3-CHLOROBENZHYDRAZIDE

3-CHLOROBENZHYDRAZIDE Property

Melting point:

155-156°C

Density 

1.323±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

11.86±0.10(Predicted)

color 

White to Light yellow

BRN 

973243

InChI

InChI=1S/C7H7ClN2O/c8-6-3-1-2-5(4-6)7(11)10-9/h1-4H,9H2,(H,10,11)

InChIKey

PHRDZSRVSVNQRN-UHFFFAOYSA-N

SMILES

C(NN)(=O)C1=CC=CC(Cl)=C1

CAS DataBase Reference

1673-47-8(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29280090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P405Store locked up.

3-CHLOROBENZHYDRAZIDE Chemical Properties,Usage,Production

Chemical Properties

White crystalline powder

Antimicrobial activity

3-Chlorobenzhydrazide is a dihedral molecule that can be classified as an antibacterial and antimycobacterial agent. The crystal x-ray diffraction study revealed that 3-chlorobenzhydrazide forms a hydrogen bond with hydroxyl groups of amino acids in proteins. This property makes it an effective antibacterial agent against Gram-positive bacteria such as staphylococci and Mycobacteria tuberculosis.

Synthesis

General procedure for the synthesis of 3-chlorobenzhydrazide from 3-chlorobenzoic acid: a mixture of 3-chlorobenzoic acid (0.5 g, 3.19 mmol), 1,3-dicyclohexylcarbodiimide (0.72 g, 3.51 mmol), and 4-dimethylaminopyridine (0.04 g, 0.32 mmol) in ethanol was stirred for 1.5 h at room temperature. The white solid was collected by filtration and the filtrate was diluted with dichloromethane (100 mL). The organic phase was washed sequentially with 1N sodium bisulfate solution (100 mL), saturated sodium bicarbonate solution (100 mL), water (100 mL) and brine (100 mL). The organic layer was dried with anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting crude product was dissolved in ethanol (15 mL) and hydrazine monohydrate (0.46 mL, 9.58 mmol) was added. The reaction mixture was stirred at room temperature overnight. Subsequently, the reaction mixture was concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography with the eluent being a dichloromethane solution of 3% methanol to give 0.29 g (53% yield) of 3-chlorobenzohydrazide as a white solid.

References

[1] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 396 - 406
[2] Patent: US2003/55085, 2003, A1
[3] Journal of Chemical Research, 2010, vol. 34, # 12, p. 680 - 683
[4] Journal of Chemical Research, 2011, vol. 35, # 4, p. 234 - 237
[5] Monatshefte fur Chemie, 2010, vol. 141, # 4, p. 479 - 484