2-[(diphenylmethylidene)amino]acetonitrile

• ChemBase ID: 150665
• Molecular Formular: C15H12N2
• Molecular Mass: 220.26918
• Monoisotopic Mass: 220.10004839
• SMILES: c1ccc(cc1)/C(=N/CC#N)/c1ccccc1
• Canonical SMILES: N#CC/N=C(/c1ccccc1)\c1ccccc1
• InChI: InChI=1S/C15H12N2/c16-11-12-17-15(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10H,12H2
• InChIKey: VRLJFRODHVSTIK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(diphenylmethylidene)amino]acetonitrile
• IUPAC Traditional name: 2-[(diphenylmethylidene)amino]acetonitrile
• Synonyms: N-(Diphenylmethylene)aminoacetonitrile; 2-((Diphenylmethylene)amino)acetonitrile; N-(二苯亚甲基)氨基乙腈

Database IDs

• CAS Number: 70591-20-7
• MDL Number: MFCD00009970
• PubChem SID: 162244826; 24855228
• PubChem CID: 612957

CALCULATED PROPERTIES

• Acid pKa: 11.921642
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.2028008
• LogD (pH = 7.4): 3.2048295
• Log P: 3.2048686
• Molar Refractivity: 68.6512 cm^3
• Polarizability: 26.032303 Å^3
• Polar Surface Area: 36.15 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 84-85 °C(lit.)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 95+%; 98%
• Linear Formula: (C6H5)2C=NCH2CN

DETAILS

Sigma Aldrich - 252654

Packaging
5 g in glass bottle
Application
Synthon for a variety of amino acids via phase-transfer-catalyzed alkylation and hydrolysis.1
Used in a key enantiodifferentiating step in a concise synthesis of dehydrocoronamic acid ethyl ester. Also used in a synthesis of γ-amino acid esters.