4-Hydroxy-2-butanone Chemical Properties

Melting point:

15°C (estimate)

Boiling point:

73-76 °C/12 mmHg (lit.)

Density 

1.023 g/mL at 25 °C (lit.)

refractive index 

1.430

Flash point:

91°F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform, Methanol (Slightly)

form 

Oil

pka

14.43±0.10(Predicted)

color 

Clear Colourless

Water Solubility 

Miscible with water, alcohol, ethanol and ether.

BRN 

1737666

InChI

1S/C4H8O2/c1-4(6)2-3-5/h5H,2-3H2,1H3

InChIKey

LVSQXDHWDCMMRJ-UHFFFAOYSA-N

SMILES

CC(=O)CCO

LogP

-1.209 at 25℃

CAS DataBase Reference

590-90-9(CAS DataBase Reference)

NIST Chemistry Reference

4-Hydroxy-2-butanone(590-90-9)

EPA Substance Registry System

2-Butanone, 4-hydroxy- (590-90-9)

Safety Information

Risk Statements 

10

Safety Statements 

16-24/25

RIDADR 

UN 1993

WGK Germany 

3

TSCA 

TSCA listed

HazardClass 

3

HS Code 

29144000

Storage Class

3 - Flammable liquids

Hazard Classifications

Flam. Liq. 3

MSDS

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4-Hydroxy-2-butanone Usage And Synthesis

Chemical Properties

Colourless to pale yellow liquid

Uses

4-Hydroxy-2-butanone is used in the preparation of fused benzazepine molecules as selective D3 receptor antagonists with pharmaceutical activity. It is also used in the preparation of verrucarin and mevalonic acid lactone. Further, it is used to prepare 3-buten-2-one through dehydration over an anatase titanium dioxide catalyst. It is also employed in the preparation of 4-methyl-5-hydroxymethylthiazole, (±)-lineatin and beta-hydroxylactones.

Application

4-Hydroxy-2-butanone has been used in the synthesis of:

• 3-buten-2-one via dehydration over anatase-TiO2 catalyst
• 4-methyl-5-hydroxymethylthiazole
• (±)-lineatin
• mevalonic acid lactone
• verrucarin
• β-hydroxylactones

Definition

ChEBI: A beta-hydroxy ketone that is butan-2-one substituted by a hydroxy group at position 4.

General Description

4-Hydroxy-2-butanone is an important pharmaceutical intermediate. Gas phase reaction of the OH radicals with 4-hydroxy-2-butanone has been investigated by absolute rate method.

Synthesis

A method for synthesizing 4-hydroxy-2-butanone, comprising the steps of:

(1) adding a certain amount of 1.3 butanediol, catalyst, water and water-carrying agent to a reaction vessel, stirring well to form a mixed solution, and raising temperature to 60-75C;

(2) continue stirring, add hydrogen peroxide with a mass concentration of 25-35% dropwise to the mixed solution, and distill and dehydrate while dropping and adding;

(3) When the content of 1.3 butanediol in the reaction vessel is detected to be less than 5% of the initial content, stop adding hydrogen peroxide dropwise, and continue stirring for 0.5-1.5h;

(4) control the temperature in the reaction vessel, and vaporize the water-carrying agent;

(5) lowering the temperature in the reaction vessel to 60-65C and distilling to obtain the target product 4-hydroxy-2-butanone.

4-Hydroxy-2-butanone(590-90-9)Related Product Information

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• Bensulfuron methyl
• 4-Cyanophenol
• Methylparaben
• 2-Butanone oxime
• Methyl acrylate
• 2-(METHYLSULFONYL)ETHANOL
• 4-Methyl-2-pentanone
• Methyl
• Parathion-methyl
• Mordant Blue 29
• 3-(2-FLUORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER
• Methyl 4-chloro-3-oxo-butanoate
• Ethyl 4,4,4-trifluoroacetoacetate
• Ethyl 2-oxocyclopentanecarboxylate
• Ethyl 2-oxocyclohexanecarboxylate
• Acetoin