2958-87-4

Basic information

• Product Name: 2,3,6-TRICHLOROQUINOXALINE
• Synonyms: 2,3,6-TRICHLOROQUINOXALINE;Quinoxaline, 2,3,6-trichloro.;2,3,6-TRICHLOROQUINOXALINE 98%;2,3,6-Trichloroquinoxaline ,98%;2,3,6-Trichloropyrimidine;NSC 203052;6-chloro-2,3-dichloroquinoxaline
• CAS NO: 2958-87-4
• Molecular Formula: C₈H₃Cl₃N₂
• Molecular Weight: 233.48
• EINECS: 220-987-3
• Mol File: 2958-87-4.mol

Chemical Properties

• Melting Point: 143-148 °C
• Boiling Point: 373.7°C (rough estimate)
• Flash Point: 160°C
• Appearance: /
• Density: 1.600
• Vapor Pressure: 0.00281mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2,3,6-TRICHLOROQUINOXALINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,6-TRICHLOROQUINOXALINE(2958-87-4)
• EPA Substance Registry System: 2,3,6-TRICHLOROQUINOXALINE(2958-87-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25
• Hazardous Substances Data: 2958-87-4(Hazardous Substances Data)

Usage

Chemical Properties

Pink-brown granular powder

InChI:InChI=1/C8H3Cl3N2/c9-4-1-2-5-6(3-4)13-8(11)7(10)12-5/h1-3H

Upstream product

• 552-32-9 o-nitroacetanilide 
• 68-12-2 N,N-dimethyl-formamide 
• 6639-79-8 6-chloroquinoxaline-2,3(1H,4H)-dione 
• 5448-43-1 6-chloroquinoxaline 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 6639-79-8 2,3-dihydroxy-6-chloroquinoxaline 
• 89-63-4 4-Chloro-2-nitroaniline 

Downstream Products

• 35251-86-6 (7-chloro-3-m-tolyl-3H-thiazolo[4,5-b]quinoxalin-2-ylidene)-m-tolyl-amine 
• 35252-25-6 (7-chloro-3-o-tolyl-3H-thiazolo[4,5-b]quinoxalin-2-ylidene)-o-tolyl-amine 
• 35251-89-9 [7-chloro-3-(3-chloro-phenyl)-3H-thiazolo[4,5-b]quinoxalin-2-ylidene]-(3-chloro-phenyl)-amine 
• 35242-76-3 (7-chloro-3-phenyl-3H-thiazolo[4,5-b]quinoxalin-2-ylidene)-phenyl-amine 
• 31102-90-6 7-chloro-3-(2-methoxy-phenyl)-3H-thiazolo[4,5-b]quinoxalin-2-ylideneamine 
• 31102-77-9 (7-chloro-thiazolo[4,5-b]quinoxalin-2-yl)-(2-methoxy-phenyl)-amine 
• 35251-88-8 [7-chloro-3-(4-chloro-phenyl)-3H-thiazolo[4,5-b]quinoxalin-2-ylidene]-(4-chloro-phenyl)-amine 
• 31200-24-5 7-chloro-3-phenyl-3H-thiazolo[4,5-b]quinoxalin-2-ylideneamine 
• 31200-20-1 (7-chloro-thiazolo[4,5-b]quinoxalin-2-yl)-phenyl-amine 
• 31102-89-3 7-chloro-3-(4-chloro-phenyl)-3H-thiazolo[4,5-b]quinoxalin-2-ylideneamine 
• 31102-76-8 (4-chloro-phenyl)-(7-chloro-thiazolo[4,5-b]quinoxalin-2-yl)-amine 
• 55686-96-9 2,6-Dichloro-3-phenylsulfanyl-quinoxaline 
• 91895-34-0 2,6-dichloro-3-hydrazinoquinoxaline 
• 61611-37-8 9-chloroditetrazolo[1,5-a:5',1'-c]quinoxaline 

Relevant articles and documents

Novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and preparation and application thereof

The invention provides a novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and a preparation method and application thereof, and belongs to the field of chemical medicines. The derivative is a compound as shown in a formula I, or a salt thereof, or a stereoisomer thereof. The compound is low in toxicity or basically non-toxic to normal cells, has an obvious inhibition effect to tumor cell lines, particularly has good lipid toxicity selectivity to tumor cells such as liver cancer, lung cancer and the like in vivo, and has an obvious inhibition effect; meanwhile, the compound can effectively activate SREBP1 and PPAR gamma, inhibit lipid transport MTTP, cause lipid aggregation in tumor cells and cause lipid toxicity of the tumor cells. The compound can be used for treating liver cancer, lung cancer and the like in a molecular targeting manner, is low in toxicity or even non-toxic, and has a good application prospect.

A One-pot Facile Synthesis of 2,3-Dihydroxyquinoxaline and 2,3-Dichloroquinoxaline Derivatives Using Silica Gel as an Efficient Catalyst

An efficient one-pot reaction has been developed for the synthesis of 2,3-dichloroquinoxaline derivatives 3a–n. The reaction was performed in two steps via a silica gel catalyzed tandem process from o-phenylenediamine and oxalic acid, followed by addition of phosphorus oxychloride (POCl3). A variety of 2,3-dichloroquinoxalines have been obtained in good to excellent overall yields. Eight known compounds 3a–3h were characterized by IR, 1H-NMR, and mass spectroscopies. Compounds 3i–3n without spectroscopic data were characterized by IR, 1H-NMR, 13C-NMR, and mass spectroscopies.

Method for preparing 2,3-dichloro-quinoxaline derivative through one-pot procedure

The invention belongs to the field of drug synthesis, and specifically relates to a new method for preparing 2,3-dichloro-quinoxaline derivative through one-pot procedure. According to the method, cheap o-phenylenediamine and oxalic acid are adopted as raw materials, and the cheap and easily available and environmentally friendly silica gel or methanesulfonic acid is adopted as a catalyst while steps of intermediate separation and purification are omitted; the method has the advantages of easiness in operation, low cost, mild reaction conditions and environmental friendliness and promotes industrial mass production.

A new small molecule inhibitor of soluble guanylate cyclase

Soluble guanylate cyclase (sGC) is a haem containing enzyme that regulates cardiovascular homeostasis and multiple mechanisms in the central and peripheral nervous system. Commonly used inhibitors of sGC activity act through oxidation of the haem moiety, however they also bind haemoglobin and this limits their bioavailability for in vivo studies. We have discovered a new class of small molecule inhibitors of sGC and have characterised a compound designated D12 (compound 10) which binds to the catalytic domain of the enzyme with a KD of 11 μM in a SPR assay.

HETEROCYCLIC INHIBITORS OF HISTAMINE RECEPTORS FOR THE TREATMENT OF DISEASE

The present invention relates to compounds and methods which may be useful as inhibitors of H1R and/or H4R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.

HETEROCYCLIC INHIBITORS OF HISTAMINE RECEPTORS FOR THE TREATMENT OF DISEASE

The present invention relates to compounds and methods which may be useful as inhibitors of H1R and/or H4R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.

Synthesis of 2,3-dichloroquinoxalines via vilsmeier reagent chlorination

A convenient and high-yielding synthesis of 2,3-dichloroquinoxalines from the corresponding 2,3- dihydroxyquinoxalines has been developed. Treatment of a slurry of the 2,3-dihydroxyquinoxaline 1a-j with N,N-dimethylformamide in the presence of excess thionylchloride in 1,2-dichloroethane results in the rapid and high-yielding formation of the 2,3-dichloroquinoxaline derivatives 2a-j. Simplified workup and purification procedures for these compounds are also described.

Fragment based design of new H4 receptor-ligands with anti-inflammatory properties in vivo

Using a previously reported flexible alignment model we have designed, synthesized, and evaluated a series of compounds at the human histamine H 4 receptor (H4R) from which 2-(4-methyl-piperazin-l-yl)- quinoxaline (3) was identified as a new lead structure for H4R ligands. Exploration of the structure-activity relationship (SAR) of this scaffold led to the identification of 6,7-dichloro 3-(4-methylpiperazin-l-yl) quinoxalin-2(1H)-one (VUF 10214, 57) and 2-benzyl-3-(4-methyl-piperazin-l-yl) quinoxaline (VUF 10148, 20) as potent H4R ligands with nanomolar affinities. In vivo studies in the rat reveal that compound 57 has significant anti-inflammatory properties in the carrageenan-induced paw-edema model.

Quinoxaline compounds

Quinoxaline compounds, compositions, methods of making them, and methods of using them in leukocyte recruitment inhibition, in modulating an H4 receptor, and in treating conditions such as inflammation, H4 receptor-mediated conditions, and related conditions.

Synthesis and Some Reactions of 3-Chloro-2-(cyanomethylene)-1,2-dihydroquinoxalines

2,3-Dichloroquinoxaline and some of its derivatives have been reacted with malononitrile and ethyl cyanoacetate to yield a variety of 3-chloro-2-(cyanomethylene)-1,2-dihydroquinoxaline derivatives. The reaction of 3-chloro-2-(dicyanomethylene)-1,2-dihydroquinoxaline (2e) with pyridine and its methyl derivatives led to the zwitterionic structures 6a-c. The structures of the newly synthesized compounds were assigned by spectroscopic data and elemental analyses.