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157449

β-Bromostyrene

97%

Synonym(s):

beta-Bromostyrene, 1-Bromo-2-phenylethylene

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Pack SizeSKUAvailabilityPrice
5 g

Available to ship TODAYfromMILWAUKEE

$77.20

About This Item

Linear Formula:
C6H5CH=CHBr
CAS Number:
103-64-0
Molecular Weight:
183.05
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24849679
EC Number:
203-131-3
Beilstein/REAXYS Number:
2038495
MDL number:
MFCD00000185
Assay:
97%
Form:
liquid

$77.20

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Quality Level

100

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

General description

β-Bromostyrene is an α,β-unsaturated aromatic halide. It can be synthesized by catalytic Hunsdiecker reaction (CHR) of cinnamic acid. It is commonly utilized as a precursor for preparing substituted alkenes, corresponding acetylenes and also in the total synthesis of natural compounds and antibiotics.

Application

β-Bromostyrene was used in the one-pot method for the preparation of cinnamonitriles. It was also used in the preparation of pure ethyl Z- and E-α,α-difluoro-4-phenyl-3-butenoate[1] and 1,3-diphenyl-1-butene. 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. It may also be used to prepare γ-but-2-enolactone by reacting with nickel carbonyl in the presence of alkynes.

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124141523054132683
β-Bromostyrene 97%

Sigma-Aldrich

157449

β-Bromostyrene

4-Bromostyrene contains 0.05% 3,5-di-tert-butylcatechol as inhibitor, 97%

Sigma-Aldrich

124141

4-Bromostyrene

4-Bromo-2-methylanisole 98%

Sigma-Aldrich

523054

4-Bromo-2-methylanisole

2-Bromostyrene contains 0.1% 3,5-di-tert-butylcatechol as inhibitor, 97%

Sigma-Aldrich

132683

2-Bromostyrene

assay

97%

assay

97%

assay

98%

assay

97%

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

200

density

1.427 g/mL at 25 °C (lit.)

density

1.4 g/mL at 25 °C (lit.)

density

-

density

1.46 g/mL at 25 °C (lit.)

bp

110-112 °C/20 mmHg (lit.)

bp

89 °C/16 mmHg (lit.)

bp

-

bp

102-104 °C/22 mmHg (lit.)

mp

7 °C (lit.)

mp

-

mp

66-69 °C (lit.)

mp

-

refractive index

n20/D 1.607 (lit.)

refractive index

n20/D 1.594 (lit.)

refractive index

-

refractive index

n20/D 1.592 (lit.)

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

215.6 °F - closed cup

flash_point_c

102 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3513
MKCH6181
MKBT1768V
MKBN4773V
MKBJ5110V

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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)
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)
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)
View All Related Papers

Global Trade Item Number

SKUGTIN
157449-5G04061838743367

Questions

1–4 of 4 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. WHAT IS THE STEREOCHEMISTRY OF THIS COMPOUND?

    1 answer

    1. The entire product is likely planar due to the conjugated effect between the aromatic ring and C=C double bond.

      Helpful?

  4. is there any possibility for decreacing the purity of the compound with out innert gases storage???

    1 answer

    1. 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-Values

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