13463-94-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Chlorophenylcyanamide is used as a chemical intermediate for the synthesis of N-(4-Chlorophenyl)-O-methylisourea Sulfate Salt (~90%) (C378465), a cytotoxic agent that exhibits tumor inhibitory activity. This makes it a valuable component in the development of cancer treatments, contributing to the advancement of medical therapies.

InChI:InChI=1/C7H5ClN2/c8-6-1-3-7(4-2-6)10-5-9/h1-4,10H

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 1482-62-8 1-(4-chlorophenyl)-3-cyanoguanidine 
• 917-64-6 methyl magnesium iodide 
• 926-62-5 isobutylmagnesium bromide 
• 925-90-6 ethylmagnesium bromide 
• 920-39-8 isopropylmagnesium bromide 
• 10557-57-0 propylmagnesium iodide 
• 39536-21-5 S-methyl N-(4-chlorophenyl)amidino thioether 
• 506-68-3 bromocyane 
• 106-47-8 4-chloro-aniline 
• 45964-97-4 1-(4-chlorophenyl)guanidine 
• 2386-64-3 ethylmagnesium chloride 
• 100-66-3 methoxybenzene 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 35370-37-7 N-(4-chloro-phenyl)-propionamidine 
• 14277-03-3 N-(4-chlorophenyl)acetimidamide 
• 4364-73-2 N-(4-chloro-phenyl)-N'-[4-(2-diethylamino-ethylamino)-6-methyl-pyrimidin-2-yl]-guanidine 
• 119986-59-3 benzoic acid-(4-chloro-N-cyano-anilide) 
• 3547-41-9 Kohlensaeure-<3-methoxycarbonyl-naphthyl-(2)-ester>-imid-<4-chlor-phenyl-cyanamid> 
• 3305-91-7 C₂₂H₁₄Cl₂N₆O₂ 
• 3515-02-4 Kohlensaeure-p-tolylester-imid-<(4-chlor-phenyl)-cyanamid> 
• 3547-42-0 Kohlensaeure-α-naphthylester-imid-<4-chlor-phenyl-cyanamid> 
• 3514-99-6 Kohlensaeure-<4-nitro-phenylester>-imid-<4-chlor-phenyl-cyanamid> 
• 143770-36-9 2-amino-3-<4-chlorophenyl>-4-imino-5,6,7,8-tetrahydro<1>benzothieno<2,3-d>pyrimidine 
• 128763-51-9 5-(4-Chloro-phenylamino)-4-methyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 128763-55-3 5-(4-Chloro-phenylamino)-4-ethyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 64119-13-7 C₇H₆Cl₂N₂ 
• 156361-79-4 (4-Chloro-phenyl)-prop-2-ynyl-cyanamide 

Relevant academic research and scientific papers

Oxidation of N-4-chlorophenyl-N′-hydroxyguanidine to N-(4-chlorophenyl)urea and nitric oxide by photoexcited iron porphyrins

Photochemical excitation (λ > 350 nm) of chloro[meso-tetrakis(2, 6-dichlorophenyl)porphyrin]iron(III) [FeIII(TDCPP)Cl] and chloro[meso-tetra(α,α,α,α-pivalamidophenyl)porphyrin] -iron(III) [FeIII(TpivPP)Cl] induces the oxidation of coordinated N-(4-chlorophenyl)-N′-hydroxyguanidine (1) by molecular oxygen, to give iminoxyl radicals and the FeII(O2) [or Fe III(O2.)] adduct. This complex can be accumulated in significant amounts using [FeIII(TpivPP)Cl]. The primary photoproducts give rise to secondary reactions that lead to the formation of N-4-chlorophenyl)urea (2) as the main end-product of 1. The conversion of 1 into 2 is accompanied by the formation of NO, as revealed both by an ESR spin-trapping technique and in the form of its stable end-products NO2- and NO3-. The presence of 1-methyl imidazole (1-MeIm) coordinated in axial position has a significant positive effect on the photoinduced production of 2 and NO from the hydroxyguanidine 1. The observation that radical scavengers inhibit the photooxidation process strongly supports the possibility that the reaction pathway resembles a radical-type autoxidation mechanism, where the very fast reaction of O2 with the ferrous porphyrin in the presence of the photo-generated iminoxyl radical should yield an iron-peroxo intermediate as precursor of the urea 2 and NO. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions

The iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology. All the reactions are rapid, facile, and accomplished at room temperature. A variety of substrates readily underwent the optimized reaction conditions to provide their respective target products in good to excellent yields. Furthermore, we have confirmed that no other by-products could be identified during our experimental reaction process. Graphical abstract: Iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology.[Figure not available: see fulltext.].

CF3SO2Na as a Bifunctional Reagent: Electrochemical Trifluoromethylation of Alkenes Accompanied by SO2 Insertion to Access Trifluoromethylated Cyclic N-Sulfonylimines

An unprecedented electrochemical trifluoromethylation/SO2 insertion/cyclization process has been achieved in an undivided cell in an atom-economic fashion. The protocol relies on tandem cyclization of N-cyanamide alkenes by using Langlois’ reagent as a source of both CF3 and SO2 under direct anodically oxidative conditions, in which two C?C bonds, two C?X bonds (N?S and S?C), and two rings were formed in a single operation. This transformation enabled efficient construction of various trifluoromethylated cyclic N-sulfonylimines from readily accessible materials.

Synthesis of Cyanamides via a One-Pot Oxidation-Cyanation of Primary and Secondary Amines

An operationally simple oxidation-cyanation method for the synthesis of cyanamides is described. The procedure utilizes inexpensive and commercially available N-chlorosuccinimide and Zn(CN)2 as reagents to avoid direct handling of toxic cyanogen halides. It is demonstrated to be amenable for the cyanation of a variety of primary and secondary amines and aniline derivatives as well as a complex synthetic intermediate en route to verubecestat (MK-8931). Additionally, kinetic measurements and other control experiments are reported to shed light onto the mechanism of this cyanation reaction.

A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement

A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.

Fe3O4@SiO2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water

In the present work, we have designed a novel, heterogeneous and recyclable magnetic Br?nsted acidic ionic liquid based on 5-phenyl-1H-tetrazole. The {Fe3O4@SiO2@CH2)35-phenyl-1H-tetrazole-SO3H/Cl} ([FSTet-SO3H]Cl) was prepared via the immobilization of 5-phenyl-1H-tetrazole-bonded sulfonic acid onto the surface of silica-coated magnetic nanoparticles using 3-chloropropyltriethoxysilane as a linker. The catalyst was characterized by XRD, TEM, FESEM, EDS, TG-DTA, and FT-IR. The ability and high activity of this catalyst were demonstrated in the synthesis of 1-carbamoyl-1-phenylureas with good to excellent yields via a new, simple and one-pot procedure in aqueous media under reflux conditions. This procedure has advantages such as high yields, short reaction times, a simple methodology and work-up process, green reaction conditions, high stability, catalytic activity, and easy preparation, separation and reusability of the catalyst. The synthesis of these compounds was confirmed by FT-IR, 1H NMR, 13C NMR and CHN. In addition, we investigated the biological properties of the 1-carbamoyl-1-phenylureas as newly synthesized compounds. The described catalyst could be easily separated from the reaction mixture by additional magnetic force and reused several times without a remarkable loss of its catalytic activity and any considerable changes in the product yield and the reaction time.

One-pot three-component tandem reaction: Synthesis of aryl/alkyl cyanamides libraries and their further conversion into tetrazole derivatives

We have developed methodology for the synthesis of aryl/alkyl cyanamides from amines in one-pot four steps reaction using cheap, readily available and air stable copper source as catalyst under mild reaction conditions. We have also studied the application of cyanamides. In this connection, we could construct aryl tetrazolamine from cyanamides using click reaction.

Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles

[Figure not available: see fulltext.] The synthesis of cyanamides and tetrazoles from isothiocyanates through tandem reaction using cobalt catalyst has been demonstrated. In the case of tetrazole preparation, the reaction involved addition/desulfurization/nucleophilic addition/electrocyclization, whereas aromatic cyanamides were constructed from isothiocyanates through addition/desulfurization. Cheap cobalt sulfate was used for the synthesis of various cyanamides and tetrazoles. In addition, cobalt catalyst was found to be desulfurization reagent that has not been previously reported. The final products have been obtained from starting precursors in good to high yield.

The synthesis of aryl cyanamides through C-N cross-coupling

The methodology for the preparation of aromatic cyanamides has been demonstrated. The present method involves consecutive desulphurization/C-N cross-coupling reaction. Cheap, readily available and air stable cobalt catalyst has been used for this methodology. In addition, the substrate scope has been explored.

The synthesis of arylcyanamides: A copper-catalyzed consecutive desulfurization and C-N cross-coupling strategy

A one pot highly efficient and simple protocol for the construction of aromatic cyanamides from thiourea via desulphurization/C-N cross coupling using a cheap, readily available and air stable copper source as a catalyst has been described. Various iodobenzenes could give their respective C-N cross-coupled products in good to excellent yields under optimized reaction conditions. Further, the substrate scope has been explored.