1.2- Epoxy butane

Beilstein Handbook Reference) BRN 0102411 Butane. 1,2-epoxy- CCRIS 1015 EINECS 203-438-2 DL-1,2-Epoxybutane Ethylene oxide, ethyl- Ethyl ethylene oxide Ethylethylene oxide Ethyloxirane ( )-2-Ethyloxirane ( )-Ethyloxirane HSDB 2855 n-Butene-1,2-oxide NCI-C56527 NSC 24240 Oxirane, ethyl- UN3022. Liquid bp" 63,3 d O = 0.8297 very soluble in EtOH, Me2CO, freely soluble in Et20. 

Butanedione 2,3-Butanedione. See Diacetyl Butanedione dioxime 2,3-Butanedionedioxime Butane dioxime. See Dimethyl glyoxime 2,2 -[1,4-Butanediylbis (oxymethylene)] bisoxirane. See 1,4-Butanediol diglycidyl ether Butane, 1,2-epoxy-. See 1,2-Epoxybutane Butane, 1,4-epoxy-. See Tetrahydrofuran Butane, 1,2-epoxy-4,4,4-trichloro-. See Trichlorobutylene oxide... 

Synonyms Butane, 1,2-epoxy- 1-Butene oxide But-1-ene oxide 1,2-Butene oxide n-Butene-... 

Synonyms Butane, 1,2-epoxy-4,4,4-trichloro- 1,2-Epoxy-4,4,4-trichlorobutane Oxirene, 2,2,2-trichloroethyl- TCBO 4,4,4,-Trichloro-1,2-epoxybutane Empirical C4H5CI3O Properties Yel. clear liq. m.w. 175.44 Toxicology LD50 (oral, rat) 1500 mg/kg, (IV, mouse) 56,200 pg/kg LCLo (inh., rat, 1 h) 200 g/m poison by IV route primary irritant eye and severe skin irritant may cause convulsions, dyspnea, respiratory stimulation mutagen TSCA listed... 

Butanediol, diesters with octanoic and decanoic acids. See Butylene glycol dicaprylate/dicaprate Butane, 1,2-epoxy-. See 1,2-Epoxybutane... 

S)-tert-butoxy-corbonylomino-1,2(S)-epoxy-4-phenyl-butane (I)... 

Titanium enolates.1 This Fischer carbene converts epoxides into titanium enolates. In the case of cyclohexene oxide, the product is a titanium enolate of cyclohexanone. But the enolates formed by reaction with 1,2-epoxybutane (equation I) or 2,3-epoxy butane differ from those formed from 2-butanone (Equation II). Apparently the reaction with epoxides does not involve rearrangement to the ketone but complexation of the epoxide oxygen to the metal and transfer of hydrogen from the substrate to the methylene group. 

Solvolysis of butadiene monoxide (10.102) in saline solution is a rather unexpected reaction that further documents this compound s reactivity [168]. In aqueous NaCl solution at physiological pH and temperature, butadiene monoxide disappeared rapidly to form 1,2-dichloro-3,4-epoxybutane (10.111, Fig. 10.25). There was a linear dependence of the rate of reaction on the Cl concentration (in the range investigated (34-135 mM)). The reaction pathway was described as slow solvolytic formation of the bu-tenylchloronium ion, followed by Cl attack to yield Cl2 and butadiene. Cl2 is then rapidly trapped by a second molecule of butadiene monoxide to form a different chloronium ion that also reacts with Cl to yield the final, stable dichloro product (10.111). The formation of 1,2-dichloro-3,4-epoxy-butane under physiological conditions is believed to be toxicologically significant. 

Barba and coworkers [84-91] have published a number of papers dealing with novel syntheses based on the reduction of phenacyl bromides. Electrolysis of phenacyl bromide at a mercury cathode leads to an intermediate, which reacts to give 2,4-diphenylfuran [84]. However, when a proton donor (CH3OH) is present, the reduction of phenacyl bromide yields acetophenone and 2-bromo-l,3-diphenyl-3,4-epoxy-butan-l-one. Interestingly, if phenacyl bromide is slowly introduced into an electrolysis cell so that the unreduced starting material is maintained at a low concentration, the products are different [85] (Scheme 7). 

I. 1.4.1] catalyzes the reaction of 2-methyl-3-phytyl-l,4-naphthoquinone with oxidized dithiothreitol and water to produce 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-l,4-naphthoquinone and 1,4-dithiothreitol. In the reverse reaction, vitamin K 2,3-epoxide is reduced to vitamin K and possibly to vitamin K hydroquinone by 1,4-dithioer-ythritol (which is oxidized to the disulfide). Some other dithiols and butane-4-thiol can also act as substrates. This enzyme is strongly inhibited by warfarin. 

Diepoxy-7,8-dioxabicyclo[2.2.2]octane, 2339 Endrin, 3459 t 1,2-Epoxy butane, 1609 t 3,4-Epoxy butene, 1520... 

The material is prepared by reaction of 2-tert-butylcyclohexanol with sodium hydride and 1,2-epoxy butane [115a]. 

Fig. 6. C-13 NMR Spectrum of Reaction Mass of Heated Mixture of 1,2-epoxy butane, diphenyl-methyl silanol and Alfacach 501.

Cochrane, J.E. Skopek, T.R. (1994) Mutagenicity of butadiene and its epoxide metabolites IL Mutational spectra of butadiene, 1,2-epoxy butene and diepoxy butane at the hprt locus in splenic T cells from exposed B6C3F1 mice. Carcinogenesis, 15. 719-723... 

Kohler and Tishler 6 reduced 2,3-epoxy-4-meaitoyM, 1,3-triphenyl-butane over platinum, and obtained an alcohol formulated a shown in Eq. (332). Here addition of hydrogen again ooours preferentially at dir bensylic, or moet-highiy substituted, epoxide carbon. Steric hindrance evidently prohibits reduction of the carbonyl function. 

Atom (Eq. 791)- Epoxides investigated in this manner included ethylene oxide, propylene oxide, isobutylene oxide, cm- and lmtw-2,8-epoxybutane, 2.a-opoxy-2 methylbutane1 and 2,3-epoxy-2,a dimethvl butane l4s , ... 

Other monoalkylated ethylene oxides reported to undergo ready cleavage on treatment with halogen adds (Eq. 701) include 1,2-epoxy-butane,1 1,2-epoxyhexane,1 00 and 1,2-epoxyheptane. 41 Although the last two have been said to yield only secondary alcohols, corresponding to exclusive attack of halide on the terminal epoxide carbon atom, it ie probable that isomeric alcohols are also formed in small undetected quantities... 

THF, Diethylene Oxide, Tetramethylene Oxide, Cyclotetramethylene Oxide-1,4 Epoxy Butane... 

---