Bis-4-chlorobutyl ether

Unstirred mixtures of sulfinyl chloride and tetrahydrofuran may react extremely exothermally and with gas evolution when heated to 60°C, the products of ring-scission being bis(4-chlorobutyl) ether, 1,4-dichlorobutane and sulfur dioxide. Some ratios of the two reactants enhance the tendency, and relatively confined mixtures may explode. Sufficient heat to initiate the reaction may arise from selfmixing of the layered liquids, the chloride being twice as dense as THF. 

Biphenylyl)urea, 31,10 l-(4-Biphenylyl)urea, 31, 10 Bis-4-chlorobutyl ether, 37, 55 Bischi-oromethyl ether, 36,1... 

A mixture of 132.5 g. (1.05 moles) of sodium sulfite, 99.5 g. (0.5 mole) of bis-4-chlorobutyl ether (Note 1), and 450 ml. of water is placed in a creased 1-1. three-necked flask fitted with an efficient sealed stirrer and a reflux condenser. The third neck of the flask is closed with a stopper, and the mixture is heated and stirred vigorously under reflux until the ether has dissolved (Note 2). At the end of this time, heating is discontinued, and 60 ml. of concentrated c.p. hydrochloric acid is cautiously added to the solution. The mixture is then boiled with stirring until sulfur dioxide is no longer evolved. Solid barium chloride dihydrate (or a 10% aqueous solution of this salt) is added to the hot solution (Note 3) until all sulfate has been precipitated then the barium sulfate is removed by suction filtration through a layer of filter aid. 

Hydroxy- 1-butanesulfonic acid sultone has been made through the chlorosulfonation of 1-chlorobutane,3 from 4-chlorobutyl acetate 2 4 which is prepared through the reaction of tetrahydrofuran and acetyl chloride,2 from 4-chlorobutanol,4 and from bis-4-chlorobutyl ether.2 Both 4-chlorobutanol and bis-4-chlorobutyl ether can be prepared from tetrahydrofuran.6... 

Tetrahydrofuran (1 mole), POCl3 (0.33 mole), and concentrated H2S04 (10 ml) at 80 to 100° give 70% of bis-(4-chlorobutyl) ether in an exothermic reaction.1044... 

Bis(4-chlorobutyl) ether [4,4 -dichlorodibutyl ether 1,1 -oxy di-4-chlorobutane oxybis(4-chlorobutane)] [6334-96-9] C8H16CI2O 199.14 CI-CH2-CH2-CH2-CH2- O-CH2-CH2-CH2-CH2-CI Low oral toxicity in mice target organs — central nervous system, liver, and gastrointestinal tract caused muscle contraction and ulceration LD50 oral (mice) 1250 mg/kg Noncombustible liquid... 

Bis 4-chlorobutyl ether (BCBE) 2-Chloroethyl phenyl sulfide (CEPS)... 

Treatment of bis-lactim ether 420 with BuLi, then with cw-l,4-dichloro-2-butene in the presence of Nal afforded 3,4,9,9n-tetrahydro-6//-pyrido[l,2-fl]pyrazin-4-one (421) with 96% diastereomeric excess (97TA1855). Reaction of l,2-diphenyl-6-methyl-quinoxaline with 1,4-dichlorobutane in THF in the presence of Na at —78°C afforded a 3 1 mixture of 4a,5-diphenyl-9-methyl-l,2,3,4-tetrahydro-4a//-pyrido[l,2-n]quinoxaline and 4-(4-chlorobutyl)-2,3-diphenyl-6-methyl-1,4-dihydroquinoxaline (98JHC1349). 

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