2-Chloro-6-formylbenzoic acid

Base Information

• Chemical Name: 2-Chloro-6-formylbenzoic acid
• CAS No.: 20771-97-5
• Molecular Formula: C8H5ClO3
• Molecular Weight: 184.58
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID40698506
• Wikidata: Q82628750
• Mol file: 20771-97-5.mol

Synonyms:2-chloro-6-formylbenzoic acid;20771-97-5;2-CARBOXY-3-CHLORO-BENZENALDEHYDE;2-chloro-6-formylbenzoicacid;2-chloro-6-formyl-benzoic acid;DTXSID40698506;Benzoic acid, 2-chloro-6-formyl-;AKOS006309212;EN300-344257;Z1198309744

Chemical Property of 2-Chloro-6-formylbenzoic acid

Chemical Property:

• PSA: 54.37000
• LogP: 1.85070
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 183.9927217
• Heavy Atom Count: 12
• Complexity: 193

Purity/Quality:

99%min ^*data from raw suppliers

2-CARBOXY-3-CHLORO-BENZENALDEHYDE 95.00% ^*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)C(=O)O)C=O

Technology Process of 2-Chloro-6-formylbenzoic acid

There total 8 articles about 2-Chloro-6-formylbenzoic 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:

N,N-dimethyl-formamide (68-12-2,33513-42-7) + ortho-chlorobenzoic acid (118-91-2) → 2-chloro-6-formyl-benzoic acid (20771-97-5)

Guidance literature:

ortho-chlorobenzoic acid; With (E)-N,N,N′,N′-tetramethylethene-1,2-diamine; sec.-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

N,N-dimethyl-formamide; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1081/SCC-200050946

Reference yield:

2-bromo-6-chlorobenzoic acid (93224-85-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-chloro-6-formyl-benzoic acid (20771-97-5)

Guidance literature:

2-bromo-6-chlorobenzoic acid; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.202100672

Reference yield:

7-chloroisobenzofuran-1(3H)-one (70097-45-9) → 2-chloro-6-formyl-benzoic acid (20771-97-5)

Guidance literature:

Multistep reaction; (i) NBS, CCl₄, (ii) H₂O;

DOI:10.1021/ja01018a037

upstream raw materials:

2-chloro-6-methylbenzoic acid

7-chloroisobenzofuran-1(3H)-one

5-chloro-1,2,3,4-tetrahydronaphthalene

N,N-dimethyl-formamide

Downstream raw materials:

7-chloro-3-hydroxyisobenzofuran-1(3H)-one

8-chloro-2H-phthalazin-1-one

Refernces

• 1、 Gohier, Frederic,Castanet, Anne-Sophie,Mortier, Jacques. "Ortholithiation of unprotected benzoic acids: Application for novel 2-chloro-6-substituted benzoic acid syntheses". . p. 799 - 806. Retrieved 2007/10/03.