4-Hydrazinylbenzoic Acid

English synonyms

4-Hydrazinobenzoicacid,98%;4-Hydrazinobenzoicacidpure;
Phenylhydrazine-p-carbo-xylicacid;DeferasiroxHyChemicalbookdrazinoIMpurity;
DeferasiroxImpurity11;4-hydrazino-benzoicaci;p-hydrazino-benzoicaci;
P-HYDRAZINOBENZOICACID

CAS number

619-67-0

Molecular formula

C7H8N202

Molecular weight

152.15

EINECS number

210-609-5

Melting point

218℃(dec.)(lit.)

Boiling point

274.61℃(rough estimate)

Density

1.2804(rough estimate)

Refractive index

1.5200(estimate)

Storage conditions

Keep in dark place,Inert atmosphere,Store in freezer,under -20℃

Solubility

Soluble in DMSO (slightly), methanol (slightly, heated)

Acidity coefficient (pKa)

4.14±0.10 (Predicted)

Form

Crystalline powder

Color

Light yellow to light brown

BRN

387378

Stability

Stable. Flammable. Incompatible with strong acids and strong oxidants.

InChlKey

PCNFLKVWBDNNOW-UHFFFAOYSA-N

CAS database

619-67-0(CAS DataBase Reference)

EPA chemical information

Benzoic acid,4-hydrazino-(619-67-0)

Applications

4-Hydrazinobenzoic acid and its esters can be used as pharmaceutical and material intermediates.
After the target product is synthesized, because it contains a carboxyl group,
the group can be further modified, thereby increasing the chances of discovering new drugs.

Preparation

Synthesis of methyl 4-hydrazinobenzoate hydrochloride (5)

In a 1L three-necked flask, add 300mL of water, slowly add 55mL (0.6mol) of concentrated hydrochloric acid,
then add 50g (0.27mol) of intermediate 3, cool to below -10℃, drop 50mL of aqueous solution containing 20g (0.29mol) of NaNO2,
and control the temperature of the reaction solution not to exceed 0℃. When the addition is almost complete,
frequently use starch-KI test paper to detect. After a few minutes of dropping the NaNO2 solution, if the test paper quickly turns blue,
stop dropping and continue stirring at <0℃ for use. In another 1L three-necked flask, add 280mL of water,
add 87g (0.6Chemicalbook9mol) of Na2SO3 while stirring, dissolve most of the solid, and then adjust the pH value of
the Na2SO3 solution to 6.5~6.8 with concentrated hydrochloric acid. Slowly add the above diazotized solution into the Na2SO3 solution in a thin line, and
control the temperature of the reaction solution not to exceed 20℃. After the addition, stir at room temperature for 0.5h,
then add 20ml concentrated hydrochloric acid, slowly heat to 90℃ and reflux for 3h, naturally cool to room temperature, stir at 10℃ for 0.5h,
filter, wash the filter cake with 20mL10% (mass fraction) hydrochloric acid, then wash with ice water,
and vacuum dry under reduced pressure to obtain 48.6g of yellow solid, with a yield of 90%, mp233~235℃

Synthesis of 4-hydrazinobenzoic acid (1)

In a 500mL flask, add 30g (0.148mol) of intermediate 5 and 200mL 1:1 (V/V) ethanol-water. Under stirring,
slowly add 40ml of 50% (mass fraction) NaOH solution. Under nitrogen protection, heat and reflux until there is no
raw material, which takes about 3h. Recover ethanol until it is exhausted. Cool to room temperature, adjust the reaction
solution to pH 4-4.1 with concentrated hydrochloric acid, continue stirring at 10℃ for 1h, filter,
wash with a small amount of ice water,and vacuum dry to obtain 25.5g of yellow solid, with a yield of 91%.

Hazardous Materials Symbol

Xi

Hazard Category Code

36/37/38

Safety Instructions

26-36

WGK Germany

1

RTECS Number

DH1700000

Hazard Note

Irritant

TSCA

Yes

Customs Code

29280000

Downstream products

Deferasirox, 4-(5-amino-3-TERT-butyl-pyrazole-1-YL)-benzoic acid