4578-80-7

Basic information

• Product Name: 2-(p-Chlorophenyl)-2-phenylacetonitrile
• Synonyms: 2-(p-Chlorophenyl)-2-phenylacetonitrile
• CAS NO: 4578-80-7
• Molecular Weight: 227.693
• Mol File: 4578-80-7.mol

Chemical Properties

• CAS DataBase Reference: 2-(p-Chlorophenyl)-2-phenylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(p-Chlorophenyl)-2-phenylacetonitrile(4578-80-7)
• EPA Substance Registry System: 2-(p-Chlorophenyl)-2-phenylacetonitrile(4578-80-7)

Safety Data

• Hazardous Substances Data: 4578-80-7(Hazardous Substances Data)

Usage

Type of compound

Nitrile derivative of acetophenone

Common uses

Intermediate in the synthesis of pharmaceuticals and agrochemicals

Physical state

Pale yellow solid at room temperature

Solubility

Insoluble in water, soluble in organic solvents

Potential applications

Precursor in manufacturing other organic compounds, building block in synthesis of complex molecules

Field of importance

Organic chemistry

Upstream product

• 119-56-2 (4-chlorophenyl)phenylmethanol 
• 1010720-50-9 1-chloro-4-(2,2-difluoro-1-phenylvinyl)benzene 
• 106-39-8 bromochlorobenzene 
• 140-29-4 phenylacetonitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 86409-62-3 tricarbonyl(1,4-dichlorobenzene)chromium⁽⁰⁾ 
• 53731-99-0 2-bromo-2-(4-chlorophenyl)acetonitrile 
• 532-28-5 (RS)-mandelonitrile 
• 140-53-4 p-chlorobenzyl cyanide 
• 134-85-0 4-chlorobenzophenone 
• 134-83-8 1-chloro-4-(chloro(phenyl)methyl)benzene 
• 108-90-7 chlorobenzene 
• 5798-79-8 bromo-phenyl-acetonitrile 
• 71-43-2 benzene 

Downstream Products

• 21771-88-0 α-(4-chlorophenyl)phenylacetic acid 
• 134-85-0 4-chlorobenzophenone 
• 51355-14-7 4-bromo-2-phenyl-2-(4-chlorophenyl)butyronitrile 
• 882979-07-9 4-methylpiperazine-1-carbodithioic acid 3-cyano-3-phenyl-3-(4-chlorophenyl)propyl ester 
• 1247026-26-1 C₂₈H₁₈Cl₂N₂ 
• 108240-27-3 diethyl-[2-(4-chloro-phenyl)-2-phenyl-ethyl]-amine 
• 101436-43-5 ethyl-[2-(4-chloro-phenyl)-2-phenyl-ethyl]-amine 
• 107153-92-4 [2-(4-chloro-phenyl)-2-phenyl-ethyl]-methyl-amine 
• 88875-62-1 2-[2-(4-Chloro-phenyl)-2-phenyl-acetoxy]-benzoic acid 2,2,2-trichloro-ethyl ester 
• 88875-70-1 2-[2-(4-Chloro-phenyl)-2-phenyl-acetoxy]-benzoic acid 
• 324008-33-5 2-(2-{2-[(4-chloro-phenyl)-phenyl-methyl]-thiazol-4-yl}-ethyl)-isoindole-1,3-dione 
• 22187-46-8 (p-Chlor-phenyl)-phenyl-thioacetamid 
• 6578-33-2 2-(4-chloro-phenyl)-2-phenyl-ethylamine 

Relevant articles and documents

Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti

Scalable α-Arylation of Nitriles in Aqueous Micelles using Ultrasmall Pd Nanoparticles: Surprising Formation of Carbanions in Water

A scalable synthetic method is described for both the preparation of ultrasmall palladium nanoparticles and their subsequent use in catalyzing an α-arylation reaction of nitriles in aqueous micelles. This method involves the intermediacy of carbanions or keteniminates, which are presumably stabilized by the micellar environment rather than being quenched with water. These Pd nanoparticles are thoroughly characterized. Mechanistic studies using 31P NMR spectroscopy revealed the binding of phosphine ligand with the Pd surface and control experiment confirmed the zero-oxidation state of palladium. The scope of the transformation is demonstrated over 35 examples, including one at 50 g scale.

I2/Li2CO3-promoted cyanation of diarylalcohols through a dual activation process

One-step base promoted strategy for cyanation of α,α-diaryl alcohols has been developed under mild and transition metal-free conditions. This method provides a straightforward and facile way towards the synthesis of β,γ-unsaturated nitriles and α-phenylnitiriles from α-vinyl carbinols and α,α-diaryl methanols, respectively, up to 99% yield. Moreover, various azides and ethers could also be accessed from their respective nucleophiles under standard reaction conditions.

Synthesis and structure-activity relationships of A novel class of dithiocarbamic acid esters as anticancer agent

Based on a novel lead compound 4-methylpiperazine-1-carbodithioic acid 3-cyano-3,3-diphenylpropyl ester 1, the systematic structural modification was carried out. All the synthesized compounds were evaluated for their in-vitro anticancer activities on four to six different cell lines at three different concentrations. Most of the tested compounds could selectively inhibit the growth of HL-60 and Bel-7402 cell lines at a medium concentration. Four compounds (3f, 3g, 3n, and 5) were selected for the IC50 test, and the results revealed that three compounds (3g, 3n, and 5) showed almost the same or a slightly weaker activity than compound 1 against HL-60, and three compounds (3f, 3g, and 3n) showed >2-fold higher potency than compound 1 against Bel-7402. The in-vivo efficacy of 3n · HCl was evaluated with transplanted hepatocyte carcinoma 22 as an in-vivo test model. It was found that 3n · HCl could inhibit significantly the growth of tumor, and that this effect was dose-dependent. Meanwhile, the compound 3n · HCl showed low toxicity compared with compound 1 · HCl as evidenced by the little body-weight loss. These results confirmed that compound 3n · HCl is more potent than the lead compound 1 · HCl. Preliminary structure-activity relationships indicated that: a) Both nitrile group and the cyclic amine containing at least two nitrogens were indispensable moieties to keep the activity; b) substitution of the piperazine ring is unfavorable for the improvement of activity; c) the suitable linker joining the piperazinyl dithiocarboxyl and diphenylacetonitril group should be ethylene; d) a non-coplanar arrangement of the two benzene rings appears to be essential for activity. Based on a novel lead compound 4-methyl-piperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl ester 1, the systematic structural modification was carried out. Compounds 3g and 3n were found to show more potent biological activities than lead compound 1. Some useful SARs were revealed Copyright

Synthesis and biological activity of allosteric modulators of GABA B receptors, Part 1. N-(Phenylpropyl)-1-arylethylamines

A series of 15 analogues of fendiline, and 34 derivatives of N-(3-phenylpropyl)-1-arylethylamine have been prepared for evaluation as positive allosteric modulators of GABAB receptors. The most active (EC50, 10 nM) was N-(3,3-diphenylpropyl)-1-(3-chloro-4-methoxyphenyl) ethylamine 6g. CSIRO 2006.

Histamine H1 receptor ligands - Part II. Synthesis and in vitro pharmacology of 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives

New 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives were prepared and tested in vitro as H1 receptor antagonists. The compounds with 2-phenylamino substitution with meta-halide substituents at the phenyl ring, showed weak H1-antagonistic activity (pA2: 4.62-5.04) and this activity was completely lost in the case of meta-methyl substituent (pA2 : 4). When the phenylamino group was replaced by benzhydryl groups of classic antihistamines, the resulting compounds exhibited slightly improved H1-antagonistic activity (at the meta-position pA2: 6.38-6.15; at the para-position pA2: 6.04-5.87).

Synthesis of alkylaryl-and diarylnitriles from ketones via N-(1- arylalkylidene)-cyanomethyl amines

Alkylaryl- and diarylketones (Arcor; R= alkyl, aryl, 1) can be converted into nitriles [ArCH(CN)R, 2] containing an additional carbon atom through a base-promoted reaction of N-(1-arylalkylidene)-cyanomethyl amines [ArC(=NCH2CN)R, 3].

Amine compounds, their production and use

A compound of the formula: STR1 wherein Ar 1 and Ar 2 independently represent an optionally substituted aromatic group; P and Q independently represent a divalent aliphatic hydrocarbon group having at least 2 carbon atoms and optionally having either oxygen or sulfur in the carbon chain; R 1 and R 3 independently represent --CO--R, --CONH--R (R represents a hydrocarbon group or a heterocyclic group) or a hydrocarbon group; R 2 and R 4 independently represent hydrogen or an alkyl group; R 2 and R 4 independently represent hydrogen or an alkyl group; R 1 and R 2 or R 3 and R 4, taken together with the adjacent nitrogen atom, may form a nitrogen-containing heterocyclic group; and j represents 0 or 1, or a salt thereof, has excellent GnRH-receptor antagonizing activity and is useful as a prophylactic and therapeutic agent for hormone-dependent and other diseases.

Phenyl-substituted normethadones: Synthesis and pharmacology

Phenyl-substituted normethadone derivatives were synthesized and their affinity (IC50) for opioid receptors was determined by displacement of the specific binding sites of [3H]sufentanyl on rat brain preparations. Substitution resulted in a decrease of affinity in-vitro. These results suggest that normethadone-like compounds may interact with the P subsite of the μ-opioid receptor and that the P subsite has a well-defined cavity shape of stringent dimensions.

AROMATIC NUCLEOPHILIC SUBSTITUTION ON η6-Cr(CO)3-COMPLEXED HALOGENOARENES: ARYLATION OF SECONDARY CARBANIONS

The paper deals with the aromatic nucleophilic substitution on η6-Cr(CO)3-complexed fluorobenzene and ortho-, meta-, and para-dichlorobenzenes with stabilized carbanions, both under phase-transfer conditions (PTC) and in DMSO solution.In the case of the η6-Cr(CO)3-complexed ortho-, meta-, and para-dichlorobenzenes only one chlorine atom is replaced by the carbanions.