6272-38-4

Basic information

• Product Name: 2-Benzyloxyphenol
• Synonyms: Benzyl o-hydroxyphenyl ether;o-(Benzyloxy)phenol;Phenol, o-(benzyloxy)-;2-(BENZYLOXY)PHENOL;CATECHOL MONOBENZYL ETHER;Phenol, 2-(phenylmethoxy)-;2-(phenylmethoxy)phenol;2-Benzyloxyphenol,98%
• CAS NO: 6272-38-4
• Molecular Formula: C₁₃H₁₂O₂
• Molecular Weight: 200.23
• EINECS: 228-461-5
• Product Categories: Alcohols;C9 to C30;Oxygen Compounds
• Mol File: 6272-38-4.mol

Chemical Properties

• Melting Point: 35-40°C
• Boiling Point: 215 °C / 20mmHg
• Flash Point: >230 °F
• Appearance: Colorless to pale yellow/Liquid or Low Melting
• Density: 1.143 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.12E-05mmHg at 25°C
• Refractive Index: n20/D 1.591(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.65±0.30(Predicted)
• Water Solubility: Soluble in alcohol, benzene, and diethyl ether. Insoluble in water.
• CAS DataBase Reference: 2-Benzyloxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzyloxyphenol(6272-38-4)
• EPA Substance Registry System: 2-Benzyloxyphenol(6272-38-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 1
• Hazardous Substances Data: 6272-38-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Benzyloxyphenol is used as a reagent for the synthesis of 2-(benzyloxy)hydroquinone, a compound with potential applications in various fields. It is also used to prepare sequential polypeptides, which are essential in the development of new drugs and materials.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-Benzyloxyphenol is used as a pharmaceutical intermediate, playing a crucial role in the development of new drugs. Its ability to act as a reagent for the synthesis of multidentate chelating ligands makes it a valuable component in the creation of complex pharmaceutical compounds.
Used in Chemicals Industry:
2-Benzyloxyphenol is also employed in the chemicals industry, where it is used as a building block for the synthesis of various chemical products. Its versatility and unique properties make it a valuable asset in the development of new and innovative chemical compounds.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 20, p. 880, 1977 DOI: 10.1021/jm00217a002

InChI:InChI=1/C13H12O2/c14-12-8-4-5-9-13(12)15-10-11-6-2-1-3-7-11/h1-9,14H,10H2

Upstream product

• 100-44-7 benzyl chloride 
• 120-80-9 benzene-1,2-diol 
• 7527-52-8 2-phenyl-1,3-benzodioxole 
• 6738-17-6 O-benzyl-N,N'-dicyclohexylisourea 
• 725268-38-2 (2S,3R)-2,3-Bis-benzyloxy-5-hydroxy-cyclohexanone 
• 93758-13-5 2-<(methoxymethyl)oxy>-1-(benzyloxy)benzene 
• 100-39-0 benzyl bromide 
• 69617-72-7 (3S,4S,5R,1'S)-3-bromo-5-(2'-bromo-1'-hydroxy)ethyl-4,5-dihydro-4-hydroxy-2-(3H)-furanone 
• 122204-66-4 methyl 2,6-dibromo-2,6-dideoxy-α-D-mannopyranoside 
• 189758-74-5 (2S,3S,4R,6S)-2-Bromomethyl-6-methoxy-tetrahydro-pyran-3,4-diol 
• 189758-76-7 (2S,3S,4R,6S)-3,4-Bis-benzyloxy-2-bromomethyl-6-methoxy-tetrahydro-pyran 
• 189758-77-8 methyl 3,4-di-O-benzyl-2-deoxy-5-methylene-α-D-xylopyranoside 
• 90-02-8 salicylaldehyde 
• 5896-17-3 2-(phenylmethoxy)benzaldehyde 

Downstream Products

• 154582-47-5 1-(benzyloxy)-2-(2-bromoethoxy)benzene 
• 73961-19-0 2,2'-(Ethylendioxy)diphenoldibenzylether 
• 67655-20-3 1,3-bis[2-(benzyloxy)phenoxy]propan-2-ol 
• 22530-53-6 1-(2-benzyloxyphenoxy)-2,3-propylene oxide 
• 97546-45-7 1-(2-benzyloxyphenoxy)decan-2-ol 
• 87117-73-5 2,2'bisphenol-dibenzylether 
• 86955-48-8 C₃₂H₃₄O₄ 
• 87117-71-3 2,2'-<1,2-Ethandiylbis(oxy-2,1-ethandiyloxy)>bisphenol-dibenzylether 
• 87117-66-6 2-(2'-(2''-(2'''-methoxyethoxy)ethoxy)ethoxy)-1-benzyloxybenzene 
• 98571-95-0 methyl trans-4-(2-benzyloxyphenoxy)-2-butenoate 
• 86955-49-9 2,2'-((oxybis(ethane-2,1-diyl))bis(oxy))bis((benzyloxy)benzene) 
• 133322-67-5 2α-<2-(benzyloxy)phenoxy>-5α-cholestan-3-one 
• 154878-95-2 ethyl 2-<2-(benzyloxy)phenoxy>-4,5-dimethoxyphenylacetate 
• 79306-77-7 3-dimethylamino-2-phenylpropyl acetate 

Relevant articles and documents

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The N-butyl amide group, CONHBu, has been found to be an effective promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy, and fluoro, although not with nitro and, unexpectedly, is applicable to meta as well as ortho and para isomeric series.

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Enantioselective synthesis, stereochemical correction, and biological investigation of the rodgersinine family of 1,4-benzodioxane neolignans

The enantioselective synthesis and chiroptic analysis of all members of the rodgersinine family of 1,4-benzodioxane neolignans has been achieved. ECD spectra and optical rotation analysis determined that the previously published stereochemistry of trans-rodgersinines A and B was incorrect. The cis-rodgersinines A and B did not follow the model ECD study commonly used to assign the absolute stereochemistry of 1,4-benzodioxane natural products. This finding has implications on the absolute stereochemistry of other natural products of this type. Additionally, the rodgersinines were found to have anti-HCV activities.

A study towards the regioselective synthesis of the e,e,e trisadduct of C60 via the [4+2] Diels-Alder reaction with tethers bearing orthoquinodimethane precursors

The regioselective synthesis of an e,e,e trisadduct of C60 via the Diels-Alder reaction with orthoquinodimethanes has been attempted employing the tether-directed remote functionalization approach. Opened-structure tether 10 and macrocyclic tethers 16 and 21 were synthesized for this purpose. The functionalization of C60 afforded inseparable mixtures of regiomeric trisadducts and the regioselective formation of the e,e,e trisadduct was not feasible even when the more preorganized tethers 16 and 21 were employed. The in situ thermal generation of orthoquinodimethanes from the 1,2-bis(bromomethyl)benzene precursors requires high temperatures and is followed by fast, irreversible cycloaddition with C60 to afford thermally stable products, which prevents the achievement of high regioselectivities.

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Deep eutectic solvents (such as the combination of urea and choline chloride) are found to be promising solvent and phase-transfer-media for benzylation of phenol. These methods avoided the complexity of multiple alkylations giving selectively O-alkylated aromatic products. Good to excellent yields of the corresponding benzyl phenyl ether were obtained. The non-toxic, biodegradable, inexpensive, and recyclable nature of DES make this protocol green and cost-effective.

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[Pd(L)Cl2]-catalyzed selective hydroxylation of arylboronic acids to phenols

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COMPOUNDS WITH 7-MEMBER CYCLE AND THE PHARMACEUTICAL USE THEREOF FOR PREVENTING AND TREATING DIABETES AND METABOLISM SYNDROME

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The anti-anginal drug Ranolazine, a partial fatty acid oxidation (pFOX) inhibitor, is thought to modulate the metabolism during myocardial ischemia by activating pyruvate dehydrogenase activity to promote glucose oxidation. Ranolazine and its five principal metabolites: CVT-2512, CVT-2513, CVT-2514, CVT-2738 and CVT-4786, were synthesized. The effect of Ranolazine and its metabolites on the ECG (electrocardiogram) of mice with myocardial ischemia induced by isoprenaline and their effect on alleviating the symptom of myocardial ischemia were tested and compared. The results showed that CVT-2738 and CVT-2513 could be protective against mice myocardial ischemia induced by isoprenaline. Within all the metabolites tested in this study, CVT-2738 exhibited the best potency, however, it was still less potent than Ranolazine.