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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Design, Synthesis, and Biological Activity of New N -(Phenylmethyl)-benzoxazol-2-thiones as Macrophage Migration Inhibitory Factor (MIF) Antagonists: Efficacies in Experimental Pulmonary Hypertension

Macrophage migration inhibitory factor (MIF) is a key pleiotropic mediator and a promising therapeutic target in cancer as well as in several inflammatory and cardiovascular diseases including pulmonary arterial hypertension (PAH). Here, a novel series of N-(phenylmethyl)-benzoxazol-2-thiones 5-32 designed to target the MIF tautomerase active site was synthesized and evaluated for its effects on cell survival. Investigation of structure-activity relationship (SAR) particularly at the 5-position of the benzoxazole core led to the identification of 31 that potently inhibits cell survival in DU-145 prostate cancer cells and pulmonary endothelial cells derived from patients with idiopathic PAH (iPAH-ECs), two cell lines for which survival is MIF-dependent. Molecular docking studies helped to interpret initial SAR related to MIF tautomerase inhibition and propose preferred binding mode for 31 within the MIF tautomerase active site. Interestingly, daily treatment with 31 started 2 weeks after a subcutaneous monocrotaline injection regressed established pulmonary hypertension in rats.

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.