Acetonyl chloride

Synonyms Monochloroacetone chloroprop-anone l-chloro-2-propanone acetonyl chloride... 

SYNS ACETONYL CHLORIDE A-STOFF CHLORACETONE CHLOROACETONE CHLORO-ACETONE, stabilized pOT) CHLOROPROPANONE 1-CHLORO-2-PROPANONE MONOCHLORACETONE MONOCHLOROACETONE MONOCHLORO-ACETONE, inhibited pOT) MONOCHLOROACETONE, stabilized pOT) MONOCHLOROACETONE, unstabilized pOT) TONITE... 

ACETONYL CHLORIDE (78-95-5) C3H5CIO Highly flammable liquid. Forms e losive mixture with air (flash point 80°F/27°C cc). Light can cause slow polymerization may be a fire or explosion hazard. Strong oxidizers may cause fire and... 

Beilstein Handbook Reference) A-Stoff Acetone, chloro- Acetonyl chloride BRN 0605369 CCRIS 1943 Chloracetone Chloro-2-propanone Chloroacetone Chloromethyl methyl ketone Chloropropanone EINECS 201-161-1 HSDB 1070 Monochloracetone Monochloropropanone NSC 30673 Tonite UN1695. Has been considered as a tear gas. Used In chemical manufacturing and as a catalyst Liquid mp = -44.5° bp = 119° d = 1.15 moderately soluble in H2O, organic solvents LDso (mus orl) = 127 mg/kg, (rat ori) = 100 mg/kg, LCsO (rat ihl 1 hr.) = 262 ppm. Lancaster Synthesis Co. Mallinckrodt Inc. Sigma-Aldrich Fine Chem. 

This sequence is equally applicable to keto esters. Thus, condensation of guanidine with ethyl acetoacetate gives the pyrimidone, 134. Elaboration as above gives the pyrimidine, IJ5 acylation with the sulfonyl chloride (88) followed by hydrolysis yields sulfamerazine (107). Reaction of guanidine with beta dicarbonyl compounds gives the pyrimidine directly. Condensation of the base with acetonyl acetone affords the starting amine for sulfadimidine (108). ... 

Chromatographic separation clarified the peculiarities of acetonyl-thiothiophene cyclization in the presence of duminum chloride. " Gas-liquid chromatography also allowed quantitative estimates of the relative reactivities of thiophene and the isomeric thienothiophenes 1 and... 

Acetonyl triphenyl phosphonium chloride and acetylmethylene triphenyl phosphorane see... 

Above 250 °C. significant amounts of methane, carbon monoxide, and methyl chloride are formed suggesting that acetonyl, acetonylidene, and chloroacetyl radicals are unstable at elevated temperatures. This contention is supported by the rise in the quantum yield of hydrogen chloride above unity at these temperatures. 

Hydroxyhexanal undergoes a Claisen reaction with isopropenyl acetate in the presence of iV-chlorosuccinimide and tin(ll) chloride as catalyst to afford 2-acetonyloxepane. In the case of 6-hydroxy-2-pentylhexanal, 2-acetonyl-3-pentyloxepane is obtained with 95% diastereoselectivity (Equation 30) <1994CC1123>. 

Naphthyridine underwent quaternization by l-chloro-2,4-dinitrobenzene in methanol or acetone under reflux to afford 2-(2,4 dinitrophenyl)-2,7-naphthyr-idinium chloride (58) accompanied by either 2-(2,4-dinitrophenyl)-l-meth-oxy- (59, R=OMe) (10%) or l-acetonyl-2-(2,4-dinitrophenyl)-l,2-dihydro-... 

The site of the carboxyl in voacangine was confirmed by treating 20-hydroxyvoacanginol (XXXV R=OH) with acetone containing hydrogen chloride to yield the acetonyl derivative, which was characterized as its O-acetate (XXXVI) (16). A similar reaction, starting from J3-coronaridine (see Table I), led analogously to XXXVII (40). 

To a hoi (oil bath temperature 90 C), stirred solution of PhjP (26.2 g, 0.1 mol) in anhyd benzene (110 mL) was added dropwise j-chloro-3-fluoropropan-2-one (5 ll.Og, 0.1 mol). After a while, the phosphonium chloride precipitated. At the end of the addition, stirring was continued at 90 C for 3 h. (1-Fluoro-acetonyl)triphenylphosphoniuni chloride (6) was filtered off from the cold mixture, washed with benzene, and dried under vacuum yield 28,7g (77%) mp 187 C (dec.). 

Methyl-5-methoxy-2-phenyl-2,4a,5,6,7,8-hexahydro-17/-pyrido[l,2-c] pyrimidine-l-thione was obtained in the reaction of 2-acetonyl-3-methoxypiperidine and phenyl isothiocyanate in boiling methylene chloride (55JOC136). 

Two additional bases were isolated from these extracts ace-tonyl dictysine (111), C24H37NO3, m.p. 151-153°C, and acetonyl dehydrodictysine (112), C24H32NO3, m.p. 143-145 C. These structures were assigned from the spectral data and chemical transformations. Oxidation of (111) with chromic anhydride afforded (112). Hydrolysis of (112) with 20% aqueous sulfuric acid gave (113). Acetylation of (113) with acetic anhydride produced the monoacetate (114), whereas treatment of (113) with acetyl chloride gave (115). How-... 

It should be noted that complexes of types VII-5 or VII-7 can be easily prepared by the method initially described in [30a-d], The chloride complex Pt"Cl4 - reacts at room temperature in aqueous solution with alkyl iodide to produce a o-alkyl complex of platinum(IV). Methyl [30a], ethyl [30b,c], and acetonyl [30d] complexes of Pt(IV) have been prepared by this method. An interesting feature of the reaction is that the sixth coordination site in the octahedral molecule of the product is occupied by water, while the T ion is bound to another molecule of the platinum(II) complex (Ptlj and analogous products are formed and precipitate) ... 

---