Napropamide-M

Base Information

• Chemical Name: Napropamide-M
• CAS No.: 41643-35-0
• Molecular Formula: C17H21NO2
• Molecular Weight: 271.35400
• European Community (EC) Number: 820-313-3
• UNII: QS6R71RYT5
• DSSTox Substance ID: DTXSID60194459
• Nikkaji Number: J1.895C
• Wikidata: Q27157195
• Mol file: 41643-35-0.mol

Synonyms:Napropamide-M;D-Napropamide;41643-35-0;(-)-Napropamide;(R)-Devrinol;Napropamide-M [ISO];UNII-QS6R71RYT5;QS6R71RYT5;l-N,N-Diethyl-2-(alpha-naphthoxy)propionamide;(R)-N,N-Diethyl-2-(1-naphthyloxy)propionamide;(2R)-N,N-diethyl-2-naphthalen-1-yloxypropanamide;(2R)-N,N-Diethyl-2-(1-naphthalenyloxy)propanamide;Propanamide, N,N-diethyl-2-(1-naphthalenyloxy)-, (2R)-;(R)-napropamide;Napropamide M;SCHEMBL6904715;CHEBI:83772;DTXSID60194459;WXZVAROIGSFCFJ-CYBMUJFWSA-N;AKOS040753213;(R)-N,N-diethyl-2-(naphthalen-1-yloxy)propanamide;(2R)-N,N-diethyl-2-(naphthalen-1-yloxy)propanamide;Q27157195;L-N,N-DIETHYL-2-(.ALPHA.-NAPHTHOXY)PROPIONAMIDE

Chemical Property of Napropamide-M

Chemical Property:

• PSA: 29.54000
• LogP: 3.47550
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 271.157228913
• Heavy Atom Count: 20
• Complexity: 314

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)C(C)OC1=CC=CC2=CC=CC=C21
• Isomeric SMILES: CCN(CC)C(=O)[C@@H](C)OC1=CC=CC2=CC=CC=C21
• Uses: Napropamide M is an amide chiral herbicide used in the control of the most noxious weeds like Echinochloa crus-galli causing yield losses of agricultural produce.

Technology Process of Napropamide-M

There total 3 articles about Napropamide-M which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

α-naphthol (90-15-3) + (L)-(+)-N,N-diethyl-2-chloropropionamide → (R)-napropamide (41643-35-0) + (S)-napropamide (41643-36-1)

Guidance literature:

With sodium hydroxide; In water; toluene; at 55 - 95 ℃; for 6 - 7h; Product distribution / selectivity; Heating / reflux;

Reference yield:

Napropamide (15299-99-7) → (R)-napropamide (41643-35-0) + (S)-napropamide (41643-36-1)

Guidance literature:

With Chiralpak IC; In hexane; isopropyl alcohol; at 15 ℃; Resolution of racemate;

DOI:10.1002/chir.22277

Reference yield:

α-naphthol (90-15-3) + (R)-N,N-diethyl-2-hydroxypropanamide → (R)-napropamide (41643-35-0)

Guidance literature:

(R)-N,N-diethyl-2-hydroxypropanamide; With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 65 - 87 ℃; for 4h; Inert atmosphere;

α-naphthol; With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 6h;

upstream raw materials:

Napropamide

α-naphthol

Refernces

• 1、 Qi, Yanli,Liu, Donghui,Sun, Mingjing,Di, Shanshan,Wang, Peng,Zhou, Zhiqiang. "The chiral separation and enantioselective degradation of the chiral herbicide napropamide". . p. 108 - 113. Retrieved 2014.
• 2、 Li, Yingjie,Tang, Yimin,Qin, Shili,Li, Xue,Dai, Qiang,Gao, Lidi. "Preparation and characterization of a new open-tubular capillary column for enantioseparation by capillary electrochromatography". . p. 283 - 292. Retrieved 2019/02/05.