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Merck
CN

705098

Sigma-Aldrich

(S,S)-2-Allyl-1,3-bis-(4-bromobenzyl)-2-chlorooctahydro-2-1H-1,3,2-benzodiazasilole

95%

Synonym(s):

(S,S)-1,3-Bis-[(4-bromophenyl)methyl]-2-chlorooctahydro-2-(2-propenyl)-1H-1,3,2-benzodiazasilole

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About This Item

Empirical Formula (Hill Notation):
C23H27Br2ClN2Si
Molecular Weight:
554.82
MDL number:
MFCD12546043
UNSPSC Code:
12352103
PubChem Substance ID:
329762503

Key Documents

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Assay

95%

form

solid

optical activity

[α]22/D +54°, c = 1 in chloroform

mp

94-99 °C

storage temp.

2-8°C

SMILES string

Cl[Si]1(CC=C)N(Cc2ccc(Br)cc2)[C@H]3CCCC[C@@H]3N1Cc4ccc(Br)cc4

InChI

1S/C23H27Br2ClN2Si/c1-2-15-29(26)27(16-18-7-11-20(24)12-8-18)22-5-3-4-6-23(22)28(29)17-19-9-13-21(25)14-10-19/h2,7-14,22-23H,1,3-6,15-17H2/t22-,23-/m0/s1

InChI key

JTYONYYNZDUUGN-GOTSBHOMSA-N

Application

Leighton′s Strained Silacycles: Powerful Enantioselective Allylation Reagents
An operationally simple regioselective and enantioselective allylation of beta-diketones to provide tertiary carbinols

Legal Information

U.S. Patent No. 7,534,905

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBD3877V
19899MJV
19899MJ

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Wesley A Chalifoux et al.
Nature, 487(7405), 86-89 (2012-07-06)
The enantioselective allylation of ketones is a problem of fundamental importance in asymmetric reaction design, especially given that only a very small number of methods can generate tertiary carbinols. Despite the vast amount of attention that synthetic chemists have given

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