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157449

Sigma-Aldrich

β-Bromostyrene

97%

Synonym(s):

beta-Bromostyrene, 1-Bromo-2-phenylethylene

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About This Item

Linear Formula:
C6H5CH=CHBr
CAS Number:
103-64-0
Molecular Weight:
183.05
Beilstein:
2038495
EC Number:
203-131-3
MDL number:
MFCD00000185
UNSPSC Code:
12352100
PubChem Substance ID:
24849679
NACRES:
NA.22
Pricing and availability is not currently available.

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

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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]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3513
MKCH6181
MKBT1768V
MKBN4773V
MKBJ5110V

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Sigma-Aldrich

D39029

1,4-Dibromobenzene

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)
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)
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)
New method for the synthesis of β-bromostyrenes.
Shastin AV, et al.
Russian Chemical Bulletin, 50(8), 1401-1405 (2001)
View All Related Papers

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/449/386/product-dating-information-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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