5969-12-0

Basic information

• Product Name: heptane-2,6-diol
• Synonyms: 2,6-Heptanediol
• CAS NO: 5969-12-0
• Molecular Formula: C₇H₁₆O₂
• Molecular Weight: 132.2007
• Mol File: 5969-12-0.mol

Chemical Properties

• Boiling Point: 233.2°C at 760 mmHg
• Flash Point: 119.6°C
• Density: 0.945g/cm³
• Vapor Pressure: 0.0105mmHg at 25°C
• Refractive Index: 1.448
• CAS DataBase Reference: heptane-2,6-diol(CAS DataBase Reference)
• NIST Chemistry Reference: heptane-2,6-diol(5969-12-0)
• EPA Substance Registry System: heptane-2,6-diol(5969-12-0)

Safety Data

• Hazardous Substances Data: 5969-12-0(Hazardous Substances Data)

Upstream product

• 72693-12-0 6-hydroxyheptan-2-one 
• 75-16-1 methylmagnesium bromide 
• 111-30-8 Glutaraldehyde 
• 13505-34-5 2,6-heptandione 
• 3070-53-9 1,6-heptadiene 
• 18006-13-8 methyltriisopropoxytitanium(IV) 
• 18545-19-2 6-methyltetrahydro-2H-pyran-2-ol 
• 823-22-3 5-hexanolide 

Downstream Products

• 61485-85-6 2,6-dibromoheptane 
• 72693-12-0 6-hydroxyheptan-2-one 
• 4209-63-6 rac-(2R,6S)-1-benzyl-2,6-dimethylpiperidine 
• 75767-83-8 2,6-heptaneditosylate 

Relevant articles and documents

Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes

Hydration of alkenes using first row transition metals (Fe, Co, Mn) under oxygen atmosphere (Mukaiyama-type hydration) is highly practical for alkene functionalization in complex synthesis. Different hydration protocols have been developed, however, control of the stereoselectivity remains a challenge. Herein, highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents is reported. The nitro moiety is not well explored in radical chemistry and nitroarenes are known to suppress free radical processes. Our findings show the potential of cheap nitroarenes as oxygen donors in radical transformations. Secondary and tertiary alcohols were prepared with excellent Markovnikov-selectivity. The method features large functional group tolerance and is also applicable for late-stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.

Stereoselective synthesis of alicyclic ketones: A hydrogen borrowing approach

A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane products with high levels of stereoselectivity. The origins of diastereoselectivity in the annulation reaction have been explored by a series of control experiments, which provides an explanation for how each stereocentre around the newly forged ring is controlled.

Stereoselective Synthesis of Cyclohexanes via an Iridium Catalyzed (5 + 1) Annulation Strategy

An iridium catalyzed method for the synthesis of functionalized cyclohexanes from methyl ketones and 1,5-diols is described. This process operates by two sequential hydrogen borrowing reactions, providing direct access to multisubstituted cyclic products with high levels of stereocontrol. This methodology represents a novel (5 + 1) strategy for the stereoselective construction of the cyclohexane core.

Enantiopure 1,5-diols from dynamic kinetic asymmetric transformation. useful synthetic intermediates for the preparation of chiral heterocycles

Dynamic kinetic asymmetric transformation (DYKAT) of a series of 1,5-diols has been performed in the presence of Candida antarctica lipase B (CALB), Pseudomonas cepacia lipase II (PS-C II), and ruthenium catalyst 4. The resulting optically pure 1,5-diacet

Asymmetric hydrosilylation of ketones using trans-chelating chiral peralkylbisphosphine ligands bearing primary alkyl substituents on phosphorus atoms

Asymmetric hydrosilylation of simple ketones with diphenylsilane proceeded at -40 °C in the presence of a rhodium complex (0.001 - 0.01 molar amount) coordinated with a trans-chelating chiral bisphosphine ligand bearing linear alkyl substituents on the phosphorus atoms, (R,R)-(S,S)-Et-, Pr-, or BuTRAP, giving the corresponding optically active (S)- secondary alcohols with up to 97% ee. The asymmetric hydrosilylation using TRAP ligands with bulkier P-substituents resulted in much lower enantioselectivities. The EtTRAP-rhodium catalyst was also effective for asymmetric hydrosilylation of keto esters with a coordination site for a rhodium atom (up to 98% ee). Optically active symmetrical diols were obtained with up to 99% ee from the corresponding diketones via the asymmetric reduction using 2.5 molar amounts of diphenylsilane.

Synthesis of C-Glucosides by Reactions of Glucosyl Halides with Organocuprates.

Lithium dimethylcuprate reacts with trans-2-chloro-6-methyltetrahydropyran (1) via nucleophilic substitution predominantly with inversion of configuration to afford cis-2,6-dimethyltetrahydropyran (2).Similarly, lithium dialkylcuprates displace protected α-glucosyl bromides (5) with inversion to afford the β-C-glucosides, β-1-alkyl-1,5-anhydroglucitols (6).In contrast, Grignard reagents gave mixtures of α- and β- glucosides 6 and 7, while organolithium reagents gave only elimination to 9.

Lactols in Stereoselection 1. Highly selective 1,4- and 1,5-Asymmetric Induction

Nucleophilic addition to substituted γ- and δ-lactols with titanium reagents provides 1,4-syn and 1,5-syn diols in high stereoselectivity, which represents a new and simple method for the remote asymmetric induction.