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137561

Sigma-Aldrich

3-Methyl-1-pentyn-3-ol

98%

Synonym(s):

Ethyl ethynyl methyl carbinol, Meparfynol

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About This Item

Linear Formula:
CH≡CC(OH)(CH3)CH2CH3
CAS Number:
77-75-8
Molecular Weight:
98.14
Beilstein/REAXYS Number:
969340
EC Number:
201-055-5
MDL number:
MFCD00004479
UNSPSC Code:
12352100
PubChem Substance ID:
24848336
NACRES:
NA.22

vapor density

3 (vs air)

vapor pressure

6.5 mmHg ( 20 °C)

assay

98%

form

liquid

refractive index

n20/D 1.431 (lit.)

bp

121-122 °C (lit.)

solubility

Cellosolve: miscible
Stoddard solvent: miscible
acetone: miscible
benzene: miscible
carbon tetrachloride: miscible
cyclohexanone: miscible
diethyl ether: soluble
diethylene glycol: miscible
ethanolamine: miscible
ethyl acetate: miscible
kerosene: miscible
mineral spirits: miscible
neatsfoot oil: miscible
petroleum ether: miscible
soybean oil: miscible

density

0.866 g/mL at 25 °C (lit.)

functional group

hydroxyl

SMILES string

CCC(C)(O)C#C

InChI

1S/C6H10O/c1-4-6(3,7)5-2/h1,7H,5H2,2-3H3

InChI key

QXLPXWSKPNOQLE-UHFFFAOYSA-N

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General description

3-Methyl-1-pentyn-3-ol acts as initiator during the synthesis of propargyl-terminated polylactide by bulk ring-opening polymerization.

Application

3-Methyl-1-pentyn-3-ol is propargyl alcohol that can be used as:
  • A reactant to synthesize α-methylene cyclic carbonates by reacting with carbon dioxide.
  • A reactant in the synthesis of 2,6,9-trisubstituted purine based CDK inhibitors.
  • An initiator in the synthesis of polylactide bearing terminal propargyl group via ring-opening polymerization of L-lactide.

Biochem/physiol Actions

3-Methyl-1-pentyn-3-ol is a sedative and induces hepatic P4503A in mouse.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

82.4 °F - closed cup

flash_point_c

28 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV9890
MKCP1836
MKCH7830
MKCD3994
MKBZ3269V

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H Teräväinen et al.
Journal of neurology, neurosurgery, and psychiatry, 49(2), 198-199 (1986-02-01)
Six patients with essential tremor tested in the therapeutic effectiveness of a 6-carbon alcohol, methylpentynol, 200 mg/day, against placebo in a randomised double-blind clinical cross-over trial. The effect of methylpentynol on postural tremor amplitude was not different from that of
Preparation of propargyl-terminated polylactide by the bulk ring-opening polymerization.
Liu X, et al.
Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 46(10), 937-942 (2009)
Cyclin-dependent kinase (CDK) inhibitors: development of a general strategy for the construction of 2, 6, 9-trisubstituted purine libraries. Part 3
Brun V, et al.
Tetrahedron Letters, 42(46), 8169-8171 (2001)
M I Walash et al.
Journal - Association of Official Analytical Chemists, 68(6), 1209-1212 (1985-11-01)
Titrimetric and spectrophotometric titration methods are described for the quantitative determination of acetylenic hypnotics ethchlorvynol, ethinamate, and meparfynol carbamate as pure substances and in dosage forms. The methods involve the use of different brominating agents. A known excess of the
Yanlong Gu et al.
The Journal of organic chemistry, 69(2), 391-394 (2004-01-17)
Reactions of propargylic alcohols with CO(2) in a [BMIm][PhSO(3)]/CuCl catalytic system to produce the corresponding alpha-methylene cyclic carbonates were conducted with high yields. Mild reaction conditions, enhanced rates, improved yields, and recyclable ionic liquid catalyst systems are the remarkable features
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