25561-30-2

Basic information

• Product Name: Bis(trimethylsilyl)trifluoroacetamide
• Synonyms: BSTFA containing 1% TMCS;N,O-Bis(trimethylsilyl)trifluoroacetamide, contains 10% TMCS;N,O-Bis(trimethylsilyl)trifluoroacetamide, contains 1% TMCS, ampuled under argon;Bis(trimethylsilyl)trifluoroacetamide for gas chromatography;Acetamide, 2,2,2-trifluoro-O,N-bis(trimethylsilyl)-;Ethanimidic acid, 2,2,2-trifluoro-N-(trimethylsilyl)-, trimethylsilyl ester;N,O-bis(trimehylsilyl)trifluoroacetamide;N,O-BSTFA
• CAS NO: 25561-30-2
• Molecular Formula: C₈H₁₈F₃NOSi₂
• Molecular Weight: 257.4
• EINECS: 247-103-9
• Product Categories: Analytical Chemistry;Biochemistry;GC Derivatizing Reagents;Reagents for Oligosaccharide Synthesis;Si (Classes of Silicon Compounds);Silylacetamides;Silylation (GC Derivatizing Reagents);Si-N Compounds;Trimethylsilylation (GC Derivatizing Reagents);Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Blocking Agents;Protective Agents;Silazanes;Silylating Agents;Silylation Reagents
• Mol File: 25561-30-2.mol

Chemical Properties

• Melting Point: -10°C
• Boiling Point: 45-50 °C14 mm Hg(lit.)
• Flash Point: 75 °C
• Appearance: Colorless to pale yellow/Liquid
• Density: 0.97 g/mL(lit.)
• Vapor Pressure: 0.193mmHg at 25°C
• Refractive Index: n20/D 1.384(lit.)
• Storage Temp.: 2-8°C
• Solubility: Miscible with chloroform.
• PKA: 1.82±0.50(Predicted)
• Water Solubility: hydrolyses
• Sensitive: Moisture Sensitive
• BRN: 3607620
• CAS DataBase Reference: Bis(trimethylsilyl)trifluoroacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(trimethylsilyl)trifluoroacetamide(25561-30-2)
• EPA Substance Registry System: Bis(trimethylsilyl)trifluoroacetamide(25561-30-2)

Safety Data

• Hazard Codes: C,F,T
• Statements: 11-34-10-35-14
• Safety Statements: 26-36/37/39-45-16
• RIDADR: UN 2924 3/PG 3
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 25561-30-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Bis(trimethylsilyl)trifluoroacetamide is used as a reactant for the synthesis of pharmaceutical intermediates, contributing to the development of new drugs and medications.
Used in Antitumor Compound Preparation:
BSTFA is utilized as a reactant in the preparation of pyrimidinone ribosides and their analogs, which exhibit anti-tumor properties, potentially aiding in the fight against cancer.
Used in Analytical Chemistry:
In the field of analytical chemistry, BSTFA serves as a silylation reagent useful in GC and GC-MS for the derivatization of a wide range of functional groups under mild conditions. This makes it a valuable tool for various analytical purposes and the synthesis of more complex molecules.
Used as a Chemical Reagent:
Bis(trimethylsilyl)trifluoroacetamide is used as a chemical reagent for the synthesis of more complex molecules, thanks to its reactivity with various functional groups.
Used in Metabolomics Analysis:
BSTFA has been employed for metabolomics analysis of urine, specifically for the measurement of khatamines (psychoactive amines of khat, Catha edulis Forsk), and for the measurement of acrylamide in cocoa.
Used in Enzyme Inhibition:
Bis(trimethylsilyl)trifluoroacetamide is used as a DAT (dopamine transporter) inhibitor and a SLC6A2 (sodium-dependent neurotransmitter transporter) inhibitor, playing a role in the study and regulation of these proteins.
Used in Gas Chromatography and Mass Spectrometry:
BSTFA, in combination with trimethylchlorosilane, has found application in gas chromatography (GC) and mass-spectrometry (MS) for the analysis of various compounds.
Used in HPLC-Electrochemical Detection Assay:
Bis(trimethylsilyl)trifluoroacetamide is utilized in the HPLCelectrochemical detection assay of 8-oxo-deoxyguanosine and 8-oxo-guanine, which are relevant to DNA damage and repair mechanisms.

InChI:InChI=1/C8H18F3NOSi2/c1-14(2,3)8(9,15(4,5)6)7(13)12(10)11/h1-6H3

Synthetic route

trifluoracetyl chloride (354-32-5) + sodium hexamethyldisilazane (1070-89-9) → N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2)

chloro-trimethyl-silane (75-77-4) + 2,2,2-trifluoroacetamide (354-38-1) → N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2)

Conditions	Yield
With triethylamine
With triethylamine

N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (63323-30-8, 55097-80-8, 58917-67-2, 58917-91-2, 60268-85-1, 60268-86-2, 63323-29-5, 63323-31-9, 63357-09-5, 64397-28-0, 64912-49-8, 64912-50-1, 82111-22-6) → (+/-)-7β,8α-bis(trimethylsilyloxy)-9α,10α-epoxy-7,8,9,10-tetrahydrobenzopyrene (64660-75-9, 134175-49-8)

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Ambient temperature;	100%

N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + 2-(o-chlorophenyl)-2-<(methoxycarbonyl)amino>-6-hydroxycyclohexanone (103904-70-7) → [(1S,3S)-1-(2-Chloro-phenyl)-2-oxo-3-trimethylsilanyloxy-cyclohexyl]-carbamic acid methyl ester (103904-71-8)

Conditions	Yield
With pyridine In dichloromethane for 1h; Heating;	100%

N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + phenyl (2R*,5Z,9S*,10S*,16R*)-9-hydroxy-9-methyl-10,2,10-(epoxymetheno)-1-benzazacyclododeca-5-ene-3,7-diyne-1-carboxylate → phenyl (2R*,5Z,9S*,10S*,16R*)-9-methyl-9-trimethylsilyloxy-10,2,10-(epoxymetheno)-1-benz[b]azacyclododeca-5-ene-3,7-diyne-1-carboxylate

Conditions	Yield
With pyridine at 25℃; for 44h;	100%

N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene (87751-69-7) + malonic acid dimethyl ester (108-59-8) → (E)-dimethyl (1,3-diphenylprop-2-en-1-yl)propanedioate (177468-91-6)

Conditions	Yield
With potassium acetate; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran	99%
With potassium acetate; bis(η3-allyl-μ-chloropalladium(II)) In dichloromethane	98.9%
With lithium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In toluene	94%

lithium carbonate. tert-Butyl methyl ether + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene (87751-69-7) + malonic acid dimethyl ester (108-59-8) → (E)-dimethyl (1,3-diphenylprop-2-en-1-yl)propanedioate (177468-91-6)

Conditions	Yield
bis(η3-allyl-μ-chloropalladium(II))	99%
bis(η3-allyl-μ-chloropalladium(II))	91%
bis(η3-allyl-μ-chloropalladium(II))	88%
bis(η3-allyl-μ-chloropalladium(II))	86%
bis(η3-allyl-μ-chloropalladium(II))	71%

N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + (E)-2-(o-Chlorophenyl)-6-hydroxy-2-<(methoxycarbonyl)methylamino>cyclohexanone (91003-20-2) → [(1S,3R)-1-(2-Chloro-phenyl)-2-oxo-3-trimethylsilanyloxy-cyclohexyl]-methyl-carbamic acid methyl ester (91003-26-8)

Conditions	Yield
With pyridine In dichloromethane for 2h; Heating;	96.5%

N-Boc-methylthiolincosamide (663613-82-9) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → C26H59NO7SSi4 (844504-73-0)

Conditions	Yield
With triethylamine In DMF (N,N-dimethyl-formamide) at 0 - 20℃;	95%

lithium carbonate. tert-Butyl methyl ether + rac-3-acetoxycyclohexene (76644-52-5, 76704-31-9, 14447-34-8, 62247-41-0) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + malonic acid dimethyl ester (108-59-8) → dimethyl 2-(cyclohex-2-en-1-yl)malonate (34939-28-1)

Conditions	Yield
bis(η3-allyl-μ-chloropalladium(II))	93%
bis(η3-allyl-μ-chloropalladium(II))	56%

10-Deacetylbaccatine III (32981-86-5, 71629-92-0, 92999-93-4, 115509-92-7) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → 10-TMS-10-deacetylbaccatin III

Conditions	Yield
In tetrahydrofuran at 0℃; for 5h;	91%
In tetrahydrofuran at 0℃; for 5h;	91%

10-Deacetylbaccatine III (32981-86-5, 71629-92-0, 92999-93-4, 115509-92-7) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → 10-trimethylsilyl-10-desacetylbaccatin III monohydrate

Conditions	Yield
In tetrahydrofuran at 0℃; for 5h; Under N2;	91%

N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + {(2R,3S)-3-((R)-1-Hydroxy-ethyl)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester (92133-39-6) → [(2R,3S)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-4-oxo-3-((R)-1-trimethylsilanyloxy-ethyl)-azetidin-1-yl]-oxo-acetic acid 4-nitro-benzyl ester (90629-05-3)

Conditions	Yield
dmap In tetrahydrofuran	90%

N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-2-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanylcarbonylmethyl)-4-oxo-azetidin-1-yl]-oxo-acetic acid 4-nitro-benzyl ester (92133-41-0) → [(2R,3S)-2-((S)-1-{1-[(E)-4-Nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanylcarbonylmethyl)-4-oxo-3-((R)-1-trimethylsilanyloxy-ethyl)-azetidin-1-yl]-oxo-acetic acid 4-nitro-benzyl ester (98167-71-6)

Conditions	Yield
dmap In tetrahydrofuran	90%

Glycine anhydride (106-57-0) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → 1,4-bis(trimethylsilyl)-2,5-piperazinedione (3553-95-5)

Conditions	Yield
In acetonitrile Reflux; Inert atmosphere;	90%

tetraphenylethane-1,2-diol (464-72-2) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → 1-hydroxy-2-trimethylsiloxy-1,1,2,2-tetraphenylethane

Conditions	Yield
With pyridine In acetone at 70℃; for 2h;	88.3%

lithium acetate. tert-Butyl methyl ether + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene (87751-69-7) + malonic acid dimethyl ester (108-59-8) → (E)-dimethyl (1,3-diphenylprop-2-en-1-yl)propanedioate (177468-91-6)

Conditions	Yield
bis(η3-allyl-μ-chloropalladium(II))	87%

2-chloro-6-amino-9-[3,5-di-O-(4-chlorobenzoyl)-2-deoxy-α,β-D-ribofuranosyl]-purine + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → 2-chloro-6-amino-9-[3,5-di-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-purine (908006-51-9) + 2-chloro-6-trimethylsilylamino-9-[3,5-di-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-purine (1266098-30-9)

Conditions	Yield
Stage #1: 2-chloro-6-amino-9-[3,5-di-O-(4-chlorobenzoyl)-2-deoxy-α,β-D-ribofuranosyl]-purine; N,O-Bis(trimethylsilyl)trifluoroacetamide In acetonitrile at 60℃; for 3h; Inert atmosphere; Stage #2: With trifluorormethanesulfonic acid In acetonitrile at 25 - 60℃; for 17h;	A 8.4% B 86.6%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + 2-(benzyloxy)ethoxymethyl chloride (31383-67-2) + 4,6,8-triaminoimidazo<4,5-e><1,3>diazepine (162009-79-2) → 1-benzyloxyethoxymethyl-4,6-diamino-8H-8-iminoimidazo[4,5-e][1,3]diazepine triflate salt

Conditions	Yield
Stage #1: N,O-Bis(trimethylsilyl)trifluoroacetamide; 4,6,8-triaminoimidazo<4,5-e><1,3>diazepine With pyridine In acetonitrile at 20℃; Stage #2: trimethylsilyl trifluoromethanesulfonate; 2-(benzyloxy)ethoxymethyl chloride In acetonitrile at -45 - 0℃;	86%

piperidine-2,6-dione (1121-89-7) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → N-trimethylsilylglutarimide

Conditions	Yield
In acetonitrile for 18h; Inert atmosphere; Schlenk technique;	86%
In dichloromethane at 20℃; for 2h;

carminomycin (50935-04-1) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → 4'-O-trimethylsilylcarminomycin

Conditions	Yield
In acetonitrile at 50℃; for 15h;	85%

(+)-Daunomycinone (21794-55-8) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → 7-O-trimethylsilyldaunomycinone

Conditions	Yield
In dichloromethane for 18h; Ambient temperature;	85%

sodium carbonate. tert-Butyl methyl ether + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene (87751-69-7) + malonic acid dimethyl ester (108-59-8) → (E)-dimethyl (1,3-diphenylprop-2-en-1-yl)propanedioate (177468-91-6)

Conditions	Yield
bis(η3-allyl-μ-chloropalladium(II))	84%

(S)-oxalicumone C + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → (S)-2-(2-methoxycarbonylethyl)-3-((1-methoxycarbonyl)-1-((trimethylsilyl)oxy)methyl)-7-methyl-5-((trimethylsilyl)oxy)chromone

Conditions	Yield
In benzene-d6 at 65℃; for 96h;	83%

2'-O-(t-butyldimethylsilyl)-3'N-debenzoyl-2-m-N3-benzoyl-10-deacetyltaxol + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → 2'-O-(t-butyldimethylsilyl)-3'N-debenzoyl-3'N-isovaleryl-2-debenzoyl-2-m-N3-benzoyl-10-deacetyl-10-O-(trimethylsilyl)taxol

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -20℃; for 0.166667h; Inert atmosphere;	82.6%

potassium carbonate. tert-Butyl methyl ether + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene (87751-69-7) + malonic acid dimethyl ester (108-59-8) → (E)-dimethyl (1,3-diphenylprop-2-en-1-yl)propanedioate (177468-91-6)

Conditions	Yield
bis(η3-allyl-μ-chloropalladium(II))	81%

2-amino-4-hydroxy-4-methylpentanoic acid (104302-37-6) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → C15H37NO3Si3 (128753-51-5)

Conditions	Yield
at 70 - 80℃; for 0.333333h;	80%

N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + 2-amino-4-ethyl-4-hydroxyhexanoic acid (123445-56-7) → C17H41NO3Si3 (128779-82-8)

Conditions	Yield
at 70 - 80℃; for 0.333333h;	80%

potassium acetate. tert-Butyl methyl ether + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene (87751-69-7) + malonic acid dimethyl ester (108-59-8) → (E)-dimethyl (1,3-diphenylprop-2-en-1-yl)propanedioate (177468-91-6)

Conditions	Yield
bis(η3-allyl-μ-chloropalladium(II))	80%
bis(η3-allyl-μ-chloropalladium(II))	27%

3'-N-trifluoroacetyldaunorubicin (26388-52-3) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → 3'-N-trifluoroacetyl-4'-O-trimethylsilyldaunorubicin

Conditions	Yield
In acetonitrile for 24h;	76%

guaiol (489-86-1) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → {2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]-propan-2-yl-oxy}(trimethyl)silane

Conditions	Yield
With 1,1,1,2,2,2-hexamethyldisilane; magnesium bromide ethyl etherate at 20℃; Inert atmosphere;	73%

N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) + (4R,5R,8R,9S,10R,13S,14S,17S)-17-Hydroxy-13-methyl-tetradecahydro-20-oxa-cyclopropa[4,5]cyclopenta[a]phenanthren-3-one (3941-50-2) → 3,17β-bis(trimethylsilyloxy)-4,5β-epoxyestr-2-ene (85382-37-2)

Conditions	Yield
for 48h; Heating;	70%

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 354-38-1 2,2,2-trifluoroacetamide 
• 354-32-5 trifluoracetyl chloride 
• 1070-89-9 sodium hexamethyldisilazane 

Downstream Products

• 2296-40-4 1-O-methyl-2,3,4,6-tetra-O-trimethylsilyl-β-D-glucopyranoside 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 2296-39-1 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-β-D-galactopyranoside 
• 4133-45-3 methyl 2,3,4,6-tetra-O-trimethylsilyl-α-D-galactopyranoside 
• 270585-43-8 trimethylsilyl 5,6,7,9-tetra-O-benzyl-1,2,3-trideoxy-α-D-gluco-non-1-en-4-ulopyranoside 
• 446069-79-0 4-iodo-2,6-bis(trimethylsilyloxymethyl)phenol trimethylsilyl ether 
• 10586-12-6 phloroglucinol tris(trimethylsilyl) ether 
• 33581-77-0 trimethylsilyl [(trimethylsilyl)oxy]acetate 
• 119942-64-2 C₂₇H₄₅O₆PSi₃ 
• 128753-46-8 C₉H₁₉NO₂Si 
• 80963-17-3 C₃₄H₃₈N₂O₈Si 
• 90629-05-3 [(2R,3S)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-4-oxo-3-((R)-1-trimethylsilanyloxy-ethyl)-azetidin-1-yl]-oxo-acetic acid 4-nitro-benzyl ester 

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