3-Methyl butynol Chemical Properties

Melting point:

3 °C

Boiling point:

104 °C(lit.)

Density 

0.868 g/mL at 25 °C(lit.)

vapor pressure 

15 mm Hg ( 20 °C)

refractive index 

n20/D 1.42(lit.)

Flash point:

77 °F

storage temp. 

Store below +30°C.

solubility 

Fully miscible.

form 

Powder or Crystals

pka

13.34±0.29(Predicted)

color 

White to yellow-beige to brown

PH

7 (H2O, 20℃)

explosive limit

1.8-16%(V)

Water Solubility 

miscible

Merck 

14,6034

BRN 

635746

Stability:

Stable. Flammable. Incompatible with strong oxidizing agents.

LogP

0.318 at 20-25℃

CAS DataBase Reference

115-19-5(CAS DataBase Reference)

NIST Chemistry Reference

3-Butyn-2-ol, 2-methyl-(115-19-5)

EPA Substance Registry System

2-Methyl-3-butyn-2-ol (115-19-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

10-22-41

Safety Statements 

26-39-16

RIDADR 

UN 1987 3/PG 2

WGK Germany 

1

RTECS 

ES0810000

Autoignition Temperature

662 °F

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29052990

Toxicity

LD50 orally in Rabbit: 1420 mg/kg LD50 dermal Rat > 2000 mg/kg

MSDS

• Language:English Provider:2-Methylbut-3-yn-2-ol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Methyl butynol Usage And Synthesis

Chemical Properties

colourless to light yellow liquid.
Methylbutynol (3-Methyl butynol) is a colorless, transparent, and aromatic liquid that can be consumed at room temperature. It is soluble in water and fatty acids and miscible with acetone, benzene, carbon tetrachloride, and petroleum ether but insoluble in ammonia. Methylbutynol and water form an azeotrope with an azeotropic point of 91 °C in the methylbutynol composition of 74% and the water composition of 26%. Methylbutynol is chemically active and has the common reactions of alcohol groups and unsaturated triple bonds, such as addition, polymerization, esterification, and oxidation reactions.

Uses

Stabilizer in chlorinated solvents, viscosity reducer and stabilizer, electroplating brightener, intermediate.

Uses

2-Methyl-3-butyn-2-ol is used as an intermediate in the manufacture of products for the agrochemical and specialty chemical industry.

Application

Methylbutynol (3-Methyl butynol) is used as an intermediate in the pharmaceutical industry for the synthesis of the anticancer drug citricin. It is used as a raw material for the synthesis of pyrethroids in the pesticide industry and as a raw material in the synthesis of terpene perfumes. Because methylbutynol has good corrosion inhibition and synergistic effect, it can effectively prevent hydrogen embrittlement of metal. As an essential component of high-efficiency acidification corrosion inhibitor, it is widely used in the oil and gas industry. Methylbutynol can be applied as an acetylene carrier to safely and economically transport large acetylene quantities. This usage can be accomplished in three steps: Firstly, acetylene is stored in the form of methyl butanol by reacting the former with acetone. Secondly, the resulting methylbutynol is transported from the origin of acetylene to the place of consumption. Thirdly, acetylene and acetone can be obtained by cleavage of methylbutynol and separated to yield pure products for further applications.

Preparation

3-Methyl butynol is produced from Acetone and Acetylene in liquid Ammonia with Sodamide (or in Cellosolve with Potassium hydroxide). The process yields Methylbutynol which can be hydrogenated to Methylbutenol. 

General Description

Colorless to straw yellow liquid.

Air & Water Reactions

Highly flammable.

Reactivity Profile

3-Methyl butynol is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Hazard

Flammable, dangerous fire risk.

Health Hazard

Contact will cause eye and skin irritation. Vapor exposure may cause eye and respiratory tract irritation.

Fire Hazard

Special Hazards of Combustion Products: Irritating and toxic gases, such as carbon dioxide and carbon monoxide, may be produced in fire.

Flammability and Explosibility

Highly flammable

Synthesis

Three parts of the strong basic anion exchange resin Amberlite IRA400 were suspended in 30 parts of 7% sodium hydroxide solution to change to OH type. After washing to neutral with water, the resin was suspended in methanol, and after 15–60 min, methanol was discharged. The treatment with methanol was repeated as described above until the water content of the effluent methanol was less than 0.1% and the water content of the ion exchange resin was less than 0.2%. The tubular reactor was filled with the ion exchange resin, and then acetone was saturated with acetylene, and liquid ammonia was introduced into the reactor at 2.5 MPa and 40 °C. Excess acetylene in reactants was used to reduce the side reaction of acetone. After ethynylation, the reaction solution was subjected to a flash evaporation at 50 °C. The remaining solution was distilled to obtain methylbutynol (3-methyl butynol).

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