56532-65-1

Basic information

• Product Name: Benzene, 1-chloro-2-[(4-nitrophenoxy)methyl]-
• Synonyms: 2-chlorobenzyl 4-nitrophenyl ether
• CAS NO: 56532-65-1
• Molecular Formula: C13H10ClNO3
• Molecular Weight: 263.68
• Mol File: 56532-65-1.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1-chloro-2-[(4-nitrophenoxy)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-chloro-2-[(4-nitrophenoxy)methyl]-(56532-65-1)
• EPA Substance Registry System: Benzene, 1-chloro-2-[(4-nitrophenoxy)methyl]-(56532-65-1)

Safety Data

• Hazardous Substances Data: 56532-65-1(Hazardous Substances Data)

Upstream product

• 100-02-7 4-nitro-phenol 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 824-78-2 4-nitrophenol sodium salt 

Downstream Products

• 21116-13-2 4-(2-chlorobenzoxy)phenyl amine 

Relevant articles and documents

1,3-Benzothiazoles as Antimicrobial Agents

Starting from 2-amino-1,3-mercaptobenzothiazoles recently reported (1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h), a series of the corresponding 2-mercapto-1,3-benzothiazole isosters (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h) were screened for their in vitro antibacterial and antifungal activities. Results underline that the presence of the mercapto moiety at the 2-position of the heterocyclic nucleus is crucial for activity against bacteria. The biological screening against Candida spp. identified commercial 2f as the most promising compound as antifungal against Candida albicans and tropicalis. Molecular modeling studies supported these results. Then, to enlarge structure-activity relationship (SAR) studies on series 1, newly synthesized compounds (1k, 1l, 1m, 1n, 1o, 1p) were reported. All the compounds belonging to this series and bearing a bulky substituent at the 6-position of the aryl moiety showed high antifungal activity.

Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions

A catalyst for the intramolecular direct arylation of a broad range of simple and heterocyclic arenes with aryl iodides, bromides, and chlorides has been developed. These reactions occur in excellent yield and are highly selective. Studies with aryl iodides substrates revealed that catalyst poisoning occurs due to the accumulation of iodide in the reaction media. This can be overcome by the addition of silver salts which also permits these reactions to occur at lower temperature. The utility of the methodology is illustrated by a rapid synthesis of a carbazole natural product and by the synthesis of sterically encumbered tetra-ortho-substituted biaryls via ring-opening reactions of the direct arylation products. Mechanistic investigations have provided insight into the catalyst's mode of action and show the presence of a kinetically significant C-H bond cleavage in palladium-catalyzed direct arylation of simple arenes. Knowledge garnered from these studies has led to the development of new intermolecular arylation reactions with previously inaccessible arenes, opening the door for the development of other new direct arylation processes.

High-yielding intramolecular direct arylation reactions with aryl chlorides

(Chemical Equation Presented) An N-heterocyclic carbene palladium catalyst system is used to promote direct arylation of a broad range of aryl chlorides to form six- and five-membered ring biaryls. An influence of the halide on the palladium precatalyst on catalyst activation has been revealed, as has a beneficial effect of NHC salts that allows the turnover numbers to be increased by simple addition of imidazolium salts to the reaction mixture.