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226289

Sigma-Aldrich

N,N-Dimethyltrimethylsilylamine

97%

Synonym(s):

(Dimethylamino)trimethylsilane, N-(Trimethylsilyl)dimethylamine, TMSDMA

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About This Item

Linear Formula:
(CH3)3SiN(CH3)2
CAS Number:
2083-91-2
Molecular Weight:
117.26
Beilstein:
1731861
EC Number:
218-222-3
MDL number:
MFCD00008297
UNSPSC Code:
12352100
PubChem Substance ID:
24853554
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.397 (lit.)

bp

84 °C (lit.)

density

0.732 g/mL at 25 °C (lit.)

SMILES string

CN(C)[Si](C)(C)C

InChI

1S/C5H15NSi/c1-6(2)7(3,4)5/h1-5H3

InChI key

KAHVZNKZQFSBFW-UHFFFAOYSA-N

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Application

N,N-Dimethyltrimethylsilylamine can be used as a reactant to prepare:
  • Trifluoromethylacetophenone-N,N-dimethyltrimethylsilylamine adduct, which is used as an efficient reagent for nucleophilic trifluoromethylation of carbonyl and the imine group.
  • (Dimethylamino)sulfur trifluoride (Me-DAST), which is employed as a deoxofluorinating agent for the conversion of aliphatic alcohols into their corresponding fluorides.
  • Nucleoside phosphoramidites by reacting with alkyloxy (or aryloxy)-triazolylphosphine and deoxynucleoside.

It can also be used as a silylating agent in chemical synthesis.

accessory

Product No.
Description
Pricing

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H225,H260,H314

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - Water-react 1

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

10.4 °F - closed cup

Flash Point(C)

-12 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Some studies on nucleophilic trifluoromethylation using the shelf-stable trifluoromethylacetophenone-N, N-dimethyltrimethylsilylamine adduct
Motherwell WB and Storey LJ
Journal of Fluorine Chemistry, 126(4), 489-496 (2005)
A new and general procedure for the preparation of deoxynucleoside phosphoramidites
Fourrey J-L and Varenne J
Tetrahedron Letters, 24(19), 1963-1966 (1983)
Trifluoro (N-methylmethanaminato) sulfur
Champagne PA and Paquin J-F
eEROS (Encyclopedia of Reagents for Organic Synthesis), 1-2 (2001)
A new and general procedure for the preparation of deoxynucleoside phosphoramidites.
Fourrey JL and Varenne J.
Tetrahedron Letters, 24(19), 1963-1966 (1983)
Synthesis and evaluation of novel daunomycin-phosphate-sulfate-β-glucuronide and-β-glucoside prodrugs for application in ADEPT
Leenders, Ruben GG, et al.
Bioorganic & medicinal chemistry letters, 5(24), 2975-2980 (1995)
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