3-Chloro-2-hydroxybenzonitrile

Base Information

• Chemical Name: 3-Chloro-2-hydroxybenzonitrile
• CAS No.: 13073-27-3
• Molecular Formula: C7H4ClNO
• Molecular Weight: 153.568
• Hs Code.: 2926909090
• European Community (EC) Number: 812-759-2
• DSSTox Substance ID: DTXSID40499459
• Nikkaji Number: J2.599.605D
• Wikidata: Q82350246
• Mol file: 13073-27-3.mol

Synonyms:3-CHLORO-2-HYDROXYBENZONITRILE;13073-27-3;Benzonitrile, 3-chloro-2-hydroxy-;SCHEMBL3938143;DTXSID40499459;CL9665;MFCD09999455;AKOS022966732;MB08412;AS-46449;CS-0103460;FT-0732610

Chemical Property of 3-Chloro-2-hydroxybenzonitrile

Chemical Property:

• Melting Point: 113-114 °C
• Boiling Point: 242.1±25.0 °C(Predicted)
• PKA: 5.69±0.10(Predicted)
• PSA: 44.02000
• Density: 1.41±0.1 g/cm3(Predicted)
• LogP: 1.91728
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 152.9981414
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

98%Min ^*data from raw suppliers

3-Chloro-2-hydroxybenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Cl)O)C#N

Technology Process of 3-Chloro-2-hydroxybenzonitrile

There total 7 articles about 3-Chloro-2-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: 72.0%

salicylonitrile (611-20-1) → 5-chloro-2-hydroxybenzonitrile (13589-72-5) + 3-chloro-2-hydroxybenzonitrile (13073-27-3)

Guidance literature:

With N-chloro-succinimide; C₂₄H₂₀F₁₂N₄OS; In chloroform-d1; at 20 ℃; for 12h; regioselective reaction;

DOI:10.1021/acs.orglett.6b02650

Reference yield: 71.0%

salicylonitrile (611-20-1) → 3-chloro-2-hydroxybenzonitrile (13073-27-3)

Guidance literature:

With N-chloro-succinimide; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S,2S)-2-(mesitylselanyl)-2,3-dihydro-1H-inden-1-yl)thiourea; In chloroform-d1; at 20 ℃; for 12h; regioselective reaction;

DOI:10.1021/acs.joc.0c01917

Reference yield: 70.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-monochlorophenol (95-57-8) → 3-chloro-2-hydroxybenzonitrile (13073-27-3)

Guidance literature:

formaldehyd; 2-monochlorophenol; With triethylamine; magnesium chloride; In tetrahydrofuran; Heating;

With ammonium hydroxide; In tetrahydrofuran; methanol; for 0.5h;

With ortho-iodoxybenzoic acid; In tetrahydrofuran; methanol; water; Further stages.;

DOI:10.1016/j.tetlet.2008.05.006

upstream raw materials:

7-chloro-benzo[d]isoxazole

formaldehyd

2-monochlorophenol

3-chlorosalicylaldehyde

Downstream raw materials:

7-chlorobenzo[d]oxazol-2-amine

Refernces

• 1、 Maddox, Sean M.,Dinh, Andrew N.,Armenta, Felipe,Um, Joann,Gustafson, Jeffrey L.. "The Catalyst-Controlled Regiodivergent Chlorination of Phenols". supporting information. p. 5476 - 5479. Retrieved 2016/11/17.
• 2、 Anwar, Hany F.,Hansen, Trond Vidar. "A one-pot synthesis of substituted salicylnitriles". . p. 4443 - 4445. Retrieved 2008/12/21.