129763
2-Methyl-3-butyn-2-ol
98%
Synonym(s):
Dimethyl ethynyl carbinol
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About This Item
Linear Formula:
HC≡CC(CH3)2OH
CAS Number:
Molecular Weight:
84.12
Beilstein:
635746
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
vapor pressure
15 mmHg ( 20 °C)
Quality Level
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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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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - STOT SE 3
Target Organs
Central nervous system
Storage Class Code
3 - Flammable liquids
WGK
WGK 1
Flash Point(F)
66.2 °F - closed cup
Flash Point(C)
19 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Boyall et al.
Organic letters, 2(26), 4233-4236 (2001-01-11)
We report the first example of enantioselective aldehyde additions of 2-methyl-3-butyn-2-ol, a commodity bulk chemical that is readily available. Following a facile fragmentation reaction, the addition reactions provide access to optically active terminal acetylenes as useful building blocks for asymmetric
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
Micaela Crespo-Quesada et al.
Journal of the American Chemical Society, 133(32), 12787-12794 (2011-07-14)
The activity and selectivity of structure-sensitive reactions are strongly correlated with the shape and size of the nanocrystals present in a catalyst. This correlation can be exploited for rational catalyst design, especially if each type of surface atom displays a
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 & Catalysis, 349(10), 1738-1742 (2007)
Shinji Harada et al.
Chemical communications (Cambridge, England), (9)(9), 948-950 (2007-02-22)
Indium(III)-catalyzed asymmetric alkynylation of aryl, heteroaryl, alkyl and alkenyl aldehydes with 2-methyl-3-butyn-2-ol as an ethyne equivalent donor was realized, and products were obtained in moderate to good yields (up to 97%) and high enantioselectivities (up to 99% ee) using 2-10
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