162760
2-Naphthylacetonitrile
97%
Synonym(s):
2-Naphthaleneacetonitrile
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About This Item
Linear Formula:
C10H7CH2CN
CAS Number:
Molecular Weight:
167.21
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Assay
97%
bp
303 °C (lit.)
mp
82-84 °C (lit.)
density
1.092 g/mL at 25 °C (lit.)
SMILES string
N#CCc1ccc2ccccc2c1
InChI
1S/C12H9N/c13-8-7-10-5-6-11-3-1-2-4-12(11)9-10/h1-6,9H,7H2
InChI key
LPCWDVLDJVZIHA-UHFFFAOYSA-N
General description
2-Naphthylacetonitrile undergoes three-component coupling with benzyne and DMF to yield coumarins.
Application
2-Naphthylacetonitrile was used as starting reagent in the synthesis of 2-(1-cyano-1-(2-naphthyl))methylidene-3-phenyl-thiazolidine-4,5-dione.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral
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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Hiroto Yoshida et al.
Chemical communications (Cambridge, England), 47(30), 8512-8514 (2011-05-25)
ortho-Quinone methides, arising from a formal [2+2] cycloaddition between arynes and DMF, were found to facilely undergo a [4+2] cycloaddition with ester enolates or ketenimine anions to produce diverse coumarins in a straightforward manner.
Uwe Albrecht et al.
Bioorganic & medicinal chemistry, 13(14), 4402-4407 (2005-05-21)
2-Alkylidenethiazolidine-4,5-diones were prepared by novel one-pot cyclizations of arylacetonitriles with isothiocyanates and ethyl 2-chloro-2-oxoacetate. The products show antibiotic activity against the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus.
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