| Identification | More | [Name]
Mecarbinate | [CAS]
15574-49-9 | [Synonyms]
1,2-DIMETHYL-5-HYDROXYINDOLE-2-CARBOXYLATE ETHYL
AKOS BBS-00002907
AKOS BC-3007
AURORA 23327
ETHYL 1,2-DIMETHYL-5-HYDROXYINDOLE-3-CARBOXYLATE
ETHYL 5-HYDROXY-1,2-DIMETHYL-1H-INDOLE-3-CARBOXYLATE
IFLAB-BB F1920-0014
5-hydroxy-1,2-dimethyl-1h-indole-3-carboxylicaciethylester
ba2676
dimecarbin
dimecarbine
dimekarbin
1,2-Dimethyl-5-Hydroxyindole-3-Carboxylate Ethyl
ETHYL5-HYDROXY-1,2DIMETHYLINDOLE-3-CARBOXYLATE
5-hydroxy-1,2-dimethyl-1H-Indole-3-carboxylic acid ethyl ester
5-OH-1,2-di-Me-Indole-3-carboxylic acid ester
Ethyl 1,2-dimethyl-5-hydroxyindole-2-carboxylate
Mecarbinate
1,2-DIMETHYL-5-HYDROXY-3-INDOLECARBOXYLIC ACID ETHYL ESTER
1,2-Dimethyl-3-carbetoxy-5-oxyindol | [EINECS(EC#)]
605-026-1 | [Molecular Formula]
C13H15NO3 | [MDL Number]
MFCD00451373 | [Molecular Weight]
233.26 | [MOL File]
15574-49-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
210.0 to 214.0 °C | [Boiling point ]
399.8±37.0 °C(Predicted) | [density ]
1.20±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
≥ 7.1mg/mL in DMSO | [form ]
powder to crystal | [pka]
9.26±0.40(Predicted) | [color ]
White to Orange to Green | [Detection Methods]
HPLC,NMR | [InChI]
InChI=1S/C13H15NO3/c1-4-17-13(16)12-8(2)14(3)11-6-5-9(15)7-10(11)12/h5-7,15H,4H2,1-3H3 | [InChIKey]
YTBNTDMBGXAOCG-UHFFFAOYSA-N | [SMILES]
N1(C)C2=C(C=C(O)C=C2)C(C(OCC)=O)=C1C | [CAS DataBase Reference]
15574-49-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [RTECS ]
NL6003600 | [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Toxicity]
mouse,LD,intraperitoneal,> 10gm/kg (10000mg/kg),Toksikologicheskii Vestnik. Vol. (1), Pg. 29, 1994. |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white solid | [Uses]
Mecarbinate is a chemical intermediate of arbidol hydrochloride. | [Synthesis]
Synthesis: To a 250 ml round bottom flask was added p-benzoquinone (11.89 g, 0.11 mol) and 120 ml acetone and stirred well. Subsequently, a solution containing 0.11 mol of ethyl 3-(methylamino)-2-butenoate was added slowly and dropwise. The reaction mixture was stirred at 30°C for 2 hours. After completion of the reaction, the solvent was removed by distillation. The crude product was purified by recrystallization using acetone. | [References]
[1] Patent: CN106946761, 2017, A. Location in patent: Paragraph 0047-0050
[2] Journal of Organic Chemistry, 1959, vol. 24, p. 1750
[3] Patent: US2852527, 1956,
[4] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2777,2780; engl. Ausg. S. 2742, 2744
[5] Tetrahedron Letters, 2009, vol. 50, # 28, p. 4182 - 4184 |
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