Neburon

Base Information

• Chemical Name: Neburon
• CAS No.: 555-37-3
• Molecular Formula: C12H16 Cl2 N2 O
• Molecular Weight: 275.178
• European Community (EC) Number: 209-096-0
• UNII: 4MXN71654X
• DSSTox Substance ID: DTXSID4042200
• Nikkaji Number: J1.619E
• Wikidata: Q22808466
• Metabolomics Workbench ID: 67615
• ChEMBL ID: CHEMBL75410
• Mol file: 555-37-3.mol

Synonyms:neburon

Chemical Property of Neburon

Chemical Property:

• Vapor Pressure: 3.58E-07mmHg at 25°C
• Melting Point: 103℃
• Refractive Index: 1.5490 (estimate)
• Boiling Point: 417.3°C at 760 mmHg
• PKA: 13.55±0.70(Predicted)
• Flash Point: 206.2°C
• PSA: 32.34000
• Density: 1.252g/cm³
• LogP: 4.33020
• Storage Temp.: 0-6°C
• Water Solubility.: 4.8mg/L(25 oC)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 274.0639685
• Heavy Atom Count: 17
• Complexity: 251

Purity/Quality:

99% ^*data from raw suppliers

Neburon ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCN(C)C(=O)NC1=CC(=C(C=C1)Cl)Cl
• Uses: Herbicide. Preemergence control of grasses and broad-leaved weeds in peas, beans, lucerne, garlic, beets, cereals, strawberries, ornamentals and forestry.

Technology Process of Neburon

There total 6 articles about Neburon 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: 86.0%

→ 1-Butyl-3-(3,4-dichlorophenyl)-1-methylurea (555-37-3)

Guidance literature:

With cesium fluoride; In diethylene glycol dimethyl ether; at 100 ℃; for 20h; Schlenk technique; Glovebox;

Reference yield: 79.0%

N-n-butyl-N-methylamine (110-68-9) + carbon monoxide (201230-82-2) + m,p-dichloroaniline (95-76-1) → 1-Butyl-3-(3,4-dichlorophenyl)-1-methylurea (555-37-3)

Guidance literature:

N-n-butyl-N-methylamine; carbon monoxide; m,p-dichloroaniline; With sulfur; In N,N-dimethyl-formamide; at 20 ℃; for 24h; under 750.075 Torr; Inert atmosphere;

With oxygen; In N,N-dimethyl-formamide; at 20 ℃; for 6h; under 750.075 Torr;

DOI:10.1055/s-0029-1216863

Reference yield: 64.0%

N-n-butyl-N-methylamine (110-68-9) + 3,4-dichloronitrobenzene (99-54-7) + molybdenum hexacarbonyl (13939-06-5,199620-15-0) → 1-Butyl-3-(3,4-dichlorophenyl)-1-methylurea (555-37-3)

Guidance literature:

With palladium 10% on activated carbon; sodium iodide; In 1,4-dioxane; at 120 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1039/c8nj02413h

upstream raw materials:

N-n-butyl-N-methylamine

N,N-dimethylaminododecane

methyl N-(3,4-dichlorophenyl)carbamate

carbon monoxide

Downstream raw materials:

N-n-butyl-N-methylamine

3,4-dichlorophenylisocyanate

methylamine

Refernces

• 1、 Li, Chong-Liang,Peng, Jin-Bao,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng. "Pd/C-catalyzed reductive carbonylation of nitroaromatics for the synthesis of unsymmetrical ureas: One-step synthesis of neburon". supporting information. p. 12472 - 12475. Retrieved 2018/08/04.
• 2、 Mizuno, Takumi,Nakai, Takeo,Mihara, Masatoshi. "Synthesis of unsymmetrical ureas by sulfur-assisted carbonylation with carbon monoxide and oxidation with molecular oxygen under mild conditions". experimental part. p. 2492 - 2496. Retrieved 2009/12/08.