72345-23-4

Basic information

• Product Name: (2S,4S)-(+)-PENTANEDIOL
• Synonyms: [S-(S*,S*)]-(+)-2,4-PENTANEDIOL;(S,S)-PENTANEDIOL-2,4;(S,S)-(+)-2,4-PENTANEDIOL;(2S,4S)-(+)-2,4-DIHYDROXYPENTANE;(2S,4S)-(+)-2,4-PENTANEDIOL;(2S,4S)-2,4-PENTANEDIOL;(2S,4S)-(+)-PENTANEDIOL;(2S,4S)-(+)-PENTANEDIOL 99%
• CAS NO: 72345-23-4
• Molecular Formula: C₅H₁₂O₂
• Molecular Weight: 104.15
• Product Categories: Chiral Compounds;Diols;chiral;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;organic alcohol;Chiral Oxygen
• Mol File: 72345-23-4.mol
• Article Data: 47

Chemical Properties

• Melting Point: 48-51 °C
• Boiling Point: 111-113C
• Flash Point: 215 °F
• Appearance: White/Crystalline Powder
• Density: 0.9917 (rough estimate)
• Vapor Pressure: 0.384mmHg at 25°C
• Refractive Index: 54 ° (C=10, EtOH)
• Storage Temp.: 0-6°C
• Solubility: almost transparency in EtOH
• PKA: 14.74±0.20(Predicted)
• Stability: hygroscopic
• BRN: 4123490
• CAS DataBase Reference: (2S,4S)-(+)-PENTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-(+)-PENTANEDIOL(72345-23-4)
• EPA Substance Registry System: (2S,4S)-(+)-PENTANEDIOL(72345-23-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 72345-23-4(Hazardous Substances Data)

Usage

Description

(2S,4S)-(+)-Pentanediol, also known as meso-2,4-pentanediol, is an optically active organic compound with the molecular formula C5H12O2. It is a white to light yellow crystalline powder that exhibits optical activity, meaning it can rotate plane-polarized light. This characteristic makes it a valuable reagent in various chemical and pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
(2S,4S)-(+)-Pentanediol is used as an optically active reagent for the preparation of NIP-101, a potent calcium antagonist. (2S,4S)-(+)-PENTANEDIOL plays a crucial role in the development of medications that help regulate calcium levels in the body, which can be beneficial for treating conditions such as hypertension and certain heart disorders.
Used in Chemical Synthesis:
(2S,4S)-(+)-Pentanediol, due to its unique stereochemistry and functional groups, can be employed as a building block in the synthesis of various chiral compounds. These compounds find applications in the production of pharmaceuticals, agrochemicals, and other specialty chemicals that require specific stereochemistry for their biological activity.
Used in Research and Development:
The optical activity of (2S,4S)-(+)-Pentanediol makes it an essential tool in research and development for studying the effects of stereochemistry on the properties and reactivity of molecules. It can be used to investigate the mechanisms of various chemical reactions and to develop new methods for the synthesis of enantiomerically pure compounds.

InChI:InChI=1/C5H12O2/c1-2-3-4-5(6)7/h5-7H,2-4H2,1H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 107-89-1 acetaldol 
• 4161-60-8 4-hydroxypentan-2-one 
• 123-54-6 acetylacetone 
• 17615-19-9 3,4-pentadien-2-ol 
• 63315-69-5 (-)-(4R)-4-hydroxypentan-2-one 
• 22520-29-2 syn-3,4-epoxy-2-pentanol 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 
• 17227-17-7 2,2,4,6-tetramethyl-[1,3]dioxane 
• 56-81-5 glycerol 
• 1825-14-5 DL-pentan-2,4-diol 

Downstream Products

• 504-60-9 penta-1,3-diene 
• 19398-53-9 2,4-dibromopentane 
• 101421-04-9 nitric acid-(1,3-dimethyl-propanediyl ester) 
• 107-87-9 2-Pentanone 
• 113283-75-3 [(S)-1-((4S,6S)-4,6-Dimethyl-[1,3]dioxan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 90394-16-4 (4S,6S)-4,6-Dimethyl-2-(3-phenoxy-phenyl)-[1,3]dioxane 
• 27098-14-2 (4R,6R)-4,6-Dimethyl-2-(4-trifluoromethyl-phenyl)-[1,3]dioxane 
• 27098-19-7 rel-(2S,4R,6S)-4,6-dimethyl-2-<4'-(trifluoromethyl)phenyl>-1,3-dioxane 
• 2365-00-6 2-(p-nitrophenoxy)-2-oxo-4,6-dimethyl-1,3,2λ⁵-dioxaphosphorinane 
• 132201-06-0 r-2-(p-nitrophenoxy)-2-oxo-t-4,t-6-dimethyl-1,3,2λ⁵-dioxaphosphinane 
• 132201-07-1 r-2-(p-nitrophenoxy)-2-oxo-c-4,c-6-dimethyl-1,3,2λ⁵-dioxaphosphinane 
• 136315-79-2 rel-(2S,4R,6R)-2-n-hexyl-4,6-dimethyl-1,3-dioxane 
• 137694-23-6 rel-(2S,4R,6S)-2-n-hexyl-4,6-dimethyl-1,3-dioxane 
• 142632-71-1 r-2-Diphenylphosphinoyl-t-4,t-6-dimethyl-1,3-dioxane 

Relevant articles and documents

Isolation of Racemic 2,4-Pentanediol and 2,5-Hexanediol from Commercial Mixtures of Racemic and Meso Isomers by way of Cyclic Sulfites

Enantiomerically pure diols with C2 symmetry such as 2,3-butanediol, 1, 2,4-pentanediol, 2, and 2,5-hexanediol, 3, are useful chiral auxiliaries, but they are expensive because chemists lack good synthetic routes that eliminate both the meso isomer and one enantiomer.Enzymic resolutions efficiently separate the enantiomer, but do not remove the meso isomer.To simplify enzymic resolutions of 2 and 3, we developed simple methods to isolate the racemic isomer from commercial mixtures of racemic and meso isomers 1 or 2, the meso isomer selectivity reacted with SOCl2 to give a cyclic sulfite that was removed by column chromatography to leave (+/-)-2, 92percent de, 1.4 g, 55percent yield.For 3, both meso and racemic isomers reacted with SOCl2 to give cyclic sulfites, but the sulfite derived from the meso isomer rearranged to trans-2,5-dimethyltetrahydrofuran under acidic conditions.Hydrolysis of the remaining sulfite gave (+/-)-3, 84percent de, 1.1 g, 37percent yield.Resolution of (+/-)-2 and (+/-)-3 using lipase from Pseudomonas cepacia yielded (2R,4R)-2-diacetate, 78 percent ee, >97percent de, 40percent of theory and (2R,5R)-3-diacetate, 94percent ee, >97percent de, 47percent of theory.Previously reported acetylations of 2 and 3 by lipase from Candida antarctica (CAL) or by lipase from Pseudomonas sp. (Amonolipase AK) are more enantioselective and thus, the best route to enantiomerically and diastereomerically pure 2 and 3 is removal of the meso isomer by way of cyclic sulfites followed by resolution with CAL or Amano lipase AK.

Vinylidene Homologation of Boronic Esters and its Application to the Synthesis of the Proposed Structure of Machillene

Alkenyl boronic esters are important reagents in organic synthesis. Herein, we report that these valuable products can be accessed by the homologation of boronic esters with lithiated epoxysilanes. Aliphatic and electron-rich aromatic boronic esters provided vinylidene boronic esters in moderate to high yields, while electron-deficient aromatic and vinyl boronic esters were found to give the corresponding vinyl silane products. Through DFT calculations, this divergence in mechanistic pathway has been rationalized by considering the stabilization of negative charge in the C?Si and C?B bond breaking transition states. This vinylidene homologation was used in a short six-step stereoselective synthesis of the proposed structure of machillene, however, synthetic and reported data were found to be inconsistent.

Method for preparing beta-diol from beta-diketone

The invention relates to a method for preparing beta-diol from beta-diketone. The method is characterized in that beta-diketone contacts and reacts with hydrogen in the presence of a hydrogenation catalyst under fixed bed reaction conditions, the hydrogenation catalyst comprises an active component copper and a carrier, and the hydrogenation catalyst preferably comprises an assistant component selected from VIIIB and IB group elements, the assistant is preferably selected from one or more of Ni, Co and Ag, and the carrier is SiO2. The method adopting a fixed bed hydrogenation technology and using a copper-containing supported catalyst has the advantages of no pollution to environment, mild operating conditions, and suitableness for continuous production.