5-Chloro-2-hydroxybenzonitrile

Base Information

• Chemical Name: 5-Chloro-2-hydroxybenzonitrile
• CAS No.: 13589-72-5
• Molecular Formula: C7H4ClNO
• Molecular Weight: 153.568
• Hs Code.: 2926907090
• European Community (EC) Number: 802-878-8
• DSSTox Substance ID: DTXSID00380516
• Nikkaji Number: J1.148.601K
• Wikidata: Q27455337
• Mol file: 13589-72-5.mol

Synonyms:5-chloro-2-hydroxybenzonitrile;13589-72-5;4-chloro-2-cyanophenol;MFCD00219003;2-cyano-4-chlorophenol;Benzonitrile, 5-chloro-2-hydroxy-;Benzonitrile, 5-?chloro-?2-?hydroxy-;5-chloro-2-hydroxy-benzonitrile;Benzonitrile,5-chloro-2-hydroxy-;5-Chlorosalicylonitrile;2-cyano-4-chloro-phenol;SCHEMBL584161;2-hydroxy-5-chlorobenzonitrile;DTXSID00380516;XWQDMIXVAYAZGB-UHFFFAOYSA-N;AMY28369;BBL104345;STK399951;AKOS000313174;FS-1810;AC-23050;BP-10147;SY063996;5-chloro-2-hydroxybenzonitrile, AldrichCPR;CS-0043964;FT-0620253;EN300-126809;A886921;J-514930;Q27455337;4ZC

Chemical Property of 5-Chloro-2-hydroxybenzonitrile

Chemical Property:

• Vapor Pressure: 0.00438mmHg at 25°C
• Melting Point: 152-154 °C
• Refractive Index: 1.611
• Boiling Point: 269.4 °C at 760 mmHg
• PKA: 6.72±0.18(Predicted)
• Flash Point: 116.7 °C
• Density: 1.41 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.7
• 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%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38-36
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 5-Chloro-2-hydroxybenzonitrile

There total 19 articles about 5-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: 95.0%

(E)-5-chloro-2-hydroxybenzaldehyde oxime (87974-49-0) → 5-chloro-2-hydroxybenzonitrile (13589-72-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 20 ℃; for 1h; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/jo502396u

Reference yield: 93.0%

5-chlorosalicyclaldehyde (635-93-8) → 5-chloro-2-hydroxybenzonitrile (13589-72-5)

Guidance literature:

With hydroxylamine-O-sulfonic acid; In water; at 20 - 60 ℃; for 7h;

Reference yield: 80.0%

4-chloro-2-iodo phenol (71643-66-8) → 5-chloro-2-hydroxybenzonitrile (13589-72-5)

Guidance literature:

In N,N-dimethyl-formamide;

upstream raw materials:

5-chlorobenzo[d]isoxazole

2-(acetyloxy)-5-chlorobenzonitrile

methyl thiocyanate

4-chloro-phenol

Downstream raw materials:

zoxazolamine

5-chloro-2-hydroxybenzoic acid

5-chloro-2-hydroxy-benzamide oxime

5-chlorosalicylamide

Refernces

• 1、 Hollfelder,Kirby,Tawfik. "On the magnitude and specificity of medium effects in enzyme-like catalysts for proton transfer". . p. 5866 - 5874. Retrieved 2001.
• 2、 Dinh, Andrew N.,Maddox, Sean M.,Vaidya, Sagar D.,Saputra, Mirza A.,Nalbandian, Christopher J.,Gustafson, Jeffrey L.. "Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst". . p. 13895 - 13905. Retrieved 2020/11/03.
• 3、 -. "Preparation method of piperidine compound". . . Retrieved 2017/11/04.