Fenclorim Chemical Properties

Melting point:

92-93°C

Boiling point:

235.5±33.0 °C(Predicted)

Density 

1.363±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly)

pka

-4.69±0.30(Predicted)

color 

Off-White to Pale Yellow

Water Solubility 

Insoluble in water

BRN 

142293

InChI

InChI=1S/C10H6Cl2N2/c11-8-6-9(12)14-10(13-8)7-4-2-1-3-5-7/h1-6H

InChIKey

NRFQZTCQAYEXEE-UHFFFAOYSA-N

SMILES

C1(C2=CC=CC=C2)=NC(Cl)=CC(Cl)=N1

CAS DataBase Reference

3740-92-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20-43

Safety Statements 

36/37

RIDADR 

3077

WGK Germany 

2

RTECS 

UV8258400

HS Code 

2933.59.1000

HazardClass 

9

PackingGroup 

III

Fenclorim Usage And Synthesis

Description

Fenclorim (4,6-dichloro-2-phenylpyrimidine) is a pyrimidine herbicide safener that effectively protects rice (Oryza sativa L.) from the phytotoxicity of certain herbicides. It improves rice tolerance to chloroacetanilide herbicides by enhancing the expression of detoxifying glutathione S-transferase (GST). Compared with seed treatment with safener alone, sequential seed treatment with safener and insecticide minimizes the release of fenclorim without causing residue problems in the ecosystem and harvested rice.

Chemical Properties

White to off-white solid

Uses

Herbicide safener.

Definition

ChEBI: Fenclorim is a member of pyrimidines and an organohalogen compound.

Synthesis

The general procedure for the synthesis of 4,6-dichloro-2-phenyl-pyrimidine from 2-phenylpyrimidine-4,6-diol was as follows: 300 ml of phosphoryl chloride was added to 40 g of 2-phenylpyrimidine-4,6-diol. The reaction mixture was heated to reflux at 100 °C for 48 hours. Upon completion of the reaction, the excess phosphoryl chloride was removed by distillation under reduced pressure (20 mbar). Subsequently, 200 ml of chloroform and 100 ml of ice water were added to the reaction mixture and stirred thoroughly for 30 minutes. The pH of the mixture was adjusted to 5-6 with aqueous sodium carbonate. the organic layer was separated and the aqueous phase was extracted three times with 200 mL of chloroform. All chloroform phases were combined, dried with magnesium sulfate, filtered and the chloroform was removed by evaporation under reduced pressure. The resulting crude product can be purified by distillation under reduced pressure or by column chromatography using 60 mesh silica gel (with chloroform as eluent).

References

[1] Patent: US2003/162764, 2003, A1
[2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 8, p. 2627 - 2634
[3] Patent: US6372751, 2002, B1. Location in patent: Example Pr3
[4] Australian Journal of Chemistry, 2015, vol. 68, # 5, p. 814 - 824
[5] Farmaco, 1997, vol. 52, # 1, p. 61 - 65

Fenclorim(3740-92-9)Related Product Information

• Thionyl chloride
• Sodium dichloroisocyanurate
• Dichloromethylphenylsilane
• Dichloroethane
• 4,6-Dichloropyrimidine
• Triphenylphosphine
• Quinclorac
• Dichlorodiphenylsilane
• Cloquintocet-mexyl
• FENCHLORAZOL-ETHYL
• FENCHLORAZOLE
• Phenylacetone
• 4,6-DICHLORO-2,5-DIPHENYLPYRIMIDINE
• 2-(4-BROMOPHENYL)-4,6-DICHLOROPYRIMIDINE
• 4,6-DICHLORO-2-PHENYLPYRIMIDIN-5-AMINE
• 4,6-DICHLORO-2-(4-METHOXYPHENYL)PYRIMIDINE
• 2-(4-CHLOROPHENYL)-4,6-DICHLOROPYRIMIDINE
• Fenclorim