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675725

4-Bromo-1-butyne

97%

Synonym(s):

1-Bromo-3-butyne

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About This Item

Empirical Formula (Hill Notation):
C4H5Br
CAS Number:
38771-21-0
Molecular Weight:
132.99
NACRES:
NA.22
PubChem Substance ID:
329760618
UNSPSC Code:
12352100
MDL number:
MFCD10000883
Assay:
97%
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Quality Level

100

assay

97%

refractive index

n20/D 1.481

density

1.417 g/mL at 25 °C

functional group

alkyl halide, bromo

SMILES string

BrCCC#C

InChI

1S/C4H5Br/c1-2-3-4-5/h1H,3-4H2

InChI key

XLYOGWXIKVUXCL-UHFFFAOYSA-N

General description

4-Bromo-1-butyne is commonly used as a reactant. It serves as a source of alkyl halides for the introduction of bromo functionality into the molecule.

Application

4-Bromo-1-butyne is used as a reactant in the synthesis of:
  • Macrocycles by cobalt-mediated [2+2+2] co-cyclotrimerization.
  • 2,4,5-trisubstituted oxazoles by a gold-catalyzed formal [3+2] cycloaddition.
  • Intramolecular 1,3-dipolar cycloaddition to synthesize 1,3,4-oxadiazoles.
  • Lactones bearing alkynes for reductive cyclization in the preparation of azulene derivatives.
  • Substituted α-pyrones by gold-catalyzed coupling reactions.

pictograms

FlameSkull and crossbones
GHS02,GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Flam. Liq. 3 - Skin Sens. 1

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

75.0 °F

flash_point_c

23.9 °C

ppe

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ5525
MKCT3181
MKCR6459
MKCQ0417
MKCP7730

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Intermolecular and Selective Synthesis of 2, 4, 5-Trisubstituted Oxazoles by a Gold-Catalyzed Formal [3+ 2] Cycloaddition.
Davies PW, et al.
Angewandte Chemie (International Edition in English), 50(38), 8931-8935 (2011)
Reductive Cyclization Cascades of Lactones Using SmI2- H2O.
Parmar D, et al.
Journal of the American Chemical Society, 133(8), 2418-2420 (2011)
Synthesis of macrocycles via cobalt-mediated [2+ 2+ 2] cycloadditions.
Bonaga LVR, et al.
Journal of the American Chemical Society, 127(10), 3473-3485 (2005)
View All Related Papers

Global Trade Item Number

SKUGTIN
675725-5G04061832736129