2131-63-7

Basic information

• Product Name: 3-CARBOXYPHENYL ISOTHIOCYANATE
• Synonyms: 3-Isothiocyanatobenzoic acid;3-CARBOXYPHENYL ISOTHIOCYANATE;RARECHEM AL BO 0439;Benzoic acid, 3-isothiocyanato-;3-Carboxyphenyl isothiocyate
• CAS NO: 2131-63-7
• Molecular Formula: C₈H₅NO₂S
• Molecular Weight: 179.2
• Mol File: 2131-63-7.mol

Chemical Properties

• Melting Point: 165 °C
• Boiling Point: 381.2 °C at 760 mmHg
• Flash Point: 184.4 °C
• Appearance: /
• Density: 1.3522 (rough estimate)
• Vapor Pressure: 1.72E-06mmHg at 25°C
• Refractive Index: 1.6370 (estimate)
• PKA: 3.72±0.10(Predicted)
• Water Solubility: 100.4mg/L(25 oC)
• Sensitive: Moisture Sensitive
• BRN: 2209003
• CAS DataBase Reference: 3-CARBOXYPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CARBOXYPHENYL ISOTHIOCYANATE(2131-63-7)
• EPA Substance Registry System: 3-CARBOXYPHENYL ISOTHIOCYANATE(2131-63-7)

Safety Data

• Statements: 20/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2131-63-7(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry and Drug Development:
3-Carboxyphenyl isothiocyanate is utilized as a key intermediate in the synthesis of bioactive compounds, particularly for the preparation of peptide-based bioconjugates. Its reactivity allows for the development of novel therapeutic agents that can target specific biological pathways or receptors.
Used in Organic Synthesis:
Due to its unique chemical properties, 3-Carboxyphenyl isothiocyanate is employed in the development of new materials and organic synthesis processes. Its ability to react with nucleophiles makes it a valuable component in creating a wide range of chemical products.
Used in the Synthesis of Bioconjugates:
3-Carboxyphenyl isothiocyanate is used as a coupling agent for the synthesis of bioconjugates, which are compounds that combine biological molecules with other entities, such as drugs or imaging agents. This application is crucial for enhancing the functionality of these molecules in various biomedical applications, including targeted drug delivery and diagnostics.

InChI:InChI=1/C8H5NO2S/c10-8(11)6-2-1-3-7(4-6)9-5-12/h1-4H,(H,10,11)

Upstream product

• 463-71-8 thiophosgene 
• 99-05-8 meta-aminobenzoic acid 
• 7647-01-0 hydrogenchloride 
• 90962-86-0 3,3'-thioureylene-di-benzoic acid 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 75-15-0 carbon disulfide 

Downstream Products

• 36915-57-8 3-isothiocyanato-benzoyl chloride 
• 1223-21-8 N-(3-Carboxy-phenyl)-N'-phenyl-thioharnstoff 
• 138480-75-8 3-[3-(3-Carboxy-phenyl)-thioureido]-1H-pyrazole-4-carboxylic acid ethyl ester 
• 138480-69-0 1-Benzyl-3-[3-(3-carboxy-phenyl)-thioureido]-1H-pyrazole-4-carboxylic acid ethyl ester 
• 135922-04-2 1-(3-Carbethoxy)-phenyl-7-chlor-5-hydroxy-5-phenyl-2-thioxo-3H-1,2,3,5-tetrahydro<1.2.4>triazolo<5.1-b>chinazolin 
• 77268-42-9 1-isocyanato-3-isothiocyanato-benzene 
• 611214-71-2 3-{[1-methyl-5-({2-[(methylamino)carbonyl]pyridin-4-yl}-oxy)-1H-benzimidazol-2-yl]amino}benzoic acid 
• 892492-83-0 C₁₉H₁₈N₆O₅ 
• 381216-71-3 3-{3-[5-(5,6-Dichloro-1H-indol-2-yl)-2-methoxy-phenyl]-thioureido}-benzoic Acid 
• 37182-75-5 1-(3-carboxyphenyl)-2-thiourea 

Relevant articles and documents

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

Protein CK2 has gained much interest as an anticancer drug target in the past decade. We had previously described the identification of a new allosteric site on the catalytic α-subunit, along with first small molecule ligands based on the 4-(4-phenylthiazol-2-ylamino)benzoic acid scaffold. In the present work, structure optimizations guided by a binding model led to the identification of the lead compound 2-hydroxy-4-((4-(naphthalen-2-yl)thiazol-2-yl)amino)benzoic acid (27), showing a submicromolar potency against purified CK2α (IC50 = 0.6 μM). Furthermore, 27 induced apoptosis and cell death in 786-O renal cell carcinoma cells (EC50 = 5 μM) and inhibited STAT3 activation even more potently than the ATP-competitive drug candidate CX-4945 (EC50 of 1.6 μM vs 5.3 μM). Notably, the potencies of our allosteric ligands to inhibit CK2 varied depending on the individual substrate. Altogether, the novel allosteric pocket was proved a druggable site, offering an excellent perspective to develop efficient and selective allosteric CK2 inhibitors.

METHOD FOR PRODUCING ISOTHIOCYANATE COMPOUND

The object of the present invention is to provide a novel method for producing an isothiocyanate compound having a carboxyl group(s) by a reaction of the corresponding amino compound having a carboxyl group(s), thiocarbonyldiimidazole and a base, in one s

METHOD FOR PRODUCING ISOTHIOCYANATE COMPOUND

The object of the present invention is to provide a novel method for producing an isothiocyanate compound having a carboxyl group(s) by a reaction of the corresponding amino compound having a carboxyl group(s), thiocarbonyldiimidazole and a base, in one s

METHOD FOR PRODUCING ISOTHIOCYANATE COMPOUND HAVING CARBOXYL GROUP

To provide a novel method for producing an isothiocyanate compound having a carboxyl group(s) from the corresponding amino compound having a carboxyl group(s). A method for producing an isothiocyanate compound which has a carboxyl group(s) and is represented by the formula (2). And the method comprises reacting an amino compound which has a carboxyl group(s) and is represented by the formula (1) (wherein A is e.g. a C6-14 aromatic hydrocarbon group or a C1-12 saturated hydrocarbon group, and B is e.g. a single bond, a C6-14 aromatic hydrocarbon group or a C1-12 saturated hydrocarbon group), in a solvent, with carbon disulfide (CS2) and then with a halogen as a simple substance.