Fenuron

Base Information

• Chemical Name: Fenuron
• CAS No.: 101-42-8
• Molecular Formula: C9H12 N2 O
• Molecular Weight: 164.207
• Hs Code.: 29242990
• European Community (EC) Number: 202-941-4
• UNII: O7L040435W
• DSSTox Substance ID: DTXSID7037551
• Nikkaji Number: J8.623A
• Wikidata: Q3742493
• Metabolomics Workbench ID: 67548
• ChEMBL ID: CHEMBL1492698
• Mol file: 101-42-8.mol

Synonyms:3-phenyl-1,1-dimethylurea;fenuron

Chemical Property of Fenuron

Chemical Property:

• Vapor Pressure: 0.002Pa at 60℃
• Melting Point: 131-133°
• Refractive Index: 1.5373 (estimate)
• Boiling Point: 329.8°Cat760mmHg
• PKA: 15.09±0.70(Predicted)
• Flash Point: 153.3°C
• PSA: 32.34000
• Density: 1.122g/cm³
• LogP: 1.85310
• Storage Temp.: APPROX 4°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 2.40g/L(25 oC)
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 164.094963011
• Heavy Atom Count: 12
• Complexity: 151

Purity/Quality:

98% ^*data from raw suppliers

Fenuron ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn,F
• Hazard Codes: Xi,Xn,F
• Statements: 36/37-36-20/21/22-11
• Safety Statements: 24-26-36-16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Herbicides, Urea Derivative
• Canonical SMILES: CN(C)C(=O)NC1=CC=CC=C1
• Uses: Fenuron is an phenylurea based herbicide used to control brush on chaparral watersheds.

Technology Process of Fenuron

There total 57 articles about Fenuron 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: 95.0%

phenyl isocyanate (103-71-9) + dimethyl amine (124-40-3) → fenuron (101-42-8)

Guidance literature:

In water; toluene; at 75 ℃; for 4h;

DOI:10.1002/anie.200800815

Reference yield: 95.0%

N,N-dimethylcarbamoyl bromide (15249-51-1) + aniline (62-53-3) → fenuron (101-42-8)

Guidance literature:

With sodium carbonate; In hexane; at 50 ℃; for 6h; pH=5 - 6;

DOI:10.1055/s-0028-1083340

Reference yield: 95.0%

[{Ph2P(Se)NCH2CH2NPPh2(Se)}Ti(NMe2)2] + phenyl isocyanate (103-71-9) → fenuron (101-42-8)

Guidance literature:

[{Ph₂P(Se)NCH₂CH₂NPPh₂(Se)}Ti(NMe₂)₂]; phenyl isocyanate; In toluene; at 25 ℃; for 0.166667h; Schlenk technique; Inert atmosphere;

With 2,6-diisopropylbenzenamine; In toluene; at 25 ℃; for 1h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c6dt03063g

upstream raw materials:

phenyl isocyanate

3-dimethylaminopropiophenone

N,N-diphenylurea

dimethyl amine

Downstream raw materials:

1-hydroxy-3-phenylurea

N'',N'''-Diphenyl-N,N,N',N'-tetramethylformamimidic acid anhydride

phenyl isocyanate

dimethyl amine

Refernces

• 1、 Seckinger, Karl. "On the Reaction of Bis(dimethylamino)acetonitrile with Phenylisocyanate". . p. 1958 - 1959. Retrieved 1980.
• 2、 Ramadas,Janarthanan. "New synthetic strategy for urea herbicides". . p. 2357 - 2362. Retrieved 1997.
• 3、 Gangwar,Rafiquee. "Kinetics of the alkaline hydrolysis of fenuron in aqueous and micellar media". . p. 638 - 644. Retrieved 2007.
• 4、 Manna, Manash Kumar,Hossian, Asik,Jana, Ranjan. "Merging C-H activation and alkene difunctionalization at room temperature: A palladium-catalyzed divergent synthesis of indoles and indolines". . p. 672 - 675. Retrieved 2015.
• 5、 Houlden, Chris E.,Bailey, Chris D.,Ford, J. Gair,Gagne, Michel R.,Lloyd-Jones, Guy C.,Booker-Milburn, Kevin I.. "Distinct reactivity of Pd(OTs)2: The intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes". . p. 10066 - 10067. Retrieved 2008.
• 6、 Adeppa,Rupainwar,Misra, Krishna. "Improved method for the preparation of 1,1-dimethyl-3-arylureas using chlorocarbonylsulfenyl chloride". . p. 714 - 721. Retrieved 2012.
• 7、 Xian, Ming,Lu, Jianming,Zhu, Xiaoqing,Mu, Linjing,Cheng, Jin-Pei. "A Facile and High-yielding Preparation of 1-Aryl-3,3-dialkylureas". . p. 442 - 443. Retrieved 1998.
• 8、 Zhu, Xiancui,Xu, Mengchen,Sun, Jinrong,Guo, Dianjun,Zhang, Yiwei,Zhou, Shuangliu,Wang, Shaowu. "Hydroamination and Hydrophosphination of Isocyanates/Isothiocyanates under Catalyst-Free Conditions". . p. 5213 - 5218. Retrieved 2021/10/19.
• 9、 Inaloo, Iman Dindarloo,Majnooni, Sahar. "A Fe3O4?SiO2/Schiff Base/Pd Complex as an Efficient Heterogeneous and Recyclable Nanocatalyst for One-Pot Domino Synthesis of Carbamates and Unsymmetrical Ureas". . p. 6359 - 6368. Retrieved 2019/11/05.