54745-92-5

Basic information

• Product Name: 2-QUINOXALINECARBONYL CHLORIDE
• Synonyms: 2-QUINOXALOYL CHLORIDE;2-QUINOXALINECARBONYL CHLORIDE;TIMTEC-BB SBB000309;quinoxaline-2-carbonyl chloride;2-Quinoxalinecarbonyl chloride (7CI, 9CI);2-Quinoxaloyl chloride,97+%;2-(Chlorocarbonyl)quinoxaline, 1,4-Benzodiazine-2-carbonyl chloride;2-Quinoxoyl chloride
• CAS NO: 54745-92-5
• Molecular Formula: C₉H₅ClN₂O
• Molecular Weight: 192.6
• EINECS: 259-315-9
• Product Categories: ACIDHALIDE
• Mol File: 54745-92-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 113-115 °C(lit.)
• Boiling Point: 324.4 °C at 760 mmHg
• Flash Point: 150 °C
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.411 g/cm³
• Vapor Pressure: 0.000246mmHg at 25°C
• Refractive Index: 1.662
• Storage Temp.: Store below 4
• CAS DataBase Reference: 2-QUINOXALINECARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-QUINOXALINECARBONYL CHLORIDE(54745-92-5)
• EPA Substance Registry System: 2-QUINOXALINECARBONYL CHLORIDE(54745-92-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 54745-92-5(Hazardous Substances Data)

Usage

Description

2-Quinoxaloyl chloride is an off-white to tan crystalline powder that is a reactant involved in the synthesis of a variety of inhibitors and ligands. It reacts with chiral α-hydroxy carboxylic acids to yield UV and fluorescent derivatives, making it a versatile compound in the field of chemical research and pharmaceutical development.

Uses

Used in Pharmaceutical Industry:
2-Quinoxaloyl chloride is used as a reactant for the synthesis of various inhibitors, including:
1. Gelatinase inhibitors for cancer treatments: These inhibitors play a crucial role in controlling the activity of enzymes that contribute to tumor invasion and metastasis.
2. mGluR5 non-competitive antagonists: These antagonists are involved in the modulation of glutamate receptors, which can have potential applications in treating neurological disorders.
3. Hetercyclic analogs used as SIRT1 activators: SIRT1 activators are known to have potential benefits in the treatment of age-related diseases and promoting cellular health.
4. 3rd Generation multidrug resistance modulators: These modulators help in overcoming resistance to certain drugs, enhancing the effectiveness of chemotherapy in cancer treatment.
Used in Medical Imaging:
2-Quinoxaloyl chloride is used as a reactant in the preparation of PET ligands for breast cancer resistance protein imaging. This application aids in the detection and monitoring of breast cancer progression, allowing for more accurate diagnosis and treatment planning.

InChI:InChI=1/C9H5ClN2O/c10-9(13)8-5-11-6-3-1-2-4-7(6)12-8/h1-5H

Upstream product

• 879-65-2 quinoxaline-2-carboxylic acid 
• 4711-06-2 (1R,2S,3R)-1-(quinoxalin-2-yl)butane-1,2,3,4-tetraol 

Downstream Products

• 7065-23-8 ethyl quinoxaline-2-carboxylate 
• 54571-06-1 quinoxaline-2-carbohydrazide 
• 78186-11-5 2,MeAla⁶>-Des-N-tetramethyltriostin A 
• 112369-27-4 Quinoxaline-2-carboxylic acid phenethyl-amide 
• 7066-32-2 N-benzylquinoxaline-2-carboxamide 
• 611210-62-9 1,4-bis[2-(2-quinoxaloyloxy)ethyl 4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-α-D-arabino-hexopyranosid-3-ylmethyl]benzene 
• 212790-56-2 Quinoxaline-2-carboxylic acid {(S)-1-[(2S,4R)-4-(3-fluoro-3-methyl-butyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-amide 
• 624736-64-7 trifluoro-acetic acid 3-(5-{2-(3-fluoro-phenyl)-1-[(quinoxaline-2-carbonyl)-amino]-ethyl}-2-oxo-tetrahydrofuran-3-yl)-1,1-dimethyl-propyl ester 

Relevant articles and documents

Design and Discovery of Novel Antifungal Quinoline Derivatives with Acylhydrazide as a Promising Pharmacophore

Inspired by natural 2-quinolinecarboxylic acid derivatives, a series of quinoline compounds containing acylhydrazine, acylhydrazone, sulfonylhydrazine, oxadiazole, thiadiazole, or triazole moieties were synthesized and evaluated for their fungicidal activity. Most of these compounds exhibited excellent fungicidal activity in vitro. Significantly, compound 2e displayed the superior in vitro antifungal activity against Sclerotinia sclerotiorum, Rhizoctonia solani, Botrytis cinerea, and Fusarium graminearum with the EC50 values of 0.39, 0.46, 0.19, and 0.18 μg/mL, respectively, and were more potent than those of carbendazim (EC50, 0.68, 0.14, >100, and 0.65 μg/mL, respectively). Moreover, compound 2e could inhibit spore germination of F. graminearum. Preliminary mechanistic studies showed that compound 2e could cause abnormal morphology of cell walls and vacuoles, loss of mitochondrion, increases in membrane permeability, and release of cellular contents. These results indicate that compound 2e displayed superior fungicidal activities and could be a potential fungicidal candidate against plant fungal diseases.

Chemical modifications on 4-arylpiperazine-ethyl carboxamide derivatives differentially modulate affinity for 5-HT1A, D4.2, and α2A receptors: Synthesis and in vitro radioligand binding studies

A series of substituted 4-aryl-piperazine-ethyl heteroarylcarboxamides were prepared and tested in in vitro radioligand binding studies. The presence of a quinoxaline has a favourable impact in terms of serotonin 5-HT1A versus dopamine D4.2 receptor selectivity. Compounds with a 3-CF3 group at the distal phenyl ring are the most effective in terms of affinity and selectivity for 5-HT1A versus D4.2 receptors. A 4-phenyl-1,2,3,6- tetrahydropyridine in place of the corresponding 4-phenyl-piperazine side chain is also favourable not only for the affinity for 5-HT1A and D4.2 receptors but also in some cases for α2A-adrenoceptors.

Discovery of a potent class I selective ketone histone deacetylase inhibitor with antitumor activity in vivo and optimized pharmacokinetic properties

The optimization of a potent, class I selective ketone HDAC inhibitor is shown. It possesses optimized pharmacokinetic properties in preclinical species, has a clean off-target profile, and is negative in a microbial mutagenicity (Ames) test. In a mouse xenograft model it shows efficacy comparable to that of vorinostat at a 10-fold reduced dose.