252654
N-(Diphenylmethylene)aminoacetonitrile
98%
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About This Item
Linear Formula:
(C6H5)2C=NCH2CN
CAS Number:
Molecular Weight:
220.27
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
Assay
98%
mp
84-85 °C (lit.)
solubility
95% ethanol: soluble 50 mg/mL, clear, colorless to faintly yellow
storage temp.
2-8°C
SMILES string
N#CC\N=C(\c1ccccc1)c2ccccc2
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
InChI key
VRLJFRODHVSTIK-UHFFFAOYSA-N
General description
N-(Diphenylmethylene)aminoacetonitrile is a synthon for a variety of amino acids via phase-transfer-catalyzed alkylation and hydrolysis.
Application
N-(Diphenylmethylene)aminoacetonitrile has been used in:
- synthesis of ring-substituted phenylalanine amides and o-carboranylalanine, a potential analog of phenylalanine
- a key enantiodifferentiating step in concise synthesis of dehydrocoronamic acid ethyl ester
- synthesis of γ-amino acid esters
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Tetrahedron Letters, 4625-4625 (1978)
A general, convenient way to carborane-containing amino acids for boron neutron capture therapy.
Wyzlic IM and Soloway AH.
Tetrahedron Letters, 33(49), 7489-7490 (1992)
Synthesis, 918-918 (2007)
J J Knittel et al.
Peptide research, 3(4), 176-181 (1990-07-01)
A convenient approach to the synthesis of ring-substituted phenylalanine amides is described. Phase transfer alkylation of N-(diphenylmethylene)amino acetonitrile or N-(diphenylmethylene)glycine ethyl ester provides alpha-substituted imines 2 and 6. After acid hydrolysis and esterification, resolution with alpha-chymotrypsin provided 3'-substituted phenylalanine analogs
Tetrahedron Letters, 48, 945-945 (2007)
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