2- methylallyl chloride

Methylallyl Chloride. MethaUyl chloiide [563-47-3] is the piincipal product when isobutylene and chlorine react over a wide range of temperatures (123). Veryhtde addition takes place. 

Chemical Designations - Synonyms gamma-Chloroisobutylene 3-Chloro-2-methylpropene beta-Methallyl chloride beta-Methylallyl chloride Chemical Formula CH2=C(CH3)CH2C1. 

The nucleophilic displacement reactions of organolithium compounds with alkyl halides are second order insofar as the rates have been measured, but there are unexplained examples of autocatalysis and non-reproducable rate constants. The product of the reaction in the case of the methylallyl chlorides is the same mixture regardless of... 

Mercaptobutane 2-Mercaptoethanethiol 2-Methallyl Chloride 2-Methylallyl Chloride 2-Methyl-Allylchlorid 2-Methylbutanoic Acid 2-Methylbutyric Acid... 

Methyl acrylate, 58, 82 Methylallyl, chloride, 57, 36 p-Methylbenzenesulfonyl cyanide, 57, 89 Methyl bromide, 58,43 Methyl bromoacetate, 57, 60 Methyl carbazate, 58, 102, 103,106 Methyl chloride diphenyl-, 55, 94 Methyl chloride polystyrene, 56, 96 2-Wethylcyclohexanone, 57, 70 2-Methyl-2-cvclohexenone, 58, 158, 159, 162, 163... 

SYNTHESIS To a solution of 43.2 g flaked KOH in 250 mL hot EtQH there was added 96 g 4-methoxyphenol followed by 90 g 2-methylallyl chloride over the courseof2h. The mixture was held at reflux for 24 h, then added to 1.6 L H20. There was sufficient 25% NaOH added to make the phase strongly basic, and this was then extracted with 3x200 mL CHjCly The pooled extracts were washed with H20, and the solvent removed under vacuum. The residue, 125 g of a pale amber oil, was crude 4-(2-methylaUyloxy)anisole and was used without further purification in the following reaction. 

Thus, while alpha-methylallyl chloride yields only a small amount of "abnormal" product with ethoxide ion in ethanol (10),... 

Beta-Methylallyl Chloride, Methyl Allyl Chloride, 2-Chlorobutene-2 Description... 

Muthuraman, G. and Pillai, K.C. (2006) Dechlorination of fS-methylallyl chloride by electrogenerated [Co(I) (bipyridine)3]+ An electrochemical study in the presence of cationic surfactants. J. Colloid Interface Sci. 297, 687-695. 

Terpenoid Synthesis from Isoprene.—Interest continues in new syntheses of iso-prene and its derivatives the dioxan (37) is obtained108 in good yield by the Prins reaction of methylallyl chloride with formaldehyde (cf. Vol. 5, p. 8) free-radical addition of isopropyl alcohol to vinyl acetate yields compound (38) which gives isoprene by acid-catalysed reaction over alumina.109 (Z)-2-Methylbut-2-en-l-ol and dimethylallyl alcohol are readily available from frans-crotyl alcohol.110... 

SYNS 3-CHLOR-2-METHYL-PROP-1-EN (GERMAN) Y-CHLOROISOBL TYLENE 3-CHLORO-2-METHYL-1-PROPENE CHLORURE de METHALLYLE (FRENCH) 3-CLORO-2-METIL-PROP-1-ENE (ITALIAN) CLORURO di METALLILE (ITALIAN) ISOBUTENYL CHLORIDE METHALLYL CHLORIDE a-METHALLYL CHLORIDE 2-METHYL-ALLYLCHLORID (GERMAN) p-METHYLALLYL CHLORIDE 2-METHYLALLYL CHLORIDE METHYL ALLYL CHLORIDE (DOT) NCI-C54820... 

METHYLALLYL CHLORIDE see CIU750 METHYL ALLYL CHLORIDE pop see CIU750 P-METHYLALLYL CHLORIDE see CIL 750 l-METHYL-5-ALLYL-5-(l-METHYL-2-PENTYNYL)BARBITURIC ACID SODIUM SALT see MDU500... 

A mixture of 358 g. (4.0 moles) of cuprous cyanide and 500 ml. of nitrobenzene is stirred and heated to 125-130° while 543 g. (6.0 moles) of /8-methylallyl chloride is added carefully in 25-50-ml. portions. The exothermic reaction from each portion of chloride is allowed to subside before the next portion is added. The mixture is heated under reflux for 30 minutes, cooled, and filtered. The filtrate is fractionally distilled to give a 58% yield (based on cuprous cyanide) of j8-methyl-allyl cyanide boiling at 136.2-136.4°, 1.4202,... 

With allylic chloroformates, substitution may also occur via a six-centred transition state. Thus Oliver and Young have demonstrated that for the pure liquids or in a variety of solvents both a-methylallyl and y-methylallyl (crotyl) chloroformate thermally decompose to yield a mixture of a-methylallyl chloride and y-methylallyl (crotyl) chlorides. At 75 °C the ratio of a-methylallyl chloride to y-methylallyl chloride produced from pure a-methylallyl chloroformate is 47 53 the corresponding ratio from y-methylallyl chloroformate is 63 37. 

Most of the early mechanistic studies that focused on the S ,j2 versus 8 2 nucleophilic substitution by an organometallic reagent were made with allylic halides. In the late 1940s, Wilson [7] showed that phenylmagnesium bromide reacted with a- and y-methylallyl chlorides 1 and 2, respectively, to afford a nearly identical mixture of primary and secondary substituted products 3 and 4, respectively, in a 75 25 ratio [Eq. (1)]. 

Methylallyl Chlorides with K.iCo(CN)r,. An aqueous solution of K3Co(CN)r> (200 ml., 0.15M cobalt, 0.35M KOH) was prepared in a nitrogen atmosphere. Addition of y-methylallyl chloride (0.06 mole) (Aldrich, b.p. 84°C., ni+ = 1.4311) resulted in the evolution of 219 ml. gas, a sample of which was taken for analysis. Similar reactions of this substrate and of a-methylallyl chloride (Columbia, b.p. 65°C., === 1.4123) carried out at cyanide to cobalt ratios of 5.1 and 7.0 resulted in the formation of butenes, whose isomer distributions are listed in Tables II and HI under deficient CoH. ... 

Z-MethylaUyl chloride. The values of AC I AS for the hydrolysis of 3-methylallyl chloride (Table 10) suggest strongly that reaction does not occur imimolecularly, unlike the hydrolysis of the more reactive 3-phenyl-derivative (see Table 4). This conclusion agrees with earlier suggestions based on other evidence (see DeWolfe and Yoimg, 1956 Valkanas et al., 1963) but these have not always been accepted. 

P-methylallyl chloride. (methallyl chloride 3-chloro-2-methyl-l-propene MAC). CH2 C(CH3)CH2C1. 

Methyl adamantane-l-carboxylate, 216 Methyl adamantane-2-carboxylate, 216 Methyl adamantanedicarboxylates, 216 Methylallyl chloride, 310 Methylamine, 175... 

METHYLALLYL CHLORIDE (563-47-3) Forms explosive mixture with air (flash point 11°F/—12°C cc). Slowly hydrolyzes in water, forming methallyl alcohol and hydrochloric acid. Strong oxidizers may cause fire and explosions. Contact with acids or acid fumes produces highly toxic chloride fumes. Aqueous solution is incompatible with sulfuric acid, alkalis, ammonia, aliphatic amines, alkanolamines, alkylene oxides, amides, boranes, epichlorohydrin, nitromethane, organic anhydrides, isocyanates, vinyl acetate. In the presence of moisture, attacks metals can cause pitting and stress corrosion in austenitic stainless steels. 

Chloro-2-butene, n-Chloro-0-butylene crotyl chloride -,-methallyl chloride v-methylallyl chloride. Ct-... 

Another complexity with allylic substrates is the potentitil tor formation of allylic isomers. Reviews by De Wolfe and Young (93). Figiderc and Franck (94). and Magid (951 are relevant to this question. Scheme 2.2 illustrates the consequences of Sx I and SET in the prototype substituted allylic system, erotyl/o -methylallyl. The new bond I onnation. at either end of the allylic system, could be subject to a memory effect due to restricted reorientation during the lifetime of a radical or ion pair. Alternatively, competition between Ss2 and S, 2 could lead to isomer mixtures (Scheme 2.3). In early work (96, rciictions of crotyl and o -methylallyl chlorides with PhMeBr led to mixtures (9 II I l 75 25) which... 

---