| Identification | More | [Name]
3-CHLOROBENZHYDRAZIDE | [CAS]
1673-47-8 | [Synonyms]
3-CHLOROBENZENE-1-CARBOHYDRAZIDE
3-CHLOROBENZHYDRAZIDE
3-CHLOROBENZOIC ACID HYDRAZIDE
3-CHLOROBENZOIC HYDRAZIDE
AKOS BBS-00004508
ASISCHEM D51116
SPECS AN-068/40169986
Benzoic acid, 3-chloro-, hydrazide
3-chlorobenzohydrazide
3-Chlorobenzenecarbohydrazide
3-Chlorobenzhydrazide, 98+%
3-CHLOROBENZOIC HYDRAZIDE, 98+% | [EINECS(EC#)]
216-812-5 | [Molecular Formula]
C7H7ClN2O | [MDL Number]
MFCD00014757 | [Molecular Weight]
170.6 | [MOL File]
1673-47-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White crystalline powder | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29280090 |
| Hazard Information | Back Directory | [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 |
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