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5076-20-0

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5076-20-0 Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 104, p. 6122, 1982 DOI: 10.1021/ja00386a051The Journal of Organic Chemistry, 46, p. 1964, 1981 DOI: 10.1021/jo00322a058Tetrahedron Letters, 24, p. 123, 1983 DOI: 10.1016/S0040-4039(00)81345-3

General Description

Colorless liquid.

Air & Water Reactions

Water soluble.

Reactivity Profile

Epoxides, such as TETRAMETHYLETHYLENE OXIDE, are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Fire Hazard

Flash point data for TETRAMETHYLETHYLENE OXIDE are not available. TETRAMETHYLETHYLENE OXIDE is probably combustible.

Check Digit Verification of cas no

The CAS Registry Mumber 5076-20-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,0,7 and 6 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 5076-20:
(6*5)+(5*0)+(4*7)+(3*6)+(2*2)+(1*0)=80
80 % 10 = 0
So 5076-20-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O/c1-5(2)6(3,4)7-5/h1-4H3

5076-20-0 Well-known Company Product Price

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  • Aldrich

  • (662100)  2,3-Dimethyl-2,3-epoxybutane  99%

  • 5076-20-0

  • 662100-5G

  • 989.82CNY

  • Detail

5076-20-0Relevant articles and documents

Red light-induced reaction of NO2 with 2,3-dimethyl-2-butene in a low-temperature argon matrix

Nakata, Munetaka

, p. 1455 - 1466 (1994)

Red light-induced oxygen atom transfer from NO2 to 2,3-dimethyl-2-butene has been investigated in a low-temperature argon matrix.The IR spectra of a reaction intermediate identified as an alkyl nitrite radical and two final products, tetramethyloxirane and 3,3-dimethyl-2-butanone (pinacolone), were observed.From analysis of the absorbance growth of the IR bands, first-order rate constants were determined by least-square fitting.Based on these results and those of our earlier works on NO2 photoreactions with other alkenes, a reaction mechanism is proposed that involves oxygen atom transfer from NO2 to the C=C bond of 2,3-dimethyl-2-butene to give a short-lived singlet oxirane biradical.Alkyl nitrite radical is produced by a recombination of the transient biradical with NO trapped in the cage of the matrix.Tetramethyloxirane and pinacolone emerge from secondary photolysis of the trapped alkyl nitrite radical.

METALLOPORPHYRIN-MEDIATED RADICAL CYCLOADDITIONS OF p-CYANO-N,N-DIMETHYLANILINE

Dicken, C. Michael,Lu, Fu-Lung,Bruice, Thomas C.

, p. 5967 - 5970 (1986)

Tetrahydroquinolines are formed via metalloporphyrin-catalyzed radical cycloadditions of olefins (2,3-dimethyl-2-butene and norbornene) and p-cyano-N,N-dimethylaniline; their synthesis, characterization and a mechanistic rationale of their formation are presented.

The reaction of permanganyl chloride with olefins: Intermediates and mechanism as derived from matrix-isolation studies and density functional theory calculations

Wistuba, Tobias,Limberg, Christian

, p. 4674 - 4685 (2001)

Density functional theory (DFT) calculations predict that the [2+3] addition of tetramethylethylene (TME) to the MnO2 moiety of MnO3Cl is thermodynamically favoured over [2+1] addition (epoxidation), while the kinetic barriers for bo

Cvetanovic

, p. 19,21 (1959)

Porphyrins in aqueous amphiphilic polymers as peroxidase mimics

Johnstone, Robert A. W.,Simpson, Anthony J.,Stocks, Paul A.

, p. 2277 - 2278 (1997)

Water-insoluble porphyrins dissolve in aqueous solutions of amphiphilic polymers to give systems which mimic the action of peroxidase enzymes.

Synthesis and reaction of cyano-substituted 1,2,4-trioxolanes

Kuwabara, Hajime,Ushigoe, Yoshihiro,Nojima, Masatomo

, p. 871 - 874 (1996)

Carbonyl oxides, derived from the ozonolyses of vinyl ethers, readily undergo [3 + 2] cycloadditions with acyl cyanides affording the corresponding cyano-substituted 1,2,4-trioxolanes in isolated yields of 34-88%. In competition experiments, a relative order of reactivity of the carbonyl oxide trapping agents was tentatively deduced; trifluoroacetophenone > α,α-diphenyl-N-methylnitrone (N-methyldiphenyl-methylideneamine N-oxide) > benzoyl cyanide > methyl benzoylformate > α,α,N-triphenylimine [N-(diphenylmethylidene)aniline] ? benzaldehyde. As expected from the electron-withdrawing ability of the cyano group, 3-cyano-3-phenyl-1,2,4-trioxolane oxidized not only triphenylphosphine but also methyl p-tolyl sulfide and 2,3-dimethylbut-2-ene very easily.

A General Regioselective Synthesis of Alcohols by Cobalt-Catalyzed Hydrogenation of Epoxides

Beller, Matthias,Junge, Kathrin,Leischner, Thomas,Li, Wu,Liu, Weiping

supporting information, p. 11321 - 11324 (2020/05/16)

A straightforward methodology for the synthesis of anti-Markovnikov-type alcohols is presented. By using a specific cobalt triphos complex in the presence of Zn(OTf)2 as an additive, the hydrogenation of epoxides proceeds with high yields and selectivities. The described protocol shows a broad substrate scope, including multi-substituted internal and terminal epoxides, as well as a good functional-group tolerance. Various natural-product derivatives, including steroids, terpenoids, and sesquiterpenoids, gave access to the corresponding alcohols in moderate-to-excellent yields.

Experimental investigation of the low temperature oxidation of the five isomers of hexane

Wang, Zhandong,Herbinet, Olivier,Cheng, Zhanjun,Husson, Benoit,Fournet, Rene,Qi, Fei,Battin-Leclerc, Frederique

, p. 5573 - 5594 (2014/08/18)

The low-temperature oxidation of the five hexane isomers (n-hexane, 2-methyl-pentane, 3-methyl-pentane, 2,2-dimethylbutane, and 2,3-dimethylbutane) was studied in a jet-stirred reactor (JSR) at atmospheric pressure under stoichiometric conditions between 550 and 1000 K. The evolution of reactant and product mole fraction profiles were recorded as a function of the temperature using two analytical methods: gas chromatography and synchrotron vacuum ultraviolet photoionization mass spectrometry (SVUV-PIMS). Experimental data obtained with both methods were in good agreement for the five fuels. These data were used to compare the reactivity and the nature of the reaction products and their distribution. At low temperature (below 800 K), n-hexane was the most reactive isomer. The two methyl-pentane isomers have about the same reactivity, which was lower than that of n-hexane. 2,2-Dimethylbutane was less reactive than the two methyl-pentane isomers, and 2,3-dimethylbutane was the least reactive isomer. These observations are in good agreement with research octane numbers given in the literature. Cyclic ethers with rings including 3, 4, 5, and 6 atoms have been identified and quantified for the five fuels. While the cyclic ether distribution was notably more detailed than in other literature of JSR studies of branched alkane oxidation, some oxiranes were missing among the cyclic ethers expected from methyl-pentanes. Using SVUV-PIMS, the formation of C 2-C3 monocarboxylic acids, ketohydroperoxides, and species with two carbonyl groups have also been observed, supporting their possible formation from branched reactants. This is in line with what was previously experimentally demonstrated from linear fuels. Possible structures and ways of decomposition of the most probable ketohydroperoxides were discussed. Above 800 K, all five isomers have about the same reactivity, with a larger formation from branched alkanes of some unsaturated species, such as allene and propyne, which are known to be soot precursors.

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