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Merck
CN

252654

N-(Diphenylmethylene)aminoacetonitrile

98%

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About This Item

Linear Formula:
(C6H5)2C=NCH2CN
CAS Number:
70591-20-7
Molecular Weight:
220.27
UNSPSC Code:
12352100
PubChem Substance ID:
24855228
MDL number:
MFCD00009970

Key Documents

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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

SMILES string

N#CC\N=C(\c1ccccc1)c2ccccc2

InChI key

VRLJFRODHVSTIK-UHFFFAOYSA-N

assay

98%

mp

84-85 °C (lit.)

solubility

95% ethanol: soluble 50 mg/mL, clear, colorless to faintly yellow

storage temp.

2-8°C

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

pictograms

Exclamation mark
GHS07

signalword

Warning

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBH1844V
32697LJV
32697LJ
08429MH
10810LH

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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
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)
Tetrahedron Letters, 4625-4625 (1978)
Synthesis, 918-918 (2007)
Tetrahedron Letters, 48, 945-945 (2007)

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