(Phenylthio)acetic acid

Base Information

• Chemical Name: (Phenylthio)acetic acid
• CAS No.: 103-04-8
• Molecular Formula: C8H8 O2 S
• Molecular Weight: 168.216
• Hs Code.: 29309090
• European Community (EC) Number: 203-073-9
• NSC Number: 9582
• UNII: M12342PPGS
• DSSTox Substance ID: DTXSID4074431
• Nikkaji Number: J25.204B
• Wikidata: Q27283331
• ChEMBL ID: CHEMBL459548
• Mol file: 103-04-8.mol

Synonyms:phenylthioacetate;thiophenoxyacetic acid

Chemical Property of (Phenylthio)acetic acid

Chemical Property:

• Appearance/Colour: Brown crystal
• Vapor Pressure: 0.000197mmHg at 25°C
• Melting Point: 60-63 °C(lit.)
• Boiling Point: 258 °C at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 109.9 °C
• PSA: 62.60000
• Density: 1.14 g/cm³
• LogP: 1.86330
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: almost transparency in Methanol
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 168.02450067
• Heavy Atom Count: 11
• Complexity: 130

Purity/Quality:

97% ^*data from raw suppliers

(Phenylthio)acetic Acid >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC=C(C=C1)SCC(=O)O
• General Description: (Phenylthio)acetic acid, also known as phenylthioglycolic acid, is an important intermediate in the synthesis of vat dyestuffs. A recent study developed an improved synthetic route for this compound via aryltriazene intermediates, achieving higher yields compared to traditional methods. The two-step process involves diazotization of substituted anilines followed by reaction with thioglycolic acid, demonstrating efficiency and potential for industrial-scale production.

Technology Process of (Phenylthio)acetic acid

There total 52 articles about (Phenylthio)acetic 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: 98.0%

(phenylsulfinyl)acetic acid (3959-08-8,60833-02-5,60833-03-6,90693-85-9) → (phenylthio)acetic acid (103-04-8)

Guidance literature:

With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; potassium iodide; for 0.0833333h; chemoselective reaction; Neat (no solvent);

DOI:10.1021/jo1011784

Reference yield: 97.0%

methyl (phenylsulfanyl)acetate (17277-58-6) → (phenylthio)acetic acid (103-04-8)

Guidance literature:

With sodium; diphenyldisulfane; In 1-methyl-pyrrolidin-2-one; at 90 ℃; for 0.5h;

DOI:10.1021/jo010611p

Reference yield: 95.0%

bromoacetic acid (79-08-3) + thiophenol (108-98-5) → (phenylthio)acetic acid (103-04-8)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In tetrahydrofuran; water; for 0.5h; Ambient temperature;

DOI:10.1021/jo00018a026

upstream raw materials:

n-butyllithium

diethyl ether

methyl-phenyl-thioether

methyllithium

Downstream raw materials:

(4-acetyl-phenylsulfanyl)-acetic acid

ethyl phenylsulfenylacetate

(phenylthio)acetic acid chloride

thioindoxyl

Refernces

New synthesis of phenylthioglycolic acids via related triazene compounds

10.1080/00304949809355295

The research focuses on developing a novel and efficient method for synthesizing phenylthioglycolic acids, which are important intermediates in the production of vat dyestuffs. The purpose of this study was to improve upon existing synthesis methods by achieving higher yields of these acids. The researchers utilized a two-step process involving the diazotization of substituted anilines followed by reaction with pyrrolidine to form aryltriazenes, which were then reacted with thioglycolic acid to yield the desired phenylthioglycolic acids. The study concluded that this new procedure resulted in higher yields compared to previously reported methods, demonstrating its effectiveness and potential for industrial applications.