| Identification | More | [Name]
4-Methylthiophenylacetic acid | [CAS]
16188-55-9 | [Synonyms]
4-(METHYLTHIO)PHENYLACETIC ACID
RARECHEM AL BO 0923
(4-METHYLSULFANYL-PHENYL)-ACETIC ACID
2-(4-(methylthio)phenyl)acetic acid
4-(Methylthio)benzeneacetic acid | [Molecular Formula]
C9H10O2S | [MDL Number]
MFCD00192325 | [Molecular Weight]
182.24 | [MOL File]
16188-55-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Cream crystalline powder | [Melting point ]
97-98 °C(lit.) | [Boiling point ]
337.4±25.0 °C(Predicted) | [density ]
1.23±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
powder to crystal | [pka]
4.34±0.10(Predicted) | [color ]
White to Yellow to Orange | [InChI]
InChI=1S/C9H10O2S/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11) | [InChIKey]
AHMLFHMRRBJCRM-UHFFFAOYSA-N | [SMILES]
C1(CC(O)=O)=CC=C(SC)C=C1 | [CAS DataBase Reference]
16188-55-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29309099 |
| Hazard Information | Back Directory | [Chemical Properties]
Cream crystalline powder | [General Description]
TiO2 photocatalytic one-electron oxidation of 4-(methylthio)phenylacetic acid has been reported by time-resolved diffuse reflectance spectroscopy. | [Synthesis]
1. 10 g of 4-bromophenylacetic acid was dissolved in 20 mL of DMF under nitrogen protection.
2. 5.0 g of sodium methanethiol and 0.5 g of copper powder were added for nitrogen displacement.
3. The reaction mixture was heated to 130 °C under nitrogen protection and the reaction was stirred for 24 hours.
4. After the reaction was completed, it was cooled to room temperature.
5. The reaction mixture was processed according to the method of Example 1 to finally obtain 4-methylthiophenylacetic acid in 79.3% yield.
Alternative steps:
1. 10 g of 4-bromophenylacetic acid was dissolved in 20 mL of DMF under nitrogen protection.
2. 5.0 g of sodium methanethiol and 0.1 g of cuprous bromide were added for nitrogen substitution.
3. The reaction mixture was heated to 130 °C under nitrogen protection and the reaction was stirred for 4 hours.
4. Upon completion of the reaction, the mixture was cooled to room temperature, 5mL of 40% NaOH solution was added and stirred for 10 minutes.
5. Extracted twice with 25mL of ethyl acetate and combined the organic phases.
6. Add 50mL of ethyl acetate and adjust pH to 2-4 with 10% dilute sulfuric acid.
7. Collect the ethyl acetate layer and wash with 10mL of water.
8. Concentrate ethyl acetate to about 20mL by distillation, add 20mL hexane.
9. Heat to reflux to completely dissolve the solid, slowly cool to room temperature and filter to obtain yellow crystals.
10. 6.38g of 4-methylthiophenylacetic acid was obtained after drying in 76.1% yield. | [References]
[1] Patent: CN105646306, 2016, A. Location in patent: Paragraph 0011 |
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