745723
3-Methyl-1-butyne
95%
Synonym(s):
1-Isopentyne, 2-Methyl-3-butyne, 3,3-Dimethyl-1-propyne, Isopropylacetylene, Isopropylethyne
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5 G
€113.00
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€339.00
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5 G
€113.00
25 G
€339.00
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
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Quality Level
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
Related Categories
Application
3-Methyl-1-butyne can be used as a reactant in the ruthenium-catalyzed synthesis of functionalized cycloheptadienes[1] and titanium-catalyzed [2+2+1] multicomponent pyrrole synthesis.[2] It is also used as a precursor in the total syntheses of (+)-frondosin A[3], (−)-citrinadin A[4], (+)-citrinadin B[5] and coraxeniolide A.[6]
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.[7]
- An alkyne carboxylic acid (Alkyne Segment C) intermediate, which is used in the total synthesis of oscillatoxin D and its analogs.[8]
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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 enantioselective total synthesis and stereochemical revision of (+)-citrinadin B.
Kong K, et al.
Journal of the American Chemical Society, 135(30), 10890-10893 (2013)
An unconventional approach to the enantioselective synthesis of caryophylloids.
Larionov, Oleg V and Corey, EJ
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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)
Intermolecular Pauson-Khand reactions of N-substituted maleimides
Brantley CL and Coombs TC
Tetrahedron Letters, 58(48), 4519-4524 (2017)
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