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Sigma-Aldrich

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
MDL number:
MFCD10000883
UNSPSC Code:
12352100
PubChem Substance ID:
329760618
NACRES:
NA.22

Quality Level

100

assay

97%

refractive index

n20/D 1.481

density

1.417 g/mL at 25 °C

SMILES string

BrCCC#C

InChI

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

InChI key

XLYOGWXIKVUXCL-UHFFFAOYSA-N

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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_germany

WGK 3

flash_point_f

75.0 °F

flash_point_c

23.9 °C

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Reductive Cyclization Cascades of Lactones Using SmI2- H2O.
Parmar D, et al.
Journal of the American Chemical Society, 133(8), 2418-2420 (2011)
Intramolecular Diels- Alder/1, 3-dipolar cycloaddition cascade of 1, 3, 4-oxadiazoles.
Elliott GI, et al.
Journal of the American Chemical Society, 128(32), 10589-10595 (2006)
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)
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)
Tuoping Luo et al.
Organic letters, 13(11), 2834-2836 (2011-05-04)
Sequential alkyne activation of terminal alkynes and propiolic acids by gold(I) catalysts yields compounds having α-pyrone skeletons. Novel cascade reactions involving propiolic acids are reported that give rise to α-pyrones with different substitution patterns.

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