5135-80-8

Basic information

• Product Name: Chloroacetaldehyde (2,4-dinitrophenyl)hydrazone
• Synonyms: Chloroacetaldehyde (2,4-dinitrophenyl)hydrazone;N-(2-chloroethylideneamino)-2,4-dinitro-aniline;Olin-1763
• CAS NO: 5135-80-8
• Molecular Formula: C₈H₇ClN₄O₄
• Molecular Weight: 258.61858
• Mol File: 5135-80-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 413.5°Cat760mmHg
• Flash Point: 203.9°C
• Appearance: /
• Density: 1.59g/cm³
• Vapor Pressure: 4.76E-07mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: Chloroacetaldehyde (2,4-dinitrophenyl)hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: Chloroacetaldehyde (2,4-dinitrophenyl)hydrazone(5135-80-8)
• EPA Substance Registry System: Chloroacetaldehyde (2,4-dinitrophenyl)hydrazone(5135-80-8)

Safety Data

• Hazardous Substances Data: 5135-80-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H7ClN4O4/c9-3-4-10-11-7-2-1-6(12(14)15)5-8(7)13(16)17/h1-2,4-5,11H,3H2

Upstream product

• 107-20-0 2-chloroethanal 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 621-62-5 chloroacetaldehyde diethyl acetal 
• 1426658-55-0 2-(2-chloroethyl)-N-methyl-1,2-bis(methylsulfonyl)-N-nitrosohydrazinecarboxamide 
• 1426658-59-4 N-(2-chloroethyl)-2-methyl-1,2-bis(methylsulfonyl)-N-nitrosohydrazinecarboxamide 

Downstream Products

• 14947-27-4 Chloressig-2.4-dinitro-phenylhydrazon-saeurebromid 

Relevant articles and documents

Chloroethylating and methylating dual function antineoplastic agents display superior cytotoxicity against repair proficient tumor cells

Two new agents based upon the structure of the clinically active prodrug laromustine were synthesized. These agents, 2-(2-chloroethyl)-N-methyl-1,2- bis(methylsulfonyl)-N-nitrosohydrazinecarboxamide (1) and N-(2-chloroethyl)-2- methyl-1,2-bis(methylsulfonyl)-N-nitrosohydrazinecarboxamide (2), were designed to retain the potent chloroethylating and DNA cross-linking functions of laromustine, and gain the ability to methylate DNA at the O-6 position of guanine, while lacking the carbamoylating activity of laromustine. The methylating arm was introduced with the intent of depleting the DNA repair protein O6-alkylguanine-DNA alkyltransferase (AGT). Compound 1 is markedly more cytotoxic than laromustine in both AGT minus EMT6 mouse mammary carcinoma cells and high AGT expressing DU145 human prostate carcinoma cells. DNA cross-linking studies indicated that its cross-linking efficiency is nearly identical to its predicted active decomposition product, 1,2-bis(methylsulfonyl) -1-(2-chloroethyl)hydrazine (90CE), which is also produced by laromustine. AGT ablation studies in DU145 cells demonstrated that 1 can efficiently deplete AGT. Studies assaying methanol and 2-chloroethanol production as a consequence of the methylation and chloroethylation of water by 1 and 2 confirmed their ability to function as methylating and chloroethylating agents and provided insights into the superior activity of 1.

Oxidation of aliphatic primary alcohols by morpholinium chlorochromate: A kinetic and mechanistic approach

The oxidation of nine aliphatic primary alcohols by morpholinium chlorochromate (MCC) in dimethylsulfoxide leads to the transformation of alcohols to the corresponding aldehydes. The reaction is first order with respect to both MCC and the alcohol both. The reaction is catalysed by hydrogen ions. The hydrogen-ion dependence has the form: kobs = a + A[H +]. The oxidation of [1,1-2H2]ethanol (MeCD2OH) exhibits a substantial primary kinetic isotope effect. The reaction has been studied in nineteen different organic solvents. The solvent effect was analysed using Taft's and Swain's multiparametric equations. The rate of oxidation is susceptible to both polar and steric effects of the substituents. A suitable mechanism has been proposed.