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115-19-5

Basic Information
CAS No.: 115-19-5
Name: 3-Methyl butynol
Article Data: 139
Molecular Structure:
Molecular Structure of 115-19-5 (3-Methyl butynol)
Formula: C5H8O
Molecular Weight: 84.1179
Synonyms: 2-Propyn-1-ol,1,1-dimethyl- (7CI);(1-Hydroxy-1-methylethyl)acetylene;1,1-Dimethyl-2-propyn-1-ol;1,1-Dimethyl-2-propynol;1,1-Dimethylpropargylalcohol;2-Ethynyl-2-propanol;2-Hydroxy-2-methyl-3-butyne;2-Methyl-2-hydroxy-3-butyne;2-Methyl-3-butyn-2-ol;2-Methyl-3-butyne-2-ol;2-Propyne-1,1,1-triol;3-Hydroxy-3-methyl-1-butyne;3-Methyl-1-butyn-3-ol;3-Methyl-3-hydroxy-1-butyne;3-Methyl-3-hydroxybutyne;AB 32;AB 32 (alcohol);Dimethylacetylenecarbinol;Dimethylacetylenylcarbinol;Dimethylethynylcarbinol;Dimethylethynylmethanol;Ethynyldimethylcarbinol;Mebynol;NSC 523;a,a-Dimethylpropargyl alcohol;3-Methyl butynol;
EINECS: 204-070-5
Density: 0.91 g/cm3
Melting Point: 3 °C
Boiling Point: 104.2 °C at 760 mmHg
Flash Point: 25 °C
Solubility: miscible in water
Appearance: colourless to light yellow liquid
Hazard Symbols: HarmfulXn
Risk Codes: 10-22-41
Safety: 26-39-16
Transport Information: UN 1987 3/PG 2
PSA: 20.23000
LogP: 0.39050
Synthetic route
67-64-1

acetone

74-86-2

acetylene

115-19-5

2-methyl-but-3-yn-2-ol

Conditions
ConditionsYield
With sodium In methanol at 0 - 5℃; for 1h; Solvent; Reagent/catalyst; Autoclave; Inert atmosphere; Large scale;99.2%
Stage #1: acetylene With sodium amide In ammonia at -50℃; for 0.5h;
Stage #2: acetone at -50 - 25℃;
87.9%
Stage #1: acetylene With potassium hydroxide monohydrate In dimethyl sulfoxide at 10 - 15℃; for 7h;
Stage #2: acetone In dimethyl sulfoxide at 10 - 15℃; for 9h; Temperature;
82%
polymethyl(3-hydroxy-3-methyl-1-butynyl)siloxane

polymethyl(3-hydroxy-3-methyl-1-butynyl)siloxane

115-19-5

2-methyl-but-3-yn-2-ol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 12h;99%
67-64-1

acetone

74-86-2

acetylene

A

115-19-5

2-methyl-but-3-yn-2-ol

B

142-30-3

2,5-dihydroxy-2,5-dimethyl-3-hexyne

Conditions
ConditionsYield
With potassium hydride In tetrahydrofuran at 30℃; under 759.826 Torr; for 2.25h;A 7%
B 91%
Stage #1: acetone; acetylene With potassium 2-methylpropan-2-olate In xylene at 28 - 35℃; for 1h;
Stage #2: With water
Stage #3: With phosphoric acid Product distribution / selectivity;
A 2.3%
B 90%
Stage #1: acetone; acetylene With potassium 2-methylpropan-2-olate In xylene at 10 - 20℃; for 1h;
Stage #2: With water
Stage #3: With phosphoric acid Product distribution / selectivity;
A 79%
B 3%
67-64-1

acetone

70277-75-7

lithium acetylide

115-19-5

2-methyl-but-3-yn-2-ol

Conditions
ConditionsYield
Stage #1: acetone; lithium acetylide; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran at 0℃; for 2h;
Stage #2: With water In tetrahydrofuran at 20℃; Product distribution / selectivity;
81%
Stage #1: acetone; lithium acetylide; naphthalene In tetrahydrofuran at 0℃; for 2h;
Stage #2: With water In tetrahydrofuran at 20℃; Product distribution / selectivity;
56.5%
78-83-1

2-methyl-propan-1-ol

67-64-1

acetone

74-86-2

acetylene

A

115-19-5

2-methyl-but-3-yn-2-ol

B

142-30-3

2,5-dihydroxy-2,5-dimethyl-3-hexyne

Conditions
ConditionsYield
Stage #1: 2-methyl-propan-1-ol With potassium hydride In tetrahydrofuran at 30℃; under 759.826 Torr; for 0.25h;
Stage #2: acetone; acetylene In tetrahydrofuran at 30℃; under 759.826 Torr; for 2.25h;
A 74%
B 22%
39807-00-6

2-methyl-3-butyn-2-ol 1-ethoxyethyl ether

115-19-5

2-methyl-but-3-yn-2-ol

Conditions
ConditionsYield
With N,4-dimethyl-N-vinylbenzenesulfonamide; picAuCl2(III) In dichloromethane at 20℃; for 0.25h; Inert atmosphere;60%
67-64-1

acetone

4301-14-8

acetylenemagnesium bromide

115-19-5

2-methyl-but-3-yn-2-ol

Conditions
ConditionsYield
In tetrahydrofuran Heating;47%
Stage #1: acetone; acetylenemagnesium bromide In tetrahydrofuran at 0 - 20℃;
Stage #2: With ammonium chloride In tetrahydrofuran; water
In tetrahydrofuran at -10 - 20℃;
123-42-2

4-Hydroxy-4-methyl-2-pentanone

1066-26-8

sodium acetylide

115-19-5

2-methyl-but-3-yn-2-ol

1066-26-8

sodium acetylide

67-64-1

acetone

115-19-5

2-methyl-but-3-yn-2-ol

sodium acetylide

67-64-1

acetone

115-19-5

2-methyl-but-3-yn-2-ol

Conditions
ConditionsYield
at -20℃;
at -20℃;
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of 2-Methyl-3-butyn-2-ol is 2-methylbut-3-yn-2-ol. With the CAS registry number 115-19-5, it is also named as 1,1-Dimethyl-2-propyn-1-ol carbamate. The product's categories are Acetylenes; Acetylenic Alcohols & Their Derivatives; Chemistry, and the other registry numbers are 140705-79-9; 67539-62-2. Besides, it is colourless to light yellow liquid, which should be stored in a cool, sealed and ventilated warehouse. It is stable, but incompatible with strong oxidizing agents. In addition, its molecular formula is C5H8O and molecular weight is 84.12.

Physical properties about 2-Methyl-3-butyn-2-ol are: (1)ACD/LogP: 0.316; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.32; (4)ACD/LogD (pH 7.4): 0.32; (5)ACD/BCF (pH 5.5): 1.02; (6)ACD/BCF (pH 7.4): 1.02; (7)ACD/KOC (pH 5.5): 35.39; (8)ACD/KOC (pH 7.4): 35.39; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.444; (13)Molar Refractivity: 24.542 cm3; (14)Molar Volume: 92.388 cm3; (15)Polarizability: 9.729 10-24cm3; (16)Surface Tension: 33.2760009765625 dyne/cm; (17)Density: 0.911 g/cm3; (18)Flash Point: 25 °C; (19)Enthalpy of Vaporization: 40.008 kJ/mol; (20)Boiling Point: 104.165 °C at 760 mmHg; (21)Vapour Pressure: 17.1840000152588 mmHg at 25°C

Preparation of 2-Methyl-3-butyn-2-ol: this chemical can be prepared by the reaction of Propan-2-one with Ethynylmagnesium bromide.

Preparation of 2-Methyl-3-butyn-2-ol

This reaction needs Tetrahydrofuran by heating. The yield is 47 %.

Uses of 2-Methyl-3-butyn-2-ol: this chemical is an intermediate used in the synthesis of pharmaceuticals, pesticides and terpeneless spice. It can also used as acid corrosion inhibitor, viscosity depressant, viscosity stabilizer, glazing agent and stabilizer of chlorinated hydrocarbons. Additionally, it is used as polymerization inhibitor in silicon rubber. Similarly, it can react with Ethoxyethene to get 3-(1-Ethoxy-ethoxy)-3-methyl-but-1-yne.



This reaction needs Sulfuric acid for 30 min. The yield is 77 %.

When you are using this chemical, please be cautious about it as the following: it is flammable. Please keep away from sources of ignition. It is also harmful if swallowed and risk of serious damage to eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And you should wear eye/face protection.

People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: CC(C)(C#C)O;
(2)InChI: InChI=1S/C5H8O/c1-4-5(2,3)6/h1,6H,2-3H3;
(3)InChIKey: CEBKHWWANWSNTI-UHFFFAOYSA-N;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 2gm/m3 (2000mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: ATAXIA
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(4), Pg. 55, 1987.
mouse LD50 oral 500mg/kg (500mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(4), Pg. 55, 1987.
mouse LD50 subcutaneous 1161mg/kg (1161mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Yakugaku Zasshi. Journal of Pharmacy. Vol. 76, Pg. 181, 1956.
rat LD50 oral 1950mg/kg (1950mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 115, Pg. 230, 1955.