Ethylene bromohydrin

Structure and functional group Br-CH2 -CH2-OH, undergoes reactions characteristic of alkyl bromide and a primary —OH functional group 

Ethylene bromohydrin is not used much for any commercial purpose. The risk of exposure to this compound arises when ethylene oxide reacts with hydrobromic acid. 

The vapors of ethylene bromohydrin are an irritant to the eyes and mucous membranes. It is corrosive to the skin. Ingestion of this compound can produce moderate to severe toxic effects. The target organs are the CNS, gastrointestinal tract, and liver. The lethal dose in mice by the intraperitoneal route was 80 mg/kg. 

Ethylene bromohydrin manifested carcinogenicity in test animals. It caused tumors in lungs and the gastrointestinal tract in mice from intraperitoneal (150 mg/kg/8 weeks) and oral (43 mg/kg/80 weeks) dosages, respectively. It is a mutagen, positive to the histidine reversion-Ames test. 

Combustible flash point 40°C (105°F) vapor density 4.3 (air = 1) vapor can form an explosive mixture with air the explosive limits are not reported. Fire-extinguishing agent alcohol foam a water spray may also be effective and should be used to cool fire-exposed containers and to dilute and flush any spill. It decomposes to hydrogen bromide (toxic) when heated above 150°C (302 F). 

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Note 8). After two distillations the fraction boiling at 55-59°/22 mm. (Note 9) is pure ethylene bromohydrin. The yield is 327-345 g. (S7-92 per cent of the theoretical amount). 

Ethylene bromohydrin has been prepared by the reaction between ethylene glycol and hydrobromic acid and phosphorus tribromide. It has also been prepared by the direct addition of hypobromous acid to ethylene, and by the reaction between ethylene and dilute bromine water. With ethylene oxide now available at a reasonable price, the method described is probably the best because of the high yields and the convenience of reaction. 

In this work on compounds containing the C—F link, it was obviously desirable to prepare 2-fluoroethanol, both for toxicity tests on the compound itself, and as a starting material for the production of other fluorine compounds. Swarts1 was unable to obtain 2-fluoroethanol by the action of silver fluoride or mercuric fluoride on either ethylene chlorohydrin or ethylene bromohydrin. He obtained acetaldehyde in each case. He ultimately obtained fluoroethanol in very poor yield by the indirect method of hydrolysing fluoroacetin (from bromoacetin and mercuric fluoride) for 80 hr. with dilute mineral acid. 

The simpliest laboratory method of preparing mononitroglycol consists in reacting ethylene bromohydrin with silver nitrate [5] in acetonitrile solution [6] ... 

The characteristic ease with which ethylene oxides undi ruu nucleophilic attack or isomerization in tbe presence of Lewie acids made them obvious substrates for tbe org nometallic reagents intro duoed by Grignard 07 around the turn of the century, and subsequently named in his hunor. The earliest disclosure of a reaction between an epoxide and a Grignard reagent, however, bears the name of Blaise,1 who noted the formation of ethylene bromohydrin on troii merit of ethylene oxide with raethylmagneeium bromide. In the years... 

Ethyl 2-cyano-3-ethoxyacrylate, el32 A-Ethyldiisopropylamine, d418 Ethylene bromohydrin, b279 Ethylene chlorohydrin, cl03 Ethylene cyanohydrin, hl69 Ethylene diacetate, el7... 

N-Ethoxycarbonylpiperazine Palladium on carbon Isoamyl nitrite Ethylene bromohydrin Methanesulfonic acid... 

The reaction of phenylmagnesium bromide with 1,3,2-dioxathioIane 2-oxide (16) gave 3.4-23% ethylene bromohydrin (131) and 42-60% diphenyl sulfoxide (132), depending on the conditions of the reaction. The bromohydrin (131) arises from a nucleophilic displacement at carbon by bromide ion, presumably via (129) and (130), while the sulfoxide (132) is formed by repeated attack of the Grignard reagent at sulfur (56JA454). 

Ethylene oxide, C2H4O, is a multi-purpose industrial chemical used, among other things, as a rocket propellant. It can be prepared by reacting ethylene bromohydrin, C2H5OBr, with sodium hydroxide. 

Grignard reagents Organomagnesium halides RMgX having a C-Mg bond, halohydrins Halo alcohols. For example, ethylene bromohydrin is BrCH2CH20H. helicenes Ortho-fused polycyclic aromatic compounds that have a helical structure. 

We shall shortly encounter other saturated compounds that are named in a similar way, as, for example, ethylene bromohydrin and ethylene glycoL These names have in common the use of two words, the first of which is the name of the alkene in this way they can be recognized as applying to compounds no longer containing the double bond. 

Substituted alkyl halides undergo, of course, the reactions characteristic of their other functional groups—nitration of benzyl chloride, oxidation of ethylene bromohydrin, addition to allyl bromide —but as halides they react very much like ethyl or isopropyl or /cr/ butyl halides. 

Problem 14.20 Describe simple chemical tests (if any) that would distinguish between (a) ethylene bromohydrin and ethylene bromide (b) 4-chloro-1-butene and / -butyl chloride (c) bromocyclohexane and bromobenzene (d) 1-chloro-2-methyl-2-propanol and l,2-dichloro-2-methylpropane. Tell exactly what you would do and see. 

Ethylene oxide, C2H4O, a fumigant sometimes used by exterminators, is synthesized in 88.1% yield by reaction of ethylene bromohydrin, C2HjOBr, with sodium hydroxide ... 

How many grams of ethylene bromohydrin are consumed in the production of 353 g of ethylene oxide, at 88.1% yield ... 

Polytetramethylene glycol of molecular weight 2000 was freeze-dried from benzene in a vacuum. The bromoethylated prepolymer was obtained by reaction of the glycol, first with adipoyl chloride, then with ethylene bromohydrin (Table II) and precipitation in water and n-hexane. Nitromethane solution of the poly-THF dioxolenium salt was prepared after filtration of silver bromide from the reaction product of bromoethylated poly-THF with silver perchlorate in nitromethane. 

Reaction of PTG and adipoyl chloride was carried out for 12 hours at room temperature further reaction with ethylene bromohydrin was for 12 hours. 

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