L-Chloropropan

Hydrogen hahdes normally add to form 1,2-dihaLides, though an abnormal addition of hydrogen bromide is known, leading to 3-bromo-l-chloropropane [109-70-6], the reaction is beUeved to proceed by a free-radical mechanism. Water can be added by treatment with sulfuric acid at ambient or lower temperatures, followed by dilution with water. The product is l-chloro-2-propanol [127-00-4]. 

The piincipal by-pioducts aie the result of direct chlorine addition to give 1,2-dichlotoptopane [78-87-5] and ether formation. The ether product is dichloropropyl ether [108-60-1] or 2,2 -oxybis(l-chloropropane). 

Replacement of one of the phenyl groups by an alkyl group of similar bulk, on the other hand, alters the biologic activity in this series. Alkylation of phenylacetonitrile with isopropyl bromide affords the substituted nitrile, 136. Treatment of the anion prepared from 136 with strong base with 2-dimethylamino-l-chloropropane gives isoaminile (137). It is of note that alkylation of this halide, isomeric with that used in the early methadone synthesis, is apparently unaccompanied by isomer formation. Isoaminile is an agent with antitussive activity. 

The initiation mechanism comprises nucleophilic attack of the metal chloride at the least-hindered carbon. Thus hydrolysis of the 1 1 reaction product of (251) with PO yields l-chloropropan-2-ol.937... 

Polymerization and oligomerization reactions. l-FIalogenopropane-2-thiones give homopolycondensation,10 in different conditions l-chloropropane-2-thi-one11 forms a polymer or a cyclic trimer. a-Oxothioketones12 15 form dimers, by [4+2] unsymmetrical Diels Alder cycloaddition (Scheme 7). a,p-Unsatu-rated thioketones,16 Scheme 3 E = S, form dimers via head-to-head (R1 = Ph, R2 = Me) and head-to-tail (R1 = R2 = Ph), while selenoketones, E = Se, dimerize17 via head-to-head . 

Synonyms AI3-18183 BCIE BCMEE Bis(p-chloroisopropyl) ether Bis(2-chloro-l-methyleth-yl) ether Bis(2-chloro-3-methylethyl) ether Bis(l-chloro-2-propyl) ether BRN 1735833 CCRIS 91 l-Chloro-2-(p-chloroisopropoxy)propane 2-Chloroisopropyl ether p Chloroisopropylether (2-Chloro-l-methylethyl) ether DCIP Dichlorodiisopropyl ether Dichloroisopropyl ether 2,2 -Dichloroisopropyl ether EINECS 203-598-3 Isopropylchlorex NCI-C50044 Nemamol Nemamort NSC 2849 2,2 -Oxybis(l-chloropropane) Pichloram RCRA waste number U027 UN 2490. 

Synonyms AI3-15634 BRN 1748601 CCRIS 5997 Chloronitropropane EINECS 1748601 Korax Lanstan Nitrochloropropane 1-Nitro-l-chloropropane NSC 8409. 

Oxitol, see 2-Ethoxyethanol Oxitol acetate, see 2-Ethoxyethyl acetate 2-Oxobornane, see Camphor Oxocyclohexane, see Cyclohexanone Oxolane, see Tetrahydrofuran Oxomethane, see Formaldehyde Oxybenzene, see Phenol 1,1 Oxybisbenzene, see Phenyl ether l,l -Oxybis(2-chloroethane), see Bis(2-chloroethyl) ether Oxybis(chloromethane), see s/m-Dichloromethyl ether 2,2 -Oxybis(l-chloropropane), see Bis(2-chloroisopropyl) ether... 

Reactions of this type have been widely used for the synthesis of 1,5-benzoxazepines by the reactions of o-aminophenols and their derivatives with a variety of functionalized three-carbon chains. Thus reaction with 3-bromo-l-chloropropane gives (360) and reaction with 3-chloropropionyl chloride gives the analogous 4-oxo derivative. Similarly a,/3-unsatur-ated Icetones give (361), /3-ketoesters give (362), l,3-oxazolid-5-ones give (363), and the reaction of the sodium salt of N-methanesulfonyl-o-aminophenol with epichlorohydrin gives... 

Exchange of chlorine with fluorine in l-chloropropan-2-ol (1) has been carried out successfully as early as 1948.75 The fluorinated alcohol 2 is used as the precursor for 1-fluoroacetone by chromic acid oxidation76 and is therefore of preparative interest. 

Chem. Abstr. Services Reg. No.. 108-60-1 Systematic name. 2,2 -Oxybis(l-chloropropane)... 

In rats receiving a single oral dose of bis(2-chloro-l-methylethyl)ether of 0.0002-300 mg/kg bw, peak blood levels of radioactivity were reached at about 2-4 h. Following administration of a dose of 30 mg/kg bw, elimination was biphasic in rhesus monkeys, with half-lives of 5 h and two days, and monophasic in rats, with a half-life of two days. In rats, total recovery of radioactivity was 75% of an oral dose of the l- C-labelled compound and 90% after an intraperitoneal dose with the 2-i<-labelled compound approximately 20% of the oral dose was exhaled as CO2 in 48 h. Also in rats, urinary excretion of radioactivity accounted for 48% of a 90 mg/kg bw oral dose of the 1- relabelled compound within 48 h and for 60% of a 30 mg/kg bw intraperitoneal dose of the 2- rC-labelled compound within 24 h. Urinary metabolites identified after administration of an oral dose of 90 mg/kg bw of the I - ( -kibcllcd compound to rats were 2-(2-chloro-1-methylethoxy)propanoic acid (17% of the dose) and N-acetyl-5 -(2-hydroxypropyl)-cysteine (approximately 9% of the dose) following an intraperitoneal dose of the 2- 4C-labelled compound, metabolites identified were l-chloropropan-2-ol, propylene oxide and 2-(2-chloro-l-methylethoxy)propanoic acid (lARC, 1986). 

Nitroso-l-chloropropane, cryst substance having a pungent odor irritating the eyes to tears mp 5 6-7° to a deep blue liq, dec 83° was obtd by reacting propionaldoxime with NOC1 in eth at low temp(Ref l,p [79] Ref 2,p 277) and... 

Nitro-l-chloropropane, col liq, bp 172-73°, 80-84° at 25 mm, d 1.2 at 18° and 2-Nitro-2-chloropropane, col liq having a pleasant aroma, separates as prisms from cold CS2 eth, bp ca 134°(with some decompn when heated cautiously), explodes violently when heated rapidly mod sol in ale or eth v si sol... 

Nitro-2-Nitroso-l-chloropropane, C1.CH2>-C(N02)(N0) CH3 blue oil, very unstable was... 

Dinitro- 1-chloropropane, CI.CH2.C(N02)2.-CH3, oil, bp 103-5°at 15.4mm, dec at 200-2°, readily volatile with steam was obtd by oxidn of 2-nitro-2-nitroso-l-chloropropane with CrOg in AcOH. Its expl props were not reported (Refs 1 2)... 

Several compounds, including many deuterated and fluoro derivatives, have been used in the published literature. These include fluorobenzene, pentafluo-robenzene, l,2-dichlorobenzene-d4, l-chloro-2-fluorobenzene, 1,4-difluoroben-zene, l,2-dichloroethane-d4, 1,4-dichlorobutane, and 2-bromo-l-chloropropane. U.S. EPA has set the tuning criteria for bromofluorobenzene and decafluorotriph-enylphosphine as tuning compounds for volatile and semivolatile organic compounds. (See Chapter 1.4)... 

Recommended surrogate/IS 2-bromo-l-chloropropane and 1,4-dichloro-butane. 

Dimethylamino-l-chloropropane Sodium amide Hydrogen chloride... 

Dimethylsulfamoylphenothiazine 3-(4-Methyl-l-piperazinyl)-l-chloropropane Sodium amide... 

A solution of 3-dimethylsulfamoylphenthiazine (5 g) in anhydrous xylene (100 cc) is heated under reflux for 1 hour with sodamide (0.67 g). 3-(4-methyl-l-piperazinyl)-l-chloropropane (3.2 g) in solution in anhydrous xylene (20 cc) is added and the mixture heated under reflux for 5 hours. After treatment of the reaction products, a crude oily base (2.5 g) is obtained after treatment. By the addition of a solution of fumaric acid in ethanol to an ethanolic solution of the base, 3-dimethylsulfamoyl-10-(3-41-methyl-ll-piperazinylpropyl)-phenthiazinediacid fumarate (2.6 g) is obtained, melting point 182°C. The base recrystallized from ethyl acetate melts at about 140°C. 

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