7501-02-2

Basic information

• Product Name: 2-(2-BIPHENYLYLOXY)ETHANOL
• Synonyms: 2-(2-BIPHENYLYLOXY)ETHANOL;2-([1,1'-Biphenyl]-2-yloxy)ethanol;2-(2-Biphenyloxy)-ethanol;2-(o-biphenylyloxy)-ethano;2-(o-biphenylyloxy)-ethylalcoho;2-(o-phenyl)phenoxy-ethylalcoho;2-biphenyl-2-yloxy-ethanol;beta-Hydroxyethyl ether of o-phenylphenol
• CAS NO: 7501-02-2
• Molecular Formula: C₁₄H₁₄O₂
• Molecular Weight: 214.26
• EINECS: 231-355-1
• Mol File: 7501-02-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 345℃
• Flash Point: 151℃
• Appearance: /
• Density: 1.111
• Vapor Pressure: 2.47E-05mmHg at 25°C
• Refractive Index: 1.575
• PKA: 14.24±0.10(Predicted)
• CAS DataBase Reference: 2-(2-BIPHENYLYLOXY)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-BIPHENYLYLOXY)ETHANOL(7501-02-2)
• EPA Substance Registry System: 2-(2-BIPHENYLYLOXY)ETHANOL(7501-02-2)

Safety Data

• Hazardous Substances Data: 7501-02-2(Hazardous Substances Data)

Usage

General Description

2-(2-BIPHENYLYLOXY)ETHANOL, also known as 2-Phenylphenol, is a chemical compound with the molecular formula C14H14O2. It is commonly used as a preservative in various products, including agricultural and food applications, as well as in the production of polymers and plastics. The compound is a white to light yellow solid with a faint odor, and it is insoluble in water but soluble in organic solvents. It is classified as a skin and eye irritant, and there is some evidence to suggest that it may have potential reproductive and developmental toxicity. Additionally, it has been found to have antimicrobial properties and is effective against a variety of fungi and bacteria.

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

Synthetic route

[1,3]-dioxolan-2-one (96-49-1) + 2-Phenylphenol (90-43-7) → 2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2)

Conditions	Yield
With potassium carbonate at 160℃; for 1h; Temperature; Reagent/catalyst;	99.2%

ethyl (<1,1'-biphenyl>-2-yloxy)acetate (107352-46-5) → 2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h;	95%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h;

2-Phenylphenol (90-43-7) + 2-chloro-ethanol (107-07-3) → 2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2)

Conditions	Yield
With potassium hydroxide

2-Phenylphenol (90-43-7) + 2-chloro-6-fluorobenzylhalide → 2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 4 h 2: LiAlH4 / tetrahydrofuran / 1 h / 0 °C View Scheme

2-Phenylphenol (90-43-7) + diphenyl ether , 4-oxy-diphenyl → 2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, RT, overnight 2: 95 percent / lithium aluminium hydride / tetrahydrofuran / 1 h / 0 °C View Scheme

9-fluorenone (486-25-9) + 2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2) → 9,9-bis(3-phenyl-4-(2-hydroxyethoxy)phenyl)fluorene

Conditions	Yield
With methanesulfonic acid; 3-mercaptopropionic acid In toluene at 50 - 80℃; for 5.5h; Time; Reagent/catalyst; Inert atmosphere;	90%
With 3-mercaptopropionic acid In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 6h; Solvent;	87%
With sulfuric acid; 3-mercaptopropionic acid In 5,5-dimethyl-1,3-cyclohexadiene at 60 - 95℃; for 64h;

N-(2-chlorethyl)morpholine (3240-94-6) + 2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2) → 4-[2-(2-biphenyl-2-yloxy-ethoxy)-ethyl]-morpholine

Conditions	Yield
With sodium; xylene

(E)-but-2-enoic acid (107-93-7) + 2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2) → trans-crotonic acid-[2-(biphenylyl-(2)-oxy)-ethyl ester]

Conditions	Yield
With benzenesulfonic acid; benzene at 90 - 120℃;

2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2) + o-carboxybenzaldehyde (119-67-5) → 3-(2-biphenyl-2-yloxy-ethoxy)-phthalide (102706-07-0)

2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2) + methanesulfonyl chloride (124-63-0) → 2-(<1,1'-biphenyl>-2-yloxy)ethanol methanesulfonate

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h; Ambient temperature;

2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2) → 2-([1,1'-biphenyl]-2-yloxy)acetaldehyde

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 20℃; for 1h;
With Dess-Martin periodane In dichloromethane at 20℃; for 4h;

2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2) + dihydroartemisinin (71939-50-9) → C29H36O6 + C29H36O6

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -10 - -5℃; for 2h;

2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2) → 1-<2-(<1,1'-biphenyl>-2-yloxy)ethyl>-1H-imidazole (107352-48-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 1 h / Ambient temperature 2: 34 percent / dimethylformamide / Ambient temperature View Scheme

11H-Benzo[b]fluoren-11-one (3074-03-1) + 2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2) → C45H36O4

Conditions	Yield
With sulfuric acid In toluene at 50℃; for 2h;

2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2) + ethyl acrylate (140-88-5) → 2-phenylphenoxyethyl acrylate (91442-24-9)

Conditions	Yield
With 2,4-dimethyl-6-tert-butylphenol; dioctyltin(IV) oxide at 78 - 120℃; for 4h; Reagent/catalyst;

Upstream product

• 90-43-7 2-Phenylphenol 
• 107-07-3 2-chloro-ethanol 
• 96-49-1 [1,3]-dioxolan-2-one 
• 107352-46-5 ethyl (<1,1'-biphenyl>-2-yloxy)acetate 

Downstream Products

• 91442-24-9 2-phenylphenoxyethyl acrylate 
• 107352-48-7 1-<2-(<1,1'-biphenyl>-2-yloxy)ethyl>-1H-imidazole 
• 102706-07-0 3-(2-biphenyl-2-yloxy-ethoxy)-phthalide 

Relevant articles and documents

Synthetic method of o-phenyl phenoxyethanol

The invention discloses a synthetic method of o-phenyl phenoxyethanol, and belongs to the field of organic synthesis. The synthetic method comprises the following steps: adding o-phenylphenol, ethylene carbonate and a carbonate catalyst into a reactor, carrying out catalytic reaction at the reaction temperature of 60 to 200 DEG C for 0.5 to 10 hours, after cooling, filtering and recycling the carbonate catalyst from the reaction system so as to obtain the o-phenyl phenoxyethanol, wherein the mass ratio of o-phenylphenol to ethylene carbonate is 1:(0.7 to 2), and the mass of the carbonate catalyst is 0.1% to 15% of the total mass of o-phenylphenol and ethylene carbonate. According to the method provided by the invention, the reaction is carried out by adopting a melting method, dangerous ethylene oxide does not need to be used, a solvent does not need to be used neither, and then the subsequent process of washing and alkali washing and solvent distillation is avoided, so that the method is short in synthetic route and simple in operation, zero emission of pollutants is realized, and the method is safer and more environmentally friendly. Moreover, the carbonate catalyst is filtered and recycled, so that the carbonate catalyst is cyclically utilized, and the energy consumption is effectively reduced.

Imidazole Anticonvulsants: Structure-Activity Relationships of imidazoles

The imidazoles were found to be potent anticonvulsants.The most potent compound of the series, 1--2-yloxy)ethyl>-1H-imidazole (4), had an ED50 of 15.5 mg/kg aggainst maximal-electroshock-induced seizures in mice after oral administration; the horizontal screen ED50 was 320 mg/kg, revealing that the compound has a protective index of 21.Homologues bearing three- and four-carbon tethers between the imidazole and biphenylyloxy moieties were also active, but their potency was attenuated relative to 4.Congeners with the imidazolyalkoxy moiety at the meta or para positions of biphenyl were also less active.All these compounds were potent potentiators of hexobarbital-induced sleeping time in mice, presumably via the well-known imidazole-mediated inhibition of cytochrome P-450.The structural features governing the anticonvulsant and sleeping-time activities appear to be distinct, but a complete dissociation of these two effects has not been achieved.Thus, the potential of these compounds as clinically useful antiepileptic drugs would appear to be limited.