26184-62-3

Basic information

• Product Name: (S)-(+)-2-Pentanol
• Synonyms: (S)-(+)-2-Pentanol ChiPros(R), produced by BASF, 98%;4-carboxy-2-oxazolidone;4-carboxyoxazolidin-2-one;L-oxo-oxazolidine-4-carboxylic acid;N,O-carbonyl-L-serine;METHYL-N-PROPYLCARBINOL;FEMA 3316;1-METHYL-1-BUTANOL
• CAS NO: 26184-62-3
• Molecular Formula: C₅H₁₂O
• Molecular Weight: 88.15
• EINECS: 227-907-6
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds;chiral;API intermediates;Building Blocks for Liquid Crystals;Chiral Building Blocks;Chiral Compounds (Building Blocks for Liquid Crystals);Functional Materials;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 26184-62-3.mol
• Article Data: 68

Chemical Properties

• Melting Point: -50 °C
• Boiling Point: 118-119 °C(lit.)
• Flash Point: 93 °F
• Appearance: Colorless to light yellow liquid
• Density: 0.812 g/mL at 25 °C(lit.)
• Vapor Density: 3 (vs air)
• Vapor Pressure: 8.05mmHg at 25°C
• Refractive Index: n20/D 1.406(lit.)
• Storage Temp.: Flammables area
• PKA: 15.31±0.20(Predicted)
• Explosive Limit: 9%
• Water Solubility: soluble
• BRN: 1718820
• CAS DataBase Reference: (S)-(+)-2-Pentanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2-Pentanol(26184-62-3)
• EPA Substance Registry System: (S)-(+)-2-Pentanol(26184-62-3)

Safety Data

• Hazard Codes: Xn,Xi,F
• Statements: 10-36/37/38-66-37-20
• Safety Statements: 46-26-16-24/25
• RIDADR: UN 1105 3/PG 3
• WGK Germany: 2
• RTECS: SA4900000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 26184-62-3(Hazardous Substances Data)

Usage

Description

(S)-(+)-2-Pentanol, also known as (S)-2-pentanol or (S)-α-pentanol, is an optically active secondary alcohol with the molecular formula C5H12O. It is a chiral molecule, meaning it exists in two different forms that are mirror images of each other, known as enantiomers. The (S)-(+)-2-Pentanol is one of these enantiomers, characterized by its specific spatial arrangement of atoms. It is a colorless to light yellow liquid at room temperature and is soluble in water.

Uses

1. Pharmaceutical Industry:
(S)-(+)-2-Pentanol is used as a building block for the synthesis of highly potent and selective intranasal toll-like receptor 7 (TLR7) agonists. These agonists are crucial in the treatment of asthma, as they help modulate the immune response and reduce inflammation in the airways.
2. Chemical Synthesis:
(S)-(+)-2-Pentanol can be used as a starting material or intermediate in the synthesis of various organic compounds, such as pharmaceuticals, agrochemicals, and specialty chemicals. Its chiral nature makes it particularly valuable in the development of enantiomerically pure compounds, which are essential for the pharmaceutical industry to ensure the desired biological activity and minimize potential side effects.
3. Flavor and Fragrance Industry:
Due to its unique odor and volatility, (S)-(+)-2-Pentanol can be used as a component in the creation of artificial flavors and fragrances. It can contribute to the development of new and complex scents for the perfume, cosmetics, and food industries.
4. Solvent Applications:
(S)-(+)-2-Pentanol, being a polar liquid, can be employed as a solvent in various chemical processes, such as extraction, purification, and reaction media. Its ability to dissolve a wide range of substances makes it a versatile choice for many industrial applications.
5. Research and Development:
(S)-(+)-2-Pentanol is also used in academic and research settings to study the effects of chirality on chemical reactions and biological activities. It serves as a valuable tool for understanding the role of stereochemistry in drug design, synthesis, and pharmacology.

InChI:InChI=1/C5H12O/c1-3-4-5(2)6/h5-6H,3-4H2,1-2H3/t5-/m1/s1

Upstream product

• 6032-29-7 (+/-)-2-pentanol 
• 60-29-7 diethyl ether 
• 925-90-6 ethylmagnesium bromide 
• 75-56-9 methyloxirane 
• 534-22-5 2-methylfuran 
• 64-19-7 acetic acid 
• 29117-43-9 (R)-2-chloro-pentane 
• 29117-45-1 (R)-2-iodo-pentane 
• 2146-67-0 (dichloromethyl)lithium 
• 85167-09-5 (s)-pinanediol propylboronate 
• 1569-50-2 (2S,3E)-pent-3-en-2-ol 
• 765-43-5 Cyclopropyl methyl ketone 
• 64-17-5 ethanol 
• 107-81-3 2-bromopentane 

Downstream Products

• 20412-35-5 2-pentyloxycarbonyl chloride 
• 18536-95-3 silicic acid di-tert-butyl ester-bis-(1-methyl-butyl ester) 
• 634924-84-8 chlorosulfurous acid-(1-methyl-butyl ester) 
• 1809-16-1 phosphonic acid bis-(1-methyl-butyl) ester 
• 16973-46-9 silicic acid tetrakis-(1-methyl-butyl) ester 
• 29117-43-9 (R)-2-chloro-pentane 
• 107-81-3 2-bromopentane 
• 1809-10-5 3-bromopentane 
• 29117-44-0 (R)-2-bromopentane 
• 637-97-8 2-iodopentane 
• 1809-05-8 3-pentyl iodide 
• 29117-45-1 (R)-2-iodo-pentane 
• 26378-10-9 sulfurous acid bis-(1-methyl-butyl ester) 
• 94159-12-3 methacrylic acid-(1-methyl-butyl ester) 

Relevant articles and documents

Caffeic acid esters and lignans from piper sanguineispicum

Three new caffeic acid esters (1-3), four new lignans (4-7), and the known compounds (7′S)-parabenzlactone (8), dihydrocubebin (9), and justiflorinol (10) have been isolated from leaves of Piper sanguineispicum. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRCIMS, CD experiments, and chemical methods. Compounds 1-10 were assessed for their antileishmanial potential against axenic amastigote forms of Leishmania amazonensis. Caffeic acid esters 1 and 3 exhibited the best antileishmanial activity (IC50 2.0 and 1.8 μM, respectively) with moderate cytotoxicity on murine macrophages.

Facile Stereoselective Reduction of Prochiral Ketones by using an F420-dependent Alcohol Dehydrogenase

Effective procedures for the synthesis of optically pure alcohols are highly valuable. A commonly employed method involves the biocatalytic reduction of prochiral ketones. This is typically achieved by using nicotinamide cofactor-dependent reductases. In this work, we demonstrate that a rather unexplored class of enzymes can also be used for this. We used an F420-dependent alcohol dehydrogenase (ADF) from Methanoculleus thermophilicus that was found to reduce various ketones to enantiopure alcohols. The respective (S) alcohols were obtained in excellent enantiopurity (>99 % ee). Furthermore, we discovered that the deazaflavoenzyme can be used as a self-sufficient system by merely using a sacrificial cosubstrate (isopropanol) and a catalytic amount of cofactor F420 or the unnatural cofactor FOP to achieve full conversion. This study reveals that deazaflavoenzymes complement the biocatalytic toolbox for enantioselective ketone reductions.

Production of chiral alcohols from racemic mixtures by integrated heterogeneous chemoenzymatic catalysis in fixed bed continuous operation

Valuable chiral alcohols have been obtained from racemic mixtures with an integrated heterogeneous chemoenzymatic catalyst in a two consecutive fixed catalytic bed continuous reactor system. In the first bed the racemic mixture of alcohols is oxidized to the prochiral ketone with a Zr-Beta zeolite and using acetone as the hydrogen acceptor. In the second catalytic bed the prochiral ketone is stereoselectively reduced with an alcohol dehydrogenase (ADH) immobilized on a two dimensional (2D) zeolite. In this process, the alcohol (isopropanol) formed by the reduction of acetone in the first step reduces the cofactor in the second step, and the full reaction cycle is in this way internally closed with 100% atom economy. A conversion of about 95% with ～100% selectivity to either the (R) or the (S) alcohol has been obtained for a variety of racemic mixtures of alcohols.