66422-84-2

Basic information

• Product Name: 4-(BENZYLOXY)-3-CHLOROBENZALDEHYDE
• Synonyms: 4-(BENZYLOXY)-3-CHLOROBENZALDEHYDE
• CAS NO: 66422-84-2
• Molecular Formula: C₁₄H₁₁ClO₂
• Molecular Weight: 246.69
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 66422-84-2.mol

Chemical Properties

• Melting Point: 89-91°C
• Boiling Point: 389.1°C at 760 mmHg
• Flash Point: 162.2°C
• Appearance: /
• Density: 1.247g/cm³
• Vapor Pressure: 2.92E-06mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 4-(BENZYLOXY)-3-CHLOROBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(BENZYLOXY)-3-CHLOROBENZALDEHYDE(66422-84-2)
• EPA Substance Registry System: 4-(BENZYLOXY)-3-CHLOROBENZALDEHYDE(66422-84-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 66422-84-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(Benzyloxy)-3-chlorobenzaldehyde is utilized as an intermediate in the synthesis of various pharmaceuticals. Its unique molecular structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(Benzyloxy)-3-chlorobenzaldehyde is employed as an intermediate for the production of pesticides. Its reactivity and structural features make it suitable for the creation of compounds that can effectively control pests and protect crops.
Used in Organic Synthesis:
4-(Benzyloxy)-3-chlorobenzaldehyde is used as a building block in organic synthesis for the preparation of a wide array of chemical compounds. Its ability to react with various chemicals enables the synthesis of new compounds with different properties and potential applications in various fields.
Used in Chemical Reactions:
As a reagent, 4-(Benzyloxy)-3-chlorobenzaldehyde is involved in numerous chemical reactions, facilitating the formation of desired products in research and industrial processes. Its versatility in reacting with other chemicals makes it a valuable asset in the realm of chemical research and development.

InChI:InChI=1/C14H11ClO2/c15-13-8-12(9-16)6-7-14(13)17-10-11-4-2-1-3-5-11/h1-9H,10H2

Upstream product

• 2420-16-8 4-hydroxy-3-chlorobenzaldehyde 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 106931-79-7 4-(benzyloxy)-3-chlorobenzoic acid 
• 3964-58-7 3-chloro-4-hydroxybenzoic acid 
• 536974-87-5 (4-benzyloxy-3-chlorophenyl)methanol 
• 100-51-6 benzyl alcohol 

Downstream Products

• 84447-30-3 2'-hydroxy-3,5'-dichloro-4',6'-dimethoxy-4-benzyloxychalcone 
• 202577-85-3 3-(4-Benzyloxy-3-chloro-phenyl)-3-hydroxy-propionic acid ethyl ester 
• 536974-87-5 (4-benzyloxy-3-chlorophenyl)methanol 
• 86902-27-4 3-chloro-4-benzyloxyphenol 
• 159526-67-7 (E)-3-(4-benzyloxy-3-chlorophenyl)acrylic acid ethyl ester 
• 945244-00-8 2-(4-(benzyloxy)-3-chlorophenyl)acetonitrile 
• 1239610-88-8 5-(4-(benzyloxy)-3-chlorobenzylidene)thiazolidine-2,4-dione 
• 2315-81-3 2-chloro-4-cyanophenol 
• 943141-71-7 N-(tetrahydro-2H-pyran-2-yloxy) (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamamide 
• 943141-70-6 (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamic acid 
• 943141-64-8 5-{3-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]-(2E)-2-propenylidene}-2,4-thiazolidinedione 
• 943141-63-7 (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamaldehyde 
• 943141-62-6 (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamyl alcohol 
• 524937-26-6 ethyl (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamate 

Relevant articles and documents

Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine

The transamination of α-keto acids with 2-phenylglycine is an effective methodology for directly synthesizing unprotected α-amino acids. However, the synthesis of 2-arylglycines by transamination is problematic because the corresponding products, 2-arylglycines, transaminate the starting arylglyoxylic acids. Herein, we demonstrate the use of commercially available l-2-(2-chlorophenyl)glycine as the nitrogen source in the transamination of arylglyoxylic acids, producing the corresponding 2-arylglycines without interference from the undesired self-transamination process.

HETEROCYCLIC INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY

The present invention relates to certain heterocyclic compounds of formula (1) that have the ability to inhibit lysine biosynthesis via the diaminopimelate biosynthesis pathway in certain organisms. As a result of this activity these compounds can be used

1,2,3-triazole compounds with antitumor activity and preparation method for 1,2,3-triazole compounds

The present invention relates to three 1,2,3-triazole compounds with aryl structures on the left sides, and the general structural formulae thereof are as shown in the specification. The three compounds have good antitumor activity.

Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

Control of the intracellular levels of prostaglandin E2 through inhibition of the 15-hydroxyprostaglandin dehydrogenase for wound healing

Excessive scar formation is an aberrant form of wound healing and is an indication of an exaggerated function of fibroblasts and excess accumulation of extracellular matrix during wound healing. Much experimental data suggests that prostaglandin E2 (PGE2) plays a role in the prevention of excessive scarring. However, it has a very short half-live in blood, its oxidization to 15-ketoprostaglandins is catalyzed by 15-hydroxyprostaglandin dehydrogenase (15-PGDH). Previously, we reported that 15-PGDH inhibitors significantly increased PGE2 levels in A549 cells. In our continuing attempts to develop highly potent 15-PGDH inhibitors, we newly synthesized various thiazolidine-2,4-dione derivatives. Compound 27, 28, 29, and 30 demonstrated IC50 values of 0.048, 0.020, 0.038 and 0.048 μM, respectively. They also increased levels of PGE2 in A549 cells. Especially, compound 28 significantly increased level of PGE2 at 260 pg/mL, which was approximately fivefold higher than that of control. Scratch wounds were analyzed in confluent monolayers of HaCaT cells. Cells exposed to compound 28 showed significantly improved wound healing with respect to control.

COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

Modulators of ATP-binding cassette transporters

Compounds of the present invention and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (“CFTR”). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.

Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: Effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and inhibition of Src homology 2 domain-containing protein tyrosine phosphatase-2 activity

(E)-4-[3-(1-Adamantyl)-4′-hydroxyphenyl]-3-chlorocinnamic acid (3-Cl-AHPC) induces the cell-cycle arrest and apoptosis of leukemia and cancer cells. Studies demonstrated that 3-Cl-AHPC bound to the atypical orphan nuclear receptor small heterodimer partner (SHP). Although missing a DNA-binding domain, SHP heterodimerizes with the ligand-binding domains of other nuclear receptors to repress their abilities to induce or inhibit gene expression. 3-Cl-AHPC analogues having the 1-adamantyl and phenolic hydroxyl pharmacophoric elements replaced with isosteric groups were designed, synthesized, and evaluated for their inhibition of proliferation and induction of human cancer cell apoptosis. Structure-anticancer activity relationship studies indicated the importance of both groups to apoptotic activity. Docking of 3-Cl-AHPC and its analogues to an SHP computational model that was based on the crystal structure of ultraspiracle complexed with 1-stearoyl-2-palmitoylglycero-3-phosphoethanolamine suggested why these 3-Cl-AHPC groups could influence SHP activity. Inhibitory activity against Src homology 2 domain-containing protein tyrosine phosphatase 2 (Shp-2) was also assessed. The most active Shp-2 inhibitor was found to be the 3′-(3,3-dimethylbutynyl) analogue of 3-Cl-AHPC.

Dual aromatase-steroid sulfatase inhibitors

By introducting the steroid sulfatase inhibitory pharmacophore into aromatase inhibitor 1 (YM511), two series of single agent dual aromatase-sulfatase inhibitors (DASIs) were generated. The best DASIs in'vitro (JEG-3 cells) are 5, (IC50(aromatase) = 0.82 nM; IC 50(sulfatase) = 39 nM), and 14, (IC50(aromatase) = 0.77 nM; IC50(sulfatase) = 590 nM). X-ray crystallography of 5, and docking studies of selected compounds into an aromatase homology model and the steroid sulfatase crystal structure are presented. Both 5 and 14 inhibit aromatase and sulfatase in PMSG pretreated adult female Wistar rats potently 3 h after a single oral 10 mg/kg dose. Almost complete dual inhibition is observed for 5 but the levels were reduced to 85% (aromatase) and 72% (sulfatase) after 24 h. DASI 5 did not inhibit aldosterone synthesis. The development of a potent and selective DASI should allow the therapeutic potential of dual aromatase-sulfatase inhibition in hormone-dependent breast cancer to be assessed.

An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: Effects of modifying its carboxylate group on apoptosis, proliferation, and

Apoptotic and antiproliferative activities of small heterodimer partner (SHP) nuclear receptor ligand (E)-4-[3′-(1-adamantyl)-4′- hydroxyphenyl]-3-chlorocinnamic acid (3-Cl-AHPC), which was derived from 6-[3′-(1-adamantyl)-4′-hydroxyphenyl]-2-naphthalenec