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Merck
CN

162760

2-Naphthylacetonitrile

97%

Synonym(s):

2-Naphthaleneacetonitrile

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About This Item

Linear Formula:
C10H7CH2CN
CAS Number:
Molecular Weight:
167.21
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
231-352-5
MDL number:
Assay:
97%
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InChI key

LPCWDVLDJVZIHA-UHFFFAOYSA-N

InChI

1S/C12H9N/c13-8-7-10-5-6-11-3-1-2-4-12(11)9-10/h1-6,9H,7H2

SMILES string

N#CCc1ccc2ccccc2c1

assay

97%

bp

303 °C (lit.)

mp

82-84 °C (lit.)

density

1.092 g/mL at 25 °C (lit.)

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.

pictograms

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Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

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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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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