3381-87-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzyloxybenzyl alcohol is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its role as a protecting group for alcohols and phenols is crucial in organic synthesis, ensuring the selective protection of functional groups during multi-step reactions, which is vital for the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Benzyloxybenzyl alcohol is employed in the production of various agrochemicals. Its ability to act as a building block in the synthesis of complex organic molecules contributes to the creation of effective pesticides and other agricultural chemicals.
Used in Specialty Chemicals:
2-Benzyloxybenzyl alcohol is also used in the synthesis of specialty chemicals, where its versatility as a building block and protecting group is valuable for developing unique and specialized chemical products.
Used in Organic Synthesis Research:
As a reagent, 2-Benzyloxybenzyl alcohol is instrumental in the preparation of a multitude of other compounds, making it an essential component in organic synthesis research for both academic and industrial applications.
Used in Antimicrobial Applications:
2-Benzyloxybenzyl alcohol has been studied for its potential biological activities, including its antifungal and antibacterial properties. This makes it a candidate for use in applications requiring antimicrobial agents, such as in the development of new antibiotics or antifungal treatments.

InChI:InChI=1/C14H14O2/c15-10-13-8-4-5-9-14(13)16-11-12-6-2-1-3-7-12/h1-9,15H,10-11H2

Upstream product

• 611-20-1 salicylonitrile 
• 14389-86-7 2-benzyloxybenzoic acid 
• 74511-44-7 o-(benzyloxy)benzonitrile 
• 100-39-0 benzyl bromide 
• 90-02-8 salicylaldehyde 
• 100-44-7 benzyl chloride 
• 90-01-7 salicylic alcohol 
• 89-95-2 2-methyl-benzyl alcohol 
• 5896-17-3 2-(phenylmethoxy)benzaldehyde 

Downstream Products

• 1209470-16-5 C₃₆H₃₂O₆ 
• 1209470-18-7 4',6'-bis[2-(benzyloxy)benzyloxy]-2'-hydroxychalcone 
• 1209470-19-8 7-[2-(benzyloxy)benzyloxy]-5-hydroxyflavanone 
• 1586-01-2 (2-hydroxymethylphenyl)phenylmethanol 
• 1410807-50-9 4-(2-benzyloxyphenylmethyl)-5-methyl-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside 
• 1410807-48-5 4-(2-benzyloxyphenylmethyl)-5-trifluoromethyl-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside 
• 1410807-12-3 4-(2-benzyloxyphenylmethyl)-1,2-dihydro-5-cyclopropyl-3H-pyrazol-3-one 
• 478190-06-6 4-(2-benzyloxyphenylmethyl)-5-tert-butyl-1,2-dihydro-3H-pyrazol-3-one 
• 478190-61-3 4-(2-benzyloxyphenylmethyl)-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one 
• 478190-35-1 4-(2-benzyloxyphenylmethyl)-5-ethyl-1,2-dihydro-3H-pyrazol-3-one 
• 1410807-08-7 4-(2-benzyloxyphenylmethyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one 
• 1410806-83-5 C₂₁H₂₂O₄ 
• 1410806-81-3 C₂₂H₂₆O₄ 
• 1410806-80-2 C₂₁H₂₄O₄ 

Relevant academic research and scientific papers

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.

Cyclic analogue of S-benzylisothiourea that suppresses kynurenine production without inhibiting indoleamine 2,3-dioxygenase activity

Kynurenine is biosynthesised from tryptophan catalysed by indoleamine 2,3-dioxygenase (IDO). The abrogation of kynurenine production is considered a promising therapeutic target for immunological cancer treatment. In the course of our IDO inhibitor programme, formal cyclisation of the isothiourea moiety of the IDO inhibitor 1 afforded the 5-Cl-benzimidazole derivative 2b-6, which inhibited both recombinant human IDO (rhIDO) activity and cellular kynurenine production. Further derivatisation of 2b-6 provided the potent inhibitor of cellular kynurenine production 2i (IC50 = 0.34 μM), which unexpectedly exerted little effect on the enzymatic activity of rhIDO. Elucidation of the mechanism of action revealed that compound 2i suppresses IDO expression at the protein level by inhibiting STAT1 expression in IFN-γ-treated A431 cells. The kynurenine-production inhibitor 2i is expected to be a promising starting point for a novel approach to immunological cancer treatment.

Novel leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry

The over-expression of aminopeptidase N on diverse malignant cells is associated with the tumor angiogenesis and metastasis. In this report, one new series of leucine ureido derivatives containing the triazole moiety was designed, synthesized and evaluated as APN inhibitors. Among them, compound 13v showed the best APN inhibition with an IC50 value of 0.089 ± 0.007 μM, which was two orders of magnitude lower than that of bestatin (IC50 = 9.4 ± 0.5 μM). Compound 13v also showed dose-dependent anti-angiogenesis activities. Even at the lower concentration (10 μM), compound 13v presented similar anti-angiogenesis activity compared with bestatin at 100 μM in both the human umbilical vein endothelial cells (HUVECs) capillary tube formation assay and the rat thoracic aorta rings test. Moreover, compared with bestatin, 13v exhibited comparable, if not better in vivo anti-metastasis activity in a mouse H22 pulmonary metastasis model.

Solvent responsive catalyst improves NMR sensitivity: Via efficient magnetisation transfer

A bidentate iridium carbene complex, Ir(κC,O-L1)(COD), has been synthesised which contains a strongly electron donating carbene ligand that is functionalised by a cis-spanning phenolate group. This complex acts as a precursor to effective magne

Highly Active Multidentate Ligand-Based Alkyne Metathesis Catalysts

Alkyne metathesis catalysts composed of molybdenum(VI) propylidyne and multidentate tris(2-hydroxylbenzyl)methane ligands have been developed, which exhibit excellent stability (remains active in solution for months at room temperature), high activity, an

High diastereoselectivity in the yang photocyclization via remote hydrogen abstraction reaction

1-Benzoyl-1-(o-alkoxyphenyl)cyclopropanes undergo Yang photocyclization to form dihydrobenzopyranols in a stereospecific manner. The cyclopropyl group at alpha position to carbonyls gives not only a bias in the most stable geometries of the starting ketones but also conformational restriction on geometries of biradical intermediates. More importantly, intramolecular hydrogen bonds seem to give an additional effect on conformational control of the biradical reactivity.

Synthesis of 5-arylisoxazole-3-carboxylates derived from salicylaldehyde

A procedure has been developed for the synthesis of 5-arylisoxazole-3-carboxylates on the basis of phenols and oximes derived from salicylaldehyde. Selective reduction of 4-(2-ethoxybenzylideneaminophenyl) 5-arylisoxazole-3-carboxylates afforded the corresponding amines.

Unexpected observations during the total synthesis of calothrixin B-sodium methoxide as a source of hydride

During the total synthesis of calothrixin B, various novel and unexpected results were noticed such as cleavage of C-N bond in imine using sodium cyanoborohydride, sodium methoxide as a hydride source for reduction, deformylation in the presence of bromine, and deacylation using ceric ammonium nitrate (CAN). A detailed mechanism has been proposed for the unexpected results and a few of them are generalized. Temperature dependent NMR studies have been carried out for confirmation of the structure of one of the intermediates in the synthetic sequence.

Amino acids derived benzoxazepines: Design, synthesis and antitumor activity

Two series of new benzoxazepines substituted with different alkyl amino ethyl chains were synthesized comprising synthetic steps of inter and intramolecular Mitsunobu reaction, lithium aluminium hydride (LAH) reduction, debenzylation, bimolecular nucleophilic substitution (SN2) reaction. The present study investigates the effect of a tyrosine-based benzoxazepine derivative in human breast cancer cells MCF-7 and MDA-MB-231 and in breast cancer animal model. The anti-proliferative effect of 15a on MCF-7 cells was associated with G1 cell-cycle arrest. This G1 growth arrest was followed by apoptosis as 15a dose dependently increased phosphatidylserine exposure, PARP cleavage and DNA fragmentation that are hallmarks of apoptotic cell death. Interestingly, 15a activated components of both intrinsic and extrinsic pathways of apoptosis characterized by activation of caspase-8 and -9, mitochondrial membrane depolarization and increase in Bax/Bcl2 ratio. However, use of selective caspase inhibitors revealed that the caspase-8-dependent pathway is the major contributor to 15a-induced apoptosis. Compound 15a also significantly reduced the growth of MCF-7 xenograft tumors in athymic nude mice. Together, 15a could serve as a base for the development of a new group of effective breast cancer therapeutics.

Neighboring lithium-assisted [1,2]-wittig rearrangement: Practical access to diarylmethanol-based 1,4-diols and optically active binol derivatives with axial and sp3-central chirality

A facile and practical methodology for the synthesis of synthetically useful diarylmethanol-based 1,4-diols and enantiomerically pure BINOL-derived diols with axial and sp3-central chirality has been developed through neighboring lithium-promot