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493023

Sigma-Aldrich

3-Methyl-1-penten-4-yn-3-ol

98%

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Synonym(s):
Ethynyl methyl vinyl carbinol
Linear Formula:
HC≡CC(CH3)(OH)CH=CH2
CAS Number:
Molecular Weight:
96.13
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.446 (lit.)

bp

63-65 °C/100 mmHg (lit.)

density

0.89 g/mL at 25 °C (lit.)

SMILES string

CC(O)(C=C)C#C

InChI

1S/C6H8O/c1-4-6(3,7)5-2/h1,5,7H,2H2,3H3

InChI key

VBATUBQIYXCZPA-UHFFFAOYSA-N

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1 of 4

This Item
111279P8602244430
4-Penten-1-ol 99%

Sigma-Aldrich

111279

4-Penten-1-ol

1-Penten-3-ol 99%

Sigma-Aldrich

P8602

1-Penten-3-ol

3-Hexyn-1-ol 98%

Sigma-Aldrich

244430

3-Hexyn-1-ol

refractive index

n20/D 1.446 (lit.)

refractive index

n20/D 1.429 (lit.)

refractive index

n20/D 1.424 (lit.)

refractive index

n20/D 1.454 (lit.)

bp

63-65 °C/100 mmHg (lit.)

bp

134-137 °C (lit.)

bp

114-115 °C (lit.)

bp

63-64 °C/12 mmHg (lit.)

density

0.89 g/mL at 25 °C (lit.)

density

0.834 g/mL at 25 °C (lit.)

density

0.838 g/mL at 20 °C (lit.), 0.839 g/mL at 25 °C (lit.)

density

0.898 g/mL at 25 °C (lit.)

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

General description

3-Methyl-1-penten-4-yn-3-ol is an acetylenic alcohol. It reacts with ruthenium vinyl carbene to form a ten-membered η2-olefin coordinated ruthenacycle. The efficiency of different palladium catalysts for the hydrogenation of 3-methyl-1-penten-4-yn-3-ol under continuous-flow liquid-phase conditions has been evaluated. It undergoes allylic rearrangement to form cis and trans isomers of 3-methyl-2-penten-4-yn-l-ol.

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

90.0 °F - closed cup

Flash Point(C)

32.2 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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1,2-Migration in the reactions of ruthenium vinyl carbene with propargyl alcohols.
Zhou X, et al.
Organic Chemistry Frontiers : An International Journal of Organic Chemistry / Royal Society of Chemistry, 1(9), 1077-1082 (2014)
From the Lindlar Catalyst to Supported Ligand-Modified Palladium Nanoparticles: Selectivity Patterns and Accessibility Constraints in the Continuous-Flow Three-Phase Hydrogenation of Acetylenic Compounds.
Vile G, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 20(20), 5926-5937 (2014)
Allyl rearrangement of 3-methyl-1-penten-4-yn-3-ol.
Skoda A, et al.
Chemical Papers, 43(6), 743-751 (1989)

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