Isopropyl iodide

Mix 30 g. (38 ml.) of iaopropyl alcohol with 450 g. (265 ml.) of constant boiling point hydriodic acid (57 per cent.) (Section 11,49,2) in a 500 ml. distilling flask, attach a condenser for downward distillation, and distil slowly (1-2 drops per second) from an air bath (compare Fig. II, 5, 3). When about half the liquid has passed over, stop the distillation. Separate the lower layer of crude iodide (80 g.). Redistil the aqueous layer and thus recover a further 5 g. of iodide from the flrst quarter of the distillate (1). Wash the combined iodides with an equal volume of concentrated hydrochloric acid, then, successively, with water, 5 per cent, sodium carbonate solution, and water. Dry with anhydrous calcium chloride and distil. The isopropyl iodide distils constantly at 89°. 

Isopropyl iodide (2-iodopropane) [75-30-9] M 170.0, b 88.9 , d 1.70, n 1.4987. Treated with bromine, followed by extraction of free halogen with aqueous Na2S203 or NaHS03, washing with water, drying (MgS04 or CaCl2) and distn. (The treatment with bromine is optional.) Other purification methods include... 

Isopropyl Iodide.—The replacement of hydroxyl by iodine in the action of phosphorus and iodine on alcohols has alieady been described (see Piep. 6, p. 68), but here the presence of an excess of hydriodic acid, which is due to the action of water on the phosphorus iodide,... 

In addition, Pfister and coworkers investigated 3-hydroxyflavone-6-carboxylic acids as histamine induced gastric secretion inhibitors. After condensing 3-acetyl-4-hydroxybenzoic acid (45) with a variety of aldehydes 46 to deliver the chalcones 47, these purified chalcones were then subjected to the standard AFO conditions to afford flavonols 48 in 51-80% yield. Subsequent alkylation of 48 with methyl iodide or isopropyl iodide followed by saponification of the corresponding esters gave the target compounds. 

The most thoroughly investigated compounds are the alkyl-pyridines. Coleman and Fuoss compared the reactions of pyridine, 4-picoline, and 4-isopropylpyridine with n-butyl bromide and found a steady increase in the rate in the order given the activation energies are 16.0,15.95, and 15.6 kcal per mole, respectively. Brown and Cahn carried out a detailed study of the reactions of 2-, 3-, and 4-alkyl-pyridines with methyl, ethyl, and isopropyl iodides in nitrobenzene the results are given in Table II. These data show the higher activation... 

O-isopropylidene-a-D-xylofuranose (CsHijO, 20037-27-4) see Stavudine isopropyl iodide... 

Schrauzer and co-workers have studied the kinetics of alkylation of Co(I) complexes by organic halides (RX) and have examined the effect of changing R, X, the equatorial, and axial ligands 148, 147). Some of their rate constants are given in Table II. They show that the rates vary with X in the order Cl < Br < I and with R in the order methyl > other primary alkyls > secondary alkyls. Moreover, the rate can be enhanced by substituents such as Ph, CN, and OMe. tert-Butyl chloride will also react slowly with [Co (DMG)2py] to give isobutylene and the Co(II) complex, presumably via the intermediate formation of the unstable (ert-butyl complex. In the case of Co(I) cobalamin, the Co(II) complex is formed in the reaction with isopropyl iodide as well as tert-butyl chloride. Solvent has only a slight effect on the rate, e.g., the rate of reaction of Co(I) cobalamin... 

A further quantity of isopropyl iodide, only slightly less than that obtained in the first distillation, may be prepared by combining the residues in the distilling flask, adding 30 g. (38 ml.) of isopropyl alcohol and repeating the distillation. Finally, the residues should be distilled and the 67 per cent, constant boiling point acid recovered. 

Diisopropyl methylphosphonate is an organophosphate compound that was first produced in the United States as a by-product of the manufacture of the nerve gas isopropyl methylphosphonofluoridate (GB, or Sarin) (ATSDR 1996 EPA 1989 Robson 1977, 1981). It is not a nerve gas and is not a metabolite or degradation product (Roberts et al. 1995). Diisopropyl methylphosphonate constitutes approximately 2-3% of the crude GB product, but it is neither a metabolite nor a degradation product of GB (EPA 1989 Rosenblatt et al. 1975b). Diisopropyl methylphosphonate is not normally produced except for its use in research. One method of producing diisopropyl methylphosphonate is to combine triisopropyl phosphite and methyl iodide. The mixture is then boiled, refluxed, and distilled, yielding diisopropyl methylphosphonate and isopropyl iodide (Ford-Moore and Perry 1951). Diisopropyl methylphosphonate may also be prepared from sodium isopropyl methylphosphonate by a reaction at 270° C, but a portion of the resulting diisopropyl methylphosphonate is converted to trimethylphosphine oxide at this temperature (EPA 1989). 

ISODEHYDROACETIC ACID, 32, 57, 76 Isomerized wood rosin, 32, 2 2-Isonitrosocyclohexanone, 32, 38 Isopropyl alcohol, 31,112 Isopropyl iodide, 30, 34 31, 33 -Isopropylphenylacetamide, 32, 94 -Isopropylphenyldichlorophosphine,... 

Isopropyl bromide Isopropyl chloride Isopropyl iodide Kerosene Linseed oil, raw Mercury Methnol, 100% Methanol, 90% Methanol, 40%... 

Isopropyl iodide, i49 Isopropyl palmitate, il09 Itaconic acid, m253... 

Some evidence to suggest that peroxo complexes can be intermediates in the oxidation of Pt(II) by 02 has been presented. As shown in Scheme 41, a Pt(IV) peroxo complex was obtained by reacting cis-PtCl2(DMSO)2 and 1,4,7-triazacyclononane (tacn) in ethanol in the presence of air (200). An alkylperoxoplatinum(IV) complex is obtained in the reaction of (phen)PtMe2 (phen = 1,10-phenanthroline) with dioxygen and isopropyl-iodide. Under conditions that favor radical formation (light or radical initiators), an isopropylperoxoplatinum(IV) compound was obtained (201,202), depicted in Scheme 42. 

Hydrogen iodide not only esterifies polyhydric alcohols but also reduces them. Thus glycerol passes by way of 1 2 3-triiodopropane into isopropyl iodide ... 

The steric rather than the inductive origin of the secondary deuterium KIE is also suggested because kH/kD = 0.994 per deuterium found in the per-deuteropyridine-methyl iodide reaction is smaller (less inverse) than the kH/kn = 0.988 per deuterium found for the 4-deuteropyridine reaction. A secondary inductive KIE should be more inverse when a deuterium is substituted for a hydrogen nearer the reaction centre, i.e. at the meta- or ortho-rather than at the para-position of the pyridine ring. Thus, if the KIE were inductive in origin, the KIE in the perdeuteropyridine reaction should be more inverse than that observed for the 4-deuteropyridine reaction. If the observed KIE were the result of a steric KIE, on the other hand, a less inverse KIE per deuterium could be found in the perdeuteropyridine reaction, i.e. a less inverse KIE per deuterium would be expected if there were little or no increase in steric hindrance around the C—H(D) bonds as the substrate was converted into the SN2 transition state. Since the KIE per D for the perdeuteropyridine reaction is less than 1%, the transition state must not be sterically crowded and the KIE must be steric in origin. Finally, the secondary deuterium KIEs observed in the reactions between 2-methyl-d3-pyridine and methyl-, ethyl- and isopropyl iodides (entries 3, 7 and 9, Table 17) are not consistent with an inductive KIE. If an inductive KIE were important in these reactions, one would expect the same KIE for all three reactions because the deuteriums would increase the nucleophilicity of the pyridine by the same amount in each reaction. The different KIEs for these three reactions are consistent with a steric KIE because the most inverse KIE is observed in the isopropyl iodide reaction, which would be expected to have the most crowded transition state, and the least inverse KIE is found in the methyl iodide reaction, where the transition state is the least crowded. 

Monoalkylation of optically active 1-phenylethylamine with benzyl bromide in N,N-dimethylpropyleneurea (249a) at 100 °C in the presence of sodium carbonate gives the enantiomerically pure A-benzyl derivative. Isopropyl iodide and neopentyl iodide behave analogously275. 

FLUOROPROPANE ISOPROPYL IODIDE n-PROPYL IODIDE ALLYAMINE PROPYLENEIMINE N,N-DIMETHYLFORMAMIDE M-METHYLACETAMIDE... 

Another example concerns the action of isopropyl iodide in isopropanol on the stable form of Paludrine 45) (see Section III N), an unfortunate choice of starting material. The product is stated to be 1-p-chlorophenyl-2-isopropylbiguanide hydriodide [p-ClC8H4NH-C( NPr>) -NHC( NH)-NHa-HI],... 

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