2-Cyanobenzoic acid

Base Information

• Chemical Name: 2-Cyanobenzoic acid
• CAS No.: 3839-22-3
• Molecular Formula: C8H5NO2
• Molecular Weight: 147.133
• Hs Code.: 29269090
• European Community (EC) Number: 675-699-4
• NSC Number: 193443
• DSSTox Substance ID: DTXSID70191732
• Nikkaji Number: J79.864I
• Wikidata: Q69754401
• Mol file: 3839-22-3.mol

Synonyms:2-Cyanobenzoic acid;3839-22-3;o-Cyanobenzoic acid;Benzoic acid, 2-cyano-;2-CyanobenzoicAcid;Cyanobenzoic acid;MFCD00045796;2-CARBOXYBENZONITRILE;2-carboxy-benzonitrile;o-Carboxybenzonitrile;2-cyano-benzoic acid;2-Cyanobenzoic acid #;SCHEMBL180853;DTXSID70191732;AMY20185;2-Cyanobenzoic acid, technical grade;NSC193443;AKOS000275074;NSC 193443;NSC-193443;AC-23088;BP-13201;SY005782;TS-01916;CS-0112283;FT-0612108;EN300-50556;A22626;J-509206

Chemical Property of 2-Cyanobenzoic acid

Chemical Property:

• Appearance/Colour: Off-white needles
• Vapor Pressure: 3.01E-05mmHg at 25°C
• Melting Point: 212 °C(lit.)
• Boiling Point: 341.9 °C at 760 mmHg
• PKA: pK1:3.14 (25°C)
• Flash Point: 160.5 °C
• PSA: 61.09000
• Density: 1.32g/cm³
• LogP: 1.25648
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Sparingly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 147.032028402
• Heavy Atom Count: 11
• Complexity: 203

Purity/Quality:

98%, ^*data from raw suppliers

2-Cyanobenzoic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C#N)C(=O)O
• Uses: 2-Cyanobenzoic acid has been used as reactant in the synthesis of T-box riboswitch antiterminator RNA-binding oxazolidinone derivatives, Benzoate modified β-cyclodextrin derivatives and Pyrrolo[1,2-f]triazines for use as JAK2 inhibitors. As a reactant involved in decarboxylation, decarboxylative halogenation and protodecarboxylation. 2-Cyanobenzoic acid may be used to synthesize phthalamidine.

Technology Process of 2-Cyanobenzoic acid

There total 51 articles about 2-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: 99.0%

2-cyano-benzoic acid ethyl ester (6525-45-7) → 2-cyanobenzoic acid (3839-22-3)

Guidance literature:

With iodine; aluminium; In acetonitrile; at 80 ℃; for 18h;

DOI:10.1021/acs.joc.1c00034

Reference yield: 95.0%

benzyl 2-cyanobenzoate → 2-cyanobenzoic acid (3839-22-3)

Guidance literature:

With palladium diacetate; sodium hydride; In N,N-dimethyl acetamide; at 60 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acscatal.8b00185

Reference yield: 92.0%

2-acetylbenzonitrile (91054-33-0) → 2-cyanobenzoic acid (3839-22-3)

Guidance literature:

With N-bromophthalimide; mercury(II) diacetate; In chloroform; at 20 ℃; for 1.5h;

DOI:10.1246/cl.2001.900

upstream raw materials:

1H-2,3-benzoxazin-1-one

3,3-dichlorophthalide

3,3-dibromo-phthalide

2-Methylbenzonitrile

Downstream raw materials:

phthalamic acid

2-Cyanobenzoyl chloride

(O-2-cyanobenzoyl)-4-methylphenyl amidoxime

2-Cyano-4'-methylbiphenyl

Refernces

• 1、 Hu, Deqing,Jiang, Xuefeng. "Stepwise benzylic oxygenation via uranyl-photocatalysis". supporting information. p. 124 - 129. Retrieved 2022/01/19.
• 2、 Zhang, Guoxiang,Zhang, Zongnan,Zeng, Rong. "Photoinduced FeCl3-Catalyzed Alkyl Aromatics Oxidation toward Degradation of Polystyrene at Room Temperature?". supporting information. p. 3225 - 3230. Retrieved 2021/09/28.