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N1909

Sigma-Aldrich

1-Naphthoic acid

96%

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Synonym(s):
1-Naphthalenecarboxylic acid
Linear Formula:
C10H7CO2H
CAS Number:
86-55-5
Molecular Weight:
172.18
Beilstein:
1908896
EC Number:
201-681-9
MDL number:
MFCD00004007
PubChem Substance ID:
24897538
NACRES:
NA.22

Assay

96%

form

powder

bp

300 °C (lit.)

mp

157-160 °C (lit.)

SMILES string

OC(=O)c1cccc2ccccc12

InChI

1S/C11H8O2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H,12,13)

InChI key

LNETULKMXZVUST-UHFFFAOYSA-N

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Application

1-Naphthoic acid can be used as a reactant to prepare:
  • Perinaphthenones by dehydrative annulation with alkynes in the presence of rhodium catalyst.
  • Isocoumarin derivatives by reacting with 2-butyne via aerobic oxidative cyclization using Rh catalyst.
  • N-Methoxy-N-methyl-1-naphthalenecarboxamide (Weinreb amide) by reacting with N,O-dimethylhydroxylamine and phosphorus trichloride.
  • 1,4-Dihydro-1-naphthalenecarboxylic acid by Birch reduction.

Other Notes

Remainder 2-naphthoic acid

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

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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S Chandra et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 74(3), 704-713 (2009-09-02)
The Fourier transform infrared gas phase spectrum of Naphthoic acid (NA) was recorded in the region 4000-400 cm(-1). The Fourier transform Raman spectrum and Fourier transform IR spectra of NA were recorded in solid phase. Quantum chemical calculations of energies
Mutual activation: Suzuki-Miyaura coupling through direct cleavage of the sp2 C-O bond of naphtholate.
Da-Gang Yu et al.
Angewandte Chemie (International ed. in English), 50(31), 7097-7100 (2011-06-29)
Qunfei Zhao et al.
Chemistry & biology, 15(7), 693-705 (2008-07-19)
Azinomycin B is a complex natural product containing densely assembled functionalities with potent antitumor activity. Cloning and sequence analysis of the azi gene cluster revealed an iterative type I polyketide synthase (PKS) gene, five nonribosomal peptide synthetases (NRPSs) genes and
Rajesh Sunasee et al.
The Journal of organic chemistry, 73(20), 8016-8020 (2008-09-26)
A method is described for converting tert-butyl benzoates or tert-butyl 1-naphthoates into derivatives having an alkyl or substituted alkyl group in a 1,4-relationship to an alkyl, aryl, alkenyl, or alkynyl group. Key steps in the sequence are (i) addition of
Josef B G Gluyas et al.
Organic & biomolecular chemistry, 10(34), 6914-6929 (2012-07-21)
Silicon chemistry offers the potential to tune the effects of biologically active organic molecules. Subtle changes in the molecular backbone caused by the exchange of a carbon atom for a silicon atom (sila-substitution) can significantly alter the biological properties. In
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