1 - Chloronaphthalene

Chloronaphthalene [91-58-7] M 162.6, m 61°, b 264-266°. Crystd from 25% EtOH/water and dried under vacuum. 

Chloronaphthalene 40 Chloronitrobenzenes, 40 Chloropentafluoroethane, 40 Chlorophacinone, 40 4-Chloro-o-phenylenediamine, 40 Chlorophenols, 40 Chlorophenols, Mono, 40 Chloropicrin, 40 Chloroplatinic acid, 41 Chloroprene, 41... 

The activation energy of substitution of an unactivated aromatic halide (e.g., fiuorobenzene and 2-chloronaphthalene ) is over 30 kcal while that of activated compounds is 5-20 kcal. For the tabulated reactions (Tables II-VIII) with alkoxide and with primary, secondary, or tertiary amines, resonance activation (cf. 278 and 279) by ortho or para nitrogens is found to be greater than inductive activation (cf. 251). This relation is qualitatively demonstrated in... 

The question of the occurrence of cine or aryne substitution in some of these reactions has been raised but not answered adequately. The normal product, 2-methoxynaphthalene was shown to be formed from 2-chloronaphthalene and methoxide ion, and the normal 6- and 8-piperidinoquinolines were proved to be products of piperidino-debromination of 6- and 8-bromoquinolines, all in unspecified yield. More highly activated compounds were then assumed not to react via the aryne mechanism. Even if the major product had been characterized, the occurrence of a substantial or predominant amount of aryne reaction may escape notice when strong orientation or steric effects lead to formation of the normal displacement product from the aryne. A substantial amoimt of concurrent aryne reaction may also escape detection if it yields an amount of cine-substituted material easily removed in purification or if the entire reaction mixture is not chromatographed Kauffman and Boettcher have demonstrated that activated compounds such as 4-chloropyridine do indeed react partially via the aryne mechanism (Section I,C,1). 

As already mentioned, there is a striking difference in the reactivity of 1- and 3-chloroisoquinoline the former reacts about 10 times faster than the latter with both piperidine and ethoxide ion at room temperature. The lower rate of ethoxy-dechlorination of the 3-isomer is due to an E which is 10 kcal higher. It is not justified to conclude that this isomer is virtually unactivated when its rate of ethoxylation is 100,000 times that of 2-chloronaphthalene and the E for this reaction is markedly decreased (by 7 kcal) relative to that of 2-chloronaphthalene. A direct comparison of reactivity with piperidine has not been made, but a rate ratio of 500 1 can be estimated by using a factor of one-fortieth (Table X, lines 1 and 4) to make the... 

Polycyclic (also called polynuclear) aromatic hydrocarbons (PAHs) are composed of multiple rings connected by shared carbon atoms (i.e., separate rings are combined by sharing two carbon atoms). All these compounds are pure hydrocarbons except for the two benzo-fluoranthenes, polychlorinated biphenyls (PCBs), and 2-chloronaphthalene. Moore and Ramamoorthy110 review the behavior of PAHs in natural waters. 

The first attempted synthesis of a benzo[ ]thiepin derivative was the solvolysis of 7,7-dichloro-3,4-benzo-2-thiabicyclo[4.1,0]heptene (19)20). Unfortunately, the reaction of 19 in hot quinoline led to 2-chloronaphthalene which suggested the reaction mechanism as shown below. In the case of the reaction of l,l-dichloro-7b-ethoxy-... 

Common Name 2-Chloronaphthalene Synonym PCN-2, (3-chloronaphthalene Chemical Name 2-chloronaphthalene CAS Registry No 91-58-7 Molecular Formula C10H7C1 Molecular Weight 162.616 Melting Point (°C) ... 

Reported vapor pressures of 2-chloronaphthalene at various temperatures and the coefficients for the vapor pressure equations... 

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

Chloromethyl) oxhane, see Epichlorohydrin 2-(Chloromethyl)oxirane, see Epichlorohydrin 4-Chloro-3-methylphenol, see p-Chloro-ro-cresol p-Chloro-3-methylphenol, see p-Chloro-ro-cresol Chloromethyl phenyl ketone, see a-Chloroacetophenone p-Chloronaphthalene, see 2-Chloronaphthalene 4-Chloronitrobenzene, see p-Chloronitrobenzene l-Chloro-4-nitrobenzene, see p-Chloronitrobenzene 4-Chloro-l-nitrobenzene, seep-Chloronitrobenzene p-Chloro-1-nitrobenzene, see p-Chloronitrobenzene Chloronitroform, see Chloropicrin Chloronitropropane, see 1-Chloro-l-nitropropane Chlorophen, see Pentachlorophenol... 

Chloro-2,3-dihydrobenzoxazol, see Fenoxaprop-ethvl 8-Chloro-l,2-dihydro-l,2-dihydroxynaphthalene, see 2-Chloronaphthalene... 

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