123493-71-0

Basic information

• Product Name: (R)-(+)-1 2-EPOXYUNDECANE 97
• Synonyms: (R)-(+)-1 2-EPOXYUNDECANE 97;(R)-(+)-1 2-EPOXYUNDECANE 97%;(R)-(+)-Nonyloxirane
• CAS NO: 123493-71-0
• Molecular Formula: C11H22O
• Molecular Weight: 170.29178
• Mol File: 123493-71-0.mol

Chemical Properties

• Boiling Point: 103 °C10 mm Hg(lit.)
• Flash Point: 158 °F
• Appearance: /
• Density: 0.842 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.171mmHg at 25°C
• Refractive Index: 1.4930 (estimate)
• CAS DataBase Reference: (R)-(+)-1 2-EPOXYUNDECANE 97(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1 2-EPOXYUNDECANE 97(123493-71-0)
• EPA Substance Registry System: (R)-(+)-1 2-EPOXYUNDECANE 97(123493-71-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 123493-71-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-1 2-EPOXYUNDECANE 97 is used as a key intermediate for the synthesis of various pharmaceuticals. Its unique chiral epoxide structure and high purity make it an ideal candidate for the development of new drugs and medications.
Used in Fragrance Industry:
In the fragrance industry, (R)-(+)-1 2-EPOXYUNDECANE 97 is used as a building block for creating complex and unique scents. Its ability to undergo further chemical manipulation allows for the creation of a wide range of fragrances.
Used in Fine Chemicals Production:
(R)-(+)-1 2-EPOXYUNDECANE 97 is also used in the production of fine chemicals, which are high-purity chemicals used in various applications, such as in the electronics, agriculture, and specialty chemical industries. Its high purity and epoxide functional group make it a valuable component in the synthesis of these chemicals.
Used in Chemical Research:
(R)-(+)-1 2-EPOXYUNDECANE 97 serves as an important compound in chemical research, particularly in the study of asymmetric synthesis and the development of new synthetic methods. Its unique properties and high purity make it an ideal subject for research and experimentation in the field of organic chemistry.

InChI:InChI=1/C11H22O/c1-2-3-4-5-6-7-8-9-11-10-12-11/h11H,2-10H2,1H3/t11-/m1/s1

Upstream product

• 821-95-4 1-undecene 
• 186581-53-3 diazomethane 
• 112-31-2 caprinaldehyde 
• 110-83-8 cyclohexene 
• 10486-19-8 tridecanal 
• 96883-16-8 (R)-1,2-dihydroxytridecane 
• 1428636-16-1 (R)-2-(tosyloxy)tridecyl benzoate 
• 17322-97-3 1,2-epoxyundecane 
• 17049-50-2 n-decyl magnesium bromide 
• 139926-09-3 (+/-)-1-chloro-2-tridecanol 
• 862848-62-2 (R)-undecane-1,2-diol 
• 922527-72-8 toluene-4-sulfonic acid 2-hydroxy-undecyl ester 
• 1731-81-3 undecyl acetate 
• 1774-47-6 trimethylsulfoxonium iodide 

Downstream Products

• 236412-69-4 (R)-(+)-1,2-epoxyundecane 
• 28254-78-6 (3R)-(-)-3-Hydroxydodecanoic acid 
• 125882-62-4 fellutamide B 
• 922527-71-7 (R)-3-hydroxydodecanenitrile 

Relevant articles and documents

Manganese acetate in pyrrolidinium ionic liquid as a robust and efficient catalytic system for epoxidation of aliphatic terminal alkenes

Green epoxides! A novel and simple ionic liquid/manganese acetate catalytic system has been developed for the rapid and selective oxidation of aliphatic terminal alkenes to epoxides. It provides an efficient, reusable, and scalable protocol for the green synthesis of epoxides from various aliphatic terminal alkenes.

Epoxidation of alkenes efficiently catalyzed by Mo salen supported on surface-modified halloysite nanotubes

Halloysite-nanotube-supported Mo salen (HNTs-Mo-SL) catalysts were successfully prepared using a facile chemical surface modification and self-assembly method. The morphologies, sizes, structure, and dispersion of the as-prepared catalysts were investigated by transmission electron microscopy, X-ray diffraction, and Fourier-transform infrared, inductively coupled plasma, and X-ray photoelectron spectroscopy, which confirmed the existence of the Mo salen structure and successful synthesis of the HNTs-Mo-SL catalyst. The immobilized catalyst was found to be highly reactive in the epoxidation of a wide range of alkenes, including linear, cyclic, and aromatic alkenes. The immobilized catalyst exhibited a higher catalytic activity for alkene epoxidation than homogeneous Mo. In contrast experiments, it was determined that the salen structure played an important role in immobilizing MoO(O2)2(DMF)2 and improving the conversion and efficiency of alkene epoxidation, which could not be obtained using other ligands, such as the N atom as a single ligand. Furthermore, the bonding between Mo and the salen ligands and the possible mechanism of alkene epoxidation catalyzed by the catalyst were determined. The catalyst could be reused several times without significant loss of catalytic activity. Given that halloysite nanotubes are cheap and easy to obtain, this catalyst offers a novel alternative for the rational design of catalysts with desired features.

Epoxidation of olefins catalyzed by manganese(III) porphyrin in a room temperature ionic liquid

The epoxidation of several alkenes catalyzed by (meso-tetrakis(pentafluorophenyl)porphinato) manganese(III) chloride (MnTFPPCl) was carried out in a 3:1 [bmim]PF6 ionic liquid/CH2Cl2 mixed solvent. The conversion and the yield of epoxide are excellent. It was also found that [bis(acetoxy)iodo]benzene [PhI(OAc)2] is a more efficient oxidant than PhIO. The catalyst in the ionic liquids can be recycled for several runs without substantial diminution in the catalytic activity.

In situ fabricated MOF-cellulose composite as an advanced ROS deactivator-convertor: Fluoroswitchable bi-phasic tweezers for free chlorine detoxification and size-exclusive catalytic insertion of aqueous H2O2

Combining the merits of structural diversity, and purposeful implantation of task-specific functionalities, metal-organic frameworks (MOFs) instigate targeted reactive oxygen species (ROS) scavenging and concurrent detoxification via self-calibrated emission modulation. Then again, grafting of catalytically active sites in MOFs can benefit developing a greener protocol to convert ROS generators to technologically important building blocks, wherein tailorable MOF-composite fabrication is highly sought for practical applications, yet unexplored. The chemo-robust and hydrogen-bonded framework encompassing free -NH2 moiety affixed pores serves as an ultra-fast and highly regenerable fluoro-probe for selective detection of toxic ROS producers hypochlorite ion (ClO-) and H2O2 with record-level nanomolar sensitivity. While the bio-relevant antioxidant l-ascorbic acid (AA) imparts notable quenching to the MOF, a significant 3.5 fold emission enhancement with bi-phasic colorimetric variation ensues when it selectively scavenges ClO- from uni-directional porous channels through an unprecedented molecular tweezer approach. Apart from a battery of experimental evidence, density functional theory (DFT) results validate "on-off-on"fluoroswitching from redistribution of MOF orbital energy levels, and show guest-mediated exclusive transition from "Tight state"to "Loose state". The coordination frustrated metal site engineered pore-wall benefits the dual-functionalized MOF in converting the potential ROS generator H2O2via selective alkene epoxidation under mild-conditions. Importantly, sterically encumbered substrates exhibit poor conversion and demonstrate first-ever pore-fitting-induced size selectivity for this benign oxidation. Judiciously planned control experiments in combination with DFT-optimized intermediates provide proof-of-concept to the ionic route of ROS conversion. Considering an effective way to broaden the advanced applications of this crystalline material, reconfigurable MOF@cotton fiber (CF) is fabricated via in situ growth, which scavenges free chlorine and concomitantly squeezes it upon exposure to AA with obvious colorimetric changes over multiple real-life platforms. Furthermore, multi-cyclic alkene epoxidation by MOF@CF paves the way to futuristic continuous flow reactors that truly serves this smart composite as a bimodal ROS deactivator-convertor and explicitly denotes it as an advanced promising analogue from contemporary state-of-the-art materials.

Proton Switch in the Secondary Coordination Sphere to Control Catalytic Events at the Metal Center: Biomimetic Oxo Transfer Chemistry of Nickel Amidate Complex

High-valent metal-oxo species are key intermediates for the oxygen atom transfer step in the catalytic cycles of many metalloenzymes. While the redox-active metal centers of such enzymes are typically supported by anionic amino acid side chains or porphyrin rings, peptide backbones might function as strong electron-donating ligands to stabilize high oxidation states. To test the feasibility of this idea in synthetic settings, we have prepared a nickel(II) complex of new amido multidentate ligand. The mononuclear nickel complex of this N5 ligand catalyzes epoxidation reactions of a wide range of olefins by using mCPBA as a terminal oxidant. Notably, a remarkably high catalytic efficiency and selectivity were observed for terminal olefin substrates. We found that protonation of the secondary coordination sphere serves as the entry point to the catalytic cycle, in which high-valent nickel species is subsequently formed to carry out oxo-transfer reactions. A conceptually parallel process might allow metalloenzymes to control the catalytic cycle in the primary coordination sphere by using proton switch in the secondary coordination sphere.

Epoxidation of Cyclooctene Using Water as the Oxygen Atom Source at Manganese Oxide Electrocatalysts

Epoxides are useful intermediates for the manufacture of a diverse set of chemical products. Current routes of olefin epoxidation either involve hazardous reagents or generate stoichiometric side products, leading to challenges in separation and significant waste streams. Here, we demonstrate a sustainable and safe route to epoxidize olefin substrates using water as the oxygen atom source at room temperature and ambient pressure. Manganese oxide nanoparticles (NPs) are shown to catalyze cyclooctene epoxidation with Faradaic efficiencies above 30%. Isotopic studies and detailed product analysis reveal an overall reaction in which water and cyclooctene are converted to cyclooctene oxide and hydrogen. Electrokinetic studies provide insights into the mechanism of olefin epoxidation, including an approximate first-order dependence on the substrate and water and a rate-determining step which involves the first electron transfer. We demonstrate that this new route can also achieve a cyclooctene conversion of ～50% over 4 h.

Enantioselective organocatalysis-based synthesis of 3-hydroxy fatty acids and fatty γ-lactones

3-Hydroxy fatty acids have attracted the interest of researchers, since some of them may interact with free fatty acid receptors more effectively than their non-hydroxylated counterparts and their determination in plasma provides diagnostic information regarding mitochondrial deficiency. We present here the development of a convenient and general methodology for the asymmetric synthesis of 3-hydroxy fatty acids. The enantioselective organocatalytic synthesis of terminal epoxides, starting from long chain aldehydes, is the key-step of our methodology, followed by ring opening with vinylmagnesium bromide. Ozonolysis and subsequent oxidation leads to the target products. MacMillan’s third generation imidazolidinone organocatalyst has been employed for the epoxide formation, ensuring products in high enantiomeric purity. Furthermore, a route for the incorporation of deuterium on the carbon atom carrying the hydroxy group was developed allowing the synthesis of deuterated derivatives, which may be useful in biological studies and in mass spectrometry studies. In addition, the synthesis of fatty γ-lactones, corresponding to 4-hydroxy fatty acids, was also explored.

Dinuclear Iron(III) and Nickel(II) Complexes Containing N-(2-Pyridylmethyl)-N′-(2-hydroxyethyl)ethylenediamine: Catalytic Oxidation and Magnetic Properties

Dinuclear FeIII and NiII complexes, [(phenO)Fe(N3)]2(NO3)2 (1) and [(phenOH)Ni(N3)2]2 (2), were prepared by treating Fe(NO3)3?9 H2O and Ni(NO3)2?6 H2O in methanol, respectively, with phenOH (=N-(2-pyridylmethyl)-N′-(2-hydroxyethyl)ethylenediamine) and NaN3; both 1 and 2 were characterized by elemental analysis, IR spectroscopy, X-ray diffraction, and magnetic susceptibility measurements. Two ethoxo-bridged FeIII and two azido-bridged NiII were observed in 1 and 2, respectively; corresponding antiferromagnetic interaction via the bridged ethoxo groups and strong ferromagnetic coupling via the bridged end-on azido ligands within the dimeric unit were observed. Complex 1 did not exhibit any catalytic activity, while 2 exhibited excellent catalytic activities for the epoxidation of aliphatic, aromatic, and terminal olefins.

Regiocontrolled syntheses of FAHFAs and LC-MS/MS differentiation of regioisomers

An efficient regiospecific total synthesis of several branched fatty acyl hydroxyl-fatty acids (FAHFA) has been achieved from available terminal alkenes and alkynes. The key steps feature a boron trifluoride mediated epoxide ring opening with acetylide carbanions, followed by hydrogenation of the alkyne function. The carboxylic acid of the hydroxylated chains is introduced at the last step of the synthesis to allow the esterification of the branched hydroxyl group by fatty acids beforehand. The chemical syntheses of a "linear" FAHFA and a branched FAHFA analog containing a Z-olefin in the hydroxyl-fatty acid chain are also reported. A LC-MS/MS method has been developed. Several reversed phase columns were compared. Regioisomers were separated.

Trinuclear nickel and cobalt complexes containing unsymmetrical tripodal tetradentate ligands: Syntheses, structural, magnetic, and catalytic properties

The coordination chemistries of the tetradentate N2O2-type ligands N-(2-pyridylmethyl)iminodiethanol (H2pmide) and N-(2-pyridylmethyl)iminodiisopropanol (H2pmidip) have been investigated with nickel(ii) and cobalt(ii/iii) ions. Three novel complexes prepared and characterized are [(Hpmide)2Ni3(CH3COO)4] (1), [(Hpmide)2Co3(CH3COO)4] (2), and [(pmidip)2Co3(CH3COO)4] (3). In 1 and 2, two terminal nickel(ii)/cobalt(ii) units are coordinated to one Hpmide- and two CH3CO2-. The terminal units are each connected to a central nickel(ii)/cobalt(ii) cation through one oxygen atom of Hpmide- and two oxygen atoms of acetate ions, giving rise to nickel(ii) and cobalt(ii) trinuclear complexes, respectively. Trinuclear complexes 1 and 2 are isomorphous. In 3, two terminal cobalt(iii) units are coordinated to pmidip2- and two CH3CO2-. The terminal units are each linked to a central cobalt(ii) cation through two oxygen atoms of pmidip2- and one oxygen atom of a bidentate acetate ion, resulting in a linear trinuclear mixed-valence cobalt complex. 1 shows a weak ferromagnetic interaction with the ethoxo and acetato groups between the nickel(ii) ions (g = 2.24, J = 2.35 cm-1). However, 2 indicates a weak antiferromagnetic coupling with the ethoxo and acetato groups between the cobalt(ii) ions (g = 2.37, J = -0.5 cm-1). Additionally, 3 behaves as a paramagnetic cobalt(ii) monomer, due to the diamagnetic cobalt(iii) ions in the terminal units (g = 2.53, =D= = 36.0 cm-1). No catalytic activity was observed in 1. However, 2 and 3 showed significant catalytic activities toward various olefins with modest to good yields. 3 was slightly less efficient toward olefin epoxidation reaction than 2. Also 2 was used for terminal olefin oxidation reaction and was oxidised to the corresponding epoxides in moderate yields (34-75%) with conversions ranging from 47-100%. The cobalt complexes 2 and 3 promoted the O-O bond cleavage to ～75% heterolysis and ～25% homolysis.