| Identification | More | [Name]
ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE | [CAS]
4506-71-2 | [Synonyms]
1-BENZOTHIOPHENE-3-CARBOXYLIC ACID, 2-AMINO-4,5,6,7-TETRAHYDRO-, ETHYL ESTER
2-AMINO-3-CARBETHOXY-4,5-TETRAMETHYLENETHIOPHENE
2-AMINO-3-ETHOXYCARBONYL-4,5-TETRAMETHYLENETHIOPHENE
2-AMINO-3-ETHOXYCARBONYL-THIENOCYCLOHEXANE
2-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER
AKOS 92528
AKOS B000472
AKOS BBB/012
AKOS BBS-00004584
AKOS MSC-0429
ART-CHEM-BB B000472
ASISCHEM N39354
CBI-BB ZERO/004885
ETHYL 2-AMINO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE
ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE
IFLAB-BB F1386-0048
TIMTEC-BB SBB000654
Ethyl-2-Amino-4,5,6,7-Tetrahydrobenzene(B)Thiophene-3-Carboxlate
Ethyl 2-amino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylate
2-Amino-3-carbethoxy-4,5-tetramethylenethiophene, GC 99% | [EINECS(EC#)]
224-823-1 | [Molecular Formula]
C11H15NO2S | [MDL Number]
MFCD00005862 | [Molecular Weight]
225.31 | [MOL File]
4506-71-2.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow fine crystalline powder | [Melting point ]
114-116 °C(lit.) | [Boiling point ]
407.5±45.0 °C(Predicted) | [density ]
1.235±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [form ]
Fine Crystalline Powder | [pka]
0.53±0.20(Predicted) | [color ]
Yellow | [InChI]
InChI=1S/C11H15NO2S/c1-2-14-11(13)9-7-5-3-4-6-8(7)15-10(9)12/h2-6,12H2,1H3 | [InChIKey]
CDYVTVLXEWMCHU-UHFFFAOYSA-N | [SMILES]
C12CCCCC=1C(C(OCC)=O)=C(N)S2 | [CAS DataBase Reference]
4506-71-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Sulfur-->Ethyl cyanoacetate-->Piperidine-->Cyclohexanone-->Ethanol-->Morpholine | [Preparation Products]
4-((3-(ethoxycarbonyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)amino)-4-oxobutanoic acid-->[1]Benzothieno[2,3-d]pyrimidin-4(1H)-one, 2,3,5,6,7,8-hexahydro-3-(3-methoxyphenyl)-2-thioxo--->[1]Benzothieno[2,3-d]pyrimidin-4(1H)-one, 2,3,5,6,7,8-hexahydro-3-(2-methoxyphenyl)-2-thioxo- |
| Hazard Information | Back Directory | [Chemical Properties]
yellow fine crystalline powder | [Uses]
Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate was used in the preparation of:
- thienopyrimidine derivatives
- azo dyes
- N-(3-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)-2-aryl hydrazono-3-oxobutanamide derivatives
- tetrahydrobenzo[b]thiophene dyes
| [Synthesis]
GENERAL METHOD: Cyclohexanone (1 mmol), ethyl cyanoacetate (1 eq.), morpholine (1 eq.), and elemental sulfur (1 eq.) were dissolved in 5 mL of ethanol at 0°C and the reaction was stirred overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was extracted three times with ethyl acetate, the organic layers were combined and dried over anhydrous sodium sulfate. After drying, the solvent was again evaporated under reduced pressure. The final product was obtained as purified ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate by recrystallization from a mixed methanol/water solvent as a yellow crystalline solid. Yield: 98%, melting point 134-135 °C. 1H NMR (400 MHz, DMSO-d6) δ 1.20 (3H, t, J = 7.1 Hz, CH3), 1.60-1.65 (4H, m, CH2), 2.35-2.37 (2H, m, CH2), 2.55-2.56 (2H, m, CH2), 4.11 (2H , q, J = 7.3 Hz, OCH2CH3), 7.14 (2H, br s, NH2).13C NMR (100 MHz, DMSO-d6) δ 14.18 (CH3), 22.34 (CH2), 22.76 (CH2), 23.88 (CH2), 26.49 (CH2), 58.71 (OCH2), 103.16 (Cq), 115.96 (Cq), 131.50 (Cq), 163.19 (Cq), 165.32 (C=O). | [References]
[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4228 - 4240
[2] Synthetic Communications, 2010, vol. 40, # 14, p. 2067 - 2074
[3] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 619 - 634
[4] Journal of Sulfur Chemistry, 2014, vol. 35, # 3, p. 261 - 269
[5] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3171 - 3172 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE(4506-71-2)MS
ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE(4506-71-2)1HNMR
ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE(4506-71-2)13CNMR
ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE(4506-71-2)IR1
ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE(4506-71-2)IR2
ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE(4506-71-2)Raman
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