7228-47-9

Basic information

• Product Name: 2-Naphthaleneethanol
• Synonyms: alpha-Methyl-2-naphthalenemethanol 2-(1-Hydroxyethyl)naphthalene;1-(naphthalen-2-yl)ethanol;a-Methyl-2-naphthalenemethanol;2-Naphthalenemethanol, alpha-methyl-;Methyl 2-naphtylcarbinol;2-(1-HYDROXYETHYL)NAPHTHALENE;2-NAPHTHYL ETHANOL;(+/-)-1-(2-NAPHTHYL)ETHANOL
• CAS NO: 7228-47-9
• Molecular Formula: C₁₂H₁₂O
• Molecular Weight: 172.22
• EINECS: 230-630-3
• Product Categories: Alcohols;C9 to C30;Oxygen Compounds
• Mol File: 7228-47-9.mol
• Article Data: 199

Chemical Properties

• Melting Point: 73-78 °C(lit.)
• Boiling Point: 180-184 °C (15 mmHg)
• Flash Point: 170°C/13mm
• Appearance: White to yellow/Powder
• Density: 1.119g/cm³
• Vapor Pressure: 2.32E-13mmHg at 25°C
• Refractive Index: 1.589
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Toluene
• PKA: 14.36±0.20(Predicted)
• BRN: 1907449
• CAS DataBase Reference: 2-Naphthaleneethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Naphthaleneethanol(7228-47-9)
• EPA Substance Registry System: 2-Naphthaleneethanol(7228-47-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 7228-47-9(Hazardous Substances Data)

Usage

Description

2-Naphthaleneethanol, also known as 1-(Naphthalen-2-yl)ethanol, is an organic compound with the molecular formula C12H10O. It is a reagent used in the chemical-enzymic preparation and resolution of β-naphthyl alcohols and is also recognized as a cinacalcet impurity. 2-Naphthaleneethanol has the ability to form complexes and multimers with methyl lactate, and upon reaction with sulfur trioxide-dimethylformamide complex and pyridine, it yields sulfated products.

Uses

Used in Chemical Synthesis:
2-Naphthaleneethanol is used as a reagent in the chemical-enzymic preparation and resolution of β-naphthyl alcohols. Its unique chemical structure allows it to participate in various chemical reactions, making it a valuable component in the synthesis of different compounds.
Used in Pharmaceutical Industry:
As a cinacalcet impurity, 2-Naphthaleneethanol plays a role in the pharmaceutical industry. Cinacalcet is a drug used to treat secondary hyperparathyroidism, and the presence of this compound can affect the drug's efficacy and safety. Therefore, its identification and control are essential in the manufacturing process of cinacalcet.
Used in Complex Formation:
2-Naphthaleneethanol is used as a component in the formation of complexes and multimers with methyl lactate. These complexes and multimers have potential applications in various fields, including materials science and chemical research.
Used in Sulfated Product Synthesis:
2-Naphthaleneethanol is used as a reactant in the synthesis of sulfated products when combined with sulfur trioxide-dimethylformamide complex and pyridine. These sulfated products may have applications in various industries, such as pharmaceuticals, agrochemicals, and other specialty chemical markets.

InChI:InChI=1/C17H26N5O3P/c1-5-8-14(26(23,24-6-2)25-7-3)9-13(4)10-22-12-21-15-16(18)19-11-20-17(15)22/h11-12H,5-8,10H2,1-4H3,(H2,18,19,20)

Upstream product

• 917-54-4 methyllithium 
• 66-99-9 β-naphthaldehyde 
• 4541-70-2 2-naphthyllithium 
• 123-38-6 propionaldehyde 
• 85880-67-7 1-(2-naphthyl)ethyl acetate 
• 827-54-3 2-naphthylethylene 
• 58464-06-5 2-(1-chloroethyl)naphthalene 
• 93-08-3 methyl 2-naphthyl ketone 
• 88773-87-9 2-(1-napthalenylethoxy)-tetrahydropyran 
• 613-54-7 2-Bromo-2'-acetonaphthone 
• 91571-04-9 2-bromo-1-(naphthalen-2-yl)ethan-1-ol 
• 939-27-5 2-ethylnaphthalene 
• 117340-81-5 (S)-2-bromo-1-(2-naphthyl)ethyl acetate 
• 114838-30-1 2-(1-deuteriovinyl)naphthalene 

Downstream Products

• 27544-18-9 (S)-1-(2-Naphthyl)ethanol 
• 52193-85-8 (R)-1-(2-Naphthyl)ethanol 
• 93-08-3 methyl 2-naphthyl ketone 
• 175692-56-5 N-[1-(2-naphthyl)ethyl]-N-phenylamine 
• 6860-93-1 (S)-1-benzoyloxy-1-(naphthyl-⁽²⁾)-ethane 
• 1737-26-4 (R)-1-[4-(trifluoromethyl)phenyl]ethan-1-ol 
• 1061606-42-5 3-(1-naphthalen-2-yl-ethoxy)-phthalic acid dimethyl ester 
• 23189-64-2 1,2,4-Trimethyl-phenanthren 
• 827-54-3 2-naphthylethylene 
• 88766-18-1 phthalic acid mono-[(S)-1-(naphthyl-⁽²⁾)-ethyl ester] 
• 88766-18-1 phthalic acid mono-[(R)-1-(naphthyl-⁽²⁾)-ethyl ester] 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 1517-70-0 (S)-1-(4-Methoxyphenyl)ethanol 

Relevant articles and documents

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Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts

A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.