182277-06-1

Basic information

• Product Name: 4-Hydroxy-5-methoxy-2-nitro-benzoyl chloride
• Synonyms: 4-Hydroxy-5-methoxy-2-nitro-benzoyl chloride
• CAS NO: 182277-06-1
• Molecular Weight: 231.592
• Mol File: 182277-06-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-Hydroxy-5-methoxy-2-nitro-benzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-5-methoxy-2-nitro-benzoyl chloride(182277-06-1)
• EPA Substance Registry System: 4-Hydroxy-5-methoxy-2-nitro-benzoyl chloride(182277-06-1)

Safety Data

• Hazardous Substances Data: 182277-06-1(Hazardous Substances Data)

Upstream product

• 60547-92-4 4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid 
• 140647-01-4 4-hydroxy-5-methoxy-2-nitrobenzoic acid 

Downstream Products

• 1263193-93-6 (S)-(2-(bis(ethylthio)methyl)piperidin-1-yl)(4-hydroxy-5-methoxy-2-nitrophenyl)methanone 
• 140647-03-6 (2S)-N-(2-amino-4-hydroxy-5-methoxybenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 175409-49-1 methyl-(2S)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxylate 
• 176387-49-8 (S)-1-(4-Hydroxy-5-methoxy-2-nitro-thiobenzoyl)-pyrrolidine-2-carbothioaldehyde 
• 123355-42-0 8-Hydroxy-7-methoxy-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one 
• 182277-11-8 (S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 166451-19-0 (S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carbaldehyde 
• 175409-51-5 (S)-1-(4-Hydroxy-5-methoxy-2-nitro-benzoyl)-pyrrolidine-2-carbaldehyde 
• 81307-24-6 (11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one 
• 176387-47-6 (S)-1-(4-Hydroxy-5-methoxy-2-nitro-benzoyl)-pyrrolidine-2-carboxylic acid 
• 140647-02-5 (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal 

Relevant articles and documents

Asymmetric syntheses of piperidino-benzodiazepines through 'cation-pool' host/guest supramolecular approach and their DNA-binding studies

The asymmetric synthetic approach to piperidino-benzodiazepine 4a (a homolog of DC-81) has been developed. The absolute stereochemistry of 4 and 5 has been assigned to be (S) at C-12a position. This procedure features the use of a 'cation-pool' strategy and also a host/guest supramolecular co-catalysis approach. In this study, the chloroformate of 8-phenylmenthyl has been employed as a chiral auxiliary and includes one-pot conditions for anodic oxidation, which are followed by nucleophilic addition to an N-acyliminium ion. In addition, intramolecular azido reductive-cyclization and nitro reductive dithioacetal deprotective tandem-cyclization approaches have also been utilized for the syntheses of these compounds 4a,b and 5a,b. Some of the representative compounds exhibited an enhanced DNA-binding ability in comparison to the natural product DC-81.

An efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via reductive cyclization

A new and convenient one-pot synthesis of pyrrolo[2,1-c][1,4]benzodiazepine (PBD) ring system has been achieved by a reductive cyclization employing N,N-dimethylhydrazine and FeCl3.6H2O in good yields.

A new route for the synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via oxidation of cycle secondary amine

The synthesis of the imine-containing pyrrolo[2,1-c][1,4]benzodiazepine DNA-binding antitumour antibiotics was achieved by a new method of oxidation of cyclic secondary amines which does not endanger the stereochemical integrity of the C-11a position.