20357-37-3

Basic information

• Product Name: 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride
• Synonyms: 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride;1-(4-Chlorobenzoyl)-2-methyl-5-methoxy-1H-indole-3-acetic acid chloride;Einecs 243-763-7;2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetyl chloride
• CAS NO: 20357-37-3
• Molecular Formula: C₁₉H₁₅Cl₂NO₃
• Molecular Weight: 376.2333
• EINECS: 243-763-7
• Mol File: 20357-37-3.mol
• Article Data: 37

Chemical Properties

• Boiling Point: 473.8°Cat760mmHg
• Flash Point: 240.4°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 3.81E-09mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride(20357-37-3)
• EPA Substance Registry System: 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride(20357-37-3)

Safety Data

• Hazardous Substances Data: 20357-37-3(Hazardous Substances Data)

Usage

General Description

1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride is a chemical compound with a complex structure. It contains a 1H-indole ring with a 5-methoxy and 2-methyl substitution, as well as an acetyl chloride and a 4-chlorobenzoyl group attached to the indole ring. 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride is likely used in organic synthesis or pharmaceutical research due to its diverse structure, which may make it a valuable building block for creating other compounds. Additionally, the presence of the acetyl chloride functional group suggests that it may be reactive and used as a reagent in chemical reactions to add an acetyl group to other compounds. Overall, this compound appears to have potential applications in the field of organic chemistry and pharmaceutical development.

InChI:InChI=1/C19H15Cl2NO3/c1-11-15(10-18(21)23)16-9-14(25-2)7-8-17(16)22(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3

Upstream product

• 123-76-2 levulinic acid 
• 13815-71-9 1-ethylidene-2-(4-methoxyphenyl)hydrazine 
• 13815-59-3 Acetaldehyd-N₁-(p-chlorbenzoyl)-p-methoxy-phenylhydrazon 
• 13815-62-8 N¹-(4-Chlorbenzoyl)-N¹-(4-methoxyphenyl)hydrazin-hydrochlorid 
• 122-01-0 4-chloro-benzoyl chloride 
• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 

Downstream Products

• 72155-44-3 [1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2-acetoxy-1-acetoxymethyl-ethyl ester 
• 59925-19-8 2-Indomethacoyl-1,3-didodecanoylglycerin 
• 76812-33-4 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-N,2-dimethyl-1H-indole-3-acetamide 
• 72155-38-5 [1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 3-{2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetoxy}-2-oxo-propyl ester 
• 59925-21-2 Butyric acid 3-butyryloxy-2-{2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetoxy}-propyl ester 
• 59925-20-1 Octanoic acid 2-{2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetoxy}-3-octanoyloxy-propyl ester 
• 72155-42-1 Decanoic acid 2-{2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetoxy}-3-decanoyloxy-propyl ester 
• 72155-40-9 2-Indomethacoyl-1,3-dipalmitoylglycerin 
• 59925-32-5 Icosanoic acid 2-{2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetoxy}-3-icosanoyloxy-propyl ester 
• 72155-35-2 1,2-bis<1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetyl>-3-<<(β,β,β-trichloroethyl)oxy>carbonyl>glyceride 
• 76812-80-1 5-<1-(4-Chlorbenzoyl)-5-methoxy-2-methylindol-3>-<3,3-di(benzyloxycarbonyl)>-laevulinsaeure-benzylester 
• 100921-91-3 (+)-2-<1-(p-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl>acetoxy-2-phenylacetic acid 
• 100921-92-4 (-)-2-<1-(p-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl>acetoxy-2-phenylacetic acid 
• 3326-40-7 N-<1-(4-Chlorbenzoyl)-5-methoxy-2-methylindol-3-acetyl>glycin-benzylester 

Relevant articles and documents

New indomethacin analogs as selective COX-2 inhibitors: Synthesis, COX-1/2 inhibitory activity, anti-inflammatory, ulcerogenicity, histopathological, and docking studies

New indomethacin analogs 4a–g, 5, 6, 8a, and 8b were synthesized to overcome the nonselectivity and ulcer liability of indomethacin. All newly synthesized compounds were more potent against cyclooxygenase 2 (COX-2; IC50 value range: 0.09–0.4 μМ) as?compared with celecoxib (IC50 = 0.89 μМ). Compounds 4a, 4b, 4d, 5, and 6 showed the highest COX-2 selectivity index (SI range = 4.07–6.33) as compared with indomethacin (SI = 1.14) and celecoxib (SI = 3.52). Additionally, 4a, 4b, 4d, 5, and 7 showed good anti-inflammatory activity with edema inhibition (79.36–88.8%), relative to celecoxib (78.96%) and indomethacin (90.43%), after 5 h. Also, ulcerogenic effects and histopathological examination were assessed for the most potent analogs,?4b, 4d, 5, and 6, to determine their safety. The results can shed light on indomethacin analog?5 as a remarkable anti-inflammatory lead compound with a good safety profile (ulcer index = 10.62) close to the nonulcerogenic drug celecoxib (ulcer index = 10.53) and better than indomethacin (ulcer index = 18.50). Docking studies were performed in the COX-2 active site for the most active compounds, to test their selectivity and to confirm their mechanism of action.

Acyloxyamines as prodrugs of anti-inflammatory carboxylic acids for improved delivery through skin

An N,N-dialkylhydroxylamine derivative of indomethacin has been synthesized. It has been shown to improve the delivery of indomethacin through mouse skin (compared to indomethacin itself) by a factor of two, to be more effective than indomethacin in inhibiting thermal inflammation (two to three times) in animal models, but to be only as effective as indomethacin in inhibiting UV-B radiation erythema in human volunteers.

Cobalt-Catalyzed Radical Hydroamination of Alkenes with N-Fluorobenzenesulfonimides

An efficient and general radical hydroamination of alkenes using Co(salen) as catalyst, N-fluorobenzenesulfonimide (NFSI) and its analogues as both nitrogen source and oxidant was successfully disclosed. A variety of alkenes, including aliphatic alkenes, styrenes, α, β-unsaturated esters, amides, acids, as well as enones, were all compatible to provide desired amination products. Mechanistic experiments suggest that the reaction underwent a metal-hydride-mediated hydrogen atom transfer (HAT) with alkene, followed by a pivotal catalyst controlled SN2-like pathway between in situ generated organocobalt(IV) species and nitrogen-based nucleophiles. Moreover, by virtue of modified chiral cobalt(II)-salen catalyst, an unprecedented asymmetric version was also achieved with good to excellent level of enantiocontrol. This novel asymmetric radical C?N bond construction opens a new door for the challenging asymmetric radical hydrofunctionalization.

A Highly Efficient Dimeric Manganese-Catalyzed Selective Hydroarylation of Internal Alkynes

We have developed a general and site-predictable manganese-catalyzed hydroarylation of internal alkynes in the presence of water, under an air atmosphere without the involvement of ligand. The unique catalytic feature of this reaction is highlighted by comparison with other widely used transition metal catalysts including palladium, rhodium, nickel, or copper. The simple operation, high efficiency and excellent functional group compatibility make this protocol practical for more than 90 structurally diverse internal alkynes, overcoming the influence of both electronic and steric effect of alkynes. Its exclusive regio- and chemoselectivity originates from the unique reactivity of the manganese-based catalyst towards an inherent double controlled strategy of sterically hindered propargyl alcohols without the installing of external directing groups. Its synthetic robustness and practicality have been illustrated by the concise synthesis of bervastatin, a hypolipidemic drug, and late-stage modification of complex alkynes with precise regioselectivity.