3-CHLORO-2,4-PENTANEDIONE

3-CHLORO-2,4-PENTANEDIONE Property

Melting point:

-15 °C

Boiling point:

49-52 °C/18 mmHg (lit.)

Density 

1.1921 g/mL at 20 °C (lit.)

vapor pressure 

15 hPa (20 °C)

refractive index 

n20/D 1.483(lit.)

Flash point:

54 °F

storage temp. 

2-8°C

solubility 

7.65g/l

form 

Liquid

pka

6.77±0.46(Predicted)

Specific Gravity

1.129

color 

Clear yellow to very deep brown

PH

3.9 (7.65g/l, H2O, 20℃)

explosive limit

2.1%(V)

BRN 

605870

CAS DataBase Reference

1694-29-7(CAS DataBase Reference)

EPA Substance Registry System

2,4-Pentanedione, 3-chloro- (1694-29-7)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

RIDADR 

UN 1224 3/PG 3

WGK Germany 

3

F 

19

Autoignition Temperature

485 °C

HS Code 

2914 79 00

HazardClass 

3.1

PackingGroup 

II

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-CHLORO-2,4-PENTANEDIONE Chemical Properties,Usage,Production

Chemical Properties

clear yellow to very deep brown liquid

Uses

3-Chloro-2,4-pentanedione was used in the synthesis of tetrathiafulvenyl-acetylacetonate (TTFSacacH), precursor of novel redox-active ligands.

General Description

The tautomeric properties of 3-chloro-2,4-pentanedione were studied using gas electron diffraction (GED) and quantum chemical calculations.

Synthesis

The general procedure for the synthesis of 3-chloro-2,4-pentanedione from acetylacetone under solvent-free conditions was as follows: first, a temperature control device was installed to maintain the reaction temperature at 15°C and the system pressure was adjusted to 1-2 atm. Acetylacetone was introduced continuously into the reaction system via a metering pump at a flow rate of 1 mol/h and chlorine at a flow rate of 1.0 mol/h. The reaction time was strictly controlled to 20 seconds. During the reaction, the temperature at the reactor outlet was gradually increased to 35 °C and the temperature at the outlet of Pipeline 2 was increased to 25 °C. The reaction lasted for 1 h and was terminated and sampled for gas phase analysis. The results showed that the reaction selectivity was 83.1% and the quantitative yield was 79.2%.

References

[1] Patent: CN105418548, 2016, A. Location in patent: Paragraph 0017
[2] Journal of the Chinese Chemical Society (Taipei, Taiwan), 1997, vol. 44, # 3, p. 309 - 312
[3] Journal of Organic Chemistry, 1995, vol. 60, # 10, p. 3074 - 3083
[4] Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 148 - 158
[5] Journal of the American Chemical Society, 1945, vol. 67, p. 395,399