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745723

Sigma-Aldrich

3-Methyl-1-butyne

95%

Synonym(s):

1-Isopentyne, 2-Methyl-3-butyne, 3,3-Dimethyl-1-propyne, Isopropylacetylene, Isopropylethyne

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About This Item

Empirical Formula (Hill Notation):
C5H8
CAS Number:
Molecular Weight:
68.12
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

95%

form

liquid

refractive index

n20/D 1.374

density

0.666 g/mL at 25 °C (lit.)

Storage temp.

2-8°C

SMILES string

C#CC(C)C

InChI

1S/C5H8/c1-4-5(2)3/h1,5H,2-3H3

InChI key

USCSRAJGJYMJFZ-UHFFFAOYSA-N

Application

3-Methyl-1-butyne can be used as a reactant in the ruthenium-catalyzed synthesis of functionalized cycloheptadienes and titanium-catalyzed [2+2+1] multicomponent pyrrole synthesis. It is also used as a precursor in the total syntheses of (+)-frondosin A, (−)-citrinadin A, (+)-citrinadin B and coraxeniolide A.
3-Methyl-1-butyne is a terminal alkyne that can be used to prepare:
  • Maleimide-fused cyclopentenones by reacting with N-substituted maleimides via Co2(CO)8-mediated Pauson−Khand reaction.
  • An alkyne carboxylic acid (Alkyne Segment C) intermediate, which is used in the total synthesis of oscillatoxin D and its analogs.

pictograms

Flame

signalword

Danger

hcodes

pcodes

Hazard Classifications

Flam. Liq. 1

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-22.0 °F

flash_point_c

-30 °C


Certificates of Analysis (COA)

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An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B.
Kong K, et al.
Journal of the American Chemical Society, 135(30), 10890-10893 (2013)
Metal carbene-promoted sequential transformations for the enantioselective synthesis of highly functionalized cycloheptadienes.
Deng L, et al.
Journal of the American Chemical Society, 127(5), 1342-1343 (2005)
An unconventional approach to the enantioselective synthesis of caryophylloids.
Larionov, Oleg V and Corey, EJ
Journal of the American Chemical Society, 130(10), 2954-2955 (2008)
Intermolecular Pauson-Khand reactions of N-substituted maleimides
Brantley CL and Coombs TC
Tetrahedron Letters, 58(48), 4519-4524 (2017)
Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+ 2+ 1] Pyrrole Synthesis.
Chiu, Hsin-Chun and Tonks, Ian A
Angewandte Chemie (International Edition in English), 57(21), 6090-6094 (2018)

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