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578932

Sigma-Aldrich

N-Allyl-N,N-bis(trimethylsilyl)amine

97%

Synonym(s):

(Prop-2-en-1-yl)bis(trimethylsilyl)amine, 1,1,1-Trimethyl-N-2-propen-1-yl-N-(trimethylsilyl)silanamine, 3-Bis(trimethylsilyl)amino-1-propene, Bis(trimethylsilyl)allylamine, N,N-Bis(trimethylsilyl)-2-propen-1-amine, N,N-Bis(trimethylsilyl)allylamine, N-Allyl-1,1,1-trimethyl-N-(trimethylsilyl)silanamine

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About This Item

Linear Formula:
CH2=CHCH2NH[Si(CH3)3]2
CAS Number:
7688-51-9
Molecular Weight:
201.46
EC Number:
231-699-2
MDL number:
MFCD00545193
UNSPSC Code:
12352103
PubChem Substance ID:
24880960
NACRES:
NA.22

assay

97%

form

liquid

refractive index

n20/D 1.440 (lit.)

bp

72 °C/15 mmHg (lit.)

density

0.816 g/mL at 25 °C (lit.)

functional group

amine

SMILES string

C[Si](C)(C)N(CC=C)[Si](C)(C)C

InChI

1S/C9H23NSi2/c1-8-9-10(11(2,3)4)12(5,6)7/h8H,1,9H2,2-7H3

InChI key

CVNCFZIIZGNVFD-UHFFFAOYSA-N

Application

N-Allyl-N,N-bis(trimethylsilyl)amine or N,N-bis(trimethylsilyl)prop-2-en-1-amine (AHMDS) can be used as a nucleophilic reagent to prepare:
  • Complex bicyclic scaffolds by reacting with aryl aldehydes via imine formation followed by efficient multicomponent reactions.
  • Dithiasuccinoyl (Dts) heterocycle by reacting with bisthiocarbamoyl chloride.
  • Allyl selenide by reacting with aryl selenium salt in the presence of a ruthenium catalyst; Allyl selenide is utilized as a key intermediate in organic synthesis.


AHMDS can also be used as a reagent in hydrosilylation and hydroboration reaction. It may be also used as an electrolyte additive.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

109.0 °F - closed cup

flash_point_c

42.78 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM3954
SHBB1356V
60396AP
43096DJ
20912JA

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Tomohiro Iimura et al.
Dalton transactions (Cambridge, England : 2003), 46(27), 8868-8874 (2017-05-16)
A platinum(0) complex bearing a cyclic (alkyl)(amino)silylene and a 1,3-divinyl-1,1,3,3-tetramethyldisiloxane (DVTMS) was synthesized and isolated in the form of colorless crystals. The single-crystal X-ray diffraction analysis of this complex in combination with theoretical calculations indicated that the Pt→Si π-back-donation in
Single-molecule spectroscopy and dynamics at room temperature
XX Sunney
Accounts of Chemical Research, 29(12), 598-606 (1996)
N, N-Bis (trimethylsilyl) prop-2-en-1-amine
Ross TM and Malachowski WP
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)

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