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167851

Sigma-Aldrich

4-Bromo-1-butene

97%

Synonym(s):

1-Bromo-3-butene, 3-Butenyl bromide, 4-Bromobut-1-ene, Allylcarbinyl bromide, But-3-en-1-yl bromide

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About This Item

Linear Formula:
BrCH2CH2CH=CH2
CAS Number:
5162-44-7
Molecular Weight:
135.00
Beilstein:
1098377
EC Number:
225-937-4
MDL number:
MFCD00000258
UNSPSC Code:
12352100
PubChem Substance ID:
24850226
NACRES:
NA.22
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Assay

97%

form

liquid

refractive index

n20/D 1.462 (lit.)

bp

98-100 °C (lit.)

density

1.33 g/mL at 25 °C (lit.)

functional group

alkyl halide
allyl
bromo

storage temp.

2-8°C

SMILES string

BrCCC=C

InChI

1S/C4H7Br/c1-2-3-4-5/h2H,1,3-4H2

InChI key

DMAYBPBPEUFIHJ-UHFFFAOYSA-N

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General description

Stereoselective epoxidation of 4-bromo-1-butene was carried out with three alkene-utilizing bacteria: Mycobacterium LI, Mycobacterium E3 and Nocardia IP1[1].

Application

  • 4-Bromo-1-butene was used in the synthesis of 4-(3-butenyloxy)benzoic acid[2].
  • It was also used in the total synthesis of largazole[3].
  • It was used in double alkylation of lactams, followed by Grubbs ring-closing metathesis, to yield gymnodimine (biotoxin)[4].
  • It was used in preparation of dienehydrazides[5].

Signal Word

Danger

Hazard Statements

H225,H317,H319,H334,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Resp. Sens. 1 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

33.8 °F - closed cup

Flash Point(C)

1 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB7049
BCBP4275V
BCBG3968V
BCBB6962V
BCBB6962

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Burcu Colak et al.
Bioconjugate chemistry, 27(9), 2111-2123 (2016-08-12)
Thiol-ene radical coupling is increasingly used for the biofunctionalization of biomaterials and the formation of 3D hydrogels enabling cell encapsulation. Indeed, thiol-ene chemistry presents interesting features that are particularly attractive for platforms requiring specific reactions of peptides or proteins, in
Tetrahedron, 60, 5613-5613 (2004)
Synthesis, 3490-3490 (2006)
Stereoselective epoxidation of 4-bromo-1-butene and 3-butene-1-ol with three alkene-utilizing bacteria.
Archelas A, et al.
Biocatalysis and Biotransformation, 1(4), 283-292 (1988)
Yongcheng Ying et al.
Journal of the American Chemical Society, 130(26), 8455-8459 (2008-05-30)
Full details of the concise and convergent synthesis (eight steps, 19% overall yield), its extension to the preparation of a series of key analogues, and the molecular target and pharmacophore of largazole are described. Central to the synthesis of largazole
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Questions

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  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

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  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

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