22148-86-3

Basic information

• Product Name: (S)-(+)-4-PHENYL-2-BUTANOL
• Synonyms: (S)-(+)-4-PHENYL-2-BUTANOL;(S)-(+)-4-PHENYLBUTAN-2-OL;(S)-(+)-4-PHENYL-2-BUTANOL, 98%&;(S)-(+)-4-PHENYL-2-BUTANOL, 99+%;(2S)-4-Phenyl-2-butanol;(S)-1-Phenylbutan-3-ol;(S)-(+)-4-Phenyl-2-butanol, 97%, ee 99%;(2S)-4-phenylbutan-2-ol
• CAS NO: 22148-86-3
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• Product Categories: Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 22148-86-3.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.)
• Vapor Pressure: 0.0147mmHg at 25°C
• Refractive Index: n20/D 1.5150(lit.)
• PKA: 15.10±0.20(Predicted)
• BRN: 4859487
• CAS DataBase Reference: (S)-(+)-4-PHENYL-2-BUTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-4-PHENYL-2-BUTANOL(22148-86-3)
• EPA Substance Registry System: (S)-(+)-4-PHENYL-2-BUTANOL(22148-86-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 22148-86-3(Hazardous Substances Data)

Usage

Description

(S)-(+)-4-PHENYL-2-BUTANOL is a chiral organic compound with the molecular formula C10H14O. It is a specific enantiomer of 4-phenyl-2-butanol, characterized by its (S) configuration, which gives it unique properties and applications compared to its (R) counterpart. (S)-(+)-4-PHENYL-2-BUTANOL can be efficiently racemized using an aminocyclopentadienyl ruthenium complex, allowing for the conversion between enantiomers when needed.

Uses

Used in Pharmaceutical Industry:
(S)-(+)-4-PHENYL-2-BUTANOL is used as an intermediate in the synthesis of antihypertensive agents, specifically bufeniode and labetalol. These medications are utilized for the treatment of high blood pressure and other cardiovascular conditions, highlighting the importance of this compound in the development of life-saving drugs.
Used in Biotechnology Research:
(S)-(+)-4-PHENYL-2-BUTANOL is employed in studies aimed at understanding the effect of glycerol on yeast, specifically Saccharomyces cerevisiae. Glycerol is a crucial component in various biological processes and industrial applications, such as biofuel production. The use of this compound in research helps to advance knowledge in the field of biotechnology and potentially improve the efficiency of yeast-based processes.

InChI:InChI=1/C10H14O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6,9,11H,7-8H2,1H3/t9-/m0/s1

Upstream product

• 64-17-5 ethanol 
• 768-56-9 4-Phenylbut-1-ene 
• 1896-62-4 (E)-benzalacetone 
• 93-91-4 1-phenylbutan-1,3-dione 
• 2344-70-9 1-phenyl-3-butanol 
• 108-05-4 vinyl acetate 
• 2146-71-6 vinyl laurate 
• 104-53-0 3-phenyl-propionaldehyde 
• 75-16-1 methylmagnesium bromide 
• 165904-22-3 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane 
• 1000995-40-3 1-methyl-3-(11-ethoxycarbonyl-undecyl)imidazolium hexafluorophosphate 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 2550-26-7 4-Phenyl-2-butanone 
• 766-77-8 Dimethylphenylsilane 

Downstream Products

• 866483-65-0 (R)-1-methyl-3-phenylpropyl diphenylphosphinite 
• 2344-70-9 1-phenyl-3-butanol 
• 1235984-29-8 C₁₈H₁₇NO₃ 
• 1338073-50-9 (R)-(3-iodobutyl)benzene 
• 116199-41-8 (S)-2-mesyloxy-4-phenylbutane 
• 2344-70-9 (R)-4-phenyl-2-butanol 
• 2344-70-9 (+)-(S)-4-phenylbutan-2-ol 
• 2550-26-7 4-Phenyl-2-butanone 
• 93963-08-7 5-Methyl-5-phenethyl-dihydro-furan-2-one 
• 83972-40-1 (R)-2-chloro-4-phenylbutane 

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%.

Tridentate nitrogen phosphine ligand containing arylamine NH as well as preparation method and application thereof

The invention discloses a tridentate nitrogen phosphine ligand containing arylamine NH as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The tridentate nitrogen phosphine ligand disclosed by the invention is the first case of tridentate nitrogen phosphine ligand containing not only a quinoline amine structure but also chiral ferrocene at present, a noble metal complex of the type of ligand shows good selectivity and extremely high catalytic activity in an asymmetric hydrogenation reaction, meanwhile, a cheap metal complex of the ligand can also show good selectivity and catalytic activity in the asymmetric hydrogenation reaction, and is very easy to modify in the aspects of electronic effect and space structure, so that the ligand has huge potential application value. A catalyst formed by the ligand and a transition metal complex can be used for catalyzing various reactions, can be used for synthesizing various drugs, and has important industrial application value.