ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE Chemical Properties

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

pka

0.53±0.20(Predicted)

form 

Fine Crystalline Powder

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 Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

36/37/39-26-22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE Usage And Synthesis

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

ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE(4506-71-2)Related Product Information

• ETHYL 2-AMINO-4-METHYLTHIOPHENE-3-CARBOXYLATE
• 2,5-Dithienylpyrrole
• 3,5-Dibromodithieno[3,2-b:2',3'-d]thiophene
• 2-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER
• ETHYL 3-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-2-CARBOXYLATE,3-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER
• 1-Benzothiophene-3-carboxylic acid