1-NAPHTHALENEACETAMIDE CAS 86-86-2
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 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) |
| pka | 16.10±0.40(Predicted) |
| color | White to Off-White |
| BRN | 1945547 |
| Major Application | agriculture environmental |
| InChI | 1S/C12H11NO/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H2,13,14) |
| InChIKey | XFNJVKMNNVCYEK-UHFFFAOYSA-N |
| SMILES | NC(=O)Cc1cccc2ccccc12 |
| CAS DataBase Reference | 86-86-2(CAS DataBase Reference) |
| NIST Chemistry Reference | 1-Naphthaleneacetamide(86-86-2) |
| EPA Substance Registry System | 1-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 Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Chronic 3 Eye Dam. 1 Repr. 2 |
| Chemical Properties | white to cream powder |
| Uses | 1-Naphthylacetamide (cas# 86-86-2) is a compound useful in organic synthesis. |
| Definition | ChEBI: 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 Uses | Plant growth regulator: 1-Naphthaleneacetamide is an agent for thinningfruit sets in apples and pear. Not currently registered foruse in EU countries (pending). Registered for use inthe U.S. |
| Trade name | AMACTONE®; AMID-THIN W®;FRUITONE®; ROOTONE® (component, withIndole-3-butyric acid and 1-Naphthaleneacetic acid);ROSETONE®; TRANSPLANTONE® (component, with1-Naphthaleneacetic acid) |
| Synthesis | 5121-00-6 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 |
1-NAPHTHALENEACETAMIDE Preparation Products And Raw materials
| Raw materials | 1-Naphthylacetonitrile-->2-(1-NAPHTHYL)ETHANOYL CHLORIDE-->1-NAPHTHOYLFORMIC ACID-->1'-Acetonaphthone-->1-Naphthaleneacetic acid-->1-Naphthol-->Chloroacetamide-->Tetrahydrofuran-->Ammonium hydroxide |
