3-Bromo-5-chloro-4-hydroxybenzonitrile

Base Information

• Chemical Name: 3-Bromo-5-chloro-4-hydroxybenzonitrile
• CAS No.: 1689-86-7
• Molecular Formula: C7H3BrClNO
• Molecular Weight: 232.464
• European Community (EC) Number: 831-048-8
• DSSTox Substance ID: DTXSID80561649
• Nikkaji Number: J728.229J
• Wikidata: Q82445490
• Mol file: 1689-86-7.mol

Synonyms:1689-86-7;3-BROMO-5-CHLORO-4-HYDROXYBENZONITRILE;Benzonitrile, 3-bromo-5-chloro-4-hydroxy-;3-Bromo-5-chloro-4-hydroxy-benzonitrile;starbld0009070;SCHEMBL11031525;DTXSID80561649;A18290;G10376;EN300-3186167;Z1416188326

Chemical Property of 3-Bromo-5-chloro-4-hydroxybenzonitrile

Chemical Property:

• Melting Point: 163-164 °C
• Boiling Point: 260.7±40.0 °C(Predicted)
• PKA: 4.84±0.23(Predicted)
• PSA: 44.02000
• Density: 1.91±0.1 g/cm3(Predicted)
• LogP: 2.67978
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 230.90865
• Heavy Atom Count: 11
• Complexity: 190

Purity/Quality:

98%min ^*data from raw suppliers

3-Bromo-5-chloro-4-hydroxybenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1Cl)O)Br)C#N

Technology Process of 3-Bromo-5-chloro-4-hydroxybenzonitrile

There total 4 articles about 3-Bromo-5-chloro-4-hydroxybenzonitrile 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: 84.0%

2-chloro-4-cyanophenol (2315-81-3) → 5-bromo-3-chloro-4-hydroxybenzonitrile (1689-86-7)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acsinfecdis.7b00218

Reference yield:

allyl n-butyl ether (3739-64-8) + 2-bromo-6-chloro-4-cyanophenyl acetate (1689-87-8) → 5-bromo-3-chloro-4-hydroxybenzonitrile (1689-86-7) + 3-(3-butoxypropyl)-5-chloro-4-hydroxybenzonitrile

Guidance literature:

allyl n-butyl ether; With borane-THF; In tetrahydrofuran; at 20 ℃; for 0.25h; Cooling with ice; Inert atmosphere;

2-bromo-6-chloro-4-cyanophenyl acetate; With potassium phosphate; palladium diacetate; ruphos; In tetrahydrofuran; water; toluene; for 16h; Sealed tube; Heating; Inert atmosphere;

DOI:10.1021/acsinfecdis.7b00218

Reference yield:

4-pentenyl ethyl ether (15193-19-8) + 2-bromo-6-chloro-4-cyanophenyl acetate (1689-87-8) → 5-bromo-3-chloro-4-hydroxybenzonitrile (1689-86-7) + 3-chloro-5-(5-ethoxypentyl)-4-hydroxybenzonitrile

Guidance literature:

4-pentenyl ethyl ether; With borane-THF; In tetrahydrofuran; at 20 ℃; for 0.25h; Cooling with ice; Inert atmosphere;

2-bromo-6-chloro-4-cyanophenyl acetate; With potassium phosphate; palladium diacetate; ruphos; In tetrahydrofuran; water; toluene; for 16h; Sealed tube; Heating; Inert atmosphere;

DOI:10.1021/acsinfecdis.7b00218

upstream raw materials:

2-chloro-4-cyanophenol

allyl n-butyl ether

2-bromo-6-chloro-4-cyanophenyl acetate

4-pentenyl ethyl ether

Downstream raw materials:

2-bromo-6-chloro-4-cyanophenyl acetate

Refernces