4-Isothiocyanatobenzoic acid

Base Information

• Chemical Name: 4-Isothiocyanatobenzoic acid
• CAS No.: 2131-62-6
• Molecular Formula: C8H5NO2S
• Molecular Weight: 179.199
• Hs Code.: 29309090
• European Community (EC) Number: 671-008-5
• NSC Number: 52064
• UNII: G83CC6APM6
• DSSTox Substance ID: DTXSID90175579
• Nikkaji Number: J265.474A
• Wikidata: Q27133300
• Metabolomics Workbench ID: 63398
• Mol file: 2131-62-6.mol

Synonyms:4-carboxy-phenyl-isothiocyanate;4-ICBA;4-isothiocyanatobenzoic acid;4-isothiocyanatobenzoic acid, sodium salt

Chemical Property of 4-Isothiocyanatobenzoic acid

Chemical Property:

• Appearance/Colour: Off-white granular solid
• Vapor Pressure: 7.34E-06mmHg at 25°C
• Melting Point: 220 °C
• Refractive Index: 1.6370 (estimate)
• Boiling Point: 361.6 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 172.5 °C
• PSA: 81.75000
• Density: 1.27 g/cm³
• LogP: 2.11910
• Storage Temp.: Keep Cold
• Water Solubility.: 19mg/L(25 oC)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 179.00409958
• Heavy Atom Count: 12
• Complexity: 215

Purity/Quality:

98%min ^*data from raw suppliers

4-CarboxyphenylIsothiocyanate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-Isothiocyanatobenzoic acid

There total 6 articles about 4-Isothiocyanatobenzoic 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: 95.0%

thiocarbonyldiimidazole + 4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-isothiocyanatobenzoic acid (2131-62-6)

Guidance literature:

thiocarbonyldiimidazole; 4-amino-benzoic acid; With triethylamine; In dichloromethane; at 5 ℃; for 1h; Cooling with ice;

With hydrogenchloride; In n-heptane; dichloromethane; at 25 - 30 ℃;

Reference yield: 90.0%

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-isothiocyanatobenzoic acid (2131-62-6)

Guidance literature:

With triethylamine; 1,1'-Thiocarbonyldiimidazole; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1039/c7md00081b

Reference yield: 87.0%

thiophosgene (463-71-8) + 4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-isothiocyanatobenzoic acid (2131-62-6)

Guidance literature:

In acetone; at 0 ℃; for 3h;

DOI:10.21577/0103-5053.20170098

upstream raw materials:

thiophosgene

4-amino-benzoic acid

carbon disulfide

Downstream raw materials:

NSC 52105-S

4-[N'-(4-acetyl-phenyl)-thioureido]-benzoic acid

4,4'-thiocarbonyldiamino-bis-benzoic acid

4-[N'-(4-sulfamoyl-phenyl)-thioureido]-benzoic acid

Refernces

• 1、 Bestgen, Beno?t,Kufareva, Irina,Seetoh, Weiguang,Abell, Chris,Hartmann, Rolf W.,Abagyan, Ruben,Le Borgne, Marc,Filhol, Odile,Cochet, Claude,Lomberget, Thierry,Engel, Matthias. "2-Aminothiazole Derivatives as Selective Allosteric Modulators of the Protein Kinase CK2. 2. Structure-Based Optimization and Investigation of Effects Specific to the Allosteric Mode of Action". . p. 1817 - 1836. Retrieved 2019/02/26.
• 2、 Zeng, Fanxun,Qi, Tiantian,Li, Chunyan,Li, Tingfang,Li, Honglin,Li, Shiliang,Zhu, Lili,Xu, Xiaoyong. "Synthesis, structure-activity relationship and binding mode analysis of 4-thiazolidinone derivatives as novel inhibitors of human dihydroorotate dehydrogenase". supporting information. p. 1297 - 1302. Retrieved 2017/07/07.