21900-23-2

Basic information

• Product Name: 3,4-DIMETHYLBENZENE-1-CARBONYL CHLORIDE
• Synonyms: 3,4-DIMETHYL-BENZOYL CHLORIDE;3,4-DIMETHYLBENZENE-1-CARBONYL CHLORIDE;Benzoyl chloride, 3,4-dimethyl- (6CI,7CI,8CI,9CI);3,4-Dimethylbenzoyl chloride 95%;4-(Chlorocarbonyl)-o-xylene, 4-(Chloroformyl)-o-xylene
• CAS NO: 21900-23-2
• Molecular Formula: C₉H₉ClO
• Molecular Weight: 168.62
• Product Categories: ACIDHALIDE
• Mol File: 21900-23-2.mol

Chemical Properties

• Boiling Point: 126 °C
• Flash Point: 112.4 °C
• Appearance: /
• Density: 1.136g/cm³
• Vapor Pressure: 0.0145mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: Store under Nitrogen
• CAS DataBase Reference: 3,4-DIMETHYLBENZENE-1-CARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHYLBENZENE-1-CARBONYL CHLORIDE(21900-23-2)
• EPA Substance Registry System: 3,4-DIMETHYLBENZENE-1-CARBONYL CHLORIDE(21900-23-2)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36
• Safety Statements: 26-36/37/39
• RIDADR: 3265
• Hazardous Substances Data: 21900-23-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-DIMETHYLBENZENE-1-CARBONYL CHLORIDE is used as a key reactant for the synthesis of various vinblastine 20'' amides. These compounds have been studied for their activity against P-glycoprotein (Pgp) overexpressing resistant cancer cell lines. Pgp is a protein that acts as a drug efflux pump, often leading to multidrug resistance in cancer cells. By targeting Pgp overexpressing cells, 3,4-DIMETHYLBENZENE-1-CARBONYL CHLORIDE contributes to the development of more effective cancer treatments.

InChI:InChI=1/C9H9ClO/c1-6-3-4-8(9(10)11)5-7(6)2/h3-5H,1-2H3

Upstream product

• 79-37-8 oxalyl dichloride 
• 95-47-6 o-xylene 
• 583-71-1 4-bromo-o-xylene 
• 95-64-7 4-amino-o-xylene 
• 619-04-5 3,4-dimethylbenzoic acid 
• 95-65-8 3,4-Dimethylphenol 
• 141-75-3 butyryl chloride 
• 255837-23-1 3,4-dimethylphenyl trifluoromethanesulfonate 

Downstream Products

• 17283-16-8 3,4-dimethylphenylacetic acid 
• 93151-43-0 3,4-dimethyl-benzoic acid-(2-diethylamino-ethylamide) 
• 164290-86-2 N-phenyl-3,4-dimethylbenzamide 
• 120-34-3 N-(4-aminophenylsulfonyl)-3,4-dimethylbenzamide 
• 860564-67-6 2,4,5,3',4'-pentamethyl-benzophenone 
• 3637-01-2 3,4-dimethylacetophenone 
• 5973-71-7 3,4-dimethylbenzaldehyde 
• 105337-17-5 (3,4-dimethyl-phenyl)-acetic acid ethyl ester 
• 57228-33-8 O,N-Di-(3,4-dimethylbenzoyl)-L-tyrosin 
• 37134-44-4 3,4-dimethyl-benzoic acid (2S,3S)-2,3-dihydroxy-3-((1S)-6-hydroxy-5-methylene-8,10-dioxo-2-oxa-7,9-diaza-bicyclo[4.2.2]dec-1-yl)-2-methyl-propyl ester 
• 4659-48-7 3,3',4,4'-tetramethylbenzophenone 
• 34824-37-8 9-(3,4-Dimethyl-benzoyl)-1,2,3,4,5,6,7,8-octahydro-phenanthren 
• 47777-03-7 C₃₀H₃₃NO₅ 
• 68429-41-4 3,4-Dimethyl-benzoic acid 2-(2,4-dimethyl-phenyl)-5,5-dimethyl-3-oxo-cyclohex-1-enyl ester 

Relevant articles and documents

ESTER COMPOUND

This ester compound is represented by formula (1) [wherein R1 to R24 are each independently a hydrogen atom, a halogen atom, a hydrocarbon group, or a heteroatom-containing hydrocarbon group; R1 to R10, R23, and R24 may be bonded to each other to form a ring, and adjacent substituents may be directly bonded to form a multiple bond; R11 to R24 may be bonded to each other to form a ring, and adjacent substituents may be bonded to each other to form a multiple bond; at least two, as a pair, of R1 to R24 are bonded to each other to form a ring structure; n2 to n5 each independently indicate an integer of 0-2; n1 and n6 each independently indicate 0 or 1; and L1 and L2 are each independently a hydrocarbon group or a heteroatom-containing hydrocarbon group].

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

Optimization of a 1,3,4-oxadiazole series for inhibition of Ca2+/calmodulin-stimulated activity of adenylyl cyclases 1 and 8 for the treatment of chronic pain

Adenylyl cyclases type 1 (AC1) and 8 (AC8) are group 1 transmembrane adenylyl cyclases (AC) that are stimulated by Ca2+/calmodulin. Studies have shown that mice depleted of AC1 have attenuated inflammatory pain response, while AC1/AC8 double-knockout mice display both attenuated pain response and opioid dependence. Thus, AC1 has emerged as a promising new target for treating chronic pain and opioid abuse. We discovered that the 1,3,4-oxadiazole scaffold inhibits Ca2+/calmodulin-stimulated cyclic adenosine 3‘,5‘-monophosphate (cAMP) production in cells stably expressing either AC1 or AC8. We then carried out structure-activity relationship studies, in which we designed and synthesized 65 analogs, to modulate potency and selectivity versus each AC isoform in cells. Furthermore, molecular docking of the analogs into an AC1 homology model suggests the molecules may bind at the ATP binding site. Finally, a prioritized analog was tested in a mouse model of inflammatory pain and exhibited modest analgesic properties. In summary, our data indicate the 1,3,4-oxadiazoles represent a novel scaffold for the cellular inhibition of Ca2+/calmodulin-stimulated AC1- and AC8 cAMP and warrant further exploration as potential lead compounds for the treatment of chronic inflammatory pain.