3695-92-9

Usage

Uses

Used in Pharmaceutical Industry:
P-Chloro-a-phenylcinnaminitrile is used as an intermediate in the synthesis of pharmaceuticals for its ability to inhibit the production of tyrosinase, an enzyme involved in the production of melanin. This makes it a potential ingredient in skin-lightening products.
Used in Agricultural Chemical Industry:
P-Chloro-a-phenylcinnaminitrile is used as a precursor in the manufacturing of agricultural chemicals, contributing to the development of various agrochemical products.
Used in Dye and Pigment Industry:
P-Chloro-a-phenylcinnaminitrile is used as a precursor in the production of dyes, pigments, and other specialty chemicals, playing a crucial role in the creation of a wide range of colorants and compounds for various applications.
It is important to handle P-Chloro-a-phenylcinnaminitrile with caution as it can cause skin and eye irritation and should be used in a well-ventilated area.

InChI:InChI=1/C15H10ClN/c16-15-8-6-12(7-9-15)10-14(11-17)13-4-2-1-3-5-13/h1-10H/b14-10-

Upstream product

• 140-29-4 phenylacetonitrile 
• 873-76-7 para-Chlorobenzyl alcohol 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 7497-44-1 (+/-)-erythro-2-(4-chloro-phenyl)-3-phenyl-succinonitrile 
• 32970-79-9 3-(4-chlorophenyl)-2-phenylpropanenitrile 
• 82234-88-6 3-cyano-4-(4-chlorophenyl)-2,3,5-triphenylpyrrolidine 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 5468-17-7 (+/-)-erythro-3-phenyl-2-(4-chloro-phenyl)-succinic acid diamide 
• 41915-63-3 (+/-)-erythro-2-(4-chloro-phenyl)-3-phenyl-succinic acid 
• 1448006-07-2 C₁₆H₁₂Cl₂N₂ 
• 70974-70-8 (Z)-3-(4-Chloro-phenyl)-3-nitro-2-phenyl-acrylonitrile 
• 949563-82-0 3-benzyl-2-(p-chlorophenyl)-2-phenylpropanenitrile 
• 949563-83-1 3-benzyl-2-(p-chlorophenyl)-2-phenylpropanoic acid 
• 949563-84-2 3-(p-chlorophenyl)-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-one 
• 949563-85-3 3-(p-cyanophenyl)-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-one 
• 949563-86-4 2-bromo-3-(p-cyanophenyl)-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-one 
• 69032-00-4 2-(4-Chlorbenzoyl)-α-phenylacetamid 

Relevant academic research and scientific papers

Pyrenedione-Catalyzed α-Olefination of Nitriles under Visible-Light Photoredox Conditions

Herein, we report a combination of pyrenedione (PD) and KOtBu to achieve facile alcohol dehydrogenation under visible-light excitation, where aerobic oxygen is utilized as the terminal oxidant. The resulting carbonyl compound can be easily converted to vinyl nitriles in a single-pot reaction, at 60 °C in 6-8 h. This environmentally benign, organocatalytic approach has distinct advantages over transition-metal-catalyzed α-olefination of nitriles, which often operate at a significantly higher temperature for an extended reaction time.

Switchable Cobalt-Catalyzed α-Olefination and α-Alkylation of Nitriles with Primary Alcohols

The first switchable α-olefination and α-alkylation of nitriles with primary alcohols catalyzed by a well-defined base transition-metal Co complex was presented. A broad variety of nitriles and primary alcohols are selectively and efficiently converted to the corresponding products by this method. It is noteworthy that the transformation is environmentally benign and atom efficient with H2and H2O being the sole byproducts.

INHIBITORS OF THE N-TERMINAL DOMAIN OF THE ANDROGEN RECEPTOR

The present disclosure provides compounds and methods for inhibiting or degrading the N-terminal domain of the androgen receptor, as well as methods for treating cancers such as prostate cancer.

Synthesis of β-Amino Diaryldienones Using the Mannich Reaction

The Mannich reaction has been used for decades to prepare many pharmaceutically important molecules. Here, using a "double-Mannich-β-elimination" synthetic sequence, we report the synthesis and the characterization details of a novel class of β-amino diaryldienones with prominent antiprostate cancer activity. Through these studies, we correct an erroneous structure in the current literature, present a discussion of the stereochemical outcome of a new reaction, and probe the mechanism(s) of byproduct formation through isotopic studies.

INHIBITORS OF THE N-TERMINAL DOMAIN OF THE ANDROGEN RECEPTOR

The present disclosure provides compounds and methods for inhibiting or degrading the N-terminal domain of the androgen receptor, as well as methods for treating cancers such as prostate cancer.

Atmosphere-Controlled Chemoselectivity: Rhodium-Catalyzed Alkylation and Olefination of Alkylnitriles with Alcohols

The chemoselective alkylation and olefination of alkylnitriles with alcohols have been developed by simply controlling the reaction atmosphere. A binuclear rhodium complex catalyzes the alkylation reaction under argon through a hydrogen-borrowing pathway and the olefination reaction under oxygen through aerobic dehydrogenation. Broad substrate scope is demonstrated, permitting the synthesis of some important organic building blocks. Mechanistic studies suggest that the alkylation product may be formed through conjugate reduction of an alkene intermediate by a rhodium hydride, whereas the formation of olefin product may be due to the oxidation of the rhodium hydride complex with molecular oxygen.

Manganese Catalyzed α-Olefination of Nitriles by Primary Alcohols

Catalytic α-olefination of nitriles using primary alcohols, via dehydrogenative coupling of alcohols with nitriles, is presented. The reaction is catalyzed by a pincer complex of an earth-abundant metal (manganese), in the absence of any additives, base, or hydrogen acceptor, liberating dihydrogen and water as the only byproducts.

Synthesis and evaluation of (Z)-2,3-diphenylacrylonitrile analogs as anti-cancer and anti-microbial agents

In the present study, a series of (Z)-2,3-diphenylacrylonitrile analogs were synthesized and then evaluated in terms of their cytotoxic activities against four human cancer cell lines, e.g. lung cancer (A549), ovarian cancer (SK-OV-3), skin cancer (SK-MEL-2), and colon cancer (HCT15), as well as anti-microbial activities against three microbes, e.g. Staphylococcus aureus, Salmonella typhi, and Aspergillus niger. The title compounds were synthesized by Knoevenagel condensation reaction of benzyl cyanide or p-nitrobenzyl cyanide with substituted benzaldehydes in good yields. Most of the compounds exhibited significant suppressive activities against the growth of all cancer cell lines. Compound 3c was most active in inhibiting the growth of A549, SK-OV-3, SK-MEL-2, and HCT15 cells lines with IC50 values of 0.57, 0.14, 0.65, and 0.34 mg/mL, respectively, followed by compounds 3f, 3i, and 3h. Compound 3c exhibited 2.4 times greater cytotoxic activity against HCT15 cells, whereas it showed similar potency against SK-OV-3 cells to that of the standard anti-cancer agent doxorubicin. Structure-activity relationship study revealed that electron-donating groups at the para-position of phenyl ring B were more favorable for improved cytotoxic activity, whereas the presence of electron-withdrawing groups was unfavorable compare to unsubstituted acrylonitrile. An optimal electron density on phenyl ring A of (Z)-2,3-diphenylacrylonitrile analogs was crucial for their cytotoxic activities against human cancer cell lines used in the present study. Qualitative structure-cytotoxic activity relationships were studied using physicochemical parameters; a good correlation between calculated polar surface area (PSA), a lipophobic parameter, and cytotoxic activity was found. Moreover, all compounds showed significant anti-bacterial activities against S. typhi, whereas compound 3k showed potent inhibition against both S. aureus and S. typhi bacterial strains.

(Z)-2-(2-bromophenyl)-3-{[4-(1-methyl-piperazine)amino]phenyl}acrylonitrile (DG172): An orally bioavailable PPARβ/δ-selective ligand with inverse agonistic properties

The ligand-regulated nuclear receptor peroxisome proliferator-activated receptor β/δ (PPARβ/δ) is a potential pharmacological target due to its role in disease-related biological processes. We used TR-FRET-based competitive ligand binding and coregulator

Synthesis and cannabinoid-1 receptor binding affinity of conformationally constrained analogs of taranabant

The design, synthesis, and binding activity of ring constrained analogs of the acyclic cannabinoid-1 receptor (CB1R) inverse agonist taranabant 1 are described. The initial inspiration for these taranabant derivatives was its conformation 1a, determined b