39516-03-5

Basic information

• Product Name: (R)-(-)-4-PHENYL-2-BUTANOL
• Synonyms: (R)-(-)-4-PHENYL-2-BUTANOL;(R)-(-)-4-PHENYLBUTAN-2-OL;(R)-(-)-4-PHENYL-2-BUTANOL,98%(99% EE/G&;(R)-(-)-4-PHENYL-2-BUTANOL, 99+%;(2R)-4-Phenyl-2-butanol;(2R)-4-Phenylbutan-2-ol;(2R)-4-Phenyl-butane-2-ol;(R)-(-)-4-Phenyl-2-butanol 98%, optical purity ee: 99% (GLC)
• CAS NO: 39516-03-5
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: -0
• Product Categories: Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 39516-03-5.mol
• Article Data: 233

Chemical Properties

• Boiling Point: 206-207 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.976 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5150(lit.)
• BRN: 5248382
• CAS DataBase Reference: (R)-(-)-4-PHENYL-2-BUTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-4-PHENYL-2-BUTANOL(39516-03-5)
• EPA Substance Registry System: (R)-(-)-4-PHENYL-2-BUTANOL(39516-03-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 39516-03-5(Hazardous Substances Data)

Usage

General Description

(R)-(-)-4-Phenyl-2-butanol is a chiral organic compound with the molecular formula C10H14O. It is a colorless liquid with a pleasant floral odor, and it is commonly used in the synthesis of pharmaceuticals and fragrances. (R)-(-)-4-PHENYL-2-BUTANOL exists in two enantiomeric forms, with the (R)-enantiomer being the natural form. (R)-(-)-4-Phenyl-2-butanol has been studied for its potential as a chiral auxiliary in asymmetric synthesis and as a chiral building block for the preparation of biologically active compounds. It is also used as a flavoring agent in the food and beverage industry. Overall, (R)-(-)-4-Phenyl-2-butanol is an important compound in organic chemistry with various applications in the fields of pharmaceuticals, fragrance, and flavoring.

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 544-97-8 dimethyl zinc(II) 
• 64-17-5 ethanol 
• 768-56-9 4-Phenylbut-1-ene 
• 2550-26-7 4-Phenyl-2-butanone 
• 1896-62-4 (E)-benzalacetone 
• 153357-82-5 (R)-N,N-di-(p-toluenesulfonyl)-1-methyl-3-phenylpropylamine 
• 93-91-4 1-phenylbutan-1,3-dione 
• 83972-42-3 Trichloro-((S)-1-methyl-3-phenyl-propyl)-silane 
• 2344-70-9 1-phenyl-3-butanol 
• 108-05-4 vinyl acetate 
• 2146-71-6 vinyl laurate 
• 75-16-1 methylmagnesium bromide 
• 1000995-40-3 1-methyl-3-(11-ethoxycarbonyl-undecyl)imidazolium hexafluorophosphate 

Downstream Products

• 866483-65-0 (R)-1-methyl-3-phenylpropyl diphenylphosphinite 
• 2344-70-9 1-phenyl-3-butanol 
• 1160843-02-6 C₁₇H₂₈N₂O 
• 1160843-04-8 (R)-4-phenylbutan-2-yl-2-phenoxyacetate 
• 116199-45-2 (S)-1-methyl-3-phenylpropyl azide 
• 1235984-29-8 C₁₈H₁₇NO₃ 
• 1338073-50-9 (R)-(3-iodobutyl)benzene 
• 2550-26-7 4-Phenyl-2-butanone 
• 4187-57-9 (S)-1-methyl-3-phenylpropylamine 
• 937-52-0 (R)-1-methyl-3-phenylpropylamine 
• 2344-70-9 (R)-4-phenyl-2-butanol 
• 2344-70-9 (+)-(S)-4-phenylbutan-2-ol 
• 1604039-68-0 2-((8-methyl-10-phenyldec-6-yn-1-yl)oxy)tetrahydro-2H-pyran 
• 93963-08-7 5-Methyl-5-phenethyl-dihydro-furan-2-one 

Relevant articles and documents

Discovery and Redesign of a Family VIII Carboxylesterase with High (S)-Selectivity toward Chiral sec-Alcohols

Highly enantioselective lipase has been widely utilized in the preparation of versatile enantiopure chiral sec-alcohols through kinetic or dynamic kinetic resolution. Lipase is intrinsically (R)-selective, and it is difficult to obtain (S)-selective lipase. Recent crystal structures of a family VIII carboxylesterase have revealed that the spatial array of its catalytic triad is the mirror image of that of lipase but with a catalytic triad that is distinct from lipase. We, therefore, hypothesized that the family VIII carboxylesterase may exhibit (S)-enantioselectivity toward sec-alcohols similar to (S)-selective serine protease, whose catalytic triad is also spatially arrayed as its mirror image. In this study, a homologous enzyme (carboxylesterase from Proteobacteria bacterium SG_bin9, PBE) of a known family VIII carboxylesterase (pdb code: 4IVK) was prepared, which showed not only moderate (S)-selectivity toward sec-alcohols such as 3-butyn-2-ol and 1-phenylethyl alcohol but also (R)-selectivity toward particular sec-alcohols among the substrates explored. Furthermore, the (S)-selectivity of PBE has been significantly improved by rational redesign based on molecular modeling. Molecular modeling identified a binding pocket composed of Ser381, Ala383, and Arg408 for the methyl substituent of (R)-1-phenylethyl acetate and suggested that larger residues may increase the enantioselectivity by interfering with the binding of the slow-reacting enantiomer. As predicted, substituting Ser381with larger residues (Phe, Tyr, and Trp) significantly improved the (S)-selectivity of PBE toward all sec-alcohols explored, even the substrates toward which the wild-type PBE exhibits (R)-selectivity. For instance, the enantioselectivity toward 3-butyn-2-ol and 1-phenylethyl alcohol was improved from E = 5.5 and 36.1 to E = 2001 and 882, respectively, by single mutagenesis (S381F).

Novel non-metal catalyst for catalyzing asymmetric hydrogenation of ketone and alpha, beta-unsaturated ketone

The invention discloses a novel non-metal catalyst for catalyzing asymmetric hydrogenation of ketone and alpha, beta-unsaturated ketone. The preparation method of a chiral alcohol compound shown as formula IV comprises the following step of: reacting a ketone compound shown as formula V with hydrogen under the catalysis of tri(4-hydrotetrafluorophenyl)boron and a chiral oxazoline compound to obtain the chiral alcohol compound shown as the formula IV; the preparation method of a chiral tetralone compound shown as formula VI comprises the following step of: under the catalysis of tri(4-hydrotetrafluorophenyl)boron and a chiral oxazoline compound, reacting an alpha, beta-unsaturated ketone compound shown as formula VII with hydrogen to obtain the chiral tetralone compound shown as the formula VI. The method has the advantages of easy synthesis of raw materials, mild reaction conditions, simple operation, high stereoselectivity and the like, the ee value of the product is up to 92%, and the yield is up to 99%.

Pickering-Droplet-Derived MOF Microreactors for Continuous-Flow Biocatalysis with Size Selectivity

Enzymatic microarchitectures with spatially controlled reactivity, engineered molecular sieving ability, favorable interior environment, and industrial productivity show great potential in synthetic protocellular systems and practical biotechnology, but their construction remains a significant challenge. Here, we proposed a Pickering emulsion interface-directed synthesis method to fabricate such a microreactor, in which a robust and defect-free MOF layer was grown around silica emulsifier stabilized droplet surfaces. The compartmentalized interior droplets can provide a biomimetic microenvironment to host free enzymes, while the outer MOF layer secludes active species from the surroundings and endows the microreactor with size-selective permeability. Impressively, the thus-designed enzymatic microreactor exhibited excellent size selectivity and long-term stability, as demonstrated by a 1000 h continuous-flow reaction, while affording completely equal enantioselectivities to the free enzyme counterpart. Moreover, the catalytic efficiency of such enzymatic microreactors was conveniently regulated through engineering of the type or thickness of the outer MOF layer or interior environments for the enzymes, highlighting their superior customized specialties. This study provides new opportunities in designing MOF-based artificial cellular microreactors for practical applications.