6085-59-2

Basic information

• Product Name: 2-Chloro-N,N-dimethyl-1,4-benzenediamine
• Synonyms: 2-Chloro-N,N-dimethyl-1,4-benzenediamine;(4-amino-2-chlorophenyl)dimethylamine(SALTDATA: 2HCl);2-Chloro-N1,N1-diMethylbenzene-1,4-diaMine
• CAS NO: 6085-59-2
• Molecular Formula: C₈H₁₁ClN₂
• Molecular Weight: 170.64
• Mol File: 6085-59-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 272.1°Cat760mmHg
• Flash Point: 118.3°C
• Appearance: /
• Density: 1.204g/cm³
• Vapor Pressure: 0.00621mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Chloro-N,N-dimethyl-1,4-benzenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-N,N-dimethyl-1,4-benzenediamine(6085-59-2)
• EPA Substance Registry System: 2-Chloro-N,N-dimethyl-1,4-benzenediamine(6085-59-2)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 6085-59-2(Hazardous Substances Data)

Usage

General Description

2-Chloro-N,N-dimethyl-1,4-benzenediamine is an organic compound with the chemical formula C8H12ClN2. It is a derivative of 1,4-benzenediamine (also known as para-phenylenediamine) and is a white to light brown crystalline solid. This chemical is mainly used in the production of dyes and pigments, particularly in the manufacture of hair dyes and colorants. It is also a commonly used intermediate in organic synthesis. 2-Chloro-N,N-dimethyl-1,4-benzenediamine has potential health hazards and should be handled with caution, as it is toxic if swallowed and can cause skin and eye irritation upon contact.

InChI:InChI=1/C8H11ClN2/c1-11(2)8-4-3-6(10)5-7(8)9/h3-5H,10H2,1-2H3

Upstream product

• 7463-28-7 N'-acetyl-N,N-dimethyl-1,4-phenylenediamine 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 350-30-1 3-chloro-4-fluoronitrobenzene 
• 103323-68-8 acetic acid-(3-chloro-4-dimethylamino-anilide) 
• 6213-19-0 3-chloro-4-(dimethylamino)nitrobenzene 

Downstream Products

• 59192-06-2 trans-3-Chlor-4-dimethylamino-azobenzol 
• 57240-08-1 N-[(4'-dimethylamino-3'-chloro)phenyl]-2,6-dimethylbenzoquinoneimine 
• 23742-50-9 Cyclopropanecarboxylic acid (3-chloro-4-dimethylamino-phenyl)-amide 
• 48125-16-2 3-chloro-4-dimethylamino-benzenediazonium; chloride 

Relevant articles and documents

1-Benzyl-3-aryl-2-thiohydantoin Derivatives as New Anti-Trypanosoma brucei Agents: SAR and in Vivo Efficacy

A high throughput screening and subsequent hit validation identified compound 1 as an inhibitor of Trypanosoma brucei parasite growth. Extensive structure-activity relationship optimization based on antiparasitic activity led to the highly potent compounds, 1-(4-fluorobenzyl)-3-(4-dimethylamino-3-chlorophenyl)-2-thiohydantoin (68) and 1-(2-chloro-4-fluorobenzyl)-3-(4-dimethylamino-3-methoxyphenyl)-2-thiohydantoin (76), with a T. brucei EC50 of 3 and 2 nM, respectively. This represents >100-fold improvement in potency compared to compound 1. In vivo efficacy experiments of 68 and 76 in an acute mouse model of Human African Trypanosomiasis showed a 100% cure rate after 4 days of oral treatment at 50 mg/kg twice per day.

Synthesis of [18F] 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (IDO5L): A novel potential PET probe for imaging of IDO1 expression

To synthesize 18F-labeled positron emission tomography (PET) ligands, reliable labeling techniques inserting 18F into a target molecule are necessary. The 18F-fluorobenzene moiety has been widely utilized in the synthesis of 18F-labeled compounds. The present study utilized [18F]-labeled aniline as intermediate in [18F]-radiolabeling chemistry for the facile radiosynthesis of 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide ([18F]IDO5L) as indoleamine 2,3-dioxygenase 1 (IDO1) targeted tracer. IDO5L is a highly potent inhibitor of IDO1 with low nanomolar IC50. [18F]IDO5L was synthesized via coupling [18F]3-chloro-4-fluoroaniline with carboximidamidoyl chloride as a potential PET probe for imaging IDO1 expression. Under the optimized labeling conditions, chemically and radiochemically pure (>98%) [18F]IDO5L was obtained with specific radioactivity ranging from 11 to 15GBq/μmol at the end of synthesis within ～90min, and the decay-corrected radiochemical yield was 18.2±2.1% (n=4).

2-Anilino-4-(thiazol-5-yl)pyrimidine CDK Inhibitors: Synthesis, SAR Analysis, X-ray Crystallography, and Biological Activity

Following the identification through virtual screening of 4-(2,4-dimethyl-thiazol-5-yl)pyrimidin-2-ylamines as moderately potent inhibitors of cyclin-dependent kinase-2 (CDK2), a CDK inhibitor analogue program was initiated. The first aims were to optimize potency and to evaluate the cellular mode of action of lead candidate molecules. Here the synthetic chemistry, the structure-guided design approach, and the structure-activity relationships (SARs) that led to the discovery of 2-anilino-4-(thiazol-5-yl)pyrimidine ATP-antagonistic CDK2 inhibitors, many with very low nM Kis against CDK2, are reported. Furthermore, X-ray crystal structures of four representative analogues from our chemical series in complex with CDK2 are presented, and these structures are used to rationalize the observed biochemical SARs. Finally results are reported that show, using the most potent CDK2 inhibitor compound from the current series, that the observed antiproliferative and proapoptotic effects are consistent with cellular CDK2 and CDK9 inhibition.