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Sigma-Aldrich

2-Methyl-3-butyn-2-ol

98%

Sinónimos:

Dimethyl ethynyl carbinol

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About This Item

Fórmula lineal:
HC≡CC(CH3)2OH
Número de CAS:
115-19-5
Peso molecular:
84.12
Beilstein/REAXYS Number:
635746
EC Number:
204-070-5
MDL number:
MFCD00004467
UNSPSC Code:
12352100
PubChem Substance ID:
24847925
NACRES:
NA.22

vapor pressure

15 mmHg ( 20 °C)

Quality Level

200

assay

98%

form

liquid

autoignition temp.

662 °F

expl. lim.

16.6 %

refractive index

n20/D 1.42 (lit.)

bp

104 °C (lit.)

mp

2.6 °C (lit.)

density

0.868 g/mL at 25 °C (lit.)

SMILES string

CC(C)(O)C#C

InChI

1S/C5H8O/c1-4-5(2,3)6/h1,6H,2-3H3

InChI key

CEBKHWWANWSNTI-UHFFFAOYSA-N

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Categorías relacionadas

General description

2-Methyl-3-butyn-2-ol (MBY) is used as a precursor in the Mannich reaction and can undergo selective semihydrogenation to produce fine chemicals.

Application

2-Methyl-3-butyn-2-ol can be used as a reactant to synthesize:,·
  • Aryl-2-methyl-3-butyn-2-ols via Pd-catalyzed Sonogashira coupling reaction with various aryl bromides.      
  • 2-Methyl-3-buten-2-ol (MBE) by Pd/γ-Al2O3 catalyzed selective hydrogenation reaction. MBE is applicable as an important intermediate in the synthesis of vitamin A.      
  • Diarylacetylenes via Pd-catalyzed Sonogashira coupling reaction with aryl chlorides in the presence of Cs2CO3 as a base. 
  • Optically active propargylic alcohols by enantioselective addition reaction with various aldehydes in the presence of Zn(OTf)2 and N-methylephedrine.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - STOT SE 3

target_organs

Central nervous system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

66.2 °F - closed cup

flash_point_c

19 °C - closed cup

ppe

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

Certificados de análisis (COA)

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Torstein Fjermestad et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(36), 10050-10057 (2011-07-21)
Density functional calculations were carried out to ascertain the origin of enantioselectivity in the brucine N-oxide (BNO)-assisted enantioselective Pauson-Khand reaction (PKR) of norbornene with 2-methyl-3-butyn-2-ol. The computed ee value in acetone is 68 % (R), which compares well to the previously
Andrea Caporale et al.
Beilstein journal of organic chemistry, 10, 384-393 (2014-03-08)
Two efficient protocols for the palladium-catalyzed synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides in the absence of copper were developed. A simple catalytic system consisting of Pd(OAc)2 and P(p-tol)3 using DBU as the base and THF as the solvent was found
Continuous 2-Methyl-3-Butyn-2-ol Selective Hydrogenation on Pd/?-Al2O3 as a Green Pathway of Vitamin A Precursor Synthesis
Fernandez-Ropero AJ, et al.
Catalysts, 11(4), 501-501 (2021)
Palladium-Catalyzed Efficient and One-Pot Synthesis of Diarylacetylenes from the Reaction of Aryl Chlorides with 2-Methyl-3-butyn-2-ol
Yi Chenyi, et al.
advanced synthesis and catalysis, 349(10), 1738-1742 (2007)
General kinetic modeling of the selective hydrogenation of 2-methyl-3-butyn-2-ol over a commercial palladium-based catalyst
Vernuccio S, et al.
Industrial & Engineering Chemistry Research, 54(46), 11543-11551 (2015)
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