2-Chloro-5-cyanobenzoic acid

Base Information

• Chemical Name: 2-Chloro-5-cyanobenzoic acid
• CAS No.: 89891-83-8
• Molecular Formula: C8H4ClNO2
• Molecular Weight: 181.578
• Hs Code.: 2926909090
• European Community (EC) Number: 823-831-8
• DSSTox Substance ID: DTXSID20557344
• Wikidata: Q82439205
• Mol file: 89891-83-8.mol

Synonyms:2-Chloro-5-cyanobenzoic acid;89891-83-8;Benzoic acid, 2-chloro-5-cyano-;2-Chloro-5-cyanobenzoicacid;SCHEMBL2225438;DTXSID20557344;OZNRJPYVSBAJLX-UHFFFAOYSA-N;MFCD11036379;AKOS006306781;AS-59365;CS-0132512;EN300-207923;A860993;AT-419/43511962;Z1198304567

Chemical Property of 2-Chloro-5-cyanobenzoic acid

Chemical Property:

• Melting Point: 178 °C
• Boiling Point: 334.7±27.0 °C(Predicted)
• PKA: 2.31±0.25(Predicted)
• PSA: 61.09000
• Density: 1.48±0.1 g/cm3(Predicted)
• LogP: 1.90988
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 180.9930561
• Heavy Atom Count: 12
• Complexity: 233

Purity/Quality:

≥95% ^*data from raw suppliers

2-chloro-5-cyanobenzoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C#N)C(=O)O)Cl

Technology Process of 2-Chloro-5-cyanobenzoic acid

There total 5 articles about 2-Chloro-5-cyanobenzoic acid 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:

2-chloro-5-nitrobenzoic acid (2516-96-3) → 2-chloro-5-cyanobenzoic acid (89891-83-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / H₂ gas / platinic oxide / ethanol / Ambient temperature

2: 1.) NaNO₂, 2N HCl; 2.) cuprous cyanide / 1.) water, 0 deg C, 35 min; 2.) water, 60 deg C, 40 min

With hydrogenchloride; hydrogen; copper(l) cyanide; sodium nitrite; platinum(IV) oxide; In ethanol;

DOI:10.1248/cpb.36.3462

Reference yield:

2-chloro-5-aminobenzoic acid (89-54-3) + copper(l) cyanide → 2-chloro-5-cyanobenzoic acid (89891-83-8)

Guidance literature:

2-chloro-5-aminobenzoic acid; With hydrogenchloride; sodium nitrite;

copper(l) cyanide; With potassium cyanide; Further stages.;

DOI:10.1021/jm0612867

Reference yield:

2-chloro-5-aminobenzoic acid (89-54-3) → 2-chloro-5-cyanobenzoic acid (89891-83-8)

Guidance literature:

With hydrogenchloride; sodium carbonate; Eintragen in eine heisse, aus Natriumcyanid, Nickel(II)-chlorid und Wasser hergestellte Loesung;

DOI:10.1039/jr9470000637

upstream raw materials:

2-chloro-5-aminobenzoic acid

potassium cyanide

2-chloro-5-nitrobenzoic acid

Downstream raw materials:

2-p-anisidino-5-cyano-benzoic acid

2-anilino-5-cyano-benzoic acid

methyl 2-<4-(2-carboxy-4-cyano)phenoxyphenyl>propionate

2-chloro-5-cyanobenzoyl chloride

Refernces

• 1、 Hino,Nakamura,Kato,Irie,Nagai,Uno. "Nonsteroidal antiinflammatory agents. III. Synthesis of the metabolites of 10,11-dihydro-8,α-dimethyl-11-oxodibenz-[b,f]oxepin-2-acetic acid (bermoprofen)". . p. 3462 - 3467. Retrieved 2007/10/02.