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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:
969340
EC Number:
201-055-5
MDL number:
MFCD00004479
UNSPSC Code:
12352100
PubChem Substance ID:
24848336
NACRES:
NA.22

vapor density

3 (vs air)

Quality Level

100

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.)

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.

Signal Word

Danger

Hazard Statements

H226,H302,H318,H412

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

82.4 °F - closed cup

Flash Point(C)

28 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
A el-Brashy et al.
Pharmaceutisch weekblad. Scientific edition, 10(2), 90-92 (1988-04-22)
A titrimetric method is described for the determination of three acetylenic hypnotics, namely ethchlorvynol, ethinamate, and methylpentynol carbamate, in bulk and in dosage forms. The method involves the use of either 1,3-dibromo-5,5-dimethylhydantoin (DBH), N-bromosuccinimide (NBS) or N-bromophthalimide (NBP) as titrants.
G J Mannering et al.
Xenobiotica; the fate of foreign compounds in biological systems, 26(5), 487-493 (1996-05-01)
1. Colupulone, a constituent of hops, was shown to be a potent inducer of hepatic P4503A in mouse. The olefin, 2-methyl-3-buten-2-ol (RC = CH2), is formed from lupulones when hops are exposed to atmospheric hydroxyl radicals. This suggested the possibility
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