13255-50-0

Basic information

• Product Name: 4-CARBOXALDEHYDE-N-ISOPROPYLBENZAMIDE
• Synonyms: 4-CARBOXALDEHYDE-N-ISOPROPYLBENZAMIDE;n-isopropyl-4-formylbenzamide;4-formyl-N-isopropylbenzamide;N-Isopropyl-p-formylbenzamide;N-Isopropylterephthalaldehydamide;4-carbaldehyde-N-isopropylbenzamide
• CAS NO: 13255-50-0
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.23
• EINECS: 236-247-8
• Mol File: 13255-50-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 367.8 °C at 760 mmHg
• Flash Point: 157.6 °C
• Appearance: /
• Density: 1.093 g/cm³
• Vapor Pressure: 1.33E-05mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.05±0.46(Predicted)
• CAS DataBase Reference: 4-CARBOXALDEHYDE-N-ISOPROPYLBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CARBOXALDEHYDE-N-ISOPROPYLBENZAMIDE(13255-50-0)
• EPA Substance Registry System: 4-CARBOXALDEHYDE-N-ISOPROPYLBENZAMIDE(13255-50-0)

Safety Data

• Hazardous Substances Data: 13255-50-0(Hazardous Substances Data)

Usage

Uses

4-Formyl-n-isopropylbenzamide is an metabolite from the oxidation of the anti-neoplastic agent in aqueous solutions.

InChI:InChI=1/C11H13NO2/c1-8(2)12-11(14)10-5-3-9(7-13)4-6-10/h3-8H,1-2H3,(H,12,14)

Upstream product

• 671-16-9 Procarbazine 
• 104-87-0 4-methyl-benzaldehyde 
• 16173-52-7 4-formylbenzoyl chloride 
• 75-31-0 isopropylamine 
• 1122-91-4 4-bromo-benzaldehyde 
• 876-08-4 p-(chloromethyl)benzoyl chloride 
• 1642-81-5 p-(chloromethyl)benzoic acid 
• 2144-17-4 N-isopropyl-4-methylbenzamide 
• 99-94-5 p-Toluic acid 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 671-16-9 Procarbazine 
• 16103-51-8 4-(hydroxymethyl)-N-isopropylbenzamide 
• 105-07-7 4-cyanobenzaldehyde 

Relevant articles and documents

Introduction of Z-GP scaffold into procarbazine reduces spermatoxicity and myelosuppression

Incorporation of carbobenzoxy-glycylprolyl (Z-GP) to either α or β position of the hydrazine moiety in procarbazine (Pcb) has been carried on in 5-steps process. The overall yield was 32.7%. The new entity Z-GP-Pcb was confirmed targeting to fibroblast activation protein-α (FAPα). Z-GP-Pcb may be hydrolyzed by either isolated rhFAPα or tumor homogenate. It was shown far less cytotoxicity against NCI-H460 cell line than Pcb. Z-GP-Pcb was displayed the potency to reduce spermatoxcity in H22-bearing mice. The mechanism may be ascribed to the blockade of dehydrogenation by α-glycerolphosphate dehydrogenase. This candidate was further proved equal antitumor activity to Pcb. However, the introduction of Z-GP scaffold decreased myelosuppression. All the evidences support that Z-GP-Pcb is a better antitumor agent than Pcb.

Synthetic method of procarbazide hydrochloride intermediate

The invention discloses a synthetic method of a procarbazide hydrochloride intermediate. The preparation method comprises the following step: in a solvent, in the presence of a hydrolysis agent, carrying out hydrolysis reaction as shown in the specification on a compound as shown in a formula II to obtain a compound as shown in a formula I. The preparation method disclosed by the invention has theadvantages of high yield, high purity and stable process, and is suitable for industrial production.

Synthetic method of procarbazine

The invention discloses a synthetic method of procarbazine (Pcb). The synthetic method comprises following steps: p-tolualdehyde is taken as an initial raw material, dibromocyanuric acid and isopropylamine are added, reaction is carried out at room temperature so as to obtain p-methyl benzoyl isopropylamine; p-methyl benzoyl isopropylamine is dissolved in an organic reagent, N-bromo-succinimide and an initiator are added, heating reflux is carried out, after reaction, the solvent is removed, acetonitrile and a hydrolysis promoter are added, heating reflux is carried out so as to obtain p-formyl benzoyl isopropylamine; p-formyl benzoyl isopropylamine and methylhydrazine sulfate are dissolved in an organic reagent, triethylamine is added for reaction, and the solvent is subjected to rotary drying, sodium cyanoborohydride is added, an obtained reaction system is heated to room temperature, reaction is carried out for more than one night so as to obtain Pcb. According to the synthetic method, bromination is carried out firstly, and then hydrolysis is carried out, p-methyl benzoyl isopropylamine is converted into p-formyl benzoyl isopropylamine, using of strong oxidizing agent and strong acid is avoided, the synthetic method is friendly to the environment, the yield is high, and the total yield of the three steps is 52.9%.