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
• Article Data: 25

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

Description

2-Benzyloxyphenol is a clear colorless liquid that serves as a versatile compound in various industries due to its unique chemical properties. It is commonly utilized in the synthesis of other compounds and acts as a pharmaceutical intermediate.

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

Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy- N-Butylbenzamides

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.

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.

Choline chloride based deep eutectic solvent as an efficient solvent for the benzylation of phenols

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.