277320
1,2-Dibromocyclopentene
97%
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About This Item
Empirical Formula (Hill Notation):
C5H6Br2
CAS Number:
Molecular Weight:
225.91
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
97%
InChI
1S/C5H6Br2/c6-4-2-1-3-5(4)7/h1-3H2
SMILES string
BrC1=C(Br)CCC1
InChI key
PNWFXPGGROADNS-UHFFFAOYSA-N
assay
97%
refractive index
n20/D 1.5558 (lit.)
bp
78 °C/5 mmHg (lit.)
density
1.895 g/mL at 25 °C (lit.)
functional group
bromo
storage temp.
2-8°C
General description
1,2-Dibromocyclopentene undergoes single Br/Mg exchange reaction with iPrMgCl LiCl to yield the corresponding β-bromocyclopentenylmagnesium reagent.
Application
1,2-Dibromocyclopentene has been used in the synthesis of cyclopentene analogs.
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
Regulatory Information
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Selective mono- and 1,2-difunctionalisation of cyclopentene derivatives via Mg and Cu intermediates.
Christina Despotopoulou et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(8), 2499-2506 (2008-01-31)
A single Br/Mg exchange of 1,2-dibromocyclopentene with iPrMgCl LiCl provides the corresponding beta-bromocyclopentenylmagnesium reagent, which can then be reacted with various electrophiles (yields: 65-82 %). In the presence of a secondary alkylmagnesium halide and Li2CuCl4 (2 mol %), these 2-bromoalkenylmagnesium
Gerard M P Giblin et al.
Bioorganic & medicinal chemistry letters, 17(2), 385-389 (2006-11-07)
The discovery of a series of selective EP1 receptor antagonists based on a 1,2-diarylcyclopentene template is described. After defining the structural requirements for EP1 potency and selectivity, heterocyclic rings were incorporated to reduce logD and improve in vitro pharmacokinetic properties.
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