ethyl 5-(benzyloxy)-1H-indole-2-carboxylate

• ChemBase ID: 35992
• Molecular Formular: C18H17NO3
• Molecular Mass: 295.33248
• Monoisotopic Mass: 295.12084341
• SMILES: c1(ccc2[nH]c(cc2c1)C(=O)OCC)OCc1ccccc1
• Canonical SMILES: CCOC(=O)c1[nH]c2c(c1)cc(cc2)OCc1ccccc1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 5-(benzyloxy)-1H-indole-2-carboxylate
• IUPAC Traditional name: ethyl 5-(benzyloxy)-1H-indole-2-carboxylate
• Synonyms: NSC 30931; 5-Benzyloxy-2-carbethoxyindole; 5-Benzyloxyindole-2-carboxylic acid ethyl ester; Ethyl 5-(benzyloxy)-1H-indole-2-carboxylate; 5-Benzyloxyindole-2-carboxylic acid ethyl ester; Ethyl 5-benzyloxyindole-2-carboxylate; 5-苄氧基吲哚-2-羧酸乙酯; 5-苄氧基吲哚-2-甲酸乙酯

Database IDs

• CAS Number: 37033-95-7
• EC Number: 253-322-0
• MDL Number: MFCD00022702
• Beilstein Number: 281129
• PubChem SID: 24891559; 160999299
• PubChem CID: 95721

CALCULATED PROPERTIES

• Acid pKa: 11.566078
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.9190953
• LogD (pH = 7.4): 3.9190698
• Log P: 3.9190958
• Molar Refractivity: 84.8717 cm^3
• Polarizability: 33.92791 Å^3
• Polar Surface Area: 51.32 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 160-165°C; 162-164°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C18H17NO3

DETAILS

Sigma Aldrich - B1126

Packaging
10 g in glass bottle
Application

• Reactant for preparation of indolyl ethanones as indoleamine 2,3-dioxygenase inhibitors1
• Reactant for preparation of histamine H3 receptor inverse agonists2
• Reactant for preparation of PPAR-γ binding agents with potential application to the treatment of osteoporosis3
• Reactant for preparation of Nonpeptide glycoprotein IIB/IIIA inhibitors4