The entire product is likely planar due to the conjugated effect between the aromatic ring and C=C double bond.
157449
β-Bromostyrene
97%
Synonym(s):
beta-Bromostyrene, 1-Bromo-2-phenylethylene
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5 G
£44.10
About This Item
Linear Formula:
C6H5CH=CHBr
CAS Number:
Molecular Weight:
183.05
Beilstein:
2038495
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
97%
form
liquid
refractive index
n20/D 1.607 (lit.)
bp
110-112 °C/20 mmHg (lit.)
mp
7 °C (lit.)
density
1.427 g/mL at 25 °C (lit.)
functional group
bromo
phenyl
storage temp.
2-8°C
SMILES string
Br\C=C\c1ccccc1
InChI
1S/C8H7Br/c9-7-6-8-4-2-1-3-5-8/h1-7H/b7-6+
InChI key
YMOONIIMQBGTDU-VOTSOKGWSA-N
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General description
β-Bromostyrene is an α,β-unsaturated aromatic halide. It can be synthesized by catalytic Hunsdiecker reaction (CHR) of cinnamic acid.[1] It is commonly utilized as a precursor for preparing substituted alkenes, corresponding acetylenes and also in the total synthesis of natural compounds and antibiotics.[2]
Application
β-Bromostyrene was used in the one-pot method for the preparation of cinnamonitriles.[3] It was also used in the preparation of pure ethyl Z- and E-α,α-difluoro-4-phenyl-3-butenoate[4] and 1,3-diphenyl-1-butene.[5] It may be used in the synthesis of β-tert-butylstyrene via cross coupling reaction with tert-butylmagnesium chloride in the presence of dichloro[1,1′-bis(diphenylphosphino)ferrocene]nickel(II) catalyst.[6] It may also be used to prepare γ-but-2-enolactone by reacting with nickel carbonyl in the presence of alkynes.[7]
Signal Word
Warning
Hazard Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
215.6 °F - closed cup
Flash Point(C)
102 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Cross-Coupling of Tertiary Alkyl Grignard Reagents with β-Bromostyrene Catalyzed by Dichloro[1,1'-bis(diphenylphosphino)ferrocene]nickel (II).
Hayashi T, et al.
Chemistry Letters (Jpn), 9(6), 767-768 (1980)
Enantioselective Preparation of C2-Symmetrical Ferrocenyl Ligands for Asymmetric Catalysis.
Schwink L and Knochel P.
Chemistry (Weinheim An Der Bergstrasse, Germany), 4(5), 950-968 (1998)
Catalytic Hunsdiecker Reaction and One-Pot Catalytic Hunsdiecker-Heck Strategy: Synthesis of α, β-Unsaturated Aromatic Halides, α-(Dihalomethyl) benzenemethanols, 5-Aryl-2, 4-pentadienoic acids, Dienoates and Dienamides.
Naskar D and Roy S.
Tetrahedron, 56(10), 1369-1377 (2000)
The reaction of ?-bromostyrene with nickel carbonyl in the presence of alkynes.
Ryang M, et al.
Journal of Organometallic Chemistry, 46(2), 375-377 (1972)
Practical one-pot conversion of aryl bromides and ?-bromostyrenes into aromatic nitriles and cinnamonitriles.
Ishii G, et al.
Tetrahedron, 69(5), 1462-1469 (2013)
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WHAT IS THE STEREOCHEMISTRY OF THIS COMPOUND?
1 answer-
Helpful?
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is there any possibility for decreacing the purity of the compound with out innert gases storage???
1 answer-
Yes, the purity of may decline over time if exposed to atmospheric oxygen. Storing the compound under inert gas, such as nitrogen or argon, prevents decomposition. Please see the link below to review additional information regarding the breakdown reaction published to PubChem:
https://pubchem.ncbi.nlm.nih.gov/compound/5314126#section=Non-Human-Toxicity-ValuesHelpful?
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