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675725

Sigma-Aldrich

4-Bromo-1-butyne

97%

Synonym(s):

1-Bromo-3-butyne

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5 G
RM 407.00

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

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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

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This Item
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4-Bromo-1-butyne 97%

675725

4-Bromo-1-butyne

1-Bromo-3-nitrobenzene 97%

775614

1-Bromo-3-nitrobenzene

4-Phenyl-3-butyn-2-ol 97%

669288

4-Phenyl-3-butyn-2-ol

3-(Bromoacetyl)thiophene 97%

738336

3-(Bromoacetyl)thiophene

assay

97%

assay

97%

assay

97%

assay

97%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

density

1.417 g/mL at 25 °C

density

-

density

1.005 g/mL at 25 °C

density

-

refractive index

n20/D 1.481

refractive index

-

refractive index

n20/D 1.5667

refractive index

-

functional group

alkyl halide

functional group

bromo, nitro

functional group

hydroxyl, phenyl

functional group

bromo, ketone

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.[1]

Application

4-Bromo-1-butyne is used as a reactant in the synthesis of:
  • Macrocycles by cobalt-mediated [2+2+2] co-cyclotrimerization.[2]
  • 2,4,5-trisubstituted oxazoles by a gold-catalyzed formal [3+2] cycloaddition.[3]
  • Intramolecular 1,3-dipolar cycloaddition to synthesize 1,3,4-oxadiazoles.[4]
  • Lactones bearing alkynes for reductive cyclization in the preparation of azulene derivatives.[5]
  • Substituted α-pyrones by gold-catalyzed coupling reactions.[6]

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Statements

H226,H301,H317

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

75.0 °F

Flash Point(C)

23.9 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves
  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    MKCQ0417
    MKCP7730
    MKCN0207
    MKCL6025
    MKCJ7315

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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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