ETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATE Chemical Properties

Melting point:

163 °C

Boiling point:

481.4±30.0 °C(Predicted)

Density 

1.225±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

pka

14?+-.0.30(Predicted)

form 

powder

Appearance

Off-white to light brown Solid

BRN 

281129

InChI

InChI=1S/C18H17NO3/c1-2-21-18(20)17-11-14-10-15(8-9-16(14)19-17)22-12-13-6-4-3-5-7-13/h3-11,19H,2,12H2,1H3

InChIKey

DCIFXYFKVKDOLL-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(OCC3=CC=CC=C3)C=C2)C=C1C(OCC)=O

CAS DataBase Reference

37033-95-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

Storage Class

13 - Non Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

ETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATE Usage And Synthesis

Uses

Reactant for preparation of indolyl ethanones as indoleamine 2,3-dioxygenase inhibitors 1 Reactant for preparation of histamine H3 receptor inverse agonists 2 Reactant for preparation of PPAR-γ binding agents with potential application to the treatment of osteoporosis 3 Reactant for preparation of Nonpeptide glycoprotein IIB/IIIA inhibitors 4

Synthesis

1.1) 80 ml of sulfuric acid was dissolved in 450 mL of ethanol and cooled to 0??C;

1.2) 359 mmol (90 g) of 4-benzyloxyphenylhydrazine hydrochloride was added to the mixture of 1.1) to form a suspension;

1.3) 43.9 mL of ethyl pyruvate was added to 90 mL of anhydrous ethanol;

1.4) the suspension of step 1.2) was added to step 1.3), magnetically stirred for 2h, warmed up to 45??C, and held to react for 16h;

1.5) the solution of step 1.4) was cooled to room temperature, 200mL of ethanol was added, filtered, and the solids were washed with ethanol, cyclohexane, and water in turn, dried, and yielded compound 3, i.e., 5-benzyloxyindole-2-carboxylic acid ethyl ester, in 72% yield ( 76.3g).

ETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATE(37033-95-7)Related Product Information

• 5-Hydroxy-2-methylindole
• Indole-2-carboxylic acid
• Methyl 2-pyrrolecarboxylate
• Indole-2-carboxaldehyde
• 5-Benzyloxyindole
• 1H-INDOL-2-YLMETHANOL
• 5-Hydroxyindole-2-carboxylic acid
• Methyl indole-2-carboxylate
• 5-Ethoxyindole
• 5-METHOXY-2-METHYLINDOLE
• Ethyl pyrrole-2-carboxylate
• 5-BENZYLOXYINDOLE-2-CARBOXYLIC ACID
• Ethyl indole-2-carboxylate
• ETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATE
• ETHYL 5-METHOXYINDOLE-2-CARBOXYLATE
• Ethyl 5-hydroxyindole-2-carboxylate
• 5-METHOXYINDOLE-2-CARBOXYLIC ACID
• 5-ETHOXY-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER