1- Chloro-2-propanol derivatives

If a diastereomeric mixture of (S,S)-2,5-dimethyl-3.4-hexanediol esters 2 and 3 reacts with methylmagnesium bromide, the result is kinetic resolution, as verified for R1 = Bn. The diastereomeric mixture was prepared from the racemic ethylene glycol a-chloro boronic ester via transesterification with chiral diol. The products isolated were (S,S)-2,5-dimethyl-3,4-hexanediol [(/ )-2-phcnyl-l-methylethyl]boronate, diastereomeric ratio >95 5 as indicated by the rotation of the (/ )- -phenyl-2-propanol derived by deboronation with hydrogen peroxide, and (S,S)-2,5-dimethyl-3.4-hexanediol methylboronate. Phenylacetaldehyde was identified by 1H NMR4. 

Chloropropanols (chlorinated propanols) are a group of three-carbon alcohols and diols with one or two chlorine atoms, which are hypothetically derived from glycerol. Six compounds, one chloro-propanol (3-chloropropan-l-ol, 12-22), two dichloropropanols (l,3-dichloropropan-2-ol, for short 1,3-DCP, 12-23 and 2,3-dichloropropan-l-ol, 2,3-DCP, 12-24), two chloropropanediols (3-chloropropane-l,2-diol, 3-CPD, also known as 3-MCPD from 3-monochloropropane-l,2-diol, 12-25, and 2-chloropropane-... 

Another possibility is that both nitrogen atoms react with a double alkylating agent. In this way fused pyrazole derivatives (pyrazolo[l,2-a]pyrazoles) like (237) can be obtained by reaction of 3,5-dimethylpyrazole with 1,3-dichloropropane or l-chloro-3-propanol (69BSF2064). More surprising is the reaction with a-chlorocarbonylphenylketene which yields the paraionic compound (238) (80JA3971) which can also be obtained from 3,5-dihydroxy-4-phenylpyrazole and /3-dicarbonyl compounds (82JOC295). 

The manufacture and uses of oxiranes are reviewed in (B-80MI50500, B-80MI50501). The industrially most important oxiranes are oxirane itself (ethylene oxide), which is made by catalyzed air-oxidation of ethylene (cf. Section 5.05.4.2.2(f)), and methyloxirane (propylene oxide), which is made by /3-elimination of hydrogen chloride from propene-derived 1-chloro-2-propanol (cf. Section 5.05.4.2.1) and by epoxidation of propene with 1-phenylethyl hydroperoxide cf. Section 5.05.4.2.2(f)) (79MI50501). 

A similar series of nucleophilic substitutions has been performed on 4-chloro[l,2,3]triazolo[4,5-c]pyridine (246) and some of its simple substituted derivatives. On compound 246 itself formic acid gives the triazolo-pyridin-4-one,192 ammonia gives the 4-amino compound,192 and hydrazine the 4-hydrazino derivative 245 hydrosulfide gives the 4-thione192 and thiourea in propanol, at first reported151 to give the 4-thione, has subsequently been... 

Hydroxy-3,4-dihydro-2//-pyrido[l,2-fl]pyrimidine hydrobromide and its 8-methyl derivative 255 (R = H, Me) were obtained in the reaction of appropriate 2-aminopyridine and l-bromo-3-chloro-2-propanol in refluxing dimethylformamide for 3.5 hours (84MI17). 

Calculation Prepare a standard curve for the summed signal areas for each of the controls against the calculated propylene chlorohydrin concentrations, in mg/kg, derived from the actual weight of chlorohydrin isomers used. Using the summed signal areas corresponding to the l-chloro-2-propanol and 2-chloro-1 -propanol from the sample, determine the concentration of mixed propylene chlorohydrins, in mg/kg, in the sample by reference to the calibration plot. 

Deuterolysis of 3-chloro-2-chloromethyl-5-methoxypyrazine over 5% palladium on alumina in the presence of sodium isopropoxide in 2-propanol afforded 3-deutero-2-monodeuteromethyl-5-methoxypyrazine (687) and methylation of the bromomagnesium derivative from 2-bromomethyl-3,5,6-trimethylpyrazine with methyl sulfate or methyl iodide gave 2-ethyl-3,5,6-trimethylpyrazine (330). 

Transformation of 1,3-diamino-2-propanol (144) into vicinal diamines has been reported. Thus, the bis(benzyloxycarbonyl) derivative of (144) was mesylated to give (145), which was converted into 1-benzyloxycarbonylaziridine (146). Acetic acid and HCl reacted at the ring carbon of (146) affording 2,3-diamino-1-propanol (147) and l-chloro-2,3-diaminopropane (148 Scheme 68). On the other hand, the reaction of (146) with Grignard reagents and sodio malonates resulted in the loss of the carbamate protecting group. In contrast, the sulfonamide derivative (149) could be converted into diamines (151) and (152) via 1-tosylaziridine (150 Scheme 68). 

Many side reactions can occur during the alkylation of an intermediate containing many nucleophilicsites. Bjoersvichetal. (254) studied the influence of various cations on the N/0 regioselectivity in the N-alkylation of acetamidotriiodoisophthalamide derivatives with 3-chloro-l-methoxy-2 propanol and found that the ion gives the best selectivity and... 

Using indolyl-based substrate analogs such as 5-bromo-4-chloro-3-indolyl-ace-tate, butyrate, or propionate (X-acetate, X-butyrate, and X-propionate) for esterases and using the p-rosaniline assay coupled with ethanol, butanol, or propanol for alcohol dehydrogenases we were able to isolate several hundred candidates in the first level of a hierarchical screen. An intermediate screen was then used to characterize and compare the esterase candidates. We used nitrophenyl and methyl-umbelliferyl derivatives to analyze esterase candidates and their preference for chain length. 

Synonyms 2-Chloro-1-propanol phosphate (3 1) 1-Propanol, 2-chloro-, phosphate (3 1) TMCP Tris (P-chloropropyl) phosphate Empirical C19H18CI3O4P Properties M.w. 447.69 Toxicology TSCA listed Uses Flame retardant for polymers Manuf./Distrib. Aceto http //www.aceto.com Trade Name Synonyms Amgard TMCP T[Rhodia/Phosphorus Perf. Derivs. http //www.rhodia-ppd.com]] Antiblaze 80 [Rhodia/Phosphorus Perf. Derivs. http //www.rhodia-ppd.com]... 

Another important derivative of 1-naphthol is propranolol, a P-receptor blocker developed by ICI and with a worldwide production of around 500 tpa. Synthesis takes place by the reaction of 1-naphthol with epichlorohydrin, followed by substitution of the chlorine in l-chloro-3-(l-naphthoxy)-2-propanol with isopropylamine to yield propranolol. 

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