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N1909

Sigma-Aldrich

1-Naphthoic acid

96%

Synonym(s):

1-Naphthalenecarboxylic acid

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About This Item

Linear Formula:
C10H7CO2H
CAS Number:
86-55-5
Molecular Weight:
172.18
Beilstein/REAXYS Number:
1908896
EC Number:
201-681-9
MDL number:
MFCD00004007
UNSPSC Code:
12352100
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

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Synthesis of perinaphthenones through rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with alkynes
Fukuyama T, et al.
Organic & Biomolecular Chemistry, 16, 7583-7587 (2018)
Hiromasa Uchiyama et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 43(1-2), 71-77 (2011-04-06)
Spray-dried particles (SDPs) with indomethacin (IND) and alpha-glycosyl transferase-treated stevia (Stevia-G) indicated extremely high dissolution rates and apparent solubility compared to particles of a ground mixture and a physical mixture of IND/Stevia-G. The apparent solubility of IND from SDPs was
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
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)
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