N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide CAS 77377-52-7
Introduction：Basic information about N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide CAS 77377-52-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide Basic information
| Product Name: | N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide |
| Synonyms: | MBDSTFA;DEUTERO-REGISIL-D18;N-TERT-BUTYLDIME.SILYL-N-ME.TRIFLUOROACE;N-TERT-BUTYLDIME.SILYL-N-ME.TRIFLUOROACE TAMIDE + 1% TBDMSCL;N-(TERT-BUTYLDIMETHYLSILYL)-N-METHYL-TRI FLUOROACETAMIDE, 97+%;N-(TERT-BUTYLDIMETHYLSILYL)-N-METHYLTRIF LUOROACETA;N-(TERT-BUTYLDIMETHYLSILYL)-N-METHYL-TRIFLUOROACETAMIDE, W/1% TBDMSCL, >=95%;N-TERT-BUTYLDIMETHYLSILYL-N-METHYL TRIFL |
| CAS: | 77377-52-7 |
| MF: | C9H18F3NOSi |
| MW: | 241.33 |
| EINECS: | 616-455-9 |
| Product Categories: | Amines;Intermediates & Fine Chemicals;Pharmaceuticals;Si-N Compounds;Silylation Reagents;Alkyldimethylsilylation (GC Derivatizing Reagents);Analytical Chemistry;GC Derivatizing Reagents;Si (Classes of Silicon Compounds);Silylacetamides;Silylation (GC Derivatizing Reagents) |
| Mol File: | 77377-52-7.mol |
N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide Chemical Properties
| Boiling point | 172-175 °C(lit.) |
| density | 1.036 g/mL at 25 °C(lit.) |
| refractive index | n |
| Fp | 127 °F |
| storage temp. | 2-8°C |
| solubility | sol most aprotic organic solvents. |
| pka | -1.50±0.70(Predicted) |
| form | Liquid |
| color | Clear colorless to slightly yellow |
| Specific Gravity | 1.023 |
| Water Solubility | decomposes |
| Sensitive | Moisture Sensitive |
| Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents |
| BRN | 3606546 |
| InChI | 1S/C9H18F3NOSi/c1-8(2,3)15(5,6)13(4)7(14)9(10,11)12/h1-6H3 |
| InChIKey | QRKUHYFDBWGLHJ-UHFFFAOYSA-N |
| SMILES | CN(C(=O)C(F)(F)F)[Si](C)(C)C(C)(C)C |
| CAS DataBase Reference | 77377-52-7(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi,F |
| Risk Statements | 10-36/37/38 |
| Safety Statements | 26-36-16-37/39-36/37/39 |
| RIDADR | UN 1993 3/PG 3 |
| WGK Germany | 3 |
| F | 10-21 |
| Hazard Note | Flammable |
| TSCA | No |
| HS Code | 2931 90 00 |
| HazardClass | 3 |
| PackingGroup | III |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Eye Irrit. 2 Flam. Liq. 3 Skin Irrit. 2 |
| Chemical Properties | clear colorless to slightly yellow liquid |
| Physical properties | bp 168–170°C; d 1.12 g cm?3. |
| Uses | N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide is a silylating agent used in the derivatization of various organic compounds (such as amino acids) for gas chromatogography-mass spectrometry (GC-MS) analysis. |
| Uses | In thepresence of 1% of t-butyldimethylchlorosilane as the catalyst,N-(t-butyldimethylsilyl)-N-methyltrifluoroacetamide (BSMTFA)functions as an extremely reactive t-butyldimethylsilylatingreagent for alcohols, amines, carboxylic acids, and thiols. Silylationis generally completed within 5 min at 25°C in acetonitrile.This amide is more reactive than N-(t-butyldimethylsilyl)-N-methylacetamide. In the protection of a hydroxy group, the resultant tbutyldimethylsilyl(TBDMS) ethers are stable under the conditionsfor acetate saponification and hydrogenation.These silylethers also remain intact towards the Jones reagent and Wittigreagents. The TBDMS ethers are approx. 10 times more stableagainst hydrolysis than the corresponding trimethylsilyl (TMS)ethers.Selective removal of the TBDMS group can be accomplishedby use of dilute acetic acid or tetra-n-butylammoniumfluoride in THF at 25°C. Silylation of ketones by use ofBSMTFAoccurs in triethylamineand DMF at 40–60°C to give the corresponding silyl enol ethersin good to excellent yields (eq 1).In addition, silyl ether formationtakes place in N-hydroxysuccinimide (88% yield) and Nhydroxypyrrole(99% yield) by use of BSMTFA in THF. |
| Uses | N-tert-Butyldimethylsilyl-N-methyltrifluoroacetamide with 1% tert-butyldimethylchlorosilane is commonly used for the preparation of N-tert-butyldimethylsilyl ethanolamines resulting from the hydrolysis of nitrogen mustards. It is also used for selective O-silylation of N,O-diacylhydroxyl amines. |
| Definition | ChEBI: An N-silyl compound that is N-methyltrifluoroacetamide in which the amide nitrogen is replaced by a tert-butyldimethylsilyl group. |
| Preparation | obtained in 91% yield by reaction ofN-methyl-2,2,2-trifluoroacetamide (1.0 equiv) in benzene andacetonitrile (1:1 v/v) with NaH (1.0 equiv) and then witht-BuMe2SiCl (1.2 equiv) at 4°C. |
| General Description | N-tert-Butyldimethylsilyl-N-methyltrifluoroacetamide is a silylating reagent which replaces the active hydrogen with tert-Butyldimethylsilyl group. The tert-Butyldimethylsilyl derivatives are found to be more resistant to hydrolysis and stable compared to trimethylsilyl (TMS) derivatives. This reagent is suitable for GC-MS analysis since it produces mass spectra, which can be easily interpreted. It is widely used for the silylation of different alcohols, thiols, phenols, carboxylic acids, amines, and amides. |
| reaction suitability | reagent type: derivatization reagent reaction type: Silylations |
N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide Preparation Products And Raw materials
