27854-88-2

Basic information

• Product Name: (R)-(+)-1-(4-PYRIDYL)ETHANOL
• Synonyms: 4-[(R)-1-Hydroxyethyl]pyridine;(R)-4-(1-Hydroxyethyl)pyridine,99+%,(99+% ee);(R)-4-(1-Hydroxyethyl)pyridine(R)-(+)-1-(4-Pyridyl)ethanol;(R)-1-(pyridin-4-yl)ethanol;(1R)-1-(pyridin-4-yl)ethan-1-ol;4-PyridineMethanol, α-Methyl-, (R)-;(aR)-a-Methyl-4-PyridineMethanol;(R)-(+)-alpha-Methyl-4-pyridinemethanol 99%
• CAS NO: 27854-88-2
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds
• Mol File: 27854-88-2.mol
• Article Data: 80

Chemical Properties

• Melting Point: 67-69 °C(lit.)
• Boiling Point: 239.718 °C at 760 mmHg
• Flash Point: 98.778 °C
• Appearance: White/Crystalline Powder or Needles
• Density: 1.083 g/cm³
• Vapor Pressure: 0.021mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 13.52±0.20(Predicted)
• BRN: 4306037
• CAS DataBase Reference: (R)-(+)-1-(4-PYRIDYL)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-(4-PYRIDYL)ETHANOL(27854-88-2)
• EPA Substance Registry System: (R)-(+)-1-(4-PYRIDYL)ETHANOL(27854-88-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 27854-88-2(Hazardous Substances Data)

Usage

Reaction

Used for the synthesis of chiral 1-(4-pyridinyl)ethylamines Precursor for intermediates of highly stable chiral (A)6-B Supramolecular Copolymers

Chemical Properties

White needles

Uses

(1R)-1-(4-Pyridyl)ethanol is a building block reagent used in the synthesis of potent GPR119 receptor agonists used in the treatment of diabetes.

Purification Methods

Purify it by recrystallisation from pet ether. The m recorded after sublimation was 59.9-60.2o, and 55o after crystallisation from *C6H6/pet ether or pet ether/*C6H6. The (-)-di-O-benzoyl tartrate salt has m 146-148o (from EtOH). [UV, ORD: Harelli & Samori J Chem Soc Perkin Trans 2 1462 1974.] The racemate recrystallises from Et2O with m 74-76o,b 90-94o/1mm. The picrate has m 125-126o (from *C6H6). [Ferles & Attia Collect Czech Chem Commun 38 611 1973, UV, NMR: Nielson et al. J Org Chem 29 2898 1964, Beilstein 21 III/IV 522, 21/2 V 217.]

InChI:InChI=1/C7H9NO/c1-6(9)7-2-4-8-5-3-7/h2-6,9H,1H3/t6-/m1/s1

Upstream product

• 1122-54-9 methyl (4-pyridyl) ketone 
• 54656-96-1 (S)-1-(4-pyridyl)ethanol 
• 27854-86-0 (1R)-1-(3-pyridyl)ethyl acetate 
• 536-75-4 4-Ethylpyridine 
• 4754-27-2 1-(3-Pyridyl)ethanol 
• 23389-75-5 rac-1-(pyridin-4-yl)ethanol 
• 108-05-4 vinyl acetate 
• 54519-07-2 vinyl ester of 3-phenylpropionic acid 
• 108-22-5 Isopropenyl acetate 
• 866417-96-1 dihydrocinnamic acid 1-pyridin-4-yl-ethyl ester 
• 330460-83-8 1-(4-Pyridyl)ethyl benzoate 
• 2555-02-4 1-(4-Pyridyl)ethyl acetate 

Downstream Products

• 600-12-4 (2R)-2-chlorobutanoic acid 
• 600-12-4 (S)-2-chlorobutyric acid 
• 134513-96-5 2-Chloro-butyric acid (R)-1-pyridin-4-yl-ethyl ester 
• 492-37-5 (+)-α-phenylpropionic acid 
• 492-37-5 (-)-2-phenylpropanoic acid 
• 16484-77-8 (R)-Mecoprop 
• 25333-13-5 (S)-mecoprop 
• 94559-04-3 (R)-2-(4-Chloro-2-methyl-phenoxy)-propionic acid (R)-1-pyridin-4-yl-ethyl ester 
• 94559-03-2 (S)-2-(4-Chloro-2-methyl-phenoxy)-propionic acid (R)-1-pyridin-4-yl-ethyl ester 
• 22204-53-1 (2S)-2-(6-methoxy(2-naphthyl))propanoic acid 
• 23979-41-1 (R)-2-(6-methoxy-2-naphthyl)propionic acid 
• 1122-54-9 methyl (4-pyridyl) ketone 
• 1351342-37-4 [(3R,4S)-4-(2,5-difluorophenyl)-1-(5-{(S)-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)piperidin-4-yl]ethylamino}pyrimidin-2-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester 
• 1351343-15-1 4-((R)-1-methanesulfonyloxy-ethyl)piperidine-1-carboxylic acid benzyl ester 

Relevant articles and documents

Bioconversion of optically active pyridyl alcohols from the corresponding racemates with plant cell cultures

A novel method for producing optically active pyridyl alcohols from the corresponding racemates was developed. When racemic pyridyl alcohol is incubated with Catharanthus roseus cell cultures, chiral alcohol is obtained in high yield with excellent enantiomeric excess (ee) (deracemization of racemate). Furthermore, the kinetic resolution of racetalc pyridyl alcohol via oxidation gave the chiral compound with high ee.

The synthesis of optically active pyridyl alcohols from the corresponding racemates by Catharanthus roseus cell cultures

A novel method for producing optically active pyridyl alcohols 1a-f from the corresponding racemates was developed. When racemic 3-pyridylphenylmethanol 1b is reacted with Catharanthus roseus cell cultures, (-)-1b is obtained in 96% yield with 100% ee.

Amino Acid-Functionalized Metal-Organic Frameworks for Asymmetric Base–Metal Catalysis

We report a strategy to develop heterogeneous single-site enantioselective catalysts based on naturally occurring amino acids and earth-abundant metals for eco-friendly asymmetric catalysis. The grafting of amino acids within the pores of a metal-organic framework (MOF), followed by post-synthetic metalation with iron precursor, affords highly active and enantioselective (>99 % ee for 10 examples) catalysts for hydrosilylation and hydroboration of carbonyl compounds. Impressively, the MOF-Fe catalyst displayed high turnover numbers of up to 10 000 and was recycled and reused more than 15 times without diminishing the enantioselectivity. MOF-Fe displayed much higher activity and enantioselectivity than its homogeneous control catalyst, likely due to the formation of robust single-site catalyst in the MOF through site-isolation.

Chiral Imidazo[1,5- a]pyridine-Oxazolines: A Versatile Family of NHC Ligands for the Highly Enantioselective Hydrosilylation of Ketones

Herein we report the synthesis and application of a versatile class of N-heterocyclic carbene ligands based on an imidazo[1,5-a]pyridine-3-ylidine backbone that is fused to a chiral oxazoline auxiliary. The key step in the synthesis of these ligands involves the installation of the oxazoline functionality via a microwave-assisted condensation of a cyano-azolium salt with a wide variety of 2-amino alcohols. The resulting chiral bidentate NHC-oxazoline ligands form stable complexes with rhodium(I) that are efficient catalysts for the enantioselective hydrosilylation of structurally diverse ketones. The corresponding secondary alcohols are isolated in good yields (typically >90%) with good to excellent enantioselectivities (80-93% ee). The reported hydrosilylation occurs at ambient temperatures (40 °C), with excellent functional group tolerability. Even ketones bearing heterocyclic substituents (e.g., pyridine or thiophene) or complex organic architectures are hydrosilylated efficiently, which is discussed further in this report.