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
• Article Data: 9

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

General Description

2-Chloro-N,N-dimethyl-4-nitroaniline, also known as 2,6-Dimethyl-4-chloro-1-nitroaniline or DCNA, is a chemical compound with the molecular formula C8H10ClN3O2. It is a yellow crystalline solid that is commonly used as an intermediate in the production of dyes and pigments. 2-Chloro-N,N-dimethyl-4-nitroaniline is considered to be a hazardous chemical and can be toxic if ingested, inhaled, or absorbed through the skin. Its production, handling, and disposal require careful safety measures to avoid environmental contamination and health risks.

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

Upstream product

• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 121-87-9 2-Chloro-4-nitroaniline 
• 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 
• 124-40-3 dimethyl amine 
• 533-17-5 N-(2-chlorophenyl)acetamide 
• 64-18-6 formic acid 
• 74-88-4 methyl iodide 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 
• 99-54-7 3,4-dichloronitrobenzene 
• 77-78-1 dimethyl sulfate 

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.

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).

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