2653-08-9

Basic information

• Product Name: NSC 49396
• Synonyms: NSC 49396;1,4-Bis(chloroacetylamino)benzene;N,N'-(1,4-Phenylene)bis(2-chloroacetamide);2-chloro-N-[4-(2-chloroethanoylamino)phenyl]ethanamide;2-chloro-N-[4-[(2-chloro-1-oxoethyl)amino]phenyl]acetamide;4-13-00-00141 (Beilstein Handbook Reference);ACETAMIDE, N,N'-(p-PHENYLENE)BIS(2-CHLOR;Acetamide, N,N'-(p-phenylene)bis[2-chloro-
• CAS NO: 2653-08-9
• Molecular Formula: C₁₀H₁₀Cl₂N₂O₂
• Molecular Weight: 261.11
• Mol File: 2653-08-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 537.2°Cat760mmHg
• Flash Point: 278.7°C
• Appearance: /
• Density: 1.463g/cm³
• CAS DataBase Reference: NSC 49396(CAS DataBase Reference)
• NIST Chemistry Reference: NSC 49396(2653-08-9)
• EPA Substance Registry System: NSC 49396(2653-08-9)

Safety Data

• Hazardous Substances Data: 2653-08-9(Hazardous Substances Data)

Usage

General Description

NSC 49396, also known as 5-Fluorouracil, is a chemotherapeutic agent used in the treatment of various cancers, including breast, colon, and skin cancer. It works by interfering with the replication and synthesis of DNA, leading to the inhibition of cancer cell growth. 5-Fluorouracil is classified as an antimetabolite, meaning it disrupts the normal metabolic processes within the cell. Common side effects of 5-Fluorouracil treatment include nausea, vomiting, diarrhea, and decreased white blood cell count. It is administered as an injection or topical cream, and its use requires close monitoring by healthcare professionals due to the potential for serious adverse effects.

Upstream product

• 79-04-9 chloroacetyl chloride 
• 106-50-3 1,4-phenylenediamine 
• 4015-58-1 monochloroacetic acid anhydride 

Downstream Products

• 112818-63-0 N,N'-bis-piperidinoacetyl-p-phenylenediamine 
• 111293-84-6 1,4-bis-[(N,N-diethyl-glycyl)-amino]-benzene 
• 100434-16-0 1,4-bis-(2-triethylammonio-acetylamino)-benzene; dichloride 

Relevant articles and documents

Synthesis and physiochemical properties of novel gemini surfactants with phenyl-1,4-bis(carbamoylmethyl) spacer

A series of novel gemini surfactants, namely, phenyl-1,4-bis[(carbamoylmethyl) N,N-dimethylalkyl ammonium chloride)] (a, b and c), was synthesized systematically and characterized by FTIR, 1H NMR, 13C NMR and MS. The surface and bulk

Efficient routes for the synthesis of novel bis(s-triazolo[3,4-b][1,3,4] thiadiazines)

Bis(triazolo[3,4-b]thiadiazine) 4 in which the fused system is linked directly to the benzene core can be synthesized in 75% yield by, firstly, preparation of bis(s-triazole) 2 followed by reaction with phenacyl bromide 3 in refluxing EtOH/DMF mixture containing piperidine. Bis(s-triazolo[3,4-b][1,3,4] thiadiazines) 8 and 11 in which the triazolothiadiazines are linked to benzene core via alkyl or ether linkage were synthesized in 70 and 72% yields, respectively, starting from dicarboxylic acids 5 and 9 upon treatment with two moles of thiocarbohydrazide 6 to give the corresponding bis(4-amino-5-mercapto- s-triazolo-3-y1) derivatives 7 and 10 and subsequent reaction with two equivalents of phenacyl bromide. Bis(6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazines) 15a, 15b, 15c, 15d, 15e, 15f, which are linked to arene cores via sulfanylmethylene spacers, were prepared by the reaction of 4-amino-4H-1,2,4- triazole-3,5-dithiol 12 with the appropriate bis(bromomethyl)benzenes 13a, 13b, 13c, 13d, 13e, 13f to give bis(4-amino-5-mercapto-4H-3-sulfanylmethyl)arenes 14a, 14b, 14c, 14d, 14e, 14f and subsequent reaction with phenacyl bromide. Compounds 15a, 15b, 15c, 15d, 15e, 15f were alternatively obtained in 60-70% yields by twofold substitution of 13a, 13b, 13c, 13d, 13e, 13f with two equivalents of 6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-3-thiol 16 in refluxing EtOH/DMF mixture containing KOH. Bis(triazolothiadiazine) 22 attached to the benzene core through the thiadiazine ring via an amine linkage was prepared in 70% yield starting from p-phenylenediamine 19 by, firstly, acylation with chloroacetyl chloride 18 followed by bis-alkylation with 1,2,4-triazole 20 and subsequent intramolecular ring closure upon treatment with phosphorus oxychloride.