P-AMINOBENZOYL-L-GLUTAMIC ACID
4-aminobenzoyl-L-glutamic acid
CAS: 4271-30-1
Molecular Formula: C12H14N2O5
P-AMINOBENZOYL-L-GLUTAMIC ACID - Names and Identifiers
| Name | 4-aminobenzoyl-L-glutamic acid |
| Synonyms | H-4-ABZ-GLU-OH P-aminobenzamide glutamic acid 4-aminobenzoyl-L-glutamic acid P-AMINOBENZOYL-L-GLUTAMIC ACID P-Amino benzamide glutamic acid P-AMINO BENZAMIDE GLUTAMIC ACID N-(p-Aminobenzoyl)glutamic acid N-(P-AMINOBENZOYL)-L-GLUTAMIC ACID N-(4-AMINOBENZOYL)-L-GLUTAMIC ACID N-(4-Aminobenzoyl)-L-glutamic acid L-Glutamic acid, N-(4-aminobenzoyl)- N-(4-Aminobenzoyl)-L-Glutaminic Acid (2R)-2-[(4-aminobenzoyl)amino]pentanedioic acid |
| CAS | 4271-30-1 |
| EINECS | 224-261-7 |
| InChI | InChI=1/C12H14N2O5/c13-8-3-1-7(2-4-8)11(17)14-9(12(18)19)5-6-10(15)16/h1-4,9H,5-6,13H2,(H,14,17)(H,15,16)(H,18,19)/t9-/m1/s1 |
| InChIKey | GADGMZDHLQLZRI-VIFPVBQESA-N |
P-AMINOBENZOYL-L-GLUTAMIC ACID - Physico-chemical Properties
| Molecular Formula | C12H14N2O5 |
| Molar Mass | 266.25 |
| Density | 1.2846 (rough estimate) |
| Melting Point | ~175°C (dec.) |
| Boling Point | 409.45°C (rough estimate) |
| Specific Rotation(α) | -15 º (c=2% in 0.1N HCl) |
| Flash Point | 320.9°C |
| Solubility | Aqueous Base (Sparingly), Aqueous Acid (Sparingly), DMSO (Sparingly), Methanol ( |
| Vapor Presure | 1.37E-15mmHg at 25°C |
| Appearance | White crystal |
| Color | White to Light Beige Waxy to |
| Merck | 14,426 |
| BRN | 2816320 |
| pKa | 3.50±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Stability | Hygroscopic |
| Refractive Index | 1.6660 (estimate) |
| MDL | MFCD00042821 |
| Physical and Chemical Properties | Colorless crystals. Melting point 173 °c. Soluble in water, slightly soluble in alcohol, insoluble in ether. |
| Use | Pharmaceutical intermediates, used in the production of methotrexate and folic acid. |
P-AMINOBENZOYL-L-GLUTAMIC ACID - Risk and Safety
| 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. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| WGK Germany | 3 |
| HS Code | 2924296000 |
P-AMINOBENZOYL-L-GLUTAMIC ACID - Introduction
Soluble in water, slightly soluble in alcohol, insoluble in ether.
Last Update：2022-10-16 17:25:12
P-AMINOBENZOYL-L-GLUTAMIC ACID - Reference Information
| uses | pharmaceutical intermediates for the production of methotrexate and folic acid. |
| production method | p-nitrobenzoyl chloride is condensed with glutamic acid, and then reduced with ammonium sulfide. the process is as follows:(1) condensation puts water, magnesium oxide and glutamic acid into a reaction tank, adjusts the pH to 8-9, and stirs to dissolve all the materials. The temperature is reduced to 20 ℃, the benzene solution of p-nitrobenzoyl chloride is slowly added dropwise, the temperature is not more than 30 ℃, the pH is not less than 7.5, and the reaction solution changes from white to purple to fading. After adding, continue stirring for 1-2h. Let it stand and stratify, take the lower aqueous solution for filtration, wash the upper benzene liquid with a small amount of water, combine the water washing liquid with the filtrate, adjust the PH to 3-3.5 with hydrochloric acid, stand still, precipitate p-nitrobenzoic acid, filter, add hydrochloric acid to the filtrate to adjust to pH = 1, stir vigorously, and then stand for 24 hours to precipitate crystallization. Filtration to obtain N-p-nitrobenzoylglutamic acid, melting point 110-112 ℃. 73% yield. (2) Reduction After mixing water and N-p-nitrobenzoyl glutamic acid, adding ammonium sulfide, stirring to dissolve, slowly heating, boiling and evaporating to 1/3 of the pH6-7 volume of the solution, stopping heating, adding activated carbon to decolorize and filter. The filtrate is naturally cooled to room temperature, adjusted to pH3-3.5 with hydrochloric acid, let stand for 24 hours, precipitate crystallization, filter, wash with water, and dry the filter cake to obtain N-p-aminobenzoyl-L-glutamic acid with a melting point of 170-172 ℃ and a yield of 58%. |
Last Update：2024-04-09 15:16:50
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