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167851

Sigma-Aldrich

4-Bromo-1-butene

97%

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Linear Formula:
BrCH2CH2CH=CH2
CAS Number:
Molecular Weight:
135.00
Beilstein:
1098377
EC Number:
MDL number:
PubChem Substance ID:

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.)

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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1 of 4

This Item
368679443743410888
4-Bromo-1-butene 97%

Sigma-Aldrich

167851

4-Bromo-1-butene

cis-1-Bromo-1-propene 97%

Sigma-Aldrich

368679

cis-1-Bromo-1-propene

3-Bromo-3-buten-1-ol 98%

Sigma-Aldrich

410888

3-Bromo-3-buten-1-ol

form

liquid

form

liquid

form

liquid

form

liquid

refractive index

n20/D 1.462 (lit.)

refractive index

n20/D 1.4545 (lit.)

refractive index

n20/D 1.401 (lit.)

refractive index

n20/D 1.499 (lit.)

bp

98-100 °C (lit.)

bp

58 °C (lit.)

bp

95-98 °C (lit.)

bp

64-65 °C/9 mmHg (lit.)

density

1.33 g/mL at 25 °C (lit.)

density

1.423 g/mL at 25 °C (lit.)

density

1.639 g/mL at 25 °C (lit.)

density

1.522 g/mL at 25 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

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.

Signal Word

Danger

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

Flash Point(C)

1 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis, 3490-3490 (2006)
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
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
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)

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