42075-32-1

Basic information

• Product Name: (2R,4R)-(-)-PENTANEDIOL
• Synonyms: (R,R)-PENTANEDIOL-2,4;[R-(R*,R*)]-(-)2,4-PENTANEDIOL;(R,R)-(-)-2,4-PENTANEDIOL;(2R,4R)-(-)-2,4-DIHYDROXYPENTANE;(2R,4R)-(-)-2,4-PENTANEDIOL;(2R,4R)-2,4-PENTANEDIOL;(2R,4R)-(-)-PENTANEDIOL;(R,R)-(-)-2,4-PENTANEDIOL 98.5+%
• CAS NO: 42075-32-1
• Molecular Formula: C₅H₁₂O₂
• Molecular Weight: 104.15
• Product Categories: Chiral Compounds;Diols;chiral;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Building Blocks;Organic Building Blocks;Polyols;organic alcohol;Chiral Oxygen
• Mol File: 42075-32-1.mol
• Article Data: 57

Chemical Properties

• Melting Point: 48-50 °C(lit.)
• Boiling Point: 111-113 °C19 mm Hg(lit.)
• Flash Point: 215 °F
• Appearance: white/crystal
• Density: 0.9917 (rough estimate)
• Vapor Pressure: 0.384mmHg at 25°C
• Refractive Index: -53.5 ° (C=10, EtOH)
• Storage Temp.: 0-6°C
• Solubility: almost transparency in EtOH
• PKA: 14.74±0.20(Predicted)
• Stability: hygroscopic
• BRN: 4290613
• CAS DataBase Reference: (2R,4R)-(-)-PENTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-(-)-PENTANEDIOL(42075-32-1)
• EPA Substance Registry System: (2R,4R)-(-)-PENTANEDIOL(42075-32-1)

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: 42075-32-1(Hazardous Substances Data)

Usage

Description

(2R,4R)-(-)-PENTANEDIOL, also known as meso-2,4-pentanediol, is a chiral secondary alcohol with a C2 symmetry. It is a colorless to light yellow liquid and is characterized by its 2R,4R configuration, which gives it unique properties and applications in various fields.

Uses

Used in Chemical Synthesis:
(2R,4R)-(-)-PENTANEDIOL is used as an acetalization reagent for ketones and β-keto esters, allowing for the selective protection of carbonyl groups in organic synthesis. This property makes it a valuable tool in the preparation of complex organic molecules.
Used in Polymer Science:
(2R,4R)-(-)-PENTANEDIOL is used as a building block in the synthesis of optically active polyesters. Its chiral nature contributes to the development of polymers with specific properties and applications, such as biodegradable plastics and materials with tailored mechanical or thermal characteristics.
Used as a Chiral Auxiliary:
In the field of asymmetric synthesis, (2R,4R)-(-)-PENTANEDIOL is used as a chiral auxiliary to induce stereoselectivity in various chemical reactions. Its C2 symmetry and unique configuration make it an effective tool for enhancing the enantioselectivity of reactions, leading to the production of optically active compounds with high purity.
Used as a Chiral Building Block:
(2R,4R)-(-)-PENTANEDIOL is also employed as a chiral building block in the construction of more complex chiral molecules. Its versatile structure allows for the creation of a wide range of chiral compounds with potential applications in pharmaceuticals, agrochemicals, and other industries.
Used as a Chiral Ligand:
In catalysis, (2R,4R)-(-)-PENTANEDIOL is used as a chiral ligand to promote enantioselective reactions. Its unique configuration enables the development of catalysts that can selectively produce one enantiomer over the other, which is crucial in the synthesis of enantiomerically pure compounds with specific biological activities.
Used in Pharmaceutical Industry:
(2R,4R)-(-)-PENTANEDIOL is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those with chiral centers. Its unique configuration allows for the development of drugs with improved efficacy and selectivity, reducing potential side effects and improving patient outcomes.
Used in Flavor and Fragrance Industry:
(2R,4R)-(-)-PENTANEDIOL is used as a chiral building block in the creation of enantiomerically pure flavors and fragrances. Its ability to impart specific scents and tastes to compounds makes it an important component in the development of high-quality, natural-smelling products.

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

Upstream product

• 107-89-1 acetaldol 
• 7664-93-9 sulfuric acid 
• 123-54-6 acetylacetone 
• 17227-17-7 2,2,4,6-tetramethyl-[1,3]dioxane 
• 56-81-5 glycerol 
• 1825-14-5 pentane-1,3-diol 
• 139696-91-6 (+)(R) 1-(p-tolylsulfinyl)-2,4-pentanedione 
• 141423-17-8 (2S,4R)-1-((R)-Toluene-4-sulfinyl)-pentane-2,4-diol 
• 127666-78-8 Hexanoic acid (1S,3S)-3-hexanoyloxy-1-methyl-butyl ester 
• 63315-69-5 (-)-(4R)-4-hydroxypentan-2-one 
• 4161-60-8 4-hydroxypentan-2-one 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 

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 
• 4161-60-8 4-hydroxypentan-2-one 
• 64-19-7 acetic acid 
• 67-64-1 acetone 
• 123-54-6 acetylacetone 
• 75-07-0 acetaldehyde 
• 67-63-0 isopropyl alcohol 
• 4233-09-4 2-phenyl-4,6-dimethyl-1,3-dioxane 
• 1356445-89-0 C₃₅H₄₅BO₂Si 
• 1356446-24-6 6-hydroxy-7-methyl-2-(triphenylsilyloxy)octan-4-one 
• 1356446-26-8 1-hydroxy-1-phenyl-5-(triphenylsilyloxy)hexan-3-one 

Relevant articles and documents

Preparation of gem-dimethylcyclopropane-fused compounds through sigmatropic rearrangements. On/off-switching of the tautomerization of 3,4-homotropilidene by steric hindrance

Cyclopropanation of 4,8,8-trimethylcycloheptatriene having an ether function at the 3-position by unsubstituted carbenoid addition resulted in a complex mixture mainly due to quick valence tautomerization of the produced 3,4-homotropilidene analogue durin

Tuning diastereoselectivity with the solvent: The asymmetric hydrogenation of simple and functionalized 1,3-diketones with ruthenium(amidophosphine-phosphinite) catalysts

Spectacular solvent effects in the asymmetric hydrogenation of methyl 3,5-dioxohexanoate (3) and 2,4-pentanedione (5) have been observed using Ru[(S)-Ph,Ph-oxoProNOP]X2 complexes (X = η3-C4H7, IIa; CF3CO2, IIb; (R)-MTPA, IIc) as catalyst precursors. β-Diketones 3 and 5 are respectively reduced to the corresponding β-diols 4 and 6. In both cases, an almost complete reversal in the diastereoselectivity of the reaction is observed when changing the solvent from CH2Cl2 (syn-4 in up to 92% de; meso-6 in up to 84% de) to a 1:1 CH2Cl2-CH3OH mixture (anti-4 and anti-6 in up to 84% de). The extent of this solvent effect is much less marked with Ru- atropisomeric diphosphine catalysts.

Water-insoluble ruthenium catalyst composition for use in aqueous hydrogenation reactions

The invention relates to a method for converting a precatalyst complex to an active catalyst complex, wherein the precatalyst complex and the active catalyst complex comprise a ruthenium atom and an optically active ligand that is insoluble in water, and the active catalyst complex furthermore comprises a monohydride and a water molecule. The method comprises the steps of providing water as an activation solvent system with a pH value equal or below 2, and solving said precatalyst complex, an acid, and hydrogen therein. The invention further relates to a method for manufacturing a catalyst composition, a method for hydrogenating a substrate molecule and a reaction mixture.

Method for preparing beta-diol from beta-diketone by hydrogenation

The invention relates to a method for preparing beta-diol from beta-diketone by hydrogenation. The method comprises the following steps: in the presence of a catalyst and under the fixed-bed hydrotreating reaction condition, enabling beta-diketone to be in contact with hydrogen, so as to obtain beta-diol, wherein the catalyst contains CuO and ZnO, preferably also contains Al2O3, and more preferably also contains alkali metal oxides. According to the method for preparing beta-diol from beta-diketone by hydrogenation, provided by the invention, the technology of continuously producing beta-diol by adopting a fixed bed device is realized, the technology is simple and convenient to operate, the utilization ratio of raw materials and the production efficiency of products are improved, the reaction does not need to be carried out under high pressure, and potential safety hazards are reduced.