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ALD00562

Sigma-Aldrich

2,3-Dibromo-propylamine, hydrobromide

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Empirical Formula (Hill Notation):
C3H8Br3N
CAS Number:
Molecular Weight:
297.81
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22

form

solid

reaction suitability

reaction type: C-C Bond Formation

SMILES string

BrCC(Br)CN.[H]Br

InChI

1S/C3H7Br2N.BrH/c4-1-3(5)2-6;/h3H,1-2,6H2;1H

InChI key

NQVQUJRBCVAMIL-UHFFFAOYSA-N

Application

In tandem with Turbo Grignard (Aldrich product 656984) and an electrophilic trap, 2,3-Dibromo-propylamine hydrobromide generates a "spring loaded" electrophile, which is a convenient reagent for the installation of azetidine to secondary amines. This product is one of several synthetic useful reagents reported by Baran and coworkers on Strain-release amination.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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The Baran Group works with Sigma-Aldrich in providing a portfolio of zinc-based reagents promoting difluoromethylation, trifluoromethylation, trifluoroethylation and isopropylation of aryl and heteroaryl motifs. Baran’s lab has also helped introduce a portable desaturase (Tz0Cl), which promotes the installation of alcohol and amine groups and leaves behind a highly useful tosyl group for further transformations.

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