- InChIKey
SIOVKLKJSOKLIF-CMDGGOBGSA-N- Molecular formula
- C8H21NOSi2
- Average molar mass
- 203.43 g/mol
Names & identifiers
- Preferred name
- N,O-bis(trimethylsilyl)acetamide
- IUPAC
- trimethylsilyl (1E)-N-trimethylsilylethanimidate
- English name
- N,O-Bis(trimethylsilyl)acetamide
- Molecular formula
- C8H21NOSi2
- Molecular weight
- 203.43
Names & synonyms
Trimethylsilyl N-trimethylsilylacetamidateR14N49I64ODTXCID1030074Ethanimidic acid, N-(trimethylsilyl)-, trimethylsilyl esterDTXSID5051525RefChem:161345233-892-710416-59-8Bis(trimethylsilyl)acetamideN,O-bis(trimethylsilyl)acetamideMFCD00008270ACETIMIDIC ACID, N-(TRIMETHYLSILYL)-, TRIMETHYLSILYL ESTER
Show more names
TMS-BAtrimethylsilyl N-trimethylsilylethanimidatetrimethylsilyl (E)-N-(trimethylsilyl)acetimidateCB2500bis(trimethylsllyl)acetamideN.O-Bis(trimethylsilyl)acetamide (BSA)
Trimethylsilyl (1E)-N-(trimethylsilyl)ethanimidateTRIMETHYLSILYL N-(TRIMETHYLSILYL)ACETIMIDATEN-(Trimethylsilyl)acetimidic acid, trimethylsilyl ester132255-83-5Dynasylan BSABSAtrimethylsilyl (1E)-N-trimethylsilylethanimidateEINECS 233-892-7
Database identifiers
- CAS
10416-59-8- PubChem CID
- 6913588
- UNII
- R14N49I64O
- EC Number
- 233-892-7
- Nikkaji
- J10.472H
Properties
Computed structural properties
- Topological polar surface area
- 21.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 176
Experimental & physicochemical properties
Chemical ClassesMetals -> Metalloid Compounds (Silicon)
Physical DescriptionColorless or pale yellow liquid; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 24 °C · 24 °C
- Boiling point
- 71 · 71-73 °C35 mm Hg(lit.)
- Density
- 0.832 g/mL · 0.832 g/mL at 20 °C(lit.)
- vapor pressure
- 10 hPa · 10 hPa (50 °C)
- refractive index
- 20 · n20/D 1.417(lit.)
- Flash point
- 53 °F · 53 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Miscible with many nonpolar and polar aprotic solvents.
- form
- Crystalline Powder, Crystals and/or Chunks
- pka
- 5.82 · 5.82±0.50(Predicted)
- Specific Gravity
- 0.832 · 0.832
Safety & regulation
GHS classification
GHS Classification
Danger
H226 (97.8%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P330, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 91 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Ethanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester
Status: Active Update: 04-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34060
Trimethylsilyl N-trimethylsilylacetamidate: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes decreased immune response in intraperitoneal lethal-dose studies of mice (LD50 = 750 mg/kg); [RTECS] Reacts violently with water; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion; [Alfa Aesar MSDS]
Hazard Classes and CategoriesFlam. Liq. 3 (97.8%)
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 10-21
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationEthanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester: ACTIVE
Applications
DescriptionClear 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.
UsesUsed 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.
UsesPowerful silylation reagent for a wide range of functional groups under mild conditions
UsesN,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.
UsesN,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.
Related reactions
235 records
Compound notes
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