51145-58-5

Basic information

• Product Name: 4-BENZYLOXYPHENYLHYDRAZINE
• Synonyms: 4-BENZYLOXYPHENYLHYDRAZINE;VITAS-BB TBB000092
• CAS NO: 51145-58-5
• Molecular Formula: C₁₃H₁₄N₂O
• Molecular Weight: 214.26
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;Miscellaneous
• Mol File: 51145-58-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 395.8°C at 760 mmHg
• Flash Point: 193.2°C
• Appearance: /
• Density: 1.185g/cm³
• Vapor Pressure: 1.79E-06mmHg at 25°C
• Refractive Index: 1.649
• CAS DataBase Reference: 4-BENZYLOXYPHENYLHYDRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXYPHENYLHYDRAZINE(51145-58-5)
• EPA Substance Registry System: 4-BENZYLOXYPHENYLHYDRAZINE(51145-58-5)

Safety Data

• Hazardous Substances Data: 51145-58-5(Hazardous Substances Data)

Usage

Uses

(4-Phenylmethoxyphenyl)hydrazine is used as a reactant in the preparation of indolyl thiazole derivatives as xanthine oxidase inhibitors and antiinflammatory drugs.

Manufacturing Process

Preparation of 4-benzyloxyphenylhydrazine: 200 grams 4-benzyloxyaniline hydrochloride was suspended in a mixture of 264 ml concentrated hydrochloric acid, 528 ml water and 732 grams crushed ice. A solution of 62.4 grams sodium nitrite in 136 ml water was added below the surface of the stirred suspension at -10-(+/-)2°C during 10 minutes. After stirring for 1 hour at 0°C, the suspension was treated with acid-washed charcoal and filtered.The filtrate was cooled and maintained at -8°C while a solution of 500 grams of stannous chloride in 760 ml concentrated hydrochloric acid was added with stirring. The mixture was stirred for 2 hours at -8°C and the 4- benzyloxyphenylhydrazine hydrochloride which separated was filtered off and washed with water. The product was crystallized by adding 800 ml hot water to a 3 liter solution in ethanol and had a MP of 185° to 189°C (yield 168.5 grams, 79%).

InChI:InChI=1/C13H14N2O/c14-15-12-6-8-13(9-7-12)16-10-11-4-2-1-3-5-11/h1-9,15H,10,14H2

Upstream product

• 123-30-8 4-amino-phenol 
• 54840-15-2 4-N-tert-butoxycarbonylaminophenol 
• 852668-28-1 (4-benzyloxyphenyl)carbamic acid tert-butyl ester 
• 6373-46-2 p-benzyloxyaniline 
• 51388-20-6 4-benzyloxyaniline hydrochloride 

Downstream Products

• 52602-38-7 6-benzyloxy-1,2,3,4-tetrahydro-carbazole 
• 7394-80-1 4-(5-benzyloxy-indol-3-yl)-butyric acid 
• 50469-23-3 acetylamino-(5-benzyloxy-indol-3-ylmethyl)-malonic acid diethyl ester 
• 100420-96-0 (R)-11-Benzyloxy-1,2,4a,5,6,7-hexahydro-4H-pyrido[3,4-d]carbazole-3-carboxylic acid ethyl ester 
• 100421-03-2 8-Benzyloxy-4,4a,5,6,11,11b-hexahydro-1H,3H-pyrido[3,4-a]carbazole-2-carboxylic acid ethyl ester 
• 145839-38-9 4-benzyloxy-(N-tert-butoxycarbonyl)phenylhydrazine 
• 20776-45-8 5-benzyloxytryptamine 
• 55581-41-4 5-benzyloxy-1H-indole-2-carboxylic acid methyl ester 
• 6640-09-1 5-benzyloxy-1H-indole-2-carboxylic acid 
• 133845-43-9 2-(5-benzyloxyindole)carboxamide 
• 374924-83-1 2-[4-(benzyloxy)phenyl]-5-methyl-2,4-dihydropyrazol-3-one 

Relevant articles and documents

Danshensu derivativeS as well as preparation method and medical application thereof

The invention discloses Danshensu derivatives as well as a preparation method and medical application thereof. The derivatives have a general structure as shown in a general formula (I) shown in the specification, wherein R1 represents OH or OCH3; R2 represents H or Ac; and R3 represents a first structure, a second structure or a third structure shown in the specification. Compared with a raw material medicine, the derivatives synthesized by the invention have the advantages that the fat solubility is increased, so that the derivatives can penetrate through the blood-brain barrier (BBB), the medicine stability is greatly improved, and the curative effect is further improved. Therefore, the derivatives disclosed by the invention can be applied to preparation of drugs for preventing, treating, treating and/or reducing the cerebral infarction volume of a patient, improving the balance coordination ability of the patient and other diseases, and a new therapeutic drug is provided for preventing and treating cerebrovascular or cranial nerve diseases.

Thrombopoietin mimetics

Non-peptide TPO mimetics are disclosed, as well as a method of treating thrombocytopenia, in a mammal, including a human, in need thereof, which comprises administering to such mammal an effective amount of a selected hydroxy-1-azo-naphthalene derivative.

Hydrazinonaphthalene and azonaphthalene thrombopoietin mimics are nonpeptidyl promoters of megakaryocytopoiesis

High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW 50 values in the region of 1-20 nM.