29644-82-4

Basic information

• Product Name: 4-chloro-2-{[(E)-phenylmethylidene]amino}phenol
• CAS NO: 29644-82-4
• Molecular Formula: C₁₃H₁₀ClNO
• Molecular Weight: 231.6776
• Mol File: 29644-82-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 418.6°C at 760 mmHg
• Flash Point: 206.9°C
• Density: 1.18g/cm³
• Vapor Pressure: 1.34E-07mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: 4-chloro-2-{[(E)-phenylmethylidene]amino}phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-2-{[(E)-phenylmethylidene]amino}phenol(29644-82-4)
• EPA Substance Registry System: 4-chloro-2-{[(E)-phenylmethylidene]amino}phenol(29644-82-4)

Safety Data

• Hazardous Substances Data: 29644-82-4(Hazardous Substances Data)

Upstream product

• 89-64-5 p-chloro-o-nitrophenol 
• 2835-06-5 phenylglycin 
• 100-52-7 benzaldehyde 
• 95-85-2 2-hydroxy-5-chloro-aniline 

Downstream Products

• 1019-90-5 5-chloro-2-phenyl-1,3-benzoxazole 
• 77434-60-7 (4-Benzyl-6-chloro-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-acetic acid methyl ester 
• 77434-52-7 2-benzylamino-4-chlorophenol 
• 1393931-16-2 diethyl 7-chloro-3-phenyl-3,4-dihydrobenzo[b][1,4]oxazine-dicarboxylate 

Relevant articles and documents

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Oxidative NHC Catalysis for the Generation of Imidoyl Azoliums: Synthesis of Benzoxazoles

N-Heterocyclic carbene (NHC)-catalyzed intramolecular cyclization of aldimines generated from 2-amino phenols and aromatic aldehydes leading to the synthesis of 2-arylbenzoxazoles under mild conditions is presented. The reaction proceeds via the generation of the aza-Breslow intermediates from imines and NHC, which under oxidative conditions form the key imidoyl azoliums and a subsequent intramolecular cyclization furnishes the product. The reaction tolerates a broad range of functional groups, and the products are formed in generally good yields.

Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation

Highly efficient synthesis of benzofused heteroaromatic compounds via aerobic oxidation catalyzed by cyanide anion has been developed. The Schiff bases derived from 2-aminophenol and aldehydes provided the corresponding benzoxazoles in high yields in the presence of a catalytic amount of cyanide in an open flask under ambient conditions without the use of any external metal co-oxidants and bases. Furthermore, we have developed a catalytic sequential one-step protocol for the synthesis of benzoxazoles by adding a catalytic amount of NaCN to Schiff bases generated in situ from 2-aminophenol and aldehydes without the isolation of imine intermediates. This one-pot protocol was further extended to the synthesis of benzothiazoles from 2-aminothiophenol and aldehydes. A variety of aldehydes could be applied to this sequential one-pot protocol and the desired benzofused azole products were obtained in high yields.