4-bromo-2-{(E)-[(2-methoxyphenyl)imino]methyl}phenol

Base Information

• Chemical Name: 4-bromo-2-{(E)-[(2-methoxyphenyl)imino]methyl}phenol
• CAS No.: 5821-04-5
• Molecular Formula: C25H36 O5
• Molecular Weight: 306.1546
• DSSTox Substance ID: DTXSID10425740
• Mol file: 5821-04-5.mol

Synonyms:5821-04-5;ZINC03131541;4-bromo-2-{(E)-[(2-methoxyphenyl)imino]methyl}phenol;DTXSID10425740;AKOS003671451;(E)-4-Bromo-2-(2-methoxyphenyliminomethyl)phenol;4-BROMO-2-((2-METHOXY-PHENYLIMINO)-METHYL)-PHENOL

Chemical Property of 4-bromo-2-{(E)-[(2-methoxyphenyl)imino]methyl}phenol

Chemical Property:

• Vapor Pressure: 5.86E-06mmHg at 25°C
• Boiling Point: 379.4°Cat760mmHg
• Flash Point: 183.3°C
• Density: 1.607g/cm³
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 305.00514
• Heavy Atom Count: 18
• Complexity: 285

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC=C1N=CC2=C(C=CC(=C2)Br)O

Technology Process of 4-bromo-2-{(E)-[(2-methoxyphenyl)imino]methyl}phenol

There total 13 articles about 4-bromo-2-{(E)-[(2-methoxyphenyl)imino]methyl}phenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

acetic anhydride (108-24-7) + (25R)-5α-spirostan-3β,12β-diol diacetate (10007-76-8) → 3β,12β-diacetoxy-5α-pregn-16-en-20-one (5821-04-5)

Guidance literature:

acetic anhydride; (25R)-5α-spirostan-3β,12β-diol diacetate; With pyridine; ammonium chloride; at 130 ℃; for 18h;

With chromium(VI) oxide; In water; acetic acid; at 0 ℃; for 0.416667h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 4h; Further stages.; Heating;

DOI:10.1021/ol000064e

Reference yield:

Acetic acid (2S,4aS,4bS,6R,6aS,6bS,9aS,10aS,10bR,12aS)-2-acetoxy-8-((R)-4-acetoxy-3-methyl-butyl)-4a,6a,7-trimethyl-2,3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-6-yl ester → 3β,12β-diacetoxy-5α-pregn-16-en-20-one (5821-04-5)

Guidance literature:

Acetic acid (2S,4aS,4bS,6R,6aS,6bS,9aS,10aS,10bR,12aS)-2-acetoxy-8-((R)-4-acetoxy-3-methyl-butyl)-4a,6a,7-trimethyl-2,3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-6-yl ester; With chromium(VI) oxide; In dichloromethane; acetic acid; at 0 ℃; for 0.25h;

With isopropyl alcohol; In dichloromethane; acetic acid; at 20 ℃; for 0.166667h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; Further stages.; Heating;

DOI:10.1021/jo011175+

Reference yield:

3β,12β-dihydroxy-(25R)-5α-spirostane (545-77-7,16653-52-4,38673-26-6,90375-72-7,90457-38-8,107297-25-6) → 3β,12β-diacetoxy-5α-pregn-16-en-20-one (5821-04-5)

Guidance literature:

ueber mehrere Stufen;

DOI:10.1039/jr9560004744

upstream raw materials:

3β,12β-dihydroxy-(25R)-5α-spirostane

acetic anhydride

(25R)-5α-spirostan-3β,12β-diol diacetate

hecogenin

Downstream raw materials:

C₅₀H₇₀O₇Si₂

3β-Hydroxy-12β-acetoxy-Δ¹⁶-5α-pregnenon-(20)