13908-40-2

Basic information

• Product Name: 1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea
• Synonyms: 1-(2-Chloroethyl)-3-(2,6-dimethylphenyl)urea; urea, N-(2-chloroethyl)-N'-(2,6-dimethylphenyl)-
• CAS NO: 13908-40-2
• Molecular Formula: C₁₁H₁₅ClN₂O
• Molecular Weight: 226.7026
• Mol File: 13908-40-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 317.3°C at 760 mmHg
• Flash Point: 145.7°C
• Density: 1.182g/cm³
• Vapor Pressure: 0.000388mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: 1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea(13908-40-2)
• EPA Substance Registry System: 1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea(13908-40-2)

Safety Data

• Hazardous Substances Data: 13908-40-2(Hazardous Substances Data)

Usage

General Description

1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea is a chemical compound with the formula C10H13ClN2O. It is a urea derivative with a 2-chloroethyl group and a 2,6-dimethylphenyl group. 1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It can also be used as a reagent in organic synthesis and as a pesticide. It is important to handle this chemical with caution and follow proper safety protocols as it can be harmful if ingested, inhaled, or comes into contact with skin and eyes.

Upstream product

• 1943-83-5 2-chloroethyl isothiocyanate 
• 87-62-7 2,6-dimethylaniline 

Downstream Products

• 13909-20-1 C₁₁H₁₄ClN₃O₂ 
• 91180-66-4 1-(2,6-dimethyl-phenyl)-imidazolidin-2-one 
• 31235-50-4 (4,5-dihydro-oxazol-2-yl)-(2,6-dimethyl-phenyl)-amine 

Relevant articles and documents

Alkylation potency and protein specificity of aromatic urea derivatives and bioisosteres as potential irreversible antagonists of the colchicine-binding site

A number of N-phenyl-N′-(2-chloroethyl)ureas (CEUs) have been shown to be potent antimitotics through their covalent binding to the colchicine-binding site on intracellular β-tubulin. The present communication aimed to evaluate the role of the electrophilic 2-chloroethyl amino moiety of CEU on cell growth inhibition and the specificity of the drugs as irreversible antagonists of the colchicine-binding site. To that end, several N-phenyl-N′-(2-ethyl)urea (EU), N-phenyl-N′-(2-chloroethyl)urea (CEU), N-aryl amino-2-oxazoline (OXA), and N-phenyl-N′-(2-chloroacetyl)urea (CAU) derivatives were prepared and tested for their antiproliferative activity, their effect on the cell cycle, and their irreversible binding to β-tubulin. EU derivatives were devoid of antiproliferative activity. CEUs (2h-2i, 2k, 2l, OXA 3e, 3h, 3i, 3k, 3l, tBCEU, and ICEU), OXA (3h, 3i, 3k, 3l, tBOXA, and IOXA), and CAU (4a-4m, tBCAU, and ICAU) had GI50 between 1.7 and 10 μM on three tumor cell lines. Cytotoxic CEU and OXA arrested the cell cycle in G2/M phase, while the corresponding CAU were not phase specific. Finally, Western blot analysis clearly showed that only CEUs 2h, 2k, 2l, tBCEU, ICEU and OXA 3h, 3i, 3k, 3l, tBOXA,and IOXA were able to bind irreversibly to the colchicine-binding site. Our results suggest that increasing the potency of the electrophilic moiety of the aromatic ureas enhances their antiproliferative activity but decreases significantly their capacity to covalently bind to the colchicine-binding site.

New substituted 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidin-4-yl derivatives with α2-adrenoceptor antagonist activity

The emergence of a novel theory concerning the role of noradrenaline in the progression and the treatment of neurodegenerative diseases such as Parkinson's and Alzheimer's diseases has provided a new impetus toward the discovery of novel compounds acting at α2-adrenoceptors. A series of substituted 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidin-4-yl derivatives bearing an amide, urea, or imidazolidinone moiety was studied. Some members of this series of compounds proved to be potent α2-adrenoceptor antagonists with good selectivity versus α1-adrenergic and D2-dopamine receptors. Particular emphasis is given to compound 33g which displays potent α2-adrenoceptor binding affinity in vitro and central effects in vivo following oral administration.

The synthesis of potential anticancer agents. XXXVI. N-nitrosoureas. II. Haloalkyl derivatives.

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