(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:

98%,99%, ^*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
• Uses: (Phenylthio)acetic acid is a reactant in the preparation of benzoxazoles, benzimidazoles, and benzothiazoles, which exhibit antimicrobial activity.

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

• 1、 Screttas, Constantinos G.,Micha-Screttas, Maria. "HEXANE-SOLUBLE COMPLEXES OF ALKYL- AND ALKENYL-SODIUM COMPOUNDS WITH MAGNESIUM ALKOXIDES". . p. 1 - 12. Retrieved 1986.
• 2、 Buglass, Alan J.,Datta, Mrityunjoy. "Arenediazothioalkanoic (Arylazothioalkanoic) acids by coupling of arenediazonium compounds with 2-Mercaptoalkanoic acids". . p. 218 - 224. Retrieved 2018.
• 3、 Fang, Lei,Zhang, Yihua,Lehmann, Jochen,Wang, You,Ji, Hui,Ding, Dayong. "Design and synthesis of furoxan-based nitric oxide-releasing glucocorticoid derivatives with potent anti-inflammatory activity and improved safety". . p. 1062 - 1066. Retrieved 2007.
• 4、 Cao, Hao,Hua, Huiming,Huang, Xiaofang,Jiao, Runwei,Li, Dahong,Li, Haonan,Li, Zhanlin,Liu, Weiwei,Xu, Fanxing,Zang, Linghe. "Antiproliferative chromone derivatives induce K562 cell death through endogenous and exogenous pathways". . p. 759 - 772. Retrieved 2020.
• 5、 Cheng, Keguang,Gao, Xiang,Hu, Xu,Hua, Huiming,Huang, Xueyan,Li, Dahong,Li, Haonan,Li, Zhanlin,Liu, Lilin,Xu, Fanxing. "Design, synthesis and apoptosis-related antiproliferative activities of chelidonine derivatives". . . Retrieved 2019.
• 6、 Fang, Yuanying,Wang, Rikang,He, Mingzhen,Huang, Hesong,Wang, Qi,Yang, Zunhua,Li, Yan,Yang, Shilin,Jin, Yi. "Nitric oxide-donating derivatives of hederacolchiside A1: Synthesis and biological evaluation in vitro and in vivo as potential anticancer agents". . p. 98 - 101. Retrieved 2017.
• 7、 Han, Tong,Li, Jia,Xue, Jingjing,Li, He,Xu, Fanxing,Cheng, Keguang,Li, Dahong,Li, Zhanlin,Gao, Ming,Hua, Huiming. "Scutellarin derivatives as apoptosis inducers: Design, synthesis and biological evaluation". . p. 270 - 281. Retrieved 2017.
• 8、 Liu, Yu-Xiu,Cui, Zhi-Peng,Zhao, Hua-Ping,Li, Yong-Hong,Gu, Yu-Cheng,Wang, Qing-Min. "Synthesis and biological activities of 3-substituted analogues of tenuazonic acid". . p. E209-E215. Retrieved 2014.
• 9、 Bao, Na,Ou, Jinfeng,Xu, Manyi,Guan, Fuqin,Shi, Wei,Sun, Jianbo,Chen, Li. "Novel NO-releasing plumbagin derivatives: Design, synthesis and evaluation of antiproliferative activity". . p. 88 - 95. Retrieved 2017.
• 10、 Fang, Yuanying,Jin, Yi,Li, Huilan,Li, Xiang,Liu, Ronghua,Tu, Liangxing,Xu, Guoliang,Yang, Zunhua. "Evaluation of novel paclitaxel-loaded NO-donating polymeric micelles for an improved therapy for gastroenteric tumor". . p. 13763 - 13774. Retrieved 2021.