835-78-9

Basic information

• Product Name: 2-PHENETHYLBENZYL ALCOHOL
• Synonyms: 2-PHENETHYLBENZYL ALCOHOL;o-phenethylbenzyl alcohol;2-(2-Phenylethyl)benzenemethanol;2-(2-Phenylethyl)benzyl alcohol;2-Phenethylbenzenemethanol;[2-(2-phenylethyl)phenyl]methanol;2-Phenethylbenzyl alcohol 98%
• CAS NO: 835-78-9
• Molecular Formula: C₁₅H₁₆O
• Molecular Weight: 212.29
• EINECS: 212-644-1
• Product Categories: Alcohols;C9 to C30;Oxygen Compounds
• Mol File: 835-78-9.mol

Chemical Properties

• Melting Point: 56-59 °C(lit.)
• Boiling Point: 330.7 °C at 760 mmHg
• Flash Point: 136.3 °C
• Appearance: /
• Density: 1.078 g/cm³
• Vapor Pressure: 6.53E-05mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-PHENETHYLBENZYL ALCOHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENETHYLBENZYL ALCOHOL(835-78-9)
• EPA Substance Registry System: 2-PHENETHYLBENZYL ALCOHOL(835-78-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 835-78-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenethylbenzyl alcohol is used as a reagent in the synthesis of non-symmetric cyclic sulfamide HIV-1 protease inhibitors. These inhibitors are essential in the development of antiretroviral drugs, which play a crucial role in the treatment and management of HIV/AIDS.
In the synthesis process, 2-phenethylbenzyl alcohol serves as a key intermediate, contributing to the formation of the desired cyclic sulfamide structure. Its presence in the reaction mixture helps achieve the desired selectivity and yield, ultimately leading to the production of effective HIV-1 protease inhibitors.
Overall, 2-phenethylbenzyl alcohol is a valuable compound in the pharmaceutical industry, particularly for the development of life-saving medications targeting HIV-1 protease. Its unique properties and applications make it an essential component in the ongoing fight against HIV/AIDS.

InChI:InChI=1/C15H16O/c16-12-15-9-5-4-8-14(15)11-10-13-6-2-1-3-7-13/h1-9,16H,10-12H2

Upstream product

• 5505-02-2 ethyl 2-phenethylbenzoate 
• 17376-04-4 2-phenethyl iodide 
• 5159-41-1 2-iodobenzyl alcohol 
• 100-39-0 benzyl bromide 
• 74785-02-7 (2-(bromomethyl)phenyl)methanol 
• 194605-53-3 methyl 2-(2-phenylethyl)benzoate 
• 4890-85-1 o-phenethylbenzoic acid 

Downstream Products

• 1268267-70-4 1,3-dimethyl-5-(2-phenethylbenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1268267-86-2 1',3'-dimethyl-3-phenyl-3,4-dihydro-1H,1'H-spiro[naphthalene-2,5'-pyrimidine]-2',4',6'(3'H)-trione 
• 194418-09-2 1-Diazomethyl-2-phenethyl-benzene 
• 78920-30-6 1-benzylbenzocyclobutene 
• 22253-11-8 2-phenyl-2,3-dihydro-1H-indene 
• 34403-05-9 1-methyl-2-phenethylbenzene 
• 194418-07-0 2-(2-phenylethyl)benzaldehyde tosylhydrazone 
• 94275-62-4 2-(2-phenylethyl)-benzyl chloride 
• 32832-96-5 2-phenethylbenzaldehyde 

Relevant articles and documents

Transformation of Trifluorotoluenes Triggered by Titanium(IV) Chloride-Catalyzed Hydrodefluorination using Hydrosilanes

The titanium tetrachloride-catalyzed hydrodefluorination reaction of trifluorotoluene derivatives was developed using triethylsilane as the reducing agent. The reaction produced various toluene derivatives with high chemoselectivities by means of readily accessible reagents. This hydrodefluorination process was extended to the intramolecular Friedel-Crafts benzylation reaction, furnishing polycyclic aromatics of various ring sizes in good yields.

Expeditious construction of a carbobicyclic skeleton via sp3-C-H functionalization: Hydride shift from an aliphatic tertiary position in an internal redox process

Described herein is the first example of an aliphatic, nonbenzylic hydride shift/cyclization sequence that contains two types of novel sp3-C-H functionalization: (1) construction of a tetraline skeleton via [1,5]-hydride shift/cyclization and (2) [1,6]-hydride shift/cyclization to form a five-membered ring (indane derivatives).

Direct synthesis of water-tolerant alkyl indium reagents and their application in palladium-catalyzed couplings with aryl halides

A direct result: Alkyl indium reagents are synthesized by the insertion of indium into alkyl halide mediated by CuCl. The synthetic utility of these reagents is demonstrated by their palladium-catalyzed coupling with aryl halides (see scheme). The reagents are compatible with various functional groups, and this makes the protocol generally useful in organic synthesis. DMA=N,N-dimethylacetamide, TBS=tert-butyldimethylsilyl.

Efficient radical coupling of organobromides using dimanganese decacarbonyl

Wurtz-type radical coupling of a variety of allylic and benzylic bromides was observed on irradiation with dimanganese decacarbonyl in excellent yield (77-99%). Efficient cross-coupling of two different bromides was also readily achieved.

Reactivity of functionalized arylcarbenes. 2-Phenylethyl side chains and hetero analogues

Phenylcarbenes with -X-CH2Ph and -CH2-X-Ph (X = CH2, O, SiMe2) groups in the ortho position were generated thermally and photolytically from diazo or tosylhydrazone precursors. Stereorandom insertion reactions with β-C-H bonds were observed, pointing to a triplet abstraction-recombination mechanism. Large kinetic and stereochemical deuterium isotope effects support this notion. The ample formation of benzocyclobutenes from 2-CH2-X-Ph substrates is due to insertion of the carbenes into ArCH2-X bonds. Addition to the terminal phenyl groups competes with C-H and C-X insertion. The results of benzophenone sensitization and of trapping with methanol suggest that the intramolecular reactions of functionalized arylcarbenes proceed, at best, competitively with spin inversion.

Modulation of pharmacological profile of diphenylethane (lefetamine- type) derivatives

With the aim to split the pharmacological properties of lefetamine (CAS 14148-99-3), some structural modifications of this compound have been studied. The basic group of lefetamine has been shifted from the alkyl chain to the vicinal phenyl ring and the N-substitution has been changed. The dimethylaminomethyl derivatives and chiefly the o-morpholinometyhl exhibited a strong anti-visceral chemical antinociception activity stripped of thermal antinociception properties and physical dependence liability. Furthermore through the introduction of a diethylaminomethyl group in the lefetamine structure some derivatives were selected exhibiting besided a significant increase in the anti-visceral chemical antinociception activity, remarkable local anesthetic properties.