4-Hydrazinobenzoic acid hydrochloride Chemical Properties

Melting point:

253 °C (dec.)(lit.)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Sparingly)

form 

Solid

color 

White to Off-White

Water Solubility 

Soluble in water.

InChI

InChI=1S/C7H8N2O2.ClH/c8-9-6-3-1-5(2-4-6)7(10)11;/h1-4,9H,8H2,(H,10,11);1H

InChIKey

XHLQMKQBCHYRLC-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

24589-77-3(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 4-hydrazino-, monohydrochloride (24589-77-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DH1700000

TSCA 

TSCA listed

HS Code 

2928009090

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Hydrazinobenzoic acid hydrochloride Usage And Synthesis

Chemical Properties

white to light yellow crystal powder     

Uses

4-Hydrazinobenzoic acid hydrochloride is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields. It may be used for the preparation of 4-(3-(2-(tert-butoxycarbonylamino)ethyl)-5-hydroxy-1H-pyrazol-1-yl)benzoic acid.

General Description

4-Hydrazinobenzoic acid (p-Hydrazinobenzoic acid, HBA) has been reported as an ingredient of the cultivated mushroom Agaricus bisporus. It is carcinogenic to rodents. Mechanism of DNA damage by 4-hydrazinobenzoic acid has been studied by using ³²P-labeled DNA fragments obtained from the human p53 and p16 tumor suppressor genes. It may be used for the preparation of 4-(3-(2-(tert-butoxycarbonylamino)ethyl)-5-hydroxy-1H-pyrazol-1-yl)benzoic acid.

Synthesis

To 600 ml beaker add water 150 ml, stirring, add p-aminobenzoic acid 27.4 g, 10N hydrochloric acid 57.5 ml, after cooling the solution to 0 ??, slowly add sodium nitrite solution (from 15 grams of sodium nitrite and 30 ml of water to formulate), add the end of the system, adjust the system pH for 1-2, control the temperature of the reaction system 5 ??, the reaction for 20 minutes, filtration and retention of the filtrate. Add 200 ml of water to a 1000 ml beaker, add 64 g of sodium metabisulfite and 78 g of sodium hydroxide with stirring, at this time, the solution pH was 7, the solution temperature was 35 ?? C. After the solution was cooled down to 15-18 ?? C, the above filtrate was added slowly, and the temperature of the solution was 20 ?? C when it was added, the pH was 7, and the reaction was carried out for 30 minutes, and then the temperature was raised to 50-60 ?? C, and 115 ml of hydrochloric acid was added to it, and the temperature continued to be raised to 97-100 ?? C, and the reaction was continued to be carried out for 20 minutes. Elevate the temperature to 97-100 ?? C, and at this temperature reaction for 30 minutes after adding 7 grams of activated carbon, decolorization after 90 ?? C filtration to retain the filtrate, cooled to 15 ?? C, add hydrochloric acid, the material precipitation, filtration, pumping dry to get the 4-carboxyphenylhydrazine hydrochloride product. The purity of 4-carboxyphenylhydrazine hydrochloride was 98.92% as measured by high performance liquid chromatography.

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