2067-58-5

Basic information

• Product Name: phenylenediamine mustard
• Synonyms: phenylenediamine mustard;N,N-Bis(2-chloroethyl)-p-phenylenediamine
• CAS NO: 2067-58-5
• Molecular Formula: C₁₀H₁₄Cl₂N₂
• Molecular Weight: 233.16
• Mol File: 2067-58-5.mol
• Article Data: 18

Chemical Properties

• Melting Point: 220 °C (decomp)
• Boiling Point: 373.25°C (rough estimate)
• Flash Point: 175°C
• Appearance: /
• Density: 1.2597 (rough estimate)
• Vapor Pressure: 1.53E-05mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• PKA: 5.87±0.50(Predicted)
• CAS DataBase Reference: phenylenediamine mustard(CAS DataBase Reference)
• NIST Chemistry Reference: phenylenediamine mustard(2067-58-5)
• EPA Substance Registry System: phenylenediamine mustard(2067-58-5)

Safety Data

• Hazardous Substances Data: 2067-58-5(Hazardous Substances Data)

Usage

Safety Profile

Poison by intraperitoneal route.An experimental teratogen. When heated todecomposition it emits very toxic fumes of Cl- and NOx.

InChI:InChI=1/C10H14Cl2N2/c11-5-7-14(8-6-12)10-3-1-9(13)2-4-10/h1-4H,5-8,13H2

Upstream product

• 120-07-0 2,2'-(phenylimino)bis[ethanol] 
• 100-00-5 4-chlorobenzonitrile 
• 3069-91-8 4--acetanilid 
• 100-01-6 4-nitro-aniline 
• 350-46-9 4-Fluoronitrobenzene 
• 23721-18-8 N,N-bis<2-<(methylsulfonyl)oxy>ethyl>-4-nitroaniline 
• 18226-17-0 N,N-bis(2-hydroxyethyl)-4-nitroaniline 
• 55743-71-0 bis(2-chloroethyl)(4-nitrophenyl)amine 
• 25843-64-5 1-Methyl-2--phenyliminomethyl>chinoliniumchlorid (IMET 3106) 
• 1215-16-3 N,N-bis(2-chloroethyl)-N'-acetyl-1,4-phenylenediamine 
• 122-80-5 N-acetyl-p-phenylenediamine 

Downstream Products

• 77337-92-9 α-p-phenylamino-α-isonitrosoacetone phenylhydrazone hydrochloride 
• 17273-11-9 N-<4-(N,N-Bis-(2-chloraethyl)-amino)-phenyl>-N'-<4-(methoxycarbonyl)-phenyl>-harnstoff 
• 2045-44-5 N-(4--phenyl)-carbaminsaeure-isopropylester 
• 1448-92-6 N-(4--phenyl)-carbaminsaeure-ethylester 
• 17273-06-2 N-(4--phenyl)-N'-<4-N,N-diethylamino)-phenyl>-harnstoff 
• 17272-95-6 N-(4--phenyl)-N'-(methoxycarbonyl-methyl)-harnstoff 
• 101269-99-2 Bernsteinsaeure-<4-(N,N-bis-(2-chlor-aethyl)-amino)-anilid>-monoaethylester 
• 13614-96-5 N,N-Bis-(2-chlor-aethyl)-N'-tricyanvinyl-p-phenylendiamin 
• 117881-69-3 4,4'-Bis--oxalsaeure-dianilid 
• 806608-18-4 4--phenyl-carbamoylchlorid 
• 67497-49-8 N,N-bis(2-chloroethyl)-N'-hexadecanoyl-1,4-phenylenediamine 
• 1215-16-3 N,N-bis(2-chloroethyl)-N'-acetyl-1,4-phenylenediamine 
• 2067-59-6 N,N-bis(2-chloroethyl)-N'-benzoyl-1,4-phenylenediamine 

Relevant articles and documents

Hypoxia-activatable nano-prodrug for fluorescently tracking drug release in mice

Chemotherapy is one of the commonly used methods to treat various types of cancers in clinic by virtue of its high efficiency and universality. However, strong side effects and low concentration of conventional drugs at the tumor site have always been important factors that plague the chemotherapy effects of patients, further precluding their practical applications. Thereof, to solve the above dilemma, by integration of anticancer drug (nitrogen mustard, NM) into an NIR fluorophore (a dicyanoisophorone derivative), an intelligent prodrug NIR-NM was developed via molecular engineering strategy. Prodrug NIR-NM stimulated in hypoxia condition exhibits significantly higher toxicity to cancer cells than normal cells, essentially reducing the collateral damage to healthy cells and tissues of nitrogen mustard. More importantly, the nanoparticle prodrug FA-lip@NIR-NM showed the advantages of the high accumulation of drug at tumor site and long-circulation capacity in vivo, which endowed it the ability to track the release of the active chemotherapeutic drug and further treat solid tumors.[Figure not available: see fulltext.].

N nitrogen mustard derivatives, two N - (2 - chloroethyl) - 1, 4 - phenylenediamine - N' - sixteen-acyl and its preparation method

The invention discloses a structural formula of a nitrogen mustard derivative N,N-di(2-chloroethyl)-N'-hexadecanoyl-1,4-phenylenediamine, and a preparation method thereof. The preparation method comprises the following steps: preparing N,N-di(2-chloroethyl)-1,4-phenylenediamine; putting the reaction raw materials comprising the N,N-di(2-chloroethyl)-1,4-phenylenediamine, dichloromethane and triethylamine into a reactor, cooling in ice-water bath, stirring, dropwise adding a mixed solution of hexadecanoyl chloride and dichloromethane into the reactor, removing the ice-water bath after addition, conducting reaction at room temperature for 12 to 14 hours, sequentially performing washing, drying and normal-pressure distillation on the reaction liquid after the reaction is conducted completely, and purifying the distilled filter cake to obtain the product. The arylamine nitrogen mustard derivative provided by the invention can effectively reduce the toxic and side effects of nitrogen mustard on the premise of enhancing the treatment index of the nitrogen mustard, and has sterilization and inflammation-diminishing curative effects to reduce the risk of complication caused by the fact that the immunity is reduced after a patient is subjected to chemical therapy.

Nitrogen mustard compounds containing hydroxamic acid groups as well as preparation method and application of nitrogen mustard compounds

The invention discloses nitrogen mustard compounds containing hydroxamic acid groups as well as a preparation method and an application of the nitrogen mustard compounds and relates to the field of medicinal chemistry. The compounds have the capability of inhibiting cancer cell proliferation, achieve the purpose of treating cancer and particularly have excellent cancer cell proliferation inhibition activity for inhibiting human cutaneous melanoma A375, human cervical carcinoma cells HeLa, human liver cancer cells HepG2, human lung cancer cells A549 and human colon cancer cells HCT116. The compounds have the structure shown in a general formula I, wherein X1, X2, X3, X4 and Z are defined in the specification.