65608-74-4

Basic information

• Product Name: N-(4-CHLOROBENZYL)UREA
• Synonyms: N-(4-CHLOROBENZYL)UREA
• CAS NO: 65608-74-4
• Molecular Formula: C₈H₉ClN₂O
• Molecular Weight: 184.62
• Mol File: 65608-74-4.mol

Chemical Properties

• Melting Point: 198-200°
• Appearance: /
• CAS DataBase Reference: N-(4-CHLOROBENZYL)UREA(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-CHLOROBENZYL)UREA(65608-74-4)
• EPA Substance Registry System: N-(4-CHLOROBENZYL)UREA(65608-74-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 65608-74-4(Hazardous Substances Data)

Upstream product

• 104-86-9 4-chlorobenzylamine 
• 95062-75-2 S-(4-bromophenyl) thiocarbamate 
• 95062-74-1 S-(4-chlorophenyl) thiocarbamate 
• 95062-72-9 S-(4-methylphenyl) thiocarbamate 
• 61642-86-2 S-phenyl thiocarbamate 
• 24827-37-0 N-(4-chlorobenzyl)thiourea 
• 42365-43-5 (4-chlorophenyl)methanamine hydrochloride 
• 57-13-6 urea 
• 556-89-8 nitrourea 
• 590-28-3 potassium cyanate 

Downstream Products

• 179486-48-7 6-amino-1-(4-chlorobenzyl)-5-nitroso-uracil 
• 179486-47-6 6-amino-1-(4-chlorobenzyl)-uracil 
• 179486-46-5 1-(4-chlorobenzyl)-3-cyanoacetyl-urea 
• 128043-68-5 [3-(4-Chloro-benzyl)-2,4,5-trioxo-imidazolidin-1-yl]-acetic acid ethyl ester 
• 40408-50-2 (4-chloro-benzyl)-imidazolidinetrione 
• 104375-81-7 N-nitroso-N-(p-chlorobenzyl)urea 
• 1616091-92-9 C₁₂H₁₄ClN₃O₃S 
• 1370686-93-3 C₁₁H₁₀ClN₃O₂S 
• 1616091-98-5 C₁₀H₈ClN₃O₂S 
• 1162748-36-8 C₂₀H₂₂ClN₅O₃ 
• 1162748-13-1 C₁₉H₁₈ClN₃O₃S 

Relevant articles and documents

Ammonium Chloride-Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation

Monosubstituted ureas are important scaffolds in organic chemistry. They appear in various biologically active compounds and serve as versatile precursors in synthesis. Monosubstituted ureas were originally prepared using toxic and hazardous phosgene equivalents. Modern methods include transamidation of urea and nucleophilic addition to cyanate salts, both of which suffer from a narrow substrate scope due to the need for a strong acid and prolonged reaction times. We hereby report that ammonium chloride can promote the reaction between amines and potassium cyanate to generate monosubstituted ureas in water. This method proceeds rapidly under microwave irradiation and tolerates a broad range of functional groups. Unlike previous strategies, it is compatible with other nucleophiles, acid-labile moieties, and most of the common protecting groups. The products precipitate out of solution, allowing facile isolation without column chromatography.

Exploring Selective Inhibition of the First Bromodomain of the Human Bromodomain and Extra-terminal Domain (BET) Proteins

A midthroughput screening follow-up program targeting the first bromodomain of the human BRD4 protein, BRD4(BD1), identified an acetylated-mimic xanthine derivative inhibitor. This compound binds with an affinity in the low micromolar range yet exerts suitable unexpected selectivity in vitro against the other members of the bromodomain and extra-terminal domain (BET) family. A structure-based program pinpointed a role of the ZA loop, paving the way for the development of potent and selective BET-BRDi probes.

Microwave-assisted synthesis of N-monosubstituted urea derivatives

An easy and rapid procedure for the preparation of N-monosubstituted ureas via reaction between potassium cyanate and a wide range of amines is described. The procedure was performed under microwave irradiation using water as solvent. This methodology is particularly attractive since it provides ureas in high yield and purity. Georg Thieme Verlag Stuttgart · New York.

Kinetics and mechanism of the aminolysis of aryl thiocarbamates: Effects of the non-leaving group

The kinetics of the aminolysis of aryl thiocarbamates [ATC: H 2NC(=O)SC6H4Z] with benzylamines (XC 6H4CH2NH2) in acetonitrile at 10.0°C have been studied. The rate order with variation of the non-leaving amino group, RNH, in RNHC(=O)SC6H4Z is NH2 s) effects of the RNH group are insignificant, and the strength of push to expel the leaving group in the tetrahedral transition state is the sole, important effect. The strong push provided by the NH2 group, the negative ρxz (-0.38) value, the size of βz (-0.54), and failure of the reactivity-selectivity principle are all consistent with the concerted mechanism. The kinetic isotope effects involving deuterated amine nucleophiles (XC6H4CH2ND2) are normal (kH/kD ≈ 1.40-1.73) suggesting a hydrogen-bonded cyclic transition state. The Royal Society of Chemistry 2005.

Aryl thioxanthines

PCT No. PCT/US95/16723 Sec. 371 Date Aug. 18, 1997 Sec. 102(e) Date Aug. 18, 1997 PCT Filed Dec. 12, 1995 PCT Pub. No. WO96/18399 PCT Pub. Date Jun. 20, 1996The present invention relates to novel compounds of the formula (I): wherein Q3R3 and Q8R8 are des

Mechanism of the formation of 1,2,4-thiadiazoles by condensation of aromatic thioamides and of N-substituted thioureas

The condensation reaction of thiobenzamide, (as well as thionicotinamide and isothionicotinamide) in the presence of dimethyl sulfoxide and of an acid, affords 3,5-diphenyl-1,2,4-thiadiazole. Under the same experimental conditions, N-substituted thioureas are also condensed to 1,2,4-thiadiazole derivatives; their structure is ascertained by spectroscopic properties and by X-ray diffraction. Some information on the mechanism of thiadiazoles formation from both starting classes of compounds, thiobenzamides and N- substituted thiourea, is collected and discussed.

Highly selective aldose reductase inhibitors. 1. 3-(Arylalkyl)-2,4,5- trioxoimidazolidine-1-acetic acids

A series of 3-(arylalkyl)-2,4,5-trioxoimidazolidine-1-acetic acids (1) was prepared and tested for aldose reductase (AR) and aldehyde reductase (ALR) inhibitory activities. These compounds showed strong inhibitory activity against AR without significant inhibitory activity for ALR. The ratio of IC50(ALR)IC50(AR) was > 1000 in some compounds. On the basis of pharmacological tests such as the recovery of reduced motor nerve conduction velocity and toxicological profile, 3-(3-nitrobenzyl)-2,4,5- trioxoimidazolidine-1-acetic acid (NZ-314) was selected as the candidate for clinical development.

Reactivity Effects on Site Selectivity in Nucleoside Aralkylation: A Model for the Factors Influencing the Sites of Carcinogen-Nucleic Acid Interactions

Product distributions are described for 15 reactions between guanosine (1) and a series of p-Y-benzyl bromides (2a-e), p-Y-benzoyl chlorides (3a-e), and N-nitroso-N-(p-Y-benzyl)ureas (4a-e) where Y = a, O2N; b, Cl; c, H; d, CH3; e, CH3O.The yields of products from reaction at the 7-position of guanosine to produce 7-(p-Y-benzyl)guanosines (5a-e), at N2 to produce N2-(p-Y-benzyl)guanosines (6a-e), at the O6-position to produce O6-(p-Y-benzyl)guanosines (7a-e), and at the 5-position to produce 4-(p-Y-benzyl)-5-guanidino-1-β-D-ribofuranosylimidazoles (8a-e) arecorrelated with the mechanism of the reaction (i.e., the SN2 or SN1 character) imposed by the para substituent and/or leaving group and the nature of the incipient charge density (i.e., the "hardness" or "softness") at the reaction center.These observations, coupled with the literature on sites of reaction of carcinogens with nucleic acid components, are used to rationalize the site selectivity differences exhibited by the alkylating and aralkylating classes of carcinogens in their nucleic acid reactions.