6213-19-0

Basic information

• Product Name: 2-CHLORO-N,N-DIMETHYL-4-NITROANILINE
• Synonyms: TIMTEC-BB SBB007974;2-chloro-n,n-dimethyl-4-nitro-benzenamin;Benzenamine, 2-chloro-N,N-dimethyl-4-nitro-;2-Chloro-N,N-dimethyl-4-nitrobenzenamine;3-Chloro-4-dimethylaminonitrobenzene;Einecs 228-280-1;N,N-Dimethyl-4-nitro-2-chloroaniline;4-nitro-2-chloro-N,N-diMethylaniline
• CAS NO: 6213-19-0
• Molecular Formula: C₈H₉ClN₂O₂
• Molecular Weight: 200.62
• EINECS: 228-280-1
• Mol File: 6213-19-0.mol

Chemical Properties

• Melting Point: 78 °C(Solv: ethanol (64-17-5))
• Boiling Point: 297.6 °C at 760 mmHg
• Flash Point: 133.8 °C
• Appearance: /Solid
• Density: 1.326 g/cm³
• Vapor Pressure: 0.00134mmHg at 25°C
• Refractive Index: 1.603
• PKA: 0.02±0.30(Predicted)
• CAS DataBase Reference: 2-CHLORO-N,N-DIMETHYL-4-NITROANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N,N-DIMETHYL-4-NITROANILINE(6213-19-0)
• EPA Substance Registry System: 2-CHLORO-N,N-DIMETHYL-4-NITROANILINE(6213-19-0)

Safety Data

• TSCA: Yes
• HazardClass: 6.1
• Hazardous Substances Data: 6213-19-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
2-Chloro-N,N-dimethyl-4-nitroaniline is used as a chemical intermediate for the production of dyes and pigments, contributing to the coloration and enhancement of various products in this sector. Its role in the synthesis process is crucial for developing a range of colorants used across different applications.
Used in Environmental Safety Measures:
Given its hazardous nature, 2-Chloro-N,N-dimethyl-4-nitroaniline is also involved in the development and implementation of safety protocols to prevent environmental contamination and health risks associated with its use. This includes the establishment of guidelines for its safe production, handling, and disposal, ensuring minimal impact on ecosystems and human health.

InChI:InChI=1/C8H9ClN2O2/c1-10(2)8-4-3-6(11(12)13)5-7(8)9/h3-5H,1-2H3

Upstream product

• 99-54-7 3,4-dichloronitrobenzene 
• 124-40-3 dimethyl amine 
• 77-78-1 dimethyl sulfate 
• 121-87-9 2-Chloro-4-nitroaniline 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 
• 333-27-7 methyl trifluoromethanesulfonate 
• 698-01-1 1-chloro-2-(dimethylamino)benzene 
• 7697-37-2 nitric acid 
• 350-30-1 3-chloro-4-fluoronitrobenzene 
• 506-59-2 N,N-dimethylammonium chloride 
• 74-88-4 methyl iodide 
• 533-17-5 N-(2-chlorophenyl)acetamide 
• 95-51-2 o-chloroaniline 

Downstream Products

• 906565-46-6 3-chloro-4-[¹⁸F]fluoroaniline 
• 7597-02-6 sulfanilic acid-(3-chloro-4-dimethylamino-anilide) 
• 6085-59-2 2-Chloro-N(1),N(1)-dimethyl-benzene-1,4-diamine 

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.

Fluorine-18 labeling of 6,7-disubstituted anilinoquinazoline derivatives for positron emission tomography (PET) imaging of tyrosine kinase receptors: Synthesis of18F-Iressa and related molecular probes

Inhibitors of tyrosine kinase enzymatic activity represent a promising new class of antineoplastic agents. Although clinical studies performed over the last decade give more insight on the potential therapeutic applications of such drugs, identification of the individual patients who might benefit from them remains a major challenge. We have developed a synthetic strategy for the production of a wide variety of radiolabeled 6,7-disubstituted 4-anilinoquinazolines suitable for noninvasive imaging of tyrosine kinase receptors to predict therapy effectiveness. Three new F-18 labeled radiopharmaceuticals based on the therapeutic agents Tarceva, Iressa, and ZD6474 were synthesized. Decay-corrected yields varied between 25 and 40% for a total synthesis time of 120 min, thus providing F-18 labeled tyrosine kinase inhibitors in quantities and times practical for use as PET radiopharmaceuticals. Copyright

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.

THE REACTION OF ACTIVATED ARYL AND HETEROARYL DIHALIDES WITH HMPA. A REGIOSELECTIVITY STUDY

A series of activated aryl and heteroaryl dihalides were reacted with HMPA at elevated temperatures.Of the eleven examples studied, all but one reacted in a regioselective manner to give a monohalo-N,N-dimethylamino derivative.

9-(P-phenylazoanilino)-7-methyl-1H-imidazo[4,5-f]quinolines

A series of 9-(substituted amino)imidazo[4,5-f]quinolines are effective anthelmintic agents; particularly in respect to the tapeworm Hymenolepis nana.