| Identification | More | [Name]
1-Naphthylacetamide | [CAS]
86-86-2 | [Synonyms]
1-NAPHTHALENEACETAMIDE
1-NAPHTHYLACETAMIDE
2-(1-NAPHTHYL)ACETAMIDE
ALPHA-NAPHTHALENEACETAMIDE
ALPHA-NAPHTHYLENE-ACETAMIDE
AMID-THIN W/ROOTONE
NAAM
N-ACETYL-1-NAPHTHYLAMINE
NAD
ROOTONE(R)
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
amidkyseliny1-naftyloctove
Amid-Thin | [EINECS(EC#)]
201-704-2 | [Molecular Formula]
C12H11NO | [MDL Number]
MFCD00004047 | [Molecular Weight]
185.22 | [MOL File]
86-86-2.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,C,F | [Risk Statements ]
R22:Harmful if swallowed.
R41:Risk of serious damage to eyes.
R34:Causes burns.
R11:Highly Flammable. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection .
S24/25:Avoid contact with skin and eyes .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S16:Keep away from sources of ignition-No smoking . | [WGK Germany ]
3
| [RTECS ]
QJ0590000
| [TSCA ]
Yes | [HS Code ]
29242990 | [Hazardous Substances Data]
86-86-2(Hazardous Substances Data) |
| Hazard Information | Back Directory | [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 thinning
fruit sets in apples and pear. Not currently registered for
use in EU countries (pending). Registered for use in
the U.S. | [Trade name]
AMACTONE®; AMID-THIN W®;
FRUITONE®; ROOTONE® (component, with
Indole-3-butyric acid and 1-Naphthaleneacetic acid);
ROSETONE®; TRANSPLANTONE® (component, with
1-Naphthaleneacetic acid) | [Synthesis]
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 |
|
|