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

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

Uses

Used in Dye and Pigment Industry:
2-Chloro-N,N-dimethyl-1,4-benzenediamine is used as a key intermediate in the production of dyes and pigments for various applications, including hair dyes and colorants. Its unique chemical structure allows for the creation of a wide range of colors and shades, making it a valuable component in the formulation of these products.
Used in Organic Synthesis:
2-Chloro-N,N-dimethyl-1,4-benzenediamine is also used as a commonly used intermediate in organic synthesis. Its versatile chemical properties enable it to be used in the synthesis of various organic compounds, contributing to the development of new materials and products across different industries.
Health Hazards:

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

Upstream product

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

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.

PET PROBES OF RADIOFLUORINATED CARBOXIMIDAMIDES FOR IDO-TARGETED IMAGING

18F labeled ID01 imaging constructs are constructed for positron emission tomography (PET). Synthetic methodology involves the coupling of a l-fluoro-2-halo-4- aminobenzene and a 4-amino-N-hydroxy-l,2,5-oxadiazole-3-carboximidoyl chloride wherein at least one of the coupled compounds comprises an 18F. The 18F labeled IDO1 imaging constructs are useful for imaging cancer cells in a patient.

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).

USE OF CONDENSED BENZO[B]THIAZINE DERIVATIVES AS CYTOPROTECTANTS

The present invention relates to arylthiazine compounds, metabolites, N-oxides, amides, esters,pharmaceutically acceptable salts, hydrates and solvates thereof and their use as cytoprotectants in the treatment or prophylaxis of diseases or states, either acute or chronic, involving aberrant cellular lipid peroxidation in the central nervous system or in the periphery of the body. The present invention also relates to a method for their preparation and to pharmaceutical composition comprising as an active ingredient one or more of the aforementioned compounds.

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.