Monalide

Base Information

• Chemical Name: Monalide
• CAS No.: 7287-36-7
• Molecular Formula: C13H18 Cl N O
• Molecular Weight: 239.745
• Hs Code.: 29242990
• European Community (EC) Number: 230-712-9
• UNII: PV4FMD17U4
• DSSTox Substance ID: DTXSID0042163
• Nikkaji Number: J2.259D
• Wikidata: Q22808454
• ChEMBL ID: CHEMBL1520034
• Mol file: 7287-36-7.mol

Synonyms:Monalide;7287-36-7;Potablan;N-(4-Chlorophenyl)-2,2-dimethylpentanamide;Schering-35830;Monalide [BSI:ISO];Caswell No. 188AA;Valeranilide, 4'-chloro-2,2-dimethyl-;4'-Chloro-2,2-dimethylvaleranilide;Pentanamide, N-(4-chlorophenyl)-2,2-dimethyl-;SN 35830;N-(4-Chlorophenyl)-2,2-dimethylvaleroamide;EINECS 230-712-9;D-90-A;UNII-PV4FMD17U4;EPA Pesticide Chemical Code 288400;BRN 5528162;PV4FMD17U4;N-(4-Chlorphenyl)-2,2-dimethylpentamid;4'-Chloro-alpha,alpha-dimethylvaleranilide;4-Chloranilid kyseliny 2,2-dimethylvalerove;CHEBI:82180;N-(4-Chlorphenyl)-2,2-dimethylpentamid [German];4-Chloranilid kyseliny 2,2-dimethylvalerove [Czech];N-(4-Chlor-phenyl)-2,2-dimethyl-valeriansaeureamid;N-(4-Chlor-phenyl)-2,2-dimethyl-valeriansaeureamid [German];N-(4-Chlorophenyl)-2,2-dimethylvaleramide;N-(4-Chlorophenyl)-.alpha.,.alpha.-Dimethylvaleramide;MONALIDE [ISO];SCHEMBL54004;CHEMBL1520034;DTXSID0042163;D 90A;D-90A;4;-Chloro-2,2-dimethylvaleranilide;AKOS015902479;NCGC00166152-01;LS-161010;Monalide, PESTANAL(R), analytical standard;C19053;N-(4-Chlorophenyl)-2,2-dimethylvaleramide (9CI);Q22808454

Chemical Property of Monalide

Chemical Property:

• Vapor Pressure: 6.46E-06mmHg at 25°C
• Melting Point: 87-88℃
• Refractive Index: 1.6330 (estimate)
• Boiling Point: 378.1°C at 760 mmHg
• PKA: 14.25±0.70(Predicted)
• Flash Point: 182.4°C
• PSA: 29.10000
• Density: 1.104g/cm³
• LogP: 4.17780
• Water Solubility.: 22.8mg/L(23 oC)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 239.1076919
• Heavy Atom Count: 16
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

Monalide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 21
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C)(C)C(=O)NC1=CC=C(C=C1)Cl
• Uses: MONALIDE is used to destroyweeds of crops such as carrots, celery, and parsley. Preemergence and postemergence control of broad-leaved weeds in parsley, carrots, dill and celery.

Technology Process of Monalide

There total 2 articles about Monalide 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: 71.0%

2-Methyl-1-pentene (763-29-1) + carbon monoxide (201230-82-2) + p-chloroaniline hydrochloride (20265-96-7) → N-(4-Chlorophenyl)-2,2-dimethylvaleramide (7287-36-7)

Guidance literature:

With bis[tri(2-methoxyphenyl)phosphine]palladium(II) dichloride; In tetrahydrofuran; at 110 ℃; for 24h; under 34202.3 Torr; regioselective reaction; Autoclave;

DOI:10.1021/jacs.1c03454

Reference yield: 65.0%

2,2-dimethylpentanol (2370-12-9) + 4-chloro-aniline (106-47-8) → N-(4-Chlorophenyl)-2,2-dimethylvaleramide (7287-36-7)

Guidance literature:

With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2,2-Trifluoroacetophenone; cesium acetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; at 80 ℃; for 24h;

DOI:10.1021/acscatal.6b02541

Reference yield: 65.0%

1,3-DIOXOLANE (646-06-0) + N-(4-Chlorophenyl)-2,2-dimethylvaleramide (7287-36-7) → N-(4-formylphenyl)-2,2-dimethylpentanamide + N-(4-(1,3-dioxolan-4-yl)phenyl)-2,2-dimethylpentanamide

Guidance literature:

1,3-DIOXOLANE; N-(4-Chlorophenyl)-2,2-dimethylvaleramide; With potassium phosphate; (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine; for 0.166667h; Glovebox;

With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; at 23 ℃; for 72h; Sealed tube; Irradiation;

With hydrogenchloride; In water; acetone; at 23 ℃;

DOI:10.1002/anie.201702079

upstream raw materials:

2,2-dimethylpentanol

4-chloro-aniline

2-Methyl-1-pentene

carbon monoxide

Refernces

• 1、 Nguyen, Trang T.,Hull, Kami L.. "Rhodium-Catalyzed oxidative amidation of sterically hindered aldehydes and alcohols". . p. 8214 - 8218. Retrieved 2018/05/23.