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Basic Information
CAS No.: 15299-99-7
Name: Napropamide
Molecular Structure:
Molecular Structure of 15299-99-7 (Napropamide)
Formula: C17H21NO2
Molecular Weight: 271.359
Synonyms: Propionamide,N,N-diethyl-2-(1-naphthyloxy)- (8CI);(?à)-Devrinol;2-(a-Naphthoxy)-N,N-diethylpropionamide;Devrinol;N,N-Diethyl-2-(1-naphthalenyloxy)propionamide;N,N-Diethyl-2-(1-naphthyloxy)propanamide;Napropamid;Napropamide;R 7465;Racemic devrinol;
EINECS: 239-333-3
Density: 1.08 g/cm3
Melting Point: 73-78 °C(lit.)
Boiling Point: 430.185 °C at 760 mmHg
Flash Point: 213.969 °C
Solubility: 73mg/L(20 oC)
Appearance: light yellow needle-like crystal
PSA: 29.54000
LogP: 3.47550
Synthetic route

Conditions
ConditionsYield
(i), (ii) COCl2, (iii) /BRN= 605268/; Multistep reaction;
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Chemistry

Molecular structure of  Propanamide,N,N-diethyl-2-(1-naphthalenyloxy)- (CAS NO.15299-99-7):

IUPAC Name: N,N-Diethyl-2-naphthalen-1-yloxypropanamide
Molecular Weight: 271.35414 [g/mol]
Molecular Formula: C17H21NO2
XLogP3: 3.4
H-Bond Acceptor: 2
Rotatable Bond Count: 5
Exact Mass: 271.157229
MonoIsotopic Mass: 271.157229
Topological Polar Surface Area: 29.5
Heavy Atom Count: 20
Complexity: 314
Index of Refraction: 1.568
Molar Refractivity: 82.28 cm3
Molar Volume: 251.3 cm3
Surface Tension: 40.6 dyne/cm
Density: 1.079 g/cm3 
Melting Point: 73-78 °C(lit.)
Flash Point: 214 °C 
Storage Temp.: 0-6 °C
Enthalpy of Vaporization: 68.56 kJ/mol
Boiling Point: 430.2 °C at 760 mmHg
Vapour Pressure: 1.32E-07 mmHg at 25 °C 
Canonical SMILES: CCN(CC)C(=O)C(C)OC1=CC=CC2=CC=CC=C21
InChI: InChI=1S/C17H21NO2/c1-4-18(5-2)17(19)13(3)20-16-12-8-10-14-9-6-7-11-15(14)16/h6-13H,4-5H2,1-3H3
InChIKey: WXZVAROIGSFCFJ-UHFFFAOYSA-N
EINECS: 239-333-3
Product Categories: HERBICIDE;Amides;Carbonyl Compounds;Organic Building Blocks;Alphabetic;D;DA - DH

Uses

 Propanamide,N,N-diethyl-2-(1-naphthalenyloxy)- (CAS NO.15299-99-7) is used as selective bud soil treatment agent. It also used for rape, radish and other vegetables, watermelons, peanuts, cotton and other crop fields, removing large crabgrass, goosegrass and other grass weeds and broadleaf weeds.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 skin > 2gm/kg (2000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A292, Pg. 1983,
mouse LD50 intraperitoneal > 1gm/kg (1000mg/kg)   Niigata Igakkai Zasshi. Niigata Medical Journal. Vol. 87, Pg. 289, 1973.
mouse LD50 oral > 5gm/kg (5000mg/kg)   Niigata Igakkai Zasshi. Niigata Medical Journal. Vol. 87, Pg. 289, 1973.
mouse LD50 subcutaneous > 1gm/kg (1000mg/kg)   Niigata Igakkai Zasshi. Niigata Medical Journal. Vol. 87, Pg. 289, 1973.
rabbit LD50 skin 4640mg/kg (4640mg/kg)   Pesticide & Toxic Chemical News. Vol. 8, Pg. 22, 1980.
rat LD50 oral 5gm/kg (5000mg/kg)   "Agricultural Chemicals," Thomson, W.T., 4 vols., Fresno, CA, Thomson Publications, 1976/77 revisionVol. 2, Pg. 59, 1977.
rat LD50 parenteral > 5gm/kg (5000mg/kg)   Defense des Vegetaux. Vol. 26, Pg. 5, 1972.

Safety Profile

WGK Germany: 2
RTECS: UE3600000

Specification

 Propanamide,N,N-diethyl-2-(1-naphthalenyloxy)- (CAS NO.15299-99-7) is also called 2-(1-Naphthoxy)-N,N-diethylpropionamide ; 2-(alpha-Naphthoxy)-N,N-diaethyl-propionsaeureamid ; 2-(alpha-Naphthoxy)-N,N-diaethyl-propionsaeureamid [German] ; 2-(alpha-Naphthoxy)-N,N-diethylpropionamide ; BRN 2217870 ; Caswell No. 590A ; Devrinol ; EPA Pesticide Chemical Code 103001 ; HSDB 6710 ; N,N-Diethyl-2-(1-naphthalenyloxy)propanamide ; N,N-Diethyl-2-(1-naphthalenyloxy)propionamide ; N,N-Diethyl-2-(1-naphthyloxy)propionamide ; Napropamid ; Napropamide ; Napropamide [ISO:PROP] ; R 7465 ; R-7465 ; R-7475 ; Racemic devrinol ; Waylay . It is lowly toxic. It will produce toxic nitrogen oxide fumes when buring. So the storage environment should be ventilate, low-temperature and dry. Keep Propanamide,N,N-diethyl-2-(1-naphthalenyloxy)- (CAS NO.15299-99-7) separate from raw materials of food.