F 2-Chloropropane

Carbon tetrachloride, 0322 Carbon tetrafluoride, 0349 Carbon tetraiodide, 0525 f 1-Chlorobutane, 1637 f 2-Chlorobutane, 1638 f Chlorocyclopentane, 1923 f l-Chloro-l,l-dilluoroethane, 0731 Chlorodilluoromethane, 0369 f Chloroethane, 0848 Chloroform, 0372 f Chloromethane, 0432 f l-Chloro-3-methylbutane, 1986 f 2-Chloro-2-methylbutane, 1987 f Chloromethyl ethyl ether, 1246 f Chloromethyl methyl ether, 0850 f l-Chloro-2-methylpropane, 1639 f 2-Chloro-2-methylpropane, 1640 f 1-Chloropentane, 1988 f 1-Chloropropane, 1243 f 2-Chloropropane, 1244 f l-Chloro-3,3,3-trifluoropropane, 1127 1,2-Dibromoethane, 0785 Dibromomethane, 0395... 

Altai, M. Munoz Embid, J. Velasco, I. Excess enthalpies and excess volumes of (1-bromobutane or 1-iodobutane -f 1 -chloropropane or 1 -chloropentane) and of (1 -iodobutane + bromoethane or 1 -bromobutane) at the temperature 298.15 K /. Chem. Thermodyn. 1994, 26,609-615... 

Prop-2-enyl trifluoromethanesulfonate, 1457 Propionyl hypobromite, 1150 Propionyl nitrite, 1181 Propiophenone, 3145 f Propyl acetate, 1971 f Propyl bromide, see 1-Bromopropane, 1237 f Propyl chloride, see 1-Chloropropane, 1239 Propylcopper(I), 1247... 

The reaction of the trimethylsilyl enol ether derived from 2-phenylcyclohexanone with the bis[trimethylsilyl(ethoxy)methyl (SEM)] ether of (/ )-BINOL, (f )-BINOL(SEM)2, was promoted in the presence of SnCU, and the (i )-a-SEM ketone was obtained in 91 % yield and 75 % ee (Table 6). In contrast, the use of the benzyloxymethyl ether gave the corresponding R adduct in 55 % yield and 43 % ee. This unique phenomenon can be explained by the interaction between silicon and a y positive charge as homohyperconjugation. Finally, the highest ee value of 94 % was achieved by performing the reaction in 1 -chloropropane at -125 °C for long periods. 

The compound 1-chloropropane, CH3CH2CH2CI, melts at 46.6 °C. What is this temperature in °F ... 

CHLOROPROPANE (540-54-5) Forms explosive mixture with air (flash point <0°F/ < —18°C). Violent reaction with strong oxidizers, alkaline earth metals, aluminum powder, potassium, sodium. Mixtures with divalent metals slowly form explosive materials. Flow or agitation of substance may generate electrostatic charges due to low conductivity. 

To improve the chemical yield of 30 or 31, ( )-( )-3-hydroxy-3,7,11-trimethyl-6,10-dodecadienyl 1-phenylacetate (35), which is less acid-sensitive than ( )-29, has been used as a substrate for cyclization with (/f)-26 SnCLi (Scheme 12.24). The enantioselectivity is higher in the order CH2CI2 toluene < chloropropane, while the chemical yield of 36 and 37 increases in the order toluene < chloropropane < C CH2CI2. Chloropropane is superior to toluene with respect to both enantioselectivity and reactivity. When a 1 1 mixed solvent of chloropropane and CH2CI2 is used, a 44 56 mixture of (—)-36 (82% ee) and (—)-37 (82% ee) is... 

The first way of synthesis is by the alkylation of 10,ll-dihydro-5//-dibenz[b,f]azepme using l-bromo-3-chloropropane in the presence of sodium amide into a chloro derivative (7.1.12) and the subsequent reaction of this with methylamine, giving desipramine (7.1.13) [18-20]. 

Reznik, G, Stinson, S.F. Ward, J.M. (1980) Respiratory pathology in rats and mice after inhalation of l,2.-dibromo-3-chloropropane or 1,2-dibromo-ethane for 13 weeks. Arch. Toxicol., 46, 233-240... 

Class 1. Characteristics (i) The decomposition in seasoned vessels exhibits first-order kinetics and there are no apparent induction periods (i7) the rate is unaffected by packing the reaction vessel or by the addition of known radical-chain inhibitors such as propene iii) the Arrhenius pre-exponential factor is of the order of 10 sec L This behaviour is consistent with a unimolecular mechanism for the decomposition. Among reactions in this class are included the dehydrohalogena-tion of monochlorinated saturated hydrocarbons containing /S-hydrogen atoms e.g., chloropropane 2-chloropropane f-butyl chloride) and of most of the secondary and tertiary monobrominated saturated hydrocarbons. 

As with nucleophilic substitution reactions, rates of dehydrohalogenation reactions will be dependent on the strength of the C-X bond being broken in the elimination process. Accordingly, it is expected that the ease of elimination of X will follow the series Br>Cl>F. The relative reactivities of Br and Cl toward elimination is evident from the hydrolysis product studies of 1,2-dibromo-3-chloropropane (DBCP Burlinson et al., 1982). DBCP has been used widely in this country as a soil fumigant for nematode control and has been detected in groundwaters (Mason et al., 1981) and subsoils (Nelson, et al., 1981). Hydrolysis kinetic studies demonstrated that the hydrolysis of DBCP is first order both in DBCP and hydroxide ion concentration above pH 7. Below pH 7, hydrolysis occurs via neutral hydrolysis however, the base-catalyzed reaction will contribute to the overall rate of hydrolysis as low as pH 5. Product studies performed at pH 9 indicate that transformation of DBCP occurs initially by E2 elimination of HBr and HCl (Figure 2.4). 

Scheme 13.6 Casillas and Townsend s synthesis of 0-methylsterigmatocystin (96). Reagents and conditions a) SbClg, 2-chloropropane b) K2CO3 c) Me0H/H20 d) SEMCl, DIPEA e) n-BuLi f) LiAlH4 g) TPAP, NMO h) n-BuLi i) BrCH2C02Et j) tartaric acid (aq) k) TIPSOTf, EtsN 1) LiAlH4 m) m-CPBA n) TPAP, NMO o) Et3N-(HP)3 p) PhSeH, Amberlyst 15 q) m-CPBA...

Scheme 6 Crombie s synthesis of (/ S,/ S)-hopromine (2) and / S,S/ )-ep/-hopromine (51). Reagents and conditions (a) 1-bromo-3-chloropropane, KOH, DMSO, rt, 18h (b) liquid NH3, 7-10 days (c) formalin, NaBHaCN, MeCN, AcOH, rt, 1 h (d) cis-1,4-dichlorobut-2-ene, KHMDS, THF, rt, 50 h (e) KHMDS, 46, THF, rt, 24 h, then NaH, rt, 10 days (f) H2 (1 atm), Pt02, MeOH, HCI, rt, 3 h. f Combined isolated yield.)...

Scheme 10 Crombie s approach toward hoprominol (3) and hopromalinol (4). Reagents and conditions (a) 72, ZnCl2, CH2CI2, rt, 20 h (b) NaBH4, MeOH, 0 °C, 1 h (c) BuLi, TBDMSCI, THF, 0 °C to rt, 6 h, then BuLi, Cul, THF, -20 °C to rt, 16 h (d) KOH, BU4NHSO3, 1-bromo-3-chloropropane, TFIF, rt, 3.5 days (e) NH3, rt, 13 days (f) formalin, NaBFl3CN, MeCN, AcOFI, rt, 1 h (g) c/s-1,4-dichlorobut-2-ene, KFIMDS, TFIF, rt, 36-48 h. Mixture of stereoisomers.)...

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