3-CHLORO-2,4-PENTANEDIONE Chemical Properties

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 Information

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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3-CHLORO-2,4-PENTANEDIONE Usage And Synthesis

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

3-CHLORO-2,4-PENTANEDIONE(1694-29-7)Related Product Information

• Loratadine
• 1-(2,6-Dichlorophenyl)-2-indolinone
• 3-CHLORO-2,4-PENTANEDIONE
• Acetylacetone
• ETHYL 3-CHLORO-2,4-DIOXOPENTANOATE
• 1,1-DIMETHYL-4-CHLORO-3,5-CYCLOHEXANEDIONE
• 2-CHLORO-2-PHENYLINDANE-1,3-DIONE
• 3-(1-Aminoethylidene)-1-chloro-2,4-pentanedione
• N1-PHENYL-3-CHLORO-4-(4-METHYLPHENYL)-2,4-DIOXOBUTANAMIDE
• AURORA KA-5384
• N-(2-CHLORO-1,3-DIOXO-2,3-DIHYDRO-1H-INDEN-2-YL)-4-(TRIFLUOROMETHYL)BENZAMIDE
• AURORA KA-5564
• 2-CHLORO-2-PHENYL-1H-PHENALENE-1,3(2H)-DIONE
• 2-ALLYL-2,4-DICHLORO-5-MORPHOLIN-4-YLCYCLOPENT-4-ENE-1,3-DIONE
• AURORA KA-4109
• AURORA KA-6510
• TETRACHLOROCYCLOPENTENE-1,3-DIONE
• 2-CHLORO-2-ETHYL-4-HYDROXY-2,3-DIHYDRO-1H-PHENALENE-1,3-DIONE