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1-NAPHTHALENEACETAMIDE

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CAS:86-86-2
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CAS:86-86-2
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  • 1-Naphthaleneacetamide
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  • 2026-03-12
  • CAS:86-86-2
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  • 1-NAPHTHALENEACETAMIDE
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  • 2025-09-25
  • CAS:86-86-2
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  • Purity: 99%
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1-NAPHTHALENEACETAMIDE Basic information
Product Name:1-NAPHTHALENEACETAMIDE
Synonyms:1-nanphthylacetamide;1-naphthaleneacetamide(nad);1-Naphthylamine, N-acetyl-;2-(1-naphthyl)ethanamide;alpha-naaamide;alpha-Naphthaleneacetic acid amide;alpha-Naphthylacetamide;Amid kyseliny 1-naftyloctove
CAS:86-86-2
MF:C12H11NO
MW:185.22
EINECS:201-704-2
Product Categories:Auxins;Biochemistry;Plant Growth Regulators;PLANT GROWTH REGULATOR;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Plant growth regulator, intermediates;Alpha sort;N;NA - NI;N-PAlphabetic;Pesticides&Metabolites
Mol File:86-86-2.mol
1-NAPHTHALENEACETAMIDE Structure
1-NAPHTHALENEACETAMIDE Chemical Properties
Melting point 180-183 °C (lit.)
Boiling point 319.45°C (rough estimate)
density 1.0936 (rough estimate)
refractive index 1.5300 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
pka16.10±0.40(Predicted)
color White to Off-White
BRN 1945547
Major Applicationagriculture
environmental
InChI1S/C12H11NO/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H2,13,14)
InChIKeyXFNJVKMNNVCYEK-UHFFFAOYSA-N
SMILESNC(=O)Cc1cccc2ccccc12
CAS DataBase Reference86-86-2(CAS DataBase Reference)
NIST Chemistry Reference1-Naphthaleneacetamide(86-86-2)
EPA Substance Registry System1-Naphthaleneacetamide (86-86-2)
Safety Information
Hazard Codes Xn,C,F
Risk Statements 22-41-34-11
Safety Statements 26-39-24/25-45-36/37/39-16
WGK Germany 3
RTECS QJ0590000
TSCA TSCA listed
HS Code 29242990
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Aquatic Chronic 3
Eye Dam. 1
Repr. 2
MSDS Information
ProviderLanguage
NAA Amide English
SigmaAldrich English
ACROS English
ALFA English
1-NAPHTHALENEACETAMIDE Usage And Synthesis
Chemical Propertieswhite to cream powder
Uses1-Naphthylacetamide (cas# 86-86-2) is a compound useful in organic synthesis.
DefinitionChEBI: 1-naphthaleneacetamide is a member of the class of naphthalenes that is naphthalene which is substituted by a 2-amino-2-oxoethyl group at position 1. It is a synthetic auxin that is widely used in agriculture to promote the growth of numerous fruits, for root cuttings and as a fruit thinning agent. It has a role as a synthetic auxin. It is a member of naphthalenes and a primary carboxamide.
Agricultural UsesPlant growth regulator: 1-Naphthaleneacetamide is an agent for thinning fruit sets in apples and pear. Not currently registered for use in EU countries (pending). Registered for use in the U.S.
Trade nameAMACTONE®; AMID-THIN W®; FRUITONE®; ROOTONE® (component, with Indole-3-butyric acid and 1-Naphthaleneacetic acid); ROSETONE®; TRANSPLANTONE® (component, with 1-Naphthaleneacetic acid)
Synthesis
2-(1-NAPHTHYL)ETHANOYL CHLORIDE

5121-00-6

1-NAPHTHALENEACETAMIDE

86-86-2

The general procedure for the synthesis of 1-naphthaleneacetamide from naphthalen-1-ylacetyl chloride was as follows: 1-naphthaleneacetic acid (93.5 mg, 0.50 mmol) was dissolved in dichloromethane (0.8 mL), a catalytic amount of DMF was added, followed by the slow, dropwise addition of oxalyl chloride (135.6 mg, 1.00 mmol, 2.00 equiv.) under stirring. The reaction mixture was stirred at room temperature for 15 minutes. Upon completion of the reaction, the solution was concentrated under vacuum and the resulting residue was dissolved in tetrahydrofuran (0.8 mL). Ammonia (28%, 450.4 mg, 7.50 mmol, 15.0 eq.) was added to this solution at 0 °C, after which the reaction mixture was transferred to room temperature and stirred for 10 min. At the end of the reaction, the solution was concentrated in vacuum and purified by silica gel column chromatography (eluent: chloroform/methanol, 10/1, Rf = 0.50) to afford the target product 1-naphthaleneacetamide (Y-015) as a white solid in 72% yield.

References[1] Patent: JP2015/89885, 2015, A. Location in patent: Paragraph 0146; 0147; 0162-0164
[2] Chimica e l'Industria (Milan, Italy), 1955, vol. 37, p. 857,860
[3] Bulletin de la Societe Chimique de France, 1965, p. 861 - 868
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 10, p. 3366 - 3376
[5] Chemistry Letters, 2015, vol. 44, # 5, p. 621 - 623
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