2,6-Difluorobenzamide Chemical Properties

Melting point:

145-148 °C (lit.)

Boiling point:

51-52C/15Tor

Density 

1,199g/cm

refractive index 

1,508

storage temp. 

Sealed in dry,Room Temperature

solubility 

ethanol: soluble5%, clear to turbid, colorless to light yellow

form 

Solid

pka

14.54±0.50(Predicted)

color 

Off-White

BRN 

2047480

InChIKey

AVRQBXVUUXHRMY-UHFFFAOYSA-N

LogP

0.011-0.25 at 25℃

CAS DataBase Reference

18063-03-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzamide, 2,6-difluoro-(18063-03-1)

EPA Substance Registry System

Benzamide, 2,6-difluoro- (18063-03-1)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20

Safety Statements 

26-37/39-36/37

WGK Germany 

1

RTECS 

CV4355050

HazardClass 

IRRITANT

HS Code 

29242990

Toxicity

rat,LC50,inhalation,> 2100mg/m3/4H (2100mg/m3),National Technical Information Service. Vol. OTS0543293,

MSDS

• Language:English Provider:2,6-Difluorobenzamide
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,6-Difluorobenzamide Usage And Synthesis

Description

2,6-Difluorobenzamide is a major metabolite of pesticide diflubenzuron and has been quantitated by HPLC/diode-array method.

Description

2,6-Difluorobenzamide is a white powdery crystal, insoluble in water. It can be obtained by hydrolysis of 2,6-difluorobenzonitrile. 2,6-Difluorobenzamide is an important intermediate in the synthesis process of benzoylurea insecticides, which is used to synthesize the next intermediate 2,6-difluorobenzoyl isocyanate, and finally obtain flubolurea, pyruron, fluridin, lice mite urea and other pesticide varieties. It can also be directly used to synthesize pyruron and flubolea. 2,6-Difluorobenzamide can inhibit the bacterial cell division protein FtsZ[1].

Chemical Properties

white to yellowish powder

Uses

2,6-Difluorobenzamide (CAS# 18063-03-1) is a useful building block used in the synthesis of (E)-3-methyleneisoindolin-1-ones via oxidative annulation acrylates. It is also used in the synthesis of pesticide intermediates, which can be used to produce various insecticides such as fluazuron, chlorpyrifos, and pyrethroids.

Preparation

2,6-Difluorobenzamide is obtained by hydrolysis of 2,6-difluorobenzonitrile.

Synthesis

General procedure for the synthesis of 2,6-difluorobenzamide from 2,6-difluorobenzonitrile: (1) 100 g (0.72 mol) of 2,6-difluorobenzonitrile was added slowly and dropwise to a mixed solution of 240 g of concentrated sulfuric acid and 24 ml of water at room temperature. The reaction mixture was stirred at 80°C to 85°C for 12 hours. After completion of the reaction, the mixture was slowly poured into 1.2 kg of ice water and stirred continuously for 30 minutes, followed by filtration. The resulting crystals were washed to neutrality with distilled water and finally dried under vacuum at 85°C. The yield was 91.0 g (80.6% yield) with a melting point of 140°C to 141.5°C.

Toxics Screening Level

The Initial Threshold Screening Level (ITSL) for 2,6-Difluorobenzamide is 11 μg/m3 based on an annual averaging time.

References

[1] Straniero V, et al. 2,6-Difluorobenzamide inhibitors of the bacterial cell division protein FtsZ: design, synthesis and Structure Activity Relationship study. ChemMedChem, 2017; 12: 1303-1318.

2,6-Difluorobenzamide(18063-03-1)Related Product Information

• 2,6-Difluorobenzoic acid
• Chlorantraniliprole
• p-Aminobenzamide
• 2,6-Difluorobenzonitrile
• Benzamide
• Difluorochloromethane
• 2,3,6-TRIFLUOROBENZAMIDE
• 4-AMINO-2,3,5,6-TETRAFLUOROBENZAMIDE
• Diflubenzuron
• Chlorfluazuron
• 2,6-Difluorobenzoyl hydrazine
• Teflubenzuron
• N-PENTAFLUOROBENZOYLIMIDAZOLE
• 2,3,4,5,6-PENTAFLUOROBENZAMIDE
• 3,5-DIFLUOROBENZAMIDE
• 2-CHLORO-3,6-DIFLUOROBENZAMIDE
• 3-CHLORO-2,6-DIFLUOROBENZAMIDE
• 2,5-DIFLUOROBENZAMIDE