N1909

Sigma-Aldrich

1-Naphthoic acid

96%

Synonym(s):
1-Naphthalenecarboxylic acid
Linear Formula:
C10H7CO2H
CAS Number:
Molecular Weight:
172.18
Beilstein/REAXYS Number:
1908896
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

assay

96%

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.

Packaging

25 g in poly bottle

Other Notes

Remainder 2-naphthoic acid

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26-36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

One-pot transition-metal-free synthesis of Weinreb amides directly from carboxylic acids
Niu T, et al.
Synthesis, 46, 320-330 (2014)
Xiao Luo et al.
Nature communications, 11(1), 28-28 (2020-01-09)
The mechanisms of triplet energy transfer across the inorganic nanocrystal/organic molecule interface remain poorly understood. Many seemingly contradictory results have been reported, mainly because of the complicated trap states characteristic of inorganic semiconductors and the ill-defined relative energetics between semiconductors...
Regioselective synthesis of isocoumarins by ruthenium-catalyzed aerobic oxidative cyclization of aromatic acids with alkynes
Kirana CR, et al.
Chemical Communications (Cambridge, England), 48, 2030-2032 (2012)
The Metal-Ammonia Reduction of 1-Naphthoic Acid
Rabideau PW, et al.
Synthetic Communications, 10, 627-632 (1980)
Debajyoti Ghosal et al.
FEMS microbiology letters, 313(2), 103-110 (2010-10-23)
The present study describes the assimilation of phenanthrene by an aerobic bacterium, Ochrobactrum sp. strain PWTJD, isolated from municipal waste-contaminated soil sample utilizing phenanthrene as a sole source of carbon and energy. The isolate was identified as Ochrobactrum sp. based...

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