104713-12-4

Basic information

• Product Name: (R)-1-PHENYL-2-PROPEN-1-OL
• Synonyms: (R)-1-PHENYL-2-PROPEN-1-OL;(R)-ALPHA-VINYLBENZYL ALCOHOL;(r)-α-vinylbenzyl alcohol;(1R)-1-Phenyl-2-propene-1-ol;(R)-1-Phenylallyl alcohol;(R)-α-Vinylbenzenemethanol;(R)-1-Phenyl-2-propen-1-ol technical, >=95% (sum of enantiomers, GC)
• CAS NO: 104713-12-4
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.18
• Mol File: 104713-12-4.mol
• Article Data: 82

Chemical Properties

• Appearance: /
• Density: 1.021 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.543
• Storage Temp.: −20°C
• CAS DataBase Reference: (R)-1-PHENYL-2-PROPEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-PHENYL-2-PROPEN-1-OL(104713-12-4)
• EPA Substance Registry System: (R)-1-PHENYL-2-PROPEN-1-OL(104713-12-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 104713-12-4(Hazardous Substances Data)

Usage

General Description

(R)-1-Phenyl-2-propen-1-ol is a chemical compound with the molecular formula C9H10O. It is also known as (R)-alpha-methylstyrene, and it is a clear, colorless liquid at room temperature. (R)-1-PHENYL-2-PROPEN-1-OL is commonly used as a fragrance ingredient and as a flavoring agent in the production of perfumes, cosmetics, and food products. It is also utilized in the synthesis of pharmaceuticals and various other organic compounds. Additionally, it has applications in the production of polymers and resins. While (R)-1-Phenyl-2-propen-1-ol has a variety of commercial uses, it should be handled and stored with care due to its potential hazards and toxicity.

Upstream product

• 27850-38-0 phthalic acid mono-((R)-1-phenyl-allyl ester) 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 69562-10-3 1-phenyl-3-phenylseleno-1-propene 
• 81422-07-3 (1R,3S,4S)-3-Bromo-7-[(2R,3R)-3-(2-chloro-5-nitro-phenyl)-oxaziridine-2-sulfonylmethyl]-1,7-dimethyl-bicyclo[2.2.1]heptan-2-one 
• 1826-67-1 vinyl magnesium bromide 
• 100-52-7 benzaldehyde 
• 1119-22-8 divinyl zinc 
• 139706-26-6 C₂₄H₃₂OSe 
• 114395-16-3 [(2S,3S)-3-phenyloxiran-2-yl]methyl 4-methylbenzenesulfonate 
• 168326-76-9 (E)-cinnamyl o-nitrophenyl selenide 
• 155486-93-4 (1S,2R)-1-phenyl-2-<(R)-p-tolylsulfinyl>-3-(trimethylsilyl)-1-propanol 
• 4541-87-1 cis-1-phenylpropene oxide 
• 4392-24-9 Cinnamyl bromide 
• 2687-12-9 cinnamyl chloride 

Downstream Products

• 1565-74-8 (R)-1-phenyl-1-propanol 
• 7217-71-2 (R)-(+)-1-acetoxy-1-phenyl-2-propylene 
• 103660-90-8 ((R)-1-Phenyl-ethyl)-carbamic acid (R)-1-phenyl-allyl ester 
• 3198-15-0 (1R,2S)-(-)-norephedrine hydrochloride 
• 53643-20-2 (1R,2R)-norephedrine hydrochloride 
• 139706-22-2 (S)-(+)-1-Phenylallyl Alcohol Mosher Ester 
• 164468-30-8 (1'S)-phenyl 2'-propenyl 2-butynoate 
• 169131-88-8 (1'R)-phenyl 2'-propenyl 2-butynoate 
• 171037-07-3 (S)-(-)-1-phenyl-prop-2-enyl methyl carbonate 
• 214280-43-0 Diphenyl-bis-((R)-1-phenyl-allyloxy)-silane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 277334-75-5 (S)-1-phenylallyl N-benzyloxycarbonyl-(S)-alanylglycinate 
• 277334-79-9 (S)-1-phenylallyl N-(tert-butyloxycarbonyl)-(S)-valyl-(RS)-alaninate 

Relevant articles and documents

Synthesis of - and -Bisferrocenyl> Diselenides and Their Application to Asymmetric Selenoxide Elimination and Sigmatropic Rearrangement

Novel optically-active bisferrocenyl> diselenides ( and ), each of which possesses two axial and two central elements of chirality, have been prepared by lithiation of commercially available chiral ferrocenes, followed by reaction with elemental selenium and air oxidation, in 77-80percent isolated yields.The structure of the -bisferrocenyl diselenide has been fully characterized by X-ray crystallography.Six chiral ferrocenyl vinylic selenides and six chiral allylic ferrocenyl selenides have been newly prepared by reaction of the diselenides with the corresponding propiolate derivatives and allylic halides.The oxidation of the vinylic selenides with m-chloroperbenzoic acid in various organic solvents produces axially chiral allenecarboxylic esters via asymmetric selenoxide elimination in 27-59percent chemical yields with high enantioselectivities (up to 89percent ee).Similar treatment of the allylic selenides afforded the corresponding chiral allylic alcohols via asymmetric sigmatropic rearrangement in 28-82percent chemical yields with high enantioselectivities (up to 89percent ee).The observed high enantioselectivities indicate that oxidation proceeds diastereoselectively, that the resultant chiral selenoxides are slow to racemize, and also that selenoxide elimination and sigmatropic rearrangement proceed with little loss of optical activity.

Characterization of a Self-Sufficient Cytochrome P450 Monooxygenase from Deinococcus apachensis for Enantioselective Benzylic Hydroxylation

A self-sufficient cytochrome P450 monooxygenase from Deinococcus apachensis (P450DA) was identified and successfully overexpressed in Escherichia coli BL21(DE3). P450DA would be a member of the CYP102D subfamily and assigned as CYP102D2 according to the phylogenetic tree and sequence alignment. Purification and characterization of the recombinant P450DA indicated both NADH and NADPH could be used by P450DA as a reducing cofactor. The recombinant E. coli (P450DA) strain was functionally active, showing excellent enantioselectivity for benzylic hydroxylation of methyl 2-phenylacetate. Further substrate scope studies revealed that P450DA is able to catalyze benzylic hydroxylation of a variety of compounds, affording the corresponding chiral benzylic alcohols in 86–99 % ee and 130–1020 total turnover numbers.

Enantioselective benzylic hydroxylation with pseudomonas monteilii TA-5: A simple method for the syntheses of (R)-benzylic alcohols containing reactive functional groups

Highly enantioselective benzylic hydroxylations of benzene derivatives (1-4) containing reactive functional groups were achieved for the first time with Pseudomonas monteilii TA-5 as biocatalyst, giving the corresponding (R)-benzylic alcohols 5-8 in 93-99% ee as the only products. Preparative biotransformations were demonstrated by the biohydroxylation of 1 and 2 with resting cells of P monteilii TA-5 to afford (R)-5 in 94% ee and 66% yield and (R)-6 in 94% ee and 56% yield, respectively. The highly enantioselective biohydroxylations represent a simple access to (R)-benzylic alcohols containing reactive functional groups that are useful pharmaceutical intermediates and versatile chiral building blocks.

Enantioselective Synthesis of Cinnamyl-1-Phenyl-2-Propenyl Ether: A Metabolite of Marine Green Algal Species Caulerpa Racemosa

The enantioselective synthesis of title compound has been achieved using a new enzyme acyl system and a mild PT catalysed etherification.The absolute configuration of natural compound has been established as R-(+) by 1H NMR analysis of MTPA esters of the

Enantioselective Preparation of sec. Alcohols from Aldehydes and Dialkyl Zinc Compounds, Generated in situ from Grignard Reagents, Using Substoichiometric Amounts of TADDOL-Titanates

Using the Schlenk trick (precipitation of MgX2 from etheral solutions by the addition of 1,4-dioxane) mixtures of a Grignard reagent RMgX (X = Cl, Br, I) and 0.5 equiv.ZnCl2 in Et2O can be converted to zinc alkyls R2Zn which in turn are added with enantioselectivities of up to 99:1 to aliphatic and aromatic aldehydes in the presence of Ti(OCHMe2)4 and a chiral titanate derived from an α,α,α',α'-tetraaryl-1,3-dioxolane-4,5-dimethanol (TADDOL).Grignard reagents containing remote double bonds, benzene rings, or acetal groups can also be employed.Different TADDOLs are compared with respect to their usefulness in this kind of enantioselective reactions.

Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition of 1,6-Enynes with Racemic Secondary Allylic Alcohols through Kinetic Resolution

It has been established that a cationic rhodium(I)/P-phos complex catalyzes the asymmetric [2+2+2] cycloaddition of 1,6-enynes with racemic secondary allylic alcohols to produce the corresponding chiral bicyclic cyclohexenes, possessing three stereogenic

A KINETIC RESOLUTION OF RACEMIC EPOXIDES BY A CHIRAL LITHIUM AMIDE

A kinetic resolution of cis-disubstituted epoxides was effectively achieved by a chiral lithium amide, prepared from (S)-2-(pyrrolidin-1-yl)-methylpyrrolidine.

Highly efficient kinetic resolution of aryl-alkenyl alcohols by ru-catalyzed hydrogen transfer

No matter through asymmetric reduction of ketones or kinetic resolution of secondary alcohols, enantioselective synthesis of the corresponding secondary alcohols is challenging when the two groups attached to the prochiral or chiral centers are spatially

An Enantioconvergent Benzylic Hydroxylation Using a Chiral Aryl Iodide in a Dual Activation Mode

The application of a triazole-substituted chiral iodoarene in a direct enantioselective hydroxylation of alkyl arenes is reported. This method allows the rapid synthesis of chiral benzyl alcohols in high yields and stereocontrol, despite its nontemplated nature. In a cascade activation consisting of an initial irradiation-induced radical C-H-bromination and a consecutive enantioconvergent hydroxylation, the iodoarene catalyst has a dual role. It initiates the radical bromination in its oxidized state through an in-situ-formed bromoiodane and in the second, Cu-catalyzed step, it acts as a chiral ligand. This work demonstrates the ability of a chiral aryl iodide catalyst acting both as an oxidant and as a chiral ligand in a highly enantioselective C-H-activating transformation. Furthermore, this concept presents an enantioconvergent hydroxylation with high selectivity using a synthetic catalyst.