| Identification | More | [Name]
Methyl 3-hydroxythiophene-2-carboxylate | [CAS]
5118-06-9 | [Synonyms]
3-HYDROXYTHIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
METHYL 3-HYDROXY-2-THIOPHENECARBOXYLATE
METHYL 3-HYDROXYTHIOPHENE-2-CARBOXYLATE
METHYL-3-HYDROXYTHIOPHENE CARBOXYLATE | [EINECS(EC#)]
692-439-5 | [Molecular Formula]
C6H6O3S | [MDL Number]
MFCD00055642 | [Molecular Weight]
158.18 | [MOL File]
5118-06-9.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
38-43 °C(lit.) | [Boiling point ]
107-109°C 13mm | [density ]
1.372±0.06 g/cm3(Predicted) | [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
9.47±0.10(Predicted) | [color ]
White to Orange to Green | [Water Solubility ]
Slightly soluble in water. | [InChI]
InChI=1S/C6H6O3S/c1-9-6(8)5-4(7)2-3-10-5/h2-3,7H,1H3 | [InChIKey]
SEMVRXMFCHXUMD-UHFFFAOYSA-N | [SMILES]
C1(C(OC)=O)SC=CC=1O | [CAS DataBase Reference]
5118-06-9(CAS DataBase Reference) |
| Questions And Answer | Back Directory | [Uses]
3-Hydroxy-2-thiophenecarboxylic Acid Methyl Ester, is used as a reactant in synthesizing nitro-products where reaction occurs with thiophenol. |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29309090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Synthesis Reference(s)]
Synthetic Communications, 9, p. 731, 1979 DOI: 10.1080/00397917908064186 | [Synthesis]
Methyl 3-hydroxy-2-thiophenecarboxylate was synthesized according to the method reported by Huddleston and Barker in Synth. Commun. 1979,9,8,731-734. The procedure was as follows: a 2 M solution of sodium methanol was prepared by adding sodium (700 mg; 30 mmol) to 15 mL of anhydrous methanol. Methyl mercaptoacetate (1.9 g; 18 mmol) was then added. The reaction solution was cooled to 0°C and methyl 2-chloroacrylate (2.1 g; 17.4 mmol) was added slowly and dropwise. The reaction mixture was stirred at room temperature overnight. After the reaction was complete, the mixture was cooled to 0°C again and the reaction was quenched with 4 M aqueous hydrochloric acid (~5 mL). Water was added and extracted twice with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2.0 g (70% yield) of brown oil, which solidified to a solid product after drying. The product could be used for subsequent reactions without further purification. The product was characterized as follows: LCMS m/z [M-H]-, retention time tR = 4.12 min, purity (UV/MS) 98/20; GCMS m/z 158 (M+), retention time tR = 4.52 min; 1H NMR (CDCl3, 400 MHz) δ 9.56 (br s, 1H, OH), 7.37 (d, 1H, J = 5.2 Hz, thiophene H), 6.74 (d, 1H, J = 5.2 Hz, thiophene H), 3.89 (s, 3H, OMe). | [References]
[1] Pesticide Science, 1996, vol. 48, # 4, p. 351 - 358
[2] Patent: WO2008/48648, 2008, A2. Location in patent: Page/Page column 70
[3] Helvetica Chimica Acta, 2002, vol. 85, # 12, p. 4485 - 4517
[4] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 20, p. 4333 - 4340
[5] Patent: US7452730, 2008, B2 |
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