427292
1-Bromo-2-butyne
≥98%
Synonym(s):
1-(Bromomethyl)-2-methylacetylene, 2-Butyn-1-yl bromide, 2-Butynyl bromide, 4-Bromobut-2-yne
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About This Item
Linear Formula:
CH3C≡CCH2Br
CAS Number:
Molecular Weight:
132.99
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
605306
Product Name
1-Bromo-2-butyne, ≥98%
InChI
1S/C4H5Br/c1-2-3-4-5/h4H2,1H3
SMILES string
CC#CCBr
InChI key
LNNXOEHOXSYWLD-UHFFFAOYSA-N
assay
≥98%
form
liquid
refractive index
n20/D 1.508 (lit.)
bp
40-41 °C/20 mmHg (lit.)
density
1.519 g/mL at 25 °C (lit.)
functional group
alkyl halide
bromo
Quality Level
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Application
1-Bromo-2-butyne was used in the alkylation of L-tryptophan methyl ester. It was used as a source to generate CH3CCCH2 radicals to investigate the reaction kinetics of these radicals with NO and NO2.
It may be used in the synthesis of the following:
It may be used in the synthesis of the following:
- 4-butynyloxybenzene sulfonyl chloride
- mono-propargylated diene derivative
- isopropylbut-2-ynylamine
- allenylcyclobutanol derivatives
- allyl-[4-(but-2-ynyloxy)phenyl]sulfane
- allenylindium
- alkynyl alcohols
- axially chiral teranyl compounds
Exploited in the synthesis of axially chiral teranyl compounds.
General description
1-Bromo-2-butyne is a propargyl bromide derivative. It is one of the constitutional isomer of bromo butyne. Its Br-loss threshold photoionization breakdown diagram has been analyzed to derive dissociative photoionization thresholds to C4H5+ production. It participates in the preparation of linagliptin.
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Kinetics of resonance stabilized CH3CCCH2 radical reactions with NO and NO2.
Rissanen MP, et al.
Chemical Physics Letters, 543, 28-33 (2012)
Takanori Shibata et al.
Journal of the American Chemical Society, 126(27), 8382-8383 (2004-07-09)
An asymmetric [2+2+2] cycloaddition of an alpha,omega-diyne, possessing ortho-substituted aryl groups on its terminus, and a monoalkyne with oxygen functionalities gave various axially chiral teraryl compounds. The coupling proceeded with extremely high enantio- (>99.5% ee) and diastereoselectivities (dl/meso = >95/5)
Imaging breakdown diagrams for bromobutyne isomers with photoelectron-photoion coincidence.
Bodi A and Hemberger P.
Physical Chemistry Chemical Physics, 16(2), 505-515 (2014)
Acetylenic TACE inhibitors. Part 1. SAR of the acyclic sulfonamide hydroxamates.
Levin JI, et al.
Bioorganic & Medicinal Chemistry Letters, 13(16), 2799-2803 (2003)
Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry.
Testero SA, et al.
ARKIVOC (Gainesville, FL, United States), 7, 221-236 (2011)
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