1565-74-8

Basic information

• Product Name: (R)-(+)-1-PHENYL-1-PROPANOL
• Synonyms: (R)-(+)-ALPHA-ETHYLBENZYL ALCOHOL;(R)-ALPHA-ETHYLBENZYL ALCOHOL;(R)-(+)-1-PHENYL-1-PROPANOL;(R)-1-PHENYLPROPAN-1-OL;(R)-1-PHENYL-PROPANOL;(R)-(+)-1-PHENYL-1-PROPANOL, 99% (99% EE /GLC);(R)-(+)-1-PHENYL-1-PROPANOL 99%;(R)-(+)-1-Phenyl-1-propanol, 98% ee, 95%
• CAS NO: 1565-74-8
• Molecular Formula: C₉H₁₂O
• Molecular Weight: 136.19
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds;Alcohols and Epoxides;CHIRAL CHEMICALS
• Mol File: 1565-74-8.mol
• Article Data: 636

Chemical Properties

• Boiling Point: 218-220 °C(lit.)
• Flash Point: 194 °F
• Appearance: Clear colorless liquid
• Density: 0.993 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0707mmHg at 25°C
• Refractive Index: n20/D 1.5196(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 10.33g/l
• PKA: 14.43±0.20(Predicted)
• BRN: 2041555
• CAS DataBase Reference: (R)-(+)-1-PHENYL-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-PHENYL-1-PROPANOL(1565-74-8)
• EPA Substance Registry System: (R)-(+)-1-PHENYL-1-PROPANOL(1565-74-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 23-24/25
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: DO5470000
• Hazardous Substances Data: 1565-74-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

Different sources of media describe the Uses of 1565-74-8 differently. You can refer to the following data:
1. For synthesis of optically active products
2. Chiral building block.

InChI:InChI=1/C9H12O/c1-2-9(10)8-6-4-3-5-7-8/h3-7,9-10H,2H2,1H3/t9-/m1/s1

Upstream product

• 108-22-5 Isopropenyl acetate 
• 93-54-9 1-Phenyl-1-propanol 
• 873-66-5 1-propenylbenzene 
• 83808-03-1 1-phenylpropyl acetate 
• 811-49-4 ethyllithium 
• 100-52-7 benzaldehyde 
• 925-90-6 ethylmagnesium bromide 
• 557-20-0 diethylzinc 
• 116809-19-9 R(+)-1-phenyl-1-propyl propionate 
• 103-65-1 phenylpropane 
• 60-29-7 diethyl ether 
• 104713-12-4 (R)-1-phenylprop-2-en-1-ol 
• 108-24-7 acetic anhydride 
• 97-94-9 triethyl borane 

Downstream Products

• 93-55-0 1-phenyl-propan-1-one 
• 1025713-29-4 (E)-ethyl 4-(1-phenylpropoxy)-2-butenoate 
• 1253941-92-2 (+)-(R)-1-phenylpropyl-4-methylbenzenesulfinate 
• 10316-10-6 (-)-(S)-(1-chloropropyl)benzene 
• 10031-86-4 (R)-1-phenylpropyl butyrate 
• 107805-98-1 1-phenyl-1-(4-methylphenylthio)propane 
• 501939-38-4 4-Nitro-benzoic acid (R)-1-phenyl-propyl ester 
• 175522-74-4 (+)-{1-(R)-[(1E)-2-methylbuta-1,3-dienyloxy]propyl}benzene 
• 136476-10-3 [(S)-1-((E)-2-Methyl-buta-1,3-dienyloxy)-propyl]-benzene 
• 162824-41-1 (R,S)-1-(1-Phenyl-1-propyl)imidazole-4,5-dicarboxylic acid 

Relevant articles and documents

ASYMMETRIC INDUCTION CATALYZED BY CONJUGATE BASES OF CHIRAL PROTON ACIDS AS LIGANDS: ENANTIOSELECTIVE ADDITION OF DIALKYLZINC-ORTHOTITANATE COMPLEX TO BENZALDEHYDE WITH CATALYTIC ABILITY OF A REMARKABLE HIGH ORDER

The addition of diethylzinc-orthotitanate complex to benzaldehyde catalyzed by 0.0001-0.04 equiv of chiral sulfonamide-titanate complex in toluene at 0- -30 deg C gives optically active 1-phenylpropanol in both high ee and chemical yields.NMR study suggests alkyltitanium is generated from diethylzinc and the titanate in situ.

Asymmetric Reduction of Aromatic Ketones with Reagents Prepared from NaBH4 and ZnCl2 in the Presence of 1,2 : 5,6-Di-O-isopropylidene-α-D-glucofuranose

Asymmetric reduction of prochiral ketones using a freshly prepared complex derived from NaBH4, 1/3 equiv of ZnCl2, and 1,2:5,6-di-O-isopropylidene-α-D-glucopyranose (1) gives an excess of the corresponding (S)-alcohols in substantial optical yields (28-69

Catalytic enantioselective alkylation of benzaldehyde with diethylzinc using chiral nonracemic (thio)-phosphoramidates

Two chiral nonracemic γ-amino alcohols, ephedrine thiol and the corresponding (thio)-phosphoramidates have been examined as catalysts for the enantioselective alkylation of benzaldehyde by diethylzinc. Addition of titanium tetraisopropoxide increases the

A General Solid-Phase Synthesis Strategy for the Preparation of 2-Pyrrolidinemethanol Ligands

-

Stereoselective synthesis and use in catalytic asymmetric addition of diethylzinc to benzaldehyde of new chiral amino alcohol complexes: Influence of the chromium complexation on the enantioselectivity

The optically active amino alcohol (arene)chromium (+)-(S,1S)-3-6 complexes were synthesized from enantiomerically pure indanone complex. As well as their uncomplexed counterparts, they have been used as chiral catalysts in the asymmetric addition of diet

Bis(ethylsulfonamide)amines via nucleophilic ring-opening ofchiral aziridines. Application to Ti-mediated addition of diethylzinc to benzaldehyde

Homochiral bis(N-trifiyl-2-alkyl-2-aminoethyl)amines, obtained from N- trifiyl-2-alkylaziridines via reaction with benzylamine, catalyze the titanium-mediated addition of diethylzinc to benzaidehyde to yield 1 - phenylpropanol in up to 78% ee in the prese

Enantioselective addition of diethylzinc to benzaldehyde catalyzed by ferrocenic amino-alcohols combining centered and planar chiralities

Diastereomeric ferrocenic amino-alcohols combining three elements of chirality (one of which is a ferrocenic plane) are tested as catalysts in the alkylation of benzaldehyde with diethylzinc. Good to excellent yields and ees were obtained and show correla

Synthesis and catalytic application of ferrocene substituted camphane-based aminoalcohols and S-containing heterocyclic analogues

A facile and practical approach was developed for the synthesis of chiral α-, β- and δ-aminoalcohols and S-containing heterocyclic analogues by using of readily available sources of chirality. The synthetic strategy involves utilization of camphor-derived

Synthesis of Novel Chiral Diazole Ligands for Enantioselective Addition of Diethylzinc to Benzaldehyde

A variety of chiral pyrazole and imidazole derivatived ligands have been prepared under high pressure conditions and their catalytic efficiency in the enantioselective addition of diethylzinc to benzaldehyde has been examined.

ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE CATALYZED BY A SMALL AMOUNT OF CHIRAL 2-AMINO-1-ALCOHOLS

The reaction of diethylzinc with benzaldehyde catalyzed by a small amount of chiral 2-amino-1-alcohols in toluene at room temperature gave optically active 1-phenylpropan-1-ol almost quantitatively in ca. 50percent ee.

Synthesis and application of C2-symmetrical bis-β-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system in the catalytic enantioselective addition of diethylzinc to benzaldehyde

Asymmetric catalytic ethylation of benzaldehyde utilizing a series of new, tetradental bis-β-amino alcohols based on the octahydro- cyclopenta[b]pyrrole system - derived from an industrial waste material - is presented. Attention is focused on steric aspects of the catalyst(-precursor) structure. Furthermore, the catalytic efficiency of the ethylene-bridged, C2-symmetrical bis-β-amino alcohols is compared to related 'monomeric' structures. Potent chiral ligands, which are highly effective even at concentrations of below 2 mol%, have been developed reaching excellent enantioselectivities up to 100% ee. (C) 1999 Elsevier Science Ltd.

"Molecular Imprinting Effect" in the Synthesis of Immobilized Rhodium Complex Catalyst (IRC cat)

A new concept has been tackled with the utilization of a polymerized rhodium complex with an asymmetric catalysic application.Furthermore, this new method of preparing heterogeneous catalyst has allowed to bring to the fore a molecular imprinting effect d

Catalytic activity of isoborneol-derived sulfides in asymmetric addition of diethylzinc to benzaldehyde

Enantioselective addition of diethylzinc to benzaldehyde in the presence of easily available, β-hydroxysulfides 1 was investigated. The use of a catalytic amount of 1 gave (S)-1-phenylpropanol in excellent yield with high enantioselectivity, ranging from

A new chiral catalyst for the enantioselective reduction of prochiral ketones with borane

A new chiral β-amino alcohol, (s)-2-amino-1,1-diphenyl-3-(2-naphthyl)-1-propanol and its use as a catalyst in the enantioselective reduction of prochiral ketones with borane were described.

Structural Insight into Guest Binding Sites in a Porous Homochiral Metal-Organic Material

An enantiomeric pair of chiral metal-organic materials (CMOMs) based upon mandelate (man) and 4,4′-bipyridine (bpy) ligands, [Co2(S-man)2(bpy)3](NO3)2·guest (1S·guest) and [Co2(R-man)2

Asymmetric Amplifying Phenomena in Enantioselective Addition of Diethylzink to Benzaldehide

-

A polymer-enlarged homogeneously soluble oxazaborolidine catalyst for the asymmetric reduction of ketones by borane

A polymer-enlarged homogeneously soluble oxazaborolidine catalyst has been prepared and used in the enantioselective borane reduction of ketones. The catalyst is derived from (2S,4R)-α,α-diphenyl-2-[(4-allyloxy)-N-benzyloxycarbonyl]-pyrrolidinemethanol 3

An optimised in situ procedure for the oxazaborolidine catalysed enantioselective reduction of prochiral ketones

A systematic study was conducted to formulate the optimal reaction parameters for the oxazaborolidine catalysed enantioselective reduction. The catalyst derived from diphenyl prolinol was found to be the best amongst several other analogues and a reductio

Improved methodology for the asymmetric alkylation of aldehydes employing bis(sulfonamide) complexes

We report an improved procedure for the asymmetric transfer of alkyl groups from zinc to aldehydes utilizing bis(sulfonamide) ligands. The new methodology is easier to perform and, in some cases, provides the alcohol products with higher enantioselectivit

N,N'-Dibenzoylcystine as an Efficient Chiral Auxiliary for Asymmetric Reduction of Ketones with Lithium Borohydride

Aromatic and α,β-unsaturated ketones were reduced enantioselectively with lithium borohydride in the presence of N,N'-dibenzoylcystine and t-butyl alcohol to afford optically active secondary alcohols with high enantiomeric excesses (76 - 90percent e.e.).

Chiral diethanolamines and their lithium alcoholates as catalysts in the enantioselective alkylation of benzaldehyde by diethylzinc

The enantioselective alkylation of benzaldehyde by diethylzinc in the presence of catalytic amounts of bis-erythro diethanolamines and their lithium alcoholates was studied. The extent of asymmetric induction was found to depend strongly upon subtle chang

Asymmetric Reduction of Aromatic Ketones with Chiral Alkoxy-amine-borane Complexes

Asymmetric reduction of prochiral aromatic ketones with chiral alkoxy-amine-borane complexes afforded the corresponding aromatic secondary alcohols in as much as 60 percent enantiomeric excess.

Asymmetric Reduction of Ketones with Asymmetric Complex Reducing Agents: *>

The reduction of selected ketones has been achieved using asymmetric zinc-containing complex reducing agents (ZnCRA*) prepared from (2S,3R)-(+)-4-dimethylamino-1,2-diphenyl-3-methyl-butan-2-ol (Chirald).

Theoretical and experimental studies of asymmetric organozinc additions to benzaldehyde catalyzed by flexible and constrained γ-amino alcohols

The cis-decalin based γ-amino alcohols, 1-5, were synthesized, resolved, and employed as catalysts in the addition of organozincs to benzaldehyde. Despite large facial differentiation in the RZn adducts of the ligands, the enantioselectivities were found

Assymmetric Reduction of Aromatic Ketone in a Continuous Flow System

When THF-borane (1/1) and aromatic ketone were supplied continuously to the column containing polymer-supported (S)-(-)-2-amino-3-(p-hydroxyphenyl)-1,1-diphenyl-1-propanol, the chiral product, secondary benzylic alcohol, could be obtained successfully (>9

Exploration of highly electron-rich manganese complexes in enantioselective oxidation catalysis; A focus on enantioselective benzylic oxidation

The direct enantioselective hydroxylation of benzylic C-H bonds to form chiral benzylic alcohols represents a challenging transformation. Herein, we report on the exploration of new biologically inspired manganese and iron complexes bearing highly electron-rich aminopyridine ligands containing 4-pyrrolidinopyridine moieties ((S,S)-1, (R,R)-1, 2 and 5) in combination with chiral bis-pyrrolidine and N,N-cyclohexanediamine backbones in enantioselective oxidation catalysis with aqueous H2O2. The current manganese complexes outperform the analogous manganese complexes containing 4-dimethylaminopyridine moieties (3 and 4) in benzylic oxidation reactions in terms of alcohol yield while keeping similar ee values (～60% ee), which is attributed to the higher basicity of the 4-pyrrolidinopyridine group. A detailed investigation of different carboxylic acid additives in enantioselective benzylic oxidation provides new insights into how to rationally enhance enantioselectivities by means of proper tuning of the environment around the catalytic active site, and has resulted in the selection of Boc-l-Tert-leucine as the preferred additive. Using these optimized conditions, manganese complex 2 was shown to be effective in the enantioselective benzylic oxidation of a series of arylalkane substrates with up to 50% alcohol yield and 62% product ee. A final set of experiments also highlights the use of the new 4-pyrrolidinopyridine-based complexes in the asymmetric epoxidation of olefins (up to 98% epoxide yield and >99% ee).

Highly Active Cooperative Lewis Acid—Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones

Enantiopure secondary alcohols are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5–3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxophilic Lewis acid within the same catalyst molecule. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an SN2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working.