2-(phenylsulfanyl)acetic acid

• ChemBase ID: 104501
• Molecular Formular: C8H8O2S
• Molecular Mass: 168.21292
• Monoisotopic Mass: 168.0245005
• SMILES: OC(=O)CSc1ccccc1
• Canonical SMILES: OC(=O)CSc1ccccc1
• InChI: InChI=1S/C8H8O2S/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
• InChIKey: MOTOSAGBNXXRRE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(phenylsulfanyl)acetic acid
• IUPAC Traditional name: phenylthio-acetic acid
• Synonyms: Thiophenoxyacetic acid; PHENYLMERCAPTOACETIC ACID; (Phenylmercapto)acetic acid; S-Phenylthioglycolic acid; (Phenylthio)acetic acid; 苯基巯基乙酸; 苯硫乙酸; 苯硫代乙酸; 苯硫基乙酸; (苯硫基)乙酸

Database IDs

• CAS Number: 103-04-8
• EC Number: 203-073-9
• MDL Number: MFCD00004355
• Beilstein Number: 2045072
• PubChem SID: 24900129; 162091646
• PubChem CID: 59541

CALCULATED PROPERTIES

• Acid pKa: 4.113577
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.36732042
• LogD (pH = 7.4): -1.3222429
• Log P: 1.7681124
• Molar Refractivity: 45.0491 cm^3
• Polarizability: 17.569117 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 60-63 °C(lit.); 61-66°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 96%; 97%; 98%
• Linear Formula: C6H5SCH2COOH

DETAILS

MP Biomedicals - 02156186

Purity: 98% Crystalline

MP Biomedicals - 05217405

MP Biomedicals Rare Chemical collection

Sigma Aldrich - T33006

Packaging
25 g in poly bottle

REFERENCES

• The dilithio-derivative can be ɑ-monoalkylated in high yield, and the process repeated to give the dialkyl derivative: J. Chem. Soc., Chem. Commun., 714 (1975). Reaction of the dianion with terminal epoxides gives -hydroxy acids which can be cyclized to ɑ-phenylthio--lactones. These can desulfurized with Raney nickel: J. Am. Chem. Soc., 108, 5352 (1986), or oxidatively, leading to butenolides: Chem. Lett., 385 (1974).