Basic information
- CAS
25561-30-2- Standard SMILES
C[Si](C)(C)N=C(O[Si](C)(C)C)C(F)(F)F- InChIKey
XCOBLONWWXQEBS-UHFFFAOYSA-N- Molecular formula
- C8H18F3NOSi2
- Average molar mass
- 257.4 g/mol
- Monoisotopic mass
- 257.08790192
Names & identifiers
- Preferred name
- Bis(trimethylsilyl)trifluoroacetamide
- IUPAC
- trimethylsilyl 2,2,2-trifluoro-N-trimethylsilylethanimidate
- English name
- Bis(trimethylsilyl)trifluoroacetamide
- Molecular formula
- C8H18F3NOSi2
- Molecular weight
- 257.4
Names & synonyms
Show more names
Database identifiers
- CAS
25561-30-2- PubChem CID
- 94358
- DTXSID
DTXSID001015789- EC Number
- 247-103-9
Properties
Computed structural properties
- Topological polar surface area
- 21.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 250
Experimental & physicochemical properties
SpringerMaterials Properties
29Si nuclear magnetic resonance spectrum
29Si nuclear magnetic resonance spectrum
Physicochemical properties
- Melting point
- -10 °C · -10°C
- Boiling point
- 45 · 45-50 °C14 mm Hg(lit.)
- Density
- 0.97 g/mL · 0.97 g/mL(lit.)
- refractive index
- 20 · n20/D 1.384(lit.)
- Flash point
- 75 °C · 75 °C
- storage temp.
- 2 · 2-8°C
- solubility
- Miscible with chloroform.
- form
- Liquid
- pka
- 1.82 · 1.82±0.50(Predicted)
- Specific Gravity
- 0.971 · 0.971
- color
- Colorless to pale yellow
- Water Solubility
- hydrolyses
- Sensitive
- Moisture Sensitive
- Hydrolytic Sensitivity
- 8 · 8: reacts rapidly with moisture, water, protic solvents
- BRN
- 3607620 · 3607620
- Stability
- Moisture Sensitive
- InChI
- 1S/C8H18F3NOSi2/c1-14(2,3)12-7(8(9,10)11)13-15(4,5)6/h1-6H3/b12-7+
- InChIKey
- XCOBLONWWXQEBS-KPKJPENVSA-N
- SMILES
- C[Si](C)(C)O\C(=N\[Si](C)(C)C)C(F)(F)F
- CAS DataBase Reference
- 25561 · 25561-30-2(CAS DataBase Reference)
- FDA UNII
- 5 T8NA426KZ · 5T8NA426KZ
- NIST Chemistry Reference
- Bis(trimethylsilyl)trifluoroacetamide(25561-30-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H302-H314
- Precautionary statements
- 210 · P210-P233-P280-P301+P312-P303+P361+P353-P305+P351+P338
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C,F,T
- Risk Statements
- 11 · 11-34-10-35-14
- Safety Statements
- 26 · 26-36/37/39-45-16
- RIDADR
- 2924 · UN 2924 3/PG 3
- WGK Germany
- 3 · 3
- F
- 10 · 10-21
- Hazard Note
- Flammable/Moisture Sensitive
- TSCA
- Yes
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29310095 · 29310095
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Flam. Liq. 2Skin Corr. 1A
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (56.7%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P332+P317, P337+P317, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 67 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 23-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21964
Bis(trimethylsilyl)trifluoroacetamide: Does not have an individual approval but may be used under an appropriate group standard
Toxicology
Safety data
- F
- 10-21
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- Yes
- ridadr
- UN 2924 3/PG 3
- hs_code
- 29310095
- risk_code
- 11-34-10-35-14
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS07
- hazard_code
- C,F,T
- hazard_note
- Flammable/Moisture Sensitive
- safety_code
- 26-36/37/39-45-16
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H225-H302-H314
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Flam. Liq. 2Skin Corr. 1A
- Precautionary statements
- P210-P233-P280-P301+P312-P303+P361+P353-P305+P351+P338
Chemistry & industry
Applications
UsesBis(trimethylsilyl)trifluoroacetamide is used for synthesis of pharmaceutical intermediates.
UsesUsed as a reactant in the preparation of pyrimidinone ribosides and analogs that show anti-tumor properties.
UsesN,O-bis(trimethylsilyl)-trifluoroacetamide (BSTFA) is similar to BSA in specificity of modification and there are several studies which have used both reagents.One study found BSTFA superior to BSA in product stability and yield of derivative. Another study compared several trimethylsilyl donors for end-capping of silica and observed that BSTFA was more reactive than BSA but less reactive than TMCim. Both BSA and BSTFA were used to prepare trimethylsilyl derivatives of pyrimidines and purines.Current work has used BSTFA for metabolomics analysis of urine,for the measurement of khatamines (psychoactive amines of khat (Catha edulis Forsk), and for the measurement of acrylamide in cocoa.
UsesN,O-Bis(trimethylsilyl)trifluoroacetamide is used for analytical purposes or as a chemical reagent for synthesis of more complex molecules. It is silylation reagent useful in GC and GC-MS for the derivatization of a wide range of functional groups under mild conditions. It is also used as DAT inhibitor and a SLC6A2 inhibitor. It is routinely used to derivatize carboxylic acids, phenols, steroids, amines, alcohols, and alkaloids and amides.
General DescriptionBis(trimethylsilyl)trifluoroacetamide with trimethylchlorosilane has found application to be used in gas chromatography (GC) and mass-spectrometry (MS). It can also be used in HPLC- electrochemical detection assay of 8-oxo-deoxyguanosine and8-oxo-guanine.
Upstream & downstream products
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: A silyl ether that is the N,O-bis(trimethylsilyl) derivative of trifluoroacetamide. N,O-bis(trimethylsilyl)trifluoroacetamide is a derivatisation agent used in gas chromatography/m ss spectrometry applications.
Related reactions
Compound notes
Loading…