10040-86-5

Basic information

• Product Name: 4-CHLOROBENZALHYDANTOIN
• Synonyms: 4-CHLOROBENZALHYDANTOIN
• CAS NO: 10040-86-5
• Molecular Formula: C₁₀H₇ClN₂O₂
• Molecular Weight: 222.63
• Mol File: 10040-86-5.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• Density: 1.45g/cm³
• Refractive Index: 1.654
• CAS DataBase Reference: 4-CHLOROBENZALHYDANTOIN(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROBENZALHYDANTOIN(10040-86-5)
• EPA Substance Registry System: 4-CHLOROBENZALHYDANTOIN(10040-86-5)

Safety Data

• Hazardous Substances Data: 10040-86-5(Hazardous Substances Data)

Usage

General Description

4-CHLOROBENZALHYDANTOIN is a chemical compound that belongs to the hydantoin class of compounds. It is a white to light yellow crystalline powder that is odorless and insoluble in water. 4-CHLOROBENZALHYDANTOIN is commonly used as a halogenating agent in organic synthesis, particularly in the modification of aromatic compounds. It is also used as a reagent in the preparation of various pharmaceuticals and is a key intermediate in the production of other organic chemicals. However, 4-CHLOROBENZALHYDANTOIN should be handled with caution, as it is a potential irritant to the skin, eyes, and respiratory system, and exposure to high concentrations can have harmful effects on health.

InChI:InChI=1/C10H7ClN2O2/c11-7-3-1-6(2-4-7)5-8-9(14)13-10(15)12-8/h1-5H,(H2,12,13,14,15)/b8-5-

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 95378-36-2 diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate 
• 461-72-3 2,4-imidazolidinedione 
• 139488-42-9 3-Acetyl-5-[1-(4-chloro-phenyl)-meth-(Z)-ylidene]-2-thioxo-imidazolidin-4-one 
• 120697-22-5 5-(p-chlorobenzylidene)hydantoin 
• 37428-88-9 5-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-2-thioxo-imidazolidin-4-one 

Downstream Products

• 867041-26-7 2-[5-(4-chloro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(3-trifluoromethyl-phenyl)-acetamide 
• 867041-32-5 2-[5-(4-chloro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide 
• 867041-17-6 2-[5-(4-chloro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(4-chloro-phenyl)-acetamide 
• 6331-81-3 5-(4-chlorobenzyl)imidazolidine-2,4-dione 
• 6331-81-3 5-(4-chlorobenzyl)imidazolidine-2,4-dione 
• 6331-81-3 5-(4-Chlorobenzyl)imidazolidine-2,4-dione 
• 127273-12-5 3-(4-chlorophenyl)-2-hydroxyacrylic acid 
• 120697-22-5 5-(p-chlorobenzylidene)hydantoin 
• 937050-04-9 C₁₆H₂₀ClN₃O₃ 
• 1388167-49-4 (Z)-5-(4-chlorobenzylidene)-3-(2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl)imidazolidine-2,4-dione 
• 1388167-36-9 (Z)-5-(4-chlorobenzylidene)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)imidazolidine-2,4-dione 
• 1388167-32-5 (Z)-5-(4-chlorobenzylidene)-3-(3-(4-(2-ethoxyphenyl)piperazin-1-yl)-2-hydroxypropyl)imidazolidine-2,4-dione 
• 1388167-21-2 C₁₃H₁₁ClN₂O₃ 

Relevant articles and documents

A new approach for the conversion of thiohydantoin to hydantoin derivatives

The reaction of thiohydantoins with 1-(bromoacetyl)benzenes afforded the corresponding hydantoin derivatives and 1-(mercaptoacetyl)benzenes instead of the expected oxoimidazothiazoles.

Synthesis of dispirooxindoles containing N-unsubstituted heterocyclic moieties and study of their anticancer activity

A convenient method is proposed for the synthesis of N-unsubstituted spiroxindoles with different heterocyclic moieties (2-thiohydantoin, hydantoin, and thiazolidine) by the regio-selective 1,3-dipolar cycloaddition of azomethine ylides, generated from is

Evaluation of α-hydroxycinnamic acids as pyruvate carboxylase inhibitors

Through a structure-based drug design project (SBDD), potent small molecule inhibitors of pyruvate carboxylase (PC) have been discovered. A series of α-keto acids (7) and α-hydroxycinnamic acids (8) were prepared and evaluated for inhibition of PC in two assays. The two most potent inhibitors were 3,3′-(1,4-phenylene)bis[2-hydroxy-2-propenoic acid] (8u) and 2-hydroxy-3-(quinoline-2-yl)propenoic acid (8v) with IC50 values of 3.0 ± 1.0 μM and 4.3 ± 1.5 μM respectively. Compound 8v is a competitive inhibitor with respect to pyruvate (Ki = 0.74 μM) and a mixed-type inhibitor with respect to ATP, indicating that it targets the unique carboxyltransferase (CT) domain of PC. Furthermore, compound 8v does not significantly inhibit human carbonic anhydrase II, matrix metalloproteinase-2, malate dehydrogenase or lactate dehydrogenase.

Design, synthesis, and biological evaluation of substrate-competitive inhibitors of C-terminal Binding Protein (CtBP)

C-terminal Binding Protein (CtBP) is a transcriptional co-regulator that downregulates the expression of many tumor-suppressor genes. Utilizing a crystal structure of CtBP with its substrate 4-methylthio-2-oxobutyric acid (MTOB) and NAD+ as a guide, we have designed, synthesized, and tested a series of small molecule inhibitors of CtBP. From our first round of compounds, we identified 2-(hydroxyimino)-3-phenylpropanoic acid as a potent CtBP inhibitor (IC50 = 0.24 μM). A structure-activity relationship study of this compound further identified the 4-chloro- (IC50 = 0.18 μM) and 3-chloro- (IC50 = 0.17 μM) analogues as additional potent CtBP inhibitors. Evaluation of the hydroxyimine analogues in a short-term cell growth/viability assay showed that the 4-chloro- and 3-chloro-analogues are 2-fold and 4-fold more potent, respectively, than the MTOB control. A functional cellular assay using a CtBP-specific transcriptional readout revealed that the 4-chloro- and 3-chloro-hydroxyimine analogues were able to block CtBP transcriptional repression activity. This data suggests that substrate-competitive inhibition of CtBP dehydrogenase activity is a potential mechanism to reactivate tumor-suppressor gene expression as a therapeutic strategy for cancer.