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Merck
CN

167851

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24850226
EC Number:
225-937-4
Beilstein/REAXYS Number:
1098377
MDL number:
MFCD00000258
Assay:
97%
Form:
liquid

Key Documents

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InChI key

DMAYBPBPEUFIHJ-UHFFFAOYSA-N

InChI

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

SMILES string

BrCCC=C

assay

97%

form

liquid

Quality Level

200

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

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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.

Application

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

33.8 °F - closed cup

flash_point_c

1 °C - closed cup

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCB7049
BCBP4275V
BCBG3968V
BCBB6962V
BCBB6962

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Synthesis, 3490-3490 (2006)
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
Tetrahedron, 60, 5613-5613 (2004)
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
Synthesis and photopolymerization of a liquid-crystalline diepoxide.
Broer DJ, et al.
Macromolecules, 26(6), 1244-1247 (1993)
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