39235-92-2

Basic information

• Product Name: N*1*-BENZYL-4-CHLORO-BENZENE-1,2-DIAMINE
• Synonyms: N-BENZYL-4-CHLORO-BENZENE-1,2-DIAMINE
• CAS NO: 39235-92-2
• Molecular Formula: C₁₃H₁₃ClN₂
• Molecular Weight: 232.70872
• Mol File: 39235-92-2.mol

Chemical Properties

• Boiling Point: 407.3 °C at 760 mmHg
• Flash Point: 200.1 °C
• Appearance: /
• Density: 1.265 g/cm³
• Vapor Pressure: 7.65E-07mmHg at 25°C
• Refractive Index: 1.68
• CAS DataBase Reference: N*1*-BENZYL-4-CHLORO-BENZENE-1,2-DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N*1*-BENZYL-4-CHLORO-BENZENE-1,2-DIAMINE(39235-92-2)
• EPA Substance Registry System: N*1*-BENZYL-4-CHLORO-BENZENE-1,2-DIAMINE(39235-92-2)

Safety Data

• Hazardous Substances Data: 39235-92-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H13ClN2/c14-11-6-7-13(12(15)8-11)16-9-10-4-2-1-3-5-10/h1-8,16H,9,15H2

Upstream product

• 2948-37-0 N-(4-chlorophenyl)benzylamine 
• 345-18-6 2-fluoro-5-chloronitrobenzene 
• 100-46-9 benzylamine 
• 100-39-0 benzyl bromide 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 100-44-7 benzyl chloride 
• 89-63-4 4-Chloro-2-nitroaniline 
• 10066-18-9 N-benzyl-4-chloro-2-nitrobenzenamine 

Downstream Products

• 2215-54-5 1-benzyl-5-chloro-1H-benzo[d]imidazol-2(3H)-one 
• 1382488-21-2 1-benzyl-5-chloro-2-[1-(4-isobutylphenyl)ethyl]-1H-benzimidazole 
• 1382488-19-8 N-(2-(benzylamino)-5-chlorophenyl)-2-(4-isobutylphenyl)propanamide 
• 1415650-63-3 1-benzyl-2-(4-(benzyloxy)phenyl)-5-chloro-1H-benzimidazole 
• 53703-87-0 2-(benzo[d] [1,3] dioxol-5-yl)-1-benzyl-5-chloro-1H-benzo[d]imidazole 

Relevant articles and documents

Novel benzimidazole-triazole hybrids as apoptosis inducing agents in lung cancer: Design, synthesis, 18F-radiolabeling & galectin-1 inhibition studies

In this study, we have synthesized a new series of benzimidazole-triazole hybrids as galectin-1 (gal-1) mediated apoptosis-inducing agents, and evaluated for their potential anticancer activity against a panel of human cancer cell lines viz. breast cancer

Synthesis of 1-benzyl-1H-benzimidazoles as galectin-1 mediated anticancer agents

In our pursuit to develop novel non-carbohydrate small molecule Galectin-1 Inhibitors, we have designed a series of 1-benzyl-1H-benzimidazole derivatives and demonstrated their anticancer activity. The compound 6g, 4-(1-benzyl-5-chloro-1H-benzo[d]imidazol

Regioselective Nitration of N-Alkyl Anilines using tert-Butyl Nitrite under Mild Condition

Regioselective ring nitration of N-alkyl anilines is reported using tert-butyl nitrite. The reactions proceed efficiently with a wide range of substrates providing synthetically useful N-nitroso N-alkyl nitroanilines in excellent yields which can be easily converted into N-alkyl phenylenediamines and N-alkyl nitroanilines using Zn-AcOH and HCl/MeOH, respectively.

Construction of Druglike 2-Amido Benzo[ d]imidazole Analogues via Desulfurative Cyclization of Thiourea Intermediate Resin on Solid-Phase

A 2-amido benzo[d]imidazole library has been constructed by solid-phase synthesis. The key step of this solid-phase synthesis involves the preparation of polymer-bound 2-amino benzo[d]imidazole resin through desulfurative cyclization of thiourea resin using 2-chloro-1,3-dimethylimidazolinium chloride and N,N-diisopropylethylamine in dichloromethane (DCM), and the resin is then functionalized by acylation at the 2-amine position to afford 2-amidobenzo[d]imidazole resin. In the case of 2-amidobenzo[d]imidazole resin having a p-I or m-NO2, the resin was further functionalized by Suzuki/Sonogashira-coupling (p-I) and reduction to the primary amine (m-NO2) followed by acylation. Finally, the functionalized 2-amido-benzo[d]imidazole resin was cleaved from the polymer support by treatment with a cocktail of trifluoroacetic acid and DCM. As a result, we obtained 2-amidobenzo[d]imidazole analogues in high yield and good purities.

Synthesis of substituted phenanthrene-9-benzimidazole conjugates: Cytotoxicity evaluation and apoptosis inducing studies

A series of new phenanthrene-9-benzimidazole conjugates has been synthesized by condensing phenanthrene aldehydes with various substituted o-phenylenediamines. The title compounds were evaluated for their in vitro cytotoxic potential against various human

Phenylquinoxalinone CFTR activator as potential prosecretory therapy for constipation

Constipation is a common condition for which current treatments can have limited efficacy. By high-throughput screening, we recently identified a phenylquinoxalinone activator of the cystic fibrosis transmembrane conductance regulator (CFTR) chloride chan

Metal-free TEMPO-promoted C(sp3)-H amination to afford multisubstituted benzimidazoles

An efficient TEMPO-air/cat. TEMPO-O2 oxidative protocol was developed to synthesize multisubstituted or fused tetracyclic benzimidazoles via a metal-free oxidative C-N coupling between the sp3 C-H and free N-H of readily available N1-benzyl/alkyl-1,2-phenylenediamines.

"All-water" one-pot diverse synthesis of 1,2-disubstituted benzimidazoles: Hydrogen bond driven 'synergistic electrophile-nucleophile dual activation' by water

A new "all-water" tandem arylaminoarylation/arylaminoalkylation- reduction-cyclisation route is reported for one-pot diversity oriented synthesis of regiodefined 1,2-disubstituted benzimidazoles. Water plays a crucial and indispensable role through hydrogen bond driven 'synergistic electrophile-nucleophile dual activation' in the formation of N-mono-aryl/aryl alkyl/alkyl/cycloalkyl o-nitroanilines under metal and base-free conditions to replace the transition metal-based C-N bond formation (aryl amination) chemistry and underlines the origin of regiodefined installation of the diverse selection of aryl, aryl alkyl, and alkyl/cycloalkyl groups as substituents on the benzimidazole scaffold to form the 1,2-disubstituted benzimidazoles. The influence of the hydrogen bond effect of water in promoting the arylaminoarylation reaction under base and metal-free conditions has been realized through observation of inferior yields in D2O compared to that obtained in water during the reaction of o-fluoronitrobenzene with aniline separately performed in water and D2O under similar experimental conditions. Water also provides assistance in promoting the subsequent nitro reduction and in the final cyclocondensation steps. The role of water in promoting the cyclocondensation reaction through hydrogen bonds is realized by the differential product yields during the reaction of mono-N-phenyl-o- phenylenediamine with benzaldehyde performed separately in water and D 2O. The better hydrogen bond donor and hydrogen bond acceptor abilities of water compared to those of the organic solvents are the contributing/deciding factors for making the new water-assisted tandem arylaminoarylation/arylaminoalkylation-reduction-cyclisation strategy for the diversified synthesis of the regiodefined 1,2-disubstituted benzimidazoles effective in an aqueous medium, making it represent a true "all-water chemistry."

Identification of novel benzimidazole derivatives as inhibitors of leukotriene biosynthesis by virtual screening targeting 5-lipoxygenase- activating protein (FLAP)

Pharmacological suppression of leukotriene biosynthesis by 5-lipoxygenase (5-LO)-activating protein (FLAP) inhibitors is a promising strategy to intervene with inflammatory, allergic and cardiovascular diseases. Virtual screening targeting FLAP based on a combined ligand- and structure-based pharmacophore model led to the identification of 1-(2-chlorobenzyl)-2-(1-(4-isobutylphenyl) ethyl)-1H-benzimidazole (7) as developable candidate. Compound 7 potently suppressed leukotriene formation in intact neutrophils (IC50 = 0.31 μM) but essentially failed to directly inhibit 5-LO suggesting that interaction with FLAP causes inhibition of leukotriene synthesis. For structural optimization, a series of 46 benzimidazole-based derivatives of 7 were synthesized leading to more potent analogues (70-72, 82) with IC50 = 0.12-0.19 μM in intact neutrophils. Together, our results disclose the benzimidazole scaffold bearing an ibuprofen fingerprint as a new chemotype for further development of anti-leukotriene agents.

Novel benzo[d]imidazole-2(3H)-thiones as potent inhibitors of the α-melanocyte stimulating hormone induced melanogenesis in melanoma B16 cells

In order to determine the optimum size of heterocycle of lead compound 1 (6-methyl-3-phenethyl-3,4-dihydro-1H-quinoline-2-thione; IC50=0.8 μM) for inhibition of melanogenesis, we have synthesized and evaluated some benzimdazole-2(3H)-thiones 5a