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

• 1825-14-5 pentane-1,3-diol 
• 141423-13-4 (+)-(R_S,2S)-1-(p-tolylsulfinyl)-2-hydroxy-4-pentanone 
• 123-54-6 acetylacetone 
• 7570-05-0 trans-4,6-dimethyl-2-oxo-1,3-dioxane 
• 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 
• 56-81-5 glycerol 
• 17227-17-7 2,2,4,6-tetramethyl-[1,3]dioxane 
• 4161-60-8 4-hydroxypentan-2-one 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 

Downstream Products

• 113283-78-6 [(S)-1-((4R,6R)-4,6-Dimethyl-[1,3]dioxan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 89238-89-1 (4R,6R)-4,6-Dimethyl-2-(4-nitro-phenyl)-[1,3]dioxane 
• 137626-21-2 rel-(2S,4R,6S)-4,6-dimethyl-2-(4'-nitrophenyl)-1,3-dioxane 
• 85029-00-1 (4R,6R)-2-cyclohexyl-4,6-dimethyl-1,3-dioxane 
• 90971-84-9 4-methoxypentan-2-ol 
• 505-22-6 1,3-dioxane 
• 504-60-9 penta-1,3-diene 
• 107-87-9 2-Pentanone 
• 4161-60-8 4-hydroxypentan-2-one 
• 64-17-5 ethanol 
• 3102-33-8 trans-3-penten-2-one 
• 67-64-1 acetone 
• 59694-09-6 2,4-pentanediol monobenzoate 
• 59694-10-9 (2R,4R)-2,4-pentanediol dibenzoate 

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.

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.

A β-diketone fixed bed hydrogenation method for preparing β-diol (by machine translation)

The invention relates to a β-diketone fixed bed hydrogenation method for preparing β-diol, including in the presence of hydrogenation catalyst under conditions and fixed bed reaction of the β-diketone reaction contact with hydrogen gas; the hydrogenation catalyst comprises active component copper and carrier, wherein in order to weight part, the content of copper is 20-35 parts, carrier is in a content of 60-80 parts. Preferably, the hydrogenation catalyst also includes selected from group IB and VIIIB additive component, more preferably the assistant is selected from Ni, Ag Co and in one or several of, the carrier is SiO 2. The method provided by the present invention which adopts a fixed bed hydrogenation process and the use of copper-containing supported catalyst, no pollution to the environment, mild operating conditions, is suitable for continuous production. (by machine translation)