4-Mercaptophenylacetic acid

Base Information

• Chemical Name: 4-Mercaptophenylacetic acid
• CAS No.: 39161-84-7
• Molecular Formula: C8H8O2S
• Molecular Weight: 168.216
• Hs Code.: 2930909090
• European Community (EC) Number: 627-721-9
• UNII: M977MK9GKO
• DSSTox Substance ID: DTXSID80392056
• Nikkaji Number: J1.549.801C
• Wikipedia: 4-Mercaptophenylacetic_acid
• Wikidata: Q20707106
• ChEMBL ID: CHEMBL257258
• Mol file: 39161-84-7.mol

Synonyms:4-mercaptophenylacetic acid

Chemical Property of 4-Mercaptophenylacetic acid

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 4.54E-05mmHg at 25°C
• Melting Point: 105-109 °C(lit.)
• Refractive Index: 1.62
• Boiling Point: 336 °C at 760 mmHg
• PKA: 4.21±0.10(Predicted)
• Flash Point: 157 °C
• PSA: 76.10000
• Density: 1.299 g/cm³
• LogP: 1.60240
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Sensitive.: Air Sensitive
• Water Solubility.: Slightly soluble in water. Soluble in Dichloromethane, Ethanol and Methanol
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 168.02450067
• Heavy Atom Count: 11
• Complexity: 139

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Mercaptophenylacetic acid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(=O)O)S
• Uses: 4-Mercaptophenylacetic acid has been used in the preparation of small ubiquitin-like modifier peptides from bis(2-sulfanylethyl)amido peptide via sequential native chemical ligation.It can be used: On-resin preparation of peptide-α thiophenylesters which are used in a chemical ligation process for the chemical synthesis of peptides.In one pot deprotection of (acetamido-methyl)cysteine following native chemical ligation and/or desulfurization method for the preparation of peptides.Palladium facilitated deprotection of N-terminal cysteine through native chemical ligation method for the preparation of synthetically challenging proteins. 4-MERCAPTOPHENYLACETIC ACID is a redox buffer that increases the folding rate of disulfide-containing proteins realative to traditional buffers such as glutathione and glutathione-disulfide. A useful synthetic intermediate for the preparation of novel antiinflammatory agents.

Technology Process of 4-Mercaptophenylacetic acid

There total 8 articles about 4-Mercaptophenylacetic 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-(4-((ethoxycarbonothioyl)thio)phenyl)acetic acid (1235544-51-0) → 4-mercaptophenylacetic acid (39161-84-7)

Guidance literature:

With water; potassium hydroxide; In ethanol; for 20h; Reflux;

Reference yield:

potassiumethyl xanthogenate + 4-aminophenylacetic acid (1197-55-3) → 4-mercaptophenylacetic acid (39161-84-7)

Guidance literature:

With hydrogenchloride; potassium hydroxide; sodium nitrite; In ethanol; water;

Reference yield:

3-carboxymethylbenzenesulphonyl chloride + 2-(4-(chlorosulfonyl)phenyl)acetic acid (22958-99-2) → 4-mercaptophenylacetic acid (39161-84-7) + 2-(3-mercaptophenyl)acetic acid (63271-86-3)

Guidance literature:

3-carboxymethylbenzenesulphonyl chloride; 2-(4-(chlorosulfonyl)phenyl)acetic acid; With phosphorus; iodine; In acetic acid; at 100 - 110 ℃; for 0.5 - 4h; Heating / reflux;

With water; at 100 ℃; for 1.5 - 2h; Product distribution / selectivity; Heating / reflux;

upstream raw materials:

(4-dimethylcarbamoylsulfanyl-phenyl)-acetic acid methyl ester

Methyl 4-hydroxyphenylacetate

(4-Dimethylthiocarbamoyloxy-phenyl)-acetic acid methyl ester

2-(4-(chlorosulfonyl)phenyl)acetic acid

Downstream raw materials:

2-[4-[[4-(carboxymethyl)phenyl]-disulfanyl]phenyl]acetic acid

2-(4-(triphenylmethylthio)phenyl)acetic acid

(4-{[2-(methoxycarbonyl)benzyl]thio}phenyl)acetic acid

(4-mercapto-phenyl)-acetic acid methyl ester

Refernces

• 1、 -. "FUSED PYRIDINE AND PYRIMIDINE DERIVATIVES AS ROR GAMMA MODULATORS". . . Retrieved 2015/06/18.
• 2、 -. "DIHYDROPYRROLOPYRIDINE INHIBITORS OF ROR-GAMMA". . . Retrieved 2015/09/23.