189439-24-5

Basic information

• Product Name: 4-(benzyloxy)-2-hydroxybenzonitrile
• Synonyms: 4-(benzyloxy)-2-hydroxybenzonitrile;Benzonitrile, 2-hydroxy-4-(phenylmethoxy)-;2-hydroxy-4-phenylmethoxybenzonitrile
• CAS NO: 189439-24-5
• Molecular Formula: C₁₄H₁₁NO₂
• Molecular Weight: 225.24264
• Mol File: 189439-24-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-(benzyloxy)-2-hydroxybenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(benzyloxy)-2-hydroxybenzonitrile(189439-24-5)
• EPA Substance Registry System: 4-(benzyloxy)-2-hydroxybenzonitrile(189439-24-5)

Safety Data

• Hazardous Substances Data: 189439-24-5(Hazardous Substances Data)

Usage

Description

4-(benzyloxy)-2-hydroxybenzonitrile is a chemical compound characterized by its molecular formula C14H11NO2. It is a white crystalline solid that features a benzene ring with a hydroxy group and a benzyloxy group attached, along with a nitrile functional group. 4-(benzyloxy)-2-hydroxybenzonitrile is pivotal in the synthesis of pharmaceuticals and other organic compounds, playing a crucial role in the development of drug compounds and biologically active molecules due to its unique structure and properties.

Uses

Used in Pharmaceutical Industry:
4-(benzyloxy)-2-hydroxybenzonitrile is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its presence in the molecular structure of target compounds allows for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic chemistry, 4-(benzyloxy)-2-hydroxybenzonitrile serves as a versatile reagent. It is employed in a range of organic reactions to facilitate the production of different organic compounds, contributing to the advancement of chemical research and the creation of novel chemical entities.
Used in the Development of Biologically Active Molecules:
Due to its structural features, 4-(benzyloxy)-2-hydroxybenzonitrile is also used in the design and synthesis of biologically active molecules. Its incorporation into these molecules can enhance their interaction with biological targets, potentially leading to the discovery of new therapeutic agents or probes for biological research.

Upstream product

• 197571-05-4 4-cyano-1,3-phenylene diacetate 
• 5399-68-8 2,4-dihydroxyphenylaldoxime 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 64419-24-5 2,4-dihydroxybenzonitrile 
• 52085-14-0 4-benzoxy-salicylaldehyde 

Downstream Products

• 719272-69-2 3-Methoxy-4-[4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazol-3-yl]phenol 
• 719273-35-5 3-[4-(benzyloxy)-2-methoxyphenyl]-4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazole 
• 719274-38-1 5-[4-(benzyloxy)-2-methoxyphenyl]-2H-tetrazole 

Relevant articles and documents

Polar Order, Mirror Symmetry Breaking, and Photoswitching of Chirality and Polarity in Functional Bent-Core Mesogens

In recent years, liquid crystals (LCs) responding to light or electrical fields have gained significant importance as multifunctional materials. Herein, two new series of photoswitchable bent-core liquid crystals (BCLCs) derived from 4-cyanoresorcinol as the central core connected to an azobenzene based wing and a phenyl benzoate wing are reported. The self-assembly of these molecules was characterized by differential scanning calorimetry (DSC), polarizing light microscopy (POM), electro-optical, dielectric, second harmonic generation (SHG) studies, and XRD. Depending on the direction of the COO group in the phenyl benzoate wing, core-fluorination, temperature, and the terminal alkyl chain length, cybotactic nematic and lamellar (smectic) LC phases were observed. The coherence length of the ferroelectric fluctuations increases continuously with decreasing temperature and adopts antipolar correlation upon the condensation into superparaelectric states of the paraelectric smectic phases. Finally, long-range polar order develops at distinct phase transitions; first leading to polarization modulated and then to nonmodulated antiferroelectric smectic phases. Conglomerates of chiral domains were observed in the high permittivity ranges of the synclinic tilted paraelectric smectic phases of these achiral molecules, indicating mirror symmetry breaking. Fine-tuning of the molecular structure leads to photoresponsive bent-core (BC)LCs exhibiting a fast and reversible photoinduced change of the mode of the switching between ferroelectric- and antiferroelectric-like as well as a light-induced switching between an achiral and a spontaneous mirror-symmetry-broken LC phase.

Discovery of phenoxybutanoic acid derivatives as potent endothelin antagonists with antihypertensive activity

A series of phenoxybutanoic acid derivatives were synthesized and tested for their antagonistic activity on the contraction of the rat thoracic aortic ring induced by endothelin-1. Preliminary screening results showed that 6e and 6g with benzoheterocycles demonstrated significant antagonistic activities when compared to the reference compound BQ123. The results from additional assays for the binding affinity and selectivity for endothelin receptors showed that 6e was a selective ETA antagonist with a nanomolar IC50. Moreover, 6e was effective in relieving hypoxia-induced pulmonary arterial hypertension and right ventricular weight ratio. Therefore, 6e may have potential for further development as a therapeutic agent for the treatment of cardiovascular diseases.

Nematic phases of bent-core mesogens

Bent-core mesogens derived from 4-cyanoresorcinol with terminal alkyl chains have been synthesized and investigated by polarizing microscopy, XRD and electro-optical methods. Short chain compounds have exclusively nematic phases which can be cooled to ambient temperature. These nematic phases are similar to ordinary nematic phases with only nearest neighbour correlation (N) whereas long chain compounds form SmC-type cybotactic clusters and these cybotactic nematic phases (NcybC) can be regarded as strongly fragmented SmC phases. The chain length dependent as well as temperature dependent structural transition from N to NcybC is continuous and associated with a change of the position and intensity of the small angle scattering in the XRD patterns. Moreover, a temperature dependent stepwise transition from cybotactic nematic phases to different types of non-polar and tilted smectic phases (SmC (I) and SmC(II)) is observed with a mesophase composed of elongated, but not yet fused cybotactic clusters (CybC) as an intermediate state of this transition. This improves the understanding of the nature and special properties of the nematic phases formed by bent-core molecules as well as their transition to smectic phases and it paves the way to new materials with spontaneous or field-induced biaxial nematic phases at ambient temperatures.