2-(5-methoxy-1H-indol-3-yl)acetonitrile

• ChemBase ID: 16373
• Molecular Formular: C11H10N2O
• Molecular Mass: 186.2099
• Monoisotopic Mass: 186.07931295
• SMILES: [nH]1cc(c2cc(ccc12)OC)CC#N
• Canonical SMILES: N#CCc1c[nH]c2c1cc(OC)cc2
• InChI: InChI=1S/C11H10N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4H2,1H3
• InChIKey: ZBQCXEREMRGOCO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(5-methoxy-1H-indol-3-yl)acetonitrile
• IUPAC Traditional name: 2-(5-methoxy-1H-indol-3-yl)acetonitrile
• Synonyms: 5-Methoxyindole-3-acetonitrile; 3-(Cyanomethyl)-5-methoxy-1H-indole; (5-Methoxy-1H-indol-3-yl)acetonitrile; 3-(Cyanomethyl)-5-methoxyindole; 5-Methoxy-3-indolylacetonitrile; 5-甲氧基吲哚-3-乙腈

Database IDs

• CAS Number: 2436-17-1
• MDL Number: MFCD02094163
• PubChem SID: 24880382; 160979680
• PubChem CID: 3564783

CALCULATED PROPERTIES

• Acid pKa: 14.361561
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.6100338
• LogD (pH = 7.4): 1.6100336
• Log P: 1.6100338
• Molar Refractivity: 53.8946 cm^3
• Polarizability: 21.585411 Å^3
• Polar Surface Area: 48.81 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 65-69 °C(lit.); 65-69°C

Safety Information

• Storage Warning: IRRITANT; Irritant/Light Sensitive/Keep Cold/Store under Argon
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 97%
• Empirical Formula (Hill Notation): C11H10N2O

DETAILS

Sigma Aldrich - 567655

Packaging
5 g in glass bottle
Application
Reactant for preparation of (-)- and (+)-debromoflustramine B and its analogues as selective butyrylcholinesterase inhibitors1Reactant for preparation of carboline analogs as potent MAPKAP-K2 inhibitors2Reactant for preparation of indole-N-acetic acid derivatives as aldose reductase inhibitors for diabetic complications treatment3Reactant for preparation of debromoflustramine B and labeled Me(3a)-13C-physostigmine4Reactant for preparation of physostigmine and physovenine5Reactant for preparation of phenethyl substituted indole derivatives as melatoninergic agonists and antagonists6