104898-06-8

Basic information

• Product Name: (R)-(+)-1,2-EPOXYHEXANE
• Synonyms: (R)-(+)-1,2-EPOXYHEXANE;(r)-2-butyloxirane;(R)-2-Butyloxirane, (R)-Hexene oxide
• CAS NO: 104898-06-8
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.16
• Mol File: 104898-06-8.mol
• Article Data: 70

Chemical Properties

• Boiling Point: 118-120 °C(lit.)
• Flash Point: 60 °F
• Appearance: /
• Density: 0.831 g/mL at 25 °C(lit.)
• Vapor Pressure: 21.1mmHg at 25°C
• Refractive Index: n20/D 1.406(lit.)
• CAS DataBase Reference: (R)-(+)-1,2-EPOXYHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1,2-EPOXYHEXANE(104898-06-8)
• EPA Substance Registry System: (R)-(+)-1,2-EPOXYHEXANE(104898-06-8)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-22-36/37/38
• Safety Statements: 16-26
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 104898-06-8(Hazardous Substances Data)

Usage

General Description

"(R)-(+)-1,2-EPOXYHEXANE" is a chemical compound with the molecular formula C6H12O. It is an epoxide, which means it contains a three-membered ring consisting of two carbon atoms and one oxygen atom. (R)-(+)-1,2-EPOXYHEXANE is chiral, meaning it has a non-superimposable mirror image, and the "(R)-(+)" designation indicates that it is the enantiomer with a positive optical rotation. (R)-(+)-1,2-EPOXYHEXANE has a wide range of industrial uses, including as a solvent, a chemical intermediate in the synthesis of pharmaceuticals and agrochemicals, and as a building block for the production of polymers and other organic compounds. However, it is important to handle this compound with care, as it is flammable and may cause skin and eye irritation.

InChI:InChI=1/C6H12O/c1-2-3-4-6-5-7-6/h6H,2-5H2,1H3/t6-/m1/s1

Upstream product

• 127911-72-2 (R)-(+)-2-hydroxyhexyl tosylate 
• 1436-34-6 1,2-Epoxyhexane 
• 592-41-6 1-hexene 
• 127911-70-0 (2S)-2-hydroxyhexyl 1-p-toluenesulfonate 
• 2426-08-6 glycidyl n-butyl ether 
• 50-30-6 2,6-dichlorobenzoic acid 
• 621-84-1 O-benzyl carbamate 
• 66-25-1 hexanal 
• 771476-44-9 (S)-2-(N-Phenyl-aminooxy)-hexan-1-ol 
• 6920-22-5 (2S)-hexane-1,2-diol 
• 930-57-4 n-butylcyclopropane 
• 93339-60-7 toluene-4-sulfonic acid (2-hydroxyhexyl) ester 
• 6920-22-5 Hexane-1,2-diol 
• 152517-47-0 (+/-)-t-butyl-(2-hydroxyhexyl)-sulfide 

Downstream Products

• 134283-34-4 (2S,4R)-4-Hydroxy-2-(4-methoxy-phenyl)-octanenitrile 
• 4938-52-7 (S)-Hept-1-en-3-ol 
• 1423808-56-3 (4S,5S,9S)-4-(benzyloxy)-7,7-diisopropyl-1-(4-methoxyphenyl)-5,9-divinyl-2,6,8-trioxa-7-silatridecane 
• 1423808-57-4 (2S,3S)-2-(benzyloxy)-3-(((S)-hept-1-en-3-yloxy)diisopropylsilyloxy)pent-4-en-1-ol 
• 1423808-58-5 (S)-2-(benzyloxy)-2-((4S,7S)-7-butyl-2,2-diisopropyl-4,7-dihydro-1,3,2-dioxasilepin-4-yl)ethanol 
• 1423808-59-6 (S,Z)-methyl 4-(benzyloxy)-4-((4S,7S)-7-butyl-2,2-diisopropyl-4,7-dihydro-1,3,2-ioxasilepin-4-yl)but-2-enoate 
• 1422040-31-0 (5S,6S)-5-(benzyloxy)-6-((S,Z)-3-hydroxyhept-1-enyl)-5,6-dihydro-2H-pyran-2-one 
• 1422040-32-1 (S,Z)-1-((2S,3S)-3-(benzyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate 
• 1437789-15-5 (5R,9S)-7,7-diisopropyl-1-(4-methoxyphenyl)-5,9-divinyl-2,6,8-trioxa-7-silatridecane 
• 1615707-79-3 1-((tert-butyldiphenylsilyl)oxy)nonane-2,5-diol 
• 1372526-20-9 C₂₅H₃₂ClNO₃ 

Relevant articles and documents

Catalytic activity and recyclability of new enantioselective chiral Co-salen complexes in the hydrolytic kinetic resolution of epichlorohydrine

Chiral Co(III) salen catalysts bearing PF6, BF4 or Br counterions proved to be reactive and enantioselective in the hydrolytic resolution of terminal epoxides. The catalysts could be recovered and reused several times without further

Enzyme Assisted Synthesis of Enantiomerically Pure δ-Lactones

Both enantiomers series of a wide variety of optically pure 6-alkylated δ-lactones - saturated as well as unsaturated - were prepared via an enzyme mediated route.The key reaction step is the nucleophilic ring opening of enantiomerically pure alkyl-oxiranes, accessible via the corresponding β-hydroxythioesters which can be obtained enantiomerically pure via enzyme catalyzed kinetic resolutions.

Tailoring the window sizes to control the local concentration and activity of (salen)Co catalysts in plugged nanochannels of SBA-15 materials

Ship shape! Chiral (salen)CoIII complexes (spheres) inside plugged nanochannels of SBA-15 materials is achieved using a ship-in-a-bottle synthesis technique. The local concentration of the metal complexes and the catalytic activity (such as the hydrolytic kinetic resolution of 1,2-epoxyalkanes; see scheme) showed a strong dependence on the size of the window. Copyright

Fluorous biphasic hydrolytic kinetic resolution of terminal epoxides

Although application of light-fluorous techniques facilitates the isolation of reaction products from the hydrolytic kinetic resolution (HKR) of terminal epoxides catalysed by cobalt complexes of salen ligands, the extension of the original fluorous biphasic approach to this reaction is far from being a trivial exercise. The nature of the counter anion has a dramatic effect on the catalytic activity of heavily fluorinated chiral (salen) cobalt(III) complexes. Excellent enantioselectivities are obtained in the fluorous biphasic HKR of 1,2-hexene oxide when fluorinated anions are introduced (e.e.s up to 99% both for the diol and the epoxide), with C8F17COO- affording reaction rates even higher than those observed with non-fluorous systems.

CrIII(salen) impregnated on silica for asymmetric ring opening reactions and its recovery via desorption/re-impregnation

The impregnation of CrIII(salen) complexes on silica resulted in a heterogeneous catalyst for the asymmetric ring opening (ARO) reaction of epoxides with good selectivity and acceptable activity. As became apparent from a series of 10 successive batch tests in the ARO reaction of 1,2-epoxyhexane, leaching was limited, while catalytic activity and selectivity were acceptable. Though the support suffered from abrasion in the batch reactor, 80% of the catalyst was easily recoverable via simple extraction from the used solid catalyst and entirely transferable onto a fresh carrier via impregnation. It was shown that 80% of the leached catalyst at the end of the tests could be transformed into a fresh heterogeneous catalyst as well.

Application of homochiral alkylated organic cages as chiral stationary phases for molecular separations by capillary gas chromatography

Molecular organic cage compounds have attracted considerable attention due to their potential applications in gas storage, catalysis, chemical sensing, molecular separations, etc. In this study, a homochiral pentyl cage compound was synthesized from a condensation reaction of (S,S)-1,2-pentyl-1,2-diaminoethane and 1,3,5-triformylbenzene. The imine-linked pentyl cage diluted with a polysiloxane (OV-1701) was explored as a novel stationary phase for high-resolution gas chromatographic separation of organic compounds. Some positional isomers were baseline separated on the pentyl cage-coated capillary column. In particular, various types of enantiomers including chiral alcohols, esters, ethers and epoxides can be resolved without derivatization on the pentyl cage-coated capillary column. The reproducibility of the pentyl cage-coated capillary column for separation was investigated using nitrochlorobenzene and styrene oxide as analytes. The results indicate that the column has good stability and separation reproducibility after being repeatedly used. This work demonstrates that molecular organic cage compounds could become a novel class of chiral separation media in the near future.

Titanium salalen catalysts based on cis-1,2-diaminocyclohexane: Enantioselective epoxidation of terminal non-conjugated olefins with H 2O2

Terminal, non-conjugated olefins, such as 1-octene, are difficult to epoxidize asymmetrically. Ti salalen complexes based on cis-1,2- diaminocyclohexane catalyze this demanding reaction giving high yields and enantioselectivities (up to 95 % ee), with H2O2 as the oxidant. The X-ray structures of the μ-oxo and peroxo complexes shed light on the coordination behavior of this novel class of ligands.

The Activation of Carboxylic Acids via Self-Assembly Asymmetric Organocatalysis: A Combined Experimental and Computational Investigation

The heterodimerizing self-assembly between a phosphoric acid catalyst and a carboxylic acid has recently been established as a new activation mode in Br?nsted acid catalysis. In this article, we present a comprehensive mechanistic investigation on this activation principle, which eventually led to its elucidation. Detailed studies are reported, including computational investigations on the supramolecular heterodimer, kinetic studies on the catalytic cycle, and a thorough analysis of transition states by DFT calculations for the rationalization of the catalyst structure-selectivity relationship. On the basis of these investigations, we developed a kinetic resolution of racemic epoxides, which proceeds with high selectivity (up to s = 93), giving the unreacted epoxides and the corresponding protected 1,2-diols in high enantiopurity. Moreover, this approach could be advanced to an unprecedented stereodivergent resolution of racemic α-chiral carboxylic acids, thus providing access to a variety of enantiopure nonsteroidal anti-inflammatory drugs and to α-amino acid derivatives.

Titanium cis-1,2-diaminocyclohexane (cis-DACH) salalen catalysts for the asymmetric epoxidation of terminal non-conjugated olefins with hydrogen peroxide

Chiral Ti salalen complexes catalyze the asymmetric epoxidation of terminal non-conjugated olefins with hydrogen peroxide. Modular ligands based on cis-1,2-diaminocyclohexane (cis-DACH) were developed, giving high yields and enantiomeric excesses (ee, up to 96%) at catalyst loadings as low as 0.1-0.5mol%, and even under solvent-free conditions.

Manganese complexes with non-porphyrin N4 ligands as recyclable catalyst for the asymmetric epoxidation of olefins

New chiral manganese complexes of N4 ligands derived from 2-acetylpyridine were prepared and used as catalysts in the enantioselective epoxidation of olefins, using H2O2 as an oxidant to give epoxides, with excellent conversions (up to 99%) and enantiomeric excess (up to 88%) within 1 h at 0°C. A detailed mechanistic study was undertaken based on the information obtained by single crystal X-ray, optical rotation, UV-Vis, CD spectra and kinetic studies, and revealed that the reaction is first order with respect to the concentration of catalyst and oxidant and independent of substrate concentration. The complex (0.1 mol%) was successfully subjected to recyclability experiments over 3 cycles in the epoxidation of styrene with H2O2 as an oxidant and acetic acid as an additive at 0°C with retention of performance.

Aromatic Donor-Acceptor Interaction-Based Co(III)-salen Self-Assemblies and Their Applications in Asymmetric Ring Opening of Epoxides

Aromatic donor-acceptor interaction as the driving force to assemble cooperative catalysts is described. Pyrene/naphthalenediimide functionalized Co(III)-salen complexes self-assembled into bimetallic catalysts through aromatic donor-acceptor interactions and showed high catalytic activity and selectivity in the asymmetric ring opening of various epoxides. Control experiments, nuclear magnetic resonance (NMR) spectroscopy titrations, mass spectrometry measurement, and X-ray crystal structure analysis confirmed that the catalysts assembled based on the aromatic donor-acceptor interaction, which can be a valuable noncovalent interaction in supramolecular catalyst development.

Hydrolytic kinetic resolution of terminal epoxides catalyzed by fluorous chiral Co(salen) complexes

Cobalt complexes of fluorous chiral salen ligands have been synthesized and tested as catalysts in the hydrolytic kinetic resolution of terminal epoxides. Whereas the activity of heavily fluorinated complexes was found to be rather low, a 'light fluorous' complex was shown to be an efficient and highly selective catalyst for this asymmetric ring-opening reaction. Several strategies for the isolation of reaction products and the recovery of the fluorous catalyst are also discussed.

Ring-expanding olefin metathesis: A route to highly active unsymmetrical macrocyclic oligomeric co-salen catalysts for the hydrolytic kinetic resolution of epoxides

In the presence of the third generation Grubbs catalyst, the ring-expanding olefin metathesis of a monocyclooct-4-en-1-yl functionalized salen ligand and the corresponding Co(II)(salen) complex at low monomer concentrations results in the exclusive formation of macrocyclic oligomeric structures with the salen moieties being attached in an unsymmetrical, flexible, pendent manner. The TOF-MALDI mass spectrometry reveals that the resulting macrocyclic oligomers consist predominantly of dimeric to tetrameric species, with detectable traces of higher homologues up to a decamer. Upon activation under aerobic and acidic conditions, these Co(salen) macrocycles exhibit extremely high reactivities and selectivities in the hydrolytic kinetic resolution (HKR) of a variety of racemic terminal epoxides under neat conditions with very low catalyst loadings. The excellent catalytic properties can be explained in terms of the new catalyst's appealing structural features, namely, the flexible oligomer backbone, the unsymmetrical pendent immobilization motif of the catalytic sites, and the high local concentration of Co(salen) species resulting from the macrocyclic framework. This ring-expanding olefin metathesis is suggested to be a simple way to prepare tethered metal complexes that are endowed with key features - (i) a high local concentration of metal complexes and (ii) a flexible, single point of attachment to the support - that facilitate rapid and efficient catalysis when a bimetallic transition state is required.

Enantioselective Resolution Copolymerization of Racemic Epoxides and Anhydrides: Efficient Approach for Stereoregular Polyesters and Chiral Epoxides

Herein we report an efficient strategy for preparing isotactic polyesters and chiral epoxides via enantioselective resolution copolymerization of racemic terminal epoxides with anhydrides, mediated by enantiopure bimetallic complexes in conjunction with a nucleophilic cocatalyst. The chirality of both the axial linker and the diamine backbones of the ligand are responsible for the chiral induction of this kinetic resolution copolymerization process. The catalyst systems exhibit exceptional levels of enantioselectivity with a kinetic resolution coefficient exceeding 300 for various racemic epoxides, affording highly isotactic copolymers (selectivity factors of more than 300) with a completely alternating structure and low polydispersity index. Most of the produced isotactic polyesters are typical semicrystalline materials with melting temperatures in the range from 77 to 160 °C.