Deferasirox Impurity 11
p-Hydrazinobenzoic acid
CAS: 619-67-0
Molecular Formula: C7H8N2O2
Deferasirox Impurity 11 - Names and Identifiers
| Name | p-Hydrazinobenzoic acid |
| Synonyms | 4-hydrazinobenzoate 4-hydrazino-benzoicaci p-hydrazino-benzoicaci Deferasirox Impurity 11 4-Hydrazinobenzoic acid P-HYDRAZINOBENZOIC ACID p-Hydrazinobenzoic acid 4-Hydrazinobenzoic acid pure Deferasirox Hydrazino IMpurity Phenylhydrazine-p-carbo-xylic acid |
| CAS | 619-67-0 |
| EINECS | 210-609-5 |
| InChI | InChI=1/C7H8N2O2/c8-9-6-3-1-5(2-4-6)7(10)11/h1-4,9H,8H2,(H,10,11)/p-1 |
| InChIKey | PCNFLKVWBDNNOW-UHFFFAOYSA-N |
Deferasirox Impurity 11 - Physico-chemical Properties
| Molecular Formula | C7H8N2O2 |
| Molar Mass | 152.15 |
| Density | 1.2804 (rough estimate) |
| Melting Point | 218 °C (dec.) (lit.) |
| Boling Point | 274.61°C (rough estimate) |
| Flash Point | 181.9°C |
| Solubility | DMSO (Slightly), Methanol (Slightly, Heated) |
| Vapor Presure | 2.32E-06mmHg at 25°C |
| Appearance | Solid |
| Color | Light yellow to light brown |
| BRN | 387378 |
| pKa | 4.14±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Stability | Stable. Combustible. Incompatible with strong acids, strong oxidizing agents. |
| Refractive Index | 1.5200 (estimate) |
| MDL | MFCD00007581 |
Deferasirox Impurity 11 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 1 |
| RTECS | DH1700000 |
| TSCA | Yes |
| HS Code | 29280000 |
| Hazard Note | Irritant |
Deferasirox Impurity 11 - Introduction
Solubility in water:< 10g/L (20°C), finely soluble in ethanol.
Last Update：2022-10-16 17:27:14
Deferasirox Impurity 11 - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Application | 4-hydrazinobenzoic acid and its esters can be used as intermediates in medicine and materials. After the target product is synthesized, because it contains a carboxyl group, the group can be further modified, thereby increasing the chance of finding a new drug. |
| preparation | synthesis of methyl p-aminobenzoate hydrochloride (3) a 1L flask was charged with ml of anhydrous methanol and cooled in an ice-water bath, 65mL thionyl chloride was slowly added dropwise, and the internal temperature was controlled not to exceed 15 °c. After dropping, stir for 15min, then add 100g of p-aminobenzoic acid at one time, slowly heat and reflux for 3.5h, cool, precipitate white solid , filter, wash with cold methanol, dry, 136.1G of intermediate 3 were obtained in almost quantitative yield. Synthesis of methyl p-hydrazinobenzoate hydrochloride (5) in a 1L three-necked flask, add 0.6 ml of water, slowly add 55ml (0.27mol) of concentrated hydrochloric acid, and then add 50g (mol) of intermediate 3, drop 50ml aqueous solution containing 20g(0.29mol) of NaNO2, and control the temperature of the reaction solution not to exceed 0 ℃, often with starch-KI test paper, when the drop NaNO2 solution added a few minutes later, if the test paper quickly turn blue, stop dropping, continue to <0 deg C stirring standby. In another 1l Three-necked flask, 0.69 of water was added and 87G (mol) of Na2SO3 was added with stirring to dissolve most of the solids, The pH of the Na2SO3 solution was then adjusted to 6.5-6.8 with concentrated hydrochloric acid. The above diazotization solution was slowly added to the Na2SO3 solution in a fine linear form, and the temperature of the reaction solution was controlled not to exceed 20 °c. After adding, stir at room temperature for 0.5h, then add 20ml of concentrated hydrochloric acid, slowly raise the temperature to 90 ℃ and reflux for 3h, naturally drop to room temperature, stir at 10 ℃ for 0.5h, and filter with suction, the filter cake was washed with 20ml of 10% (mass fraction) hydrochloric acid, then washed with ice water, and dried under reduced pressure in vacuum to obtain 48.6g of yellow solid with a yield of 90%,mp233~235 ° C. Synthesis of 4-hydrazinobenzoic acid (1) in a ml flask, 30g(0.148mol) of intermediate 5 and 200ml of 1:1(V/V) ethanol-water were added, under stirring, 40ml of 50% (mass fraction) NaOH solution was slowly added dropwise, and under the protection of nitrogen, the temperature was raised to reflux until there was no raw material, and it took about 3H to recover ethanol. Cool to room temperature, adjust the reaction solution to pH 4~4.1 with concentrated hydrochloric acid, continue to stir at 10 °c for 1H, filter, wash with a small amount of ice water, vacuum dry, get yellow solid 25.5g, the yield was 91%. |
Last Update：2024-04-09 20:48:19
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