Fenarimol

Base Information

• Chemical Name: Fenarimol
• CAS No.: 60168-88-9
• Deprecated CAS: 162707-16-6,1135442-57-7,1135442-57-7
• Molecular Formula: C17H12Cl2N2O
• Molecular Weight: 331.201
• Hs Code.: 2933599016
• European Community (EC) Number: 262-095-7
• UN Number: 3017
• UNII: O088GU930Q
• DSSTox Substance ID: DTXSID2032390
• Nikkaji Number: J18.180C
• Wikipedia: Fenarimol
• Wikidata: Q906987
• Metabolomics Workbench ID: 49107
• ChEMBL ID: CHEMBL28971
• Mol file: 60168-88-9.mol

Synonyms:alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanol;fenarimol;Rubigan 12 RC;Rubigan-4

Chemical Property of Fenarimol

Chemical Property:

• Appearance/Colour: Pure white crystalline solid
• Vapor Pressure: 4.02E-08mmHg at 25°C
• Melting Point: 117-119°C
• Refractive Index: 1.642
• Boiling Point: 502.556 °C at 760 mmHg
• PKA: 2.58
• Flash Point: 257.737 °C
• PSA: 46.01000
• Density: 1.364g/cm3
• LogP: 4.06760
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 14.6 mg l-1 (pH 3), 13.7 mg l-1 (pH 7), 13.8 mg l-1 (pH 10) at 25 °C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 330.0326684
• Heavy Atom Count: 22
• Complexity: 357
• Transport DOT Label: Poison Flammable Liquid

Purity/Quality:

99%, ^*data from raw suppliers

Fenarimol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn;N,N,Xn
• Statements: 51/53-62-63-64
• Safety Statements: 36/37-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(C2=CC=C(C=C2)Cl)(C3=CN=CN=C3)O)Cl
• Uses: Fenarimol is a broad spectrum pyrimidine carbinol fungicide with protective, curative and eradicative activities against powdery mildew (Erysiphe spp., Pudusphaera leucutricha, Uncinula necatur, Sphaerutheca spp., Leveillula spp.) and scab (Venturia spp.) in many crops. It also controls powdery mildew (Sphaerutheca pannusa) in ornamentals and Fusarium patch (Micruduccium niuale), Take-all patch (Laefisaria fuciformis), Dollar spot (Sderutina humeucavpa) and red thread (Gaeumannumyces graminis) in turf and amenity grasses. Fenarimol is a pyrimidine based fungicide which acts against rusts, blackspot and mildew fungi and it works by inhibiting the fungus’s biosynthesis of important steroid molecules.

Technology Process of Fenarimol

There total 6 articles about Fenarimol 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: 34.0%

5-bromopyrimidine (4595-59-9) + 2,4'-dichlorobenzophenone (85-29-0) → Fenarimol (60168-88-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -95 - 20 ℃;

DOI:10.1021/jm00391a016

Reference yield: 20.0%

(4-chlorophenyl)(pyrimidin-5-yl)methanone (103686-55-1) + 2-bromo-1-chlorobenzene (694-80-4) → Fenarimol (60168-88-9)

Guidance literature:

2-bromo-1-chlorobenzene; With magnesium; ethylene dibromide; In tetrahydrofuran; for 1.58333h;

(4-chlorophenyl)(pyrimidin-5-yl)methanone; With zinc(II) chloride; In tetrahydrofuran; at 20 ℃; for 0.5h;

Reference yield:

5-(4-chlorobenzyl)pyrimidine (1401217-87-5) → Fenarimol (60168-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium permanganate / ethyl acetate; water / 6 h / Reflux

2.1: magnesium / ethylene dibromide / tetrahydrofuran / 1.58 h

2.2: 0.5 h / 20 °C

With potassium permanganate; magnesium; ethylene dibromide; In tetrahydrofuran; water; ethyl acetate;

upstream raw materials:

5-bromopyrimidine

2,4'-dichlorobenzophenone

(4-chlorophenyl)(pyrimidin-5-yl)methanone

2-bromo-1-chlorobenzene

Downstream raw materials:

(2-chlorophenyl)(4-chlorophenyl)(2-isopropylpyrimidin-5-yl)methanol

(4-chlorophenyl)(2-chlorophenyl)pyrimidin-5-yl N-Oxide methanol

5-[(2-chlorophenyl)(4-chlorophenyl)methyl]pyrimidine

(+/-)-6-[(2-chlorophenyl)-(4'-chlorophenyl)pyrimidin-5-yl-methoxy]hexanoic acid

Refernces

• 1、 -. "METHOD FOR PREPARATION OF 5-SUBSTITUTED PYRIMIDINES". Page/Page column 16-17. . Retrieved 2012/10/08.
• 2、 -. "2-(Pyrazolyloxy) -pyridin-3-ylacetic acid derivatives, agents containing the same and use thereof against noxious fungi and animal parasites". . . Retrieved 2008/06/13.