17299-07-9

Basic information

• Product Name: (2R,5R)-2,5-HEXANEDIOL
• Synonyms: (2R,5R)-(-)-2,5-HEXANEDIOL;(2R,5R)-2,5-HEXANEDIOL;(2R,5R)-2,5-DIHYDROXYHEXANE;(2R,5R)-DIHYDROXYHEXANE;(2R,5R)-HEXANE-2,5-DIOL;Hexanediolcolorlessxtl;(2R,5R)-2,5-Hezanediol;(2R,5R)-(-)-2,5-Hexanediol,99%
• CAS NO: 17299-07-9
• Molecular Formula: C₆H₁₄O₂
• Molecular Weight: 118.17
• Product Categories: Chiral Compounds;Diols;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Building Blocks;Organic Building Blocks;Polyols;organic alcohol
• Mol File: 17299-07-9.mol

Chemical Properties

• Melting Point: 52-54 °C
• Boiling Point: 212-215 °C
• Flash Point: 101 °C
• Appearance: White to yellow/Crystalline Powder or Needles
• Density: 0.9843 (rough estimate)
• Vapor Pressure: 0.0364mmHg at 25°C
• Refractive Index: 1.4428 (estimate)
• Storage Temp.: 2-8°C
• Solubility: almost transparency in Methanol
• PKA: 14.87±0.20(Predicted)
• BRN: 1719251
• CAS DataBase Reference: (2R,5R)-2,5-HEXANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R)-2,5-HEXANEDIOL(17299-07-9)
• EPA Substance Registry System: (2R,5R)-2,5-HEXANEDIOL(17299-07-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 17299-07-9(Hazardous Substances Data)

Usage

Chemical Properties

white to yellow needle-like crystals

InChI:InChI=1/C6H14O2/c1-5(7)3-4-6(2)8/h5-8H,3-4H2,1-2H3/t5-,6-/m1/s1

Upstream product

• 625-72-9 (R)-3-hydroxybutyric acid 
• 97100-83-9 (R,R)-2,5-diacetoxyhexane 
• 86748-53-0 (-)-2,5-Hexanediol (-)-Dimandelate 
• 158833-94-4 (2S,5S)-1,6-Bis-((R)-toluene-4-sulfinyl)-hexane-2,5-diol 
• 110-13-4 2,5-hexanedione 
• 77489-41-9 1,2,4,6-tetra-O-p-toluenesulfonyl-D-mannitol 
• 3031-66-1 3-hexyn-2,5-diol 
• 38484-56-9 (+/-)-2,5-hexanediol 
• 876-27-7 4-chlorophenyl acetate 
• 20706-73-4 3,4-di-O-p-toluenesulfonyl-D-mannitol 
• 20706-71-2 O¹,O²;O⁵,O⁶-diisopropylidene-O³,O⁴-bis-(toluene-4-sulfonyl)-D-mannitol 
• 65709-73-1 (5R)-hydroxyhexane-2-one 
• 1888-89-7 1,5-hexadiene diepoxide 
• 1888-89-7 (2S,5S)-1,5-hexadiene diepoxide 

Downstream Products

• 65709-73-1 (5R)-hydroxyhexane-2-one 
• 147253-67-6 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene 
• 136779-26-5 1,2-bis((2S,5S)-2,5-dimethylphospholano)ethane 
• 129705-29-9 (2S,5S)-2,5-dimethyl-1-phenylphospholane 
• 137152-02-4 bis(2-((2S,5S)-2,5-dimethylphospholanoethyl))phenylphosphine 
• 959577-05-0 (2R,3R,5R,6S)-2-(((2R,5R)-5-hydroxyhexan-2-yl)oxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate 
• 110-13-4 2,5-hexanedione 
• 854670-80-7 (2R,5R)-hexane-2,5-diol di-p-toluenesulfonate 
• 1003-38-9 (-)-(R,R)-2,5-dimethyltetrahydrofurane 
• 2144-41-4 (2R,5S)-2,5-dimethyltetrahydrofuran 
• 139108-42-2 (2S,5S)-1-[(4S)-4-(tert-butyldiphenylsilyloxy)-5-vinylhept-6-enoyl]-2,5-dimethylpyrrolidine 
• 139135-92-5 (2S,5S)-1-[(4R)-4-(tert-butyldiphenylsilyloxy)-5-vinylhept-6-enoyl]-2,5-dimethylpyrrolidine 
• 618386-92-8 (2S,5S)-1-[(4R)-4-nemzoyloxy-5-vinylhept-6-enoyl]-2,5-dimethylpyrrolidine 

Relevant articles and documents

New continuous production process for enantiopure (2R,5R)-hexanediol

A new continuous production process has been developed for optically active pure (2R,5R)-hexanediol. The process uses resting whole cells of Lactobacillus kefir DSM 20587 as a biocatalyst. The reduction of (2,5)-hexanedione to (2R,5R)-hexanediol was carried out in a 2-L continuously operated membrane reactor. Conversion of (2,5)-hexanedione was nearly quantitative and the selectivity between product and intermediate was 78% for the product. Enantioselectivity and diastereoselectivity were >99% for the whole period. The productivity of L. kefir could be increased by factor 30. (2R,5R)-Hexanediol was continuously produced over 5 days with a space-time yield of 64 g·L-1·d-1.

Biocatalytical production of (5S)-hydroxy-2-hexanone

Biocatalytical approaches have been investigated in order to improve accessibility of the bifunctional chiral building block (5S)-hydroxy-2-hexanone ((S)-2). As a result, a new synthetic route starting from 2,5-hexanedione (1) was developed for (S)-2, whi

On the mechanism of the unexpected facile formation of meso-diacetate products in enzymatic acetylation of alkanediols

The mechanism of the unexpected facile formation of meso-diacetate previously observed in the enzymatic resolution of dl/meso mixtures of 2,4-pentanediol and 2,5-hexanediol with Candida antarctica lipase B has been elucidated. It was found that the formation of meso-diacetate proceeds via different mechanisms for the two diols. Enzyme-catalyzed acylation of AcO-d3 labeled (R)-monoacetates of meso-2,4-pentanediol and meso-2,5-hexanediol and analysis of the mesodiacetates obtained show that the former reaction proceeds via intramolecular acyl migration while the latter occurs via direct S-acylation of the alcohol. For the (R)-monoacetate of (R,S)-2,4-pentanediol the intramolecular acyl migration was fast and therefore direct S-acylation by the external acyl donor is suppressed. For the hexanediol monoacetate the rate ratio (pseudo E value) between (5R,2R)- and (5R,2S)-5-acetoxy-2-hexanol was experimentally determined to be kR,R/kR,S = 25, which is about 10-20 times lower than the E value for 2-pentanol and 2-octanol. In a preliminary experiment it was demonstrated that facile acyl migration in the 1,3-diol derivative can be utilized to prepare syn-1,3-diacetoxynonane (β90% syn) in high enantioselectivity (β99% ee) via a chemoenzymatic dynamic kinetic asymmetric tyransformation of a meso/dl mixture of 1,3-nonanediol.

Remote Asymmetric Induction. Stereo- and Enantioselective Synthesis of Symmetrical and Unsymmetrical 1,4-Diols

Nucleophilic addition of Grignard reagents to the tricyclic lactols 4 or 5 provides with very high selectivity syn or anti 1,4-diols, so that, starting from the scalemic lactol 1a, three of the four possible diastereoisomeric 1,4-diols 7 or 9 can be obtained.This new example of remote asymmetric induction is illustrated by the synthesis of optically pure (2R,5R)-2,5-hexanediol and (3S,6R)-4-decen-3,6-diol.

Absolute configuration for 1, n-glycols: A nonempirical approach to long-range stereochemical determination

The absolute configurations of 1,n-glycols (n = 2-12, 16) bearing two chiral centers were rapidly determined via exciton-coupled circular dichroism (ECCD) using a tris(pentafluorophenyl)porphyrin (TPFP porphyrin) tweezer system in a nonempirical fashion devoid of chemical derivatization. A unique "side-on" approach of the porphyrin tweezer relative to the diol guest molecule is suggested as the mode of complexation.

A continuously operated bimembrane reactor process for the biocatalytic production of (2R,5R)-hexanediol

Alcohol dehydrogenase-catalyzed reductions of prochiral ketones to chiral alcohols require the regeneration of consumed cofactors such as NADH or NADPH. In the substrate-coupled cofactor regeneration approach, where 2-propanol is oxidized to acetone, comp

Dynamic kinetic asymmetric transformation of 1,4-diols and the preparation of trans-2,5-disubstituted pyrrolidines

Dynamic kinetic asymmetric transformation (DYKAT) of a series of 1,4-diols is carried out with Candida antarctica lipase B (CALB), Pseudomonas cepacia lipase II (PS-C II), and a ruthenium catalyst. A β-chloro-substituted 1,4-diol is successfully transformed into an optically pure 1,4-diacetate, which is a highly useful synthetic intermediate. The usefulness of the optically pure 1,4-diacetates is demonstrated by the synthesis of enantiopure 2,5-disubstituted pyrrolidines.

Asymmetric anti-Prelog reduction of ketones catalysed by Paracoccus pantotrophus and Comamonas sp. cells via hydrogen transfer

A broad range of ketones including methyl-aryl-, methyl-alkyl-, cyclic and sterically hindered ketones were reduced to the corresponding anti-Prelog alcohols with moderate to excellent stereoselectivities by employing lyophilised cells of Paracoccus pantotrophus DSM 11072 and Comamonas sp. DSM 15091 via hydrogen transfer. The reduction equivalents were provided using 2-propanol as a hydride donor. For instance, acetophenone was reduced to the corresponding (R)-enantiomer with >99% ee.

Highly efficient synthesis of enantiopure diacetylated C 2-symmetric diols by ruthenium- and enzyme-catalyzed dynamic kinetic asymmetric transformation (DYKAT)

Highly efficient synthesis of enantiopure diacetates of 2,4-pentanediol and 2,5-hexanediol starting from commercially available mixtures of the diols (dl/ meso ≈1:1) has been realized by combining a fast ruthenium-catalyzed epimerization with an enzymatic transesterification. The in situ coupling of these two processes produces the diacetates in high yield in > 99 % enantiomeric excess.

Regio- and stereoselective reduction of diketones and oxidation of diols by biocatalytic hydrogen transfer

The asymmetric reduction of symmetrical and nonsymmetrical diketones as well as the stereoselective oxidation of various diols by biocatalytic hydrogen transfer was investigated by employing lyophilized cells of Rhodococcus ruber DSM 44541 containing alcohol dehydrogense ADH-'A'. Symmetrical and nonsymmetrical diketones at the (ω-1)- and (ω-2)-positions are reduced to the Prelog product with high stereopreference, while sterically more demanding ketone moieties, for example those at the (ω-3)-position, remain unchanged. For the oxidation mode, differentiation between primary and secondary alcohols is achieved, and the (S)-configured secondary alcohols at the (ω-1)- and (ω-2)-positions are oxidized preferentially. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.