Bis(trimethylsilyl)trifluoroacetamide

HCID 94358

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

25561-30-2N,O-Bis(trimethylsilyl)trifluoroacetamideDTXSID001015789Trimethylsilyl 2,2,2-trifluoro-N-(trimethylsilyl)acetimidateCHEBI:85067N,O-bis(TMS)3FANRefChem:899902DTXCID401473949247-103-9Bis(trimethylsilyl)trifluoroacetamideBSTFAtrimethylsilyl 2,2,2-trifluoro-N-trimethylsilylethanimidate
Show more names
N,O-BSTFAN,O-Bis(Trimethylsilyl)N,N-BIS(TRIMETHYLSILYL)TRIFLUOROACETAMIDEN,0-Bis(trimethylsilyl)trifluoroacetamideN.O-Bis(trimethylsilyl)trifluoro acetamide (BSTFA)Trimethylsilyl (E)-2,2,2-trifluoro-N-(trimethylsilyl)acetimidaten,o-bis(trimethylsilyl)trifluoroacetamide with trimethylchlorosilane
Ethanimidic acid, 2,2,2-trifluoro-N-(trimethylsilyl)-, trimethylsilyl esterN,O-Bis(trimethylsilyl)trifluoroacetamide (~90%)C8H18F3NOSi2BSTFA; N,O-Bis(trimethylsilyl)trifluoroacetamideBSTFA + TMCSAcetamide, 2,2,2-trifluoro-O,N-bis(trimethylsilyl)-BSTFA containing 1% TMCSN,O-bis-(TRIMETHYLSILYL)-TRIFLUOROACETAMIDE

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

Experimental & physicochemical properties

Chemical ClassesMetals -> Metalloid Compounds (Silicon)
PFASPFAS -> PFAS identified in REACH Regulation EC No. 1272/2008
SpringerMaterials Properties · 2 items

29Si nuclear magnetic resonance spectrum

29Si nuclear magnetic resonance spectrum

Physical DescriptionColorless liquid; [Sigma-Aldrich MSDS]

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 2 items

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

Hazards SummaryReadily hydrolyzes; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesFlam. Liq. 2 (56.7%)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

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

Chemistry & industry

Applications · 5 items

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.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

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

19 records

Compound notes

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