4773-35-7

Usage

Family

Phenylpropanoids

Physical State

Colorless liquid

Odor

Strong, sweet

Uses

a. Synthesis of pharmaceuticals
b. Synthesis of fragrances
c. Synthesis of other organic compounds
d. Intermediate in the production of various chemicals, including over-the-counter medications

Primary Use

Synthesis of illegal drugs (e.g., methcathinone and methamphetamine)

Legal Status

Controlled substance in many countries

Regulation

Production and use are strictly regulated due to potential for misuse and abuse

InChI:InChI=1/C9H9ClO/c1-7(11)9(10)8-5-3-2-4-6-8/h2-6,9H,1H3/t9-/m0/s1

Upstream product

• 103-79-7 1-phenyl-acetone 
• 41246-45-1 2,2-dichloro-1,3-diphenylpropane-1,3-diol 
• 6202-57-9 chloro-2-phenyl-2-methyl-3-oxiranne (Z) 
• 21894-15-5 (2S,3R)-2-Chloro-2-methyl-3-phenyl-oxirane 
• 98-87-3 benzylidene dichloride 
• 108-24-7 acetic anhydride 
• 86396-63-6 ((E)-2-Chloro-1-methyl-2-phenyl-vinyl)-phenyl-amine 
• 22596-45-8 2-methyl-2-nitro-3-phenyloxirane 
• 133115-84-1 1-acetylsulfanyl-1-phenyl-acetone 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 13213-36-0 1-phenylpropan-2-one oxime 
• 530-48-3 1,1-Diphenylethylene 
• 19275-80-0 1-acetoxy-1-phenyl-acetone 

Downstream Products

• 1030-23-5 2-benzoyloxypropiophenone 
• 108897-09-2 benzoic acid 2-oxo-1-phenyl-propyl ester 
• 35855-75-5 1-phenoxy-1-phenylpropan-2-one 
• 112013-79-3 1-(benzenesulfonyl)-1-phenylpropan-2-one 
• 101743-36-6 2,5-dimethyl-3,6-diphenyl-[1,4]dithiane-2,5-diol 
• 73611-98-0 2,2-dimethoxy-1-phenyl-1-propanol 
• 501-52-0 3-Phenylpropionic acid 
• 30709-67-2 2-amino-5-methyl-4-phenylthiazole 
• 28241-62-5 2-Amino-4-methyl-5-phenyl-thiazol 
• 53475-18-6 α-(methylthio)phenylacetone 
• 63200-84-0 (4-methyl-5-phenyl-selenazol-2-yl)-phenyl-amine 
• 63200-76-0 (4-methyl-5-phenyl-selenazol-2-yl)-(4-nitro-phenyl)-amine 
• 63017-09-4 1-bromo-1-chloro-1-phenyl-acetone 
• 21120-43-4 1-phenyl-1-fluoro-2-propanone 

Relevant academic research and scientific papers

Alpha-amino acid derivative containing piperidine thiazole heterocycle and preparation method and application of alpha-amino acid derivative

The invention discloses an alpha-amino acid derivative containing piperidine thiazole heterocycle. The alpha-amino acid derivative has a structural formula of formula I shown in the description, wherein in formula I, Ar is a phenyl group or a substituted phenyl group, a substituted group of the substituted phenyl group is one of a trifluoromethyl group, fluorine, chlorine or bromine, and R is oneof H and isopropyl. The invention further discloses a preparation method of the alpha-amino acid derivative and application of the alpha-amino acid derivative serving as an insecticide to prevention and control of armyworms. The novel alpha-amino acid derivative containing the piperidine thiazole heterocycle is simple in preparation method, can be used for prevention and control of armyworm insectpests, particularly has a good insecticidal activity against the armyworms, and provides bases for research and development of amino acid pesticides.

A Simple and Efficient Method for the Preparation of α-Halogenated Ketones Using Iron(III) Chloride and Iron(III) Bromide as Halogen Sources with Phenyliodonium Diacetate as Oxidant

α-Halogenated ketones are both unique structure moieties existing in biologically natural products and valuable synthetic intermediates for the preparation of functional molecules. An efficient and scalable method for the preparation of α-halogenated ketone using iron (III) chloride and iron (III) bromide as halogen sources with phenyliodonium diacetate as oxidant has been developed, featuring mild reaction conditions, environmentally friendly reagents, and wide substrate scope. Notably, the three-step synthesis of drug prasugrel was achieved using this developed method as a key step with 30% yield on gram-scale. Additionally, the reaction mechanism involving chloride cation was proposed based on some preliminary control experiments. (Figure presented.).

Peptidyl cyclopropenones: Reversible inhibitors, irreversible inhibitors, or substrates of cysteine proteases?

Peptidyl cyclopropenones were previously introduced as selective cysteine protease reversible inhibitors. In the present study we synthesized one such peptidyl cyclopropenone and investigated its interaction with papain, a prototype cysteine protease. A set of kinetics, biochemical, HPLC, MS, and 13C-NMR experiments revealed that the peptidyl cyclopropenone was an irreversible inhibitor of the enzyme, alkylating the catalytic cysteine. In parallel, this cyclopropenone also behaved as an alternative substrate of the enzyme, providing a product that was tentatively suggested to be either a spiroepoxy cyclopropanone or a gamma-lactone. Thus, a single family of compounds exhibits an unusual variety of activities, being reversible inhibitors, irreversible inhibitors and alternative substrates towards enzymes of the same family.

Pyridines from azabicyclo[3.2.0]hept-2-en-4-ones through a proposed azacyclopentadienone

Pyridines have been formed by heating azabicyclo[3.2.0]hept-2-en-4-ones in toluene. The generation of a 3-azacyclopentadienone intermediate via a [2 + 2]-cycloreversion is proposed as the key step. A Diels-Alder reaction of a styrene, extrusion of carbon monoxide, and loss of hydrogen then gives the pyridine. The process parallels the well-known synthesis of benzenes from cyclopentadienones. The azabicyclo[3.2.0]hept-2-en-4-ones were synthesized from the reaction between readily available cyclopropenones and 1-azetines, in which the cyclopropenones behave as all-carbon 1,3-dipolar equivalents.

PIPERAZINYL DERIVATIVES USEFUL AS MODULATORS OF THE NEUROPEPTIDE Y2 RECEPTOR

The present invention is directed to piperidinyl and piperazinyl derivatives of formula (II) useful as inhibitors of the NPY Y2 receptor, pharmaceutical compositions comprising said compounds, processes for the preparation of said compounds and the use of said compounds for the treatment and / or prevention of disorders, diseases and conditions mediated by the NPY Y2 receptor.

Synthesis of chiral cis-1,2,3-trisubstituted aziridines

Chiral cis-1,2,3-trisubstituted aziridines were conveniently synthesized from (1R,2S)-(-)- or (1S,2R)-(+)-norephedrine via the corresponding chiral N-(arylidene)-β-chloroamines. The enantiomeric purity of the chiral aziridines (e.e. >98%) was established by NMR spectroscopy utilizing (S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol. (C) 2000 Elsevier Science Ltd.

Reactions of alkyl methyl ketoximes with tetrasulfur tetranitride antimony pentachloride complex (S4N42.SbCl5): A regioselective formation of 3-alkyl-4-methyl-1,2,5-thiadiazoles and their mechanism of formation

Treatment of alkyl methyl ketoximes with tetrasulfur tetranitride antimony pentachloride complex (S4N4·SbCl5) in aromatic solvents such as benzene and toluene at 60 °C led to the regioselective formation of 3-alkyl- 4-methyl-1,2,5-thiadiazoles in low yields, whereas the reactions of alkyl aryl ketoximes under the same conditions gave exclusively N-arylalkanamides in good yields. A mechanism is proposed for the formation of 3-alkyl-4- methyl-1,2,5-thiadiazoles.

Indium(III) chloride-promoted rearrangement of epoxides: A selective synthesis of substituted benzylic aldehydes and ketones

A simple and efficient procedure for the rearrangement of substituted epoxides catalyzed by InCl3 has been developed. Aryl-substituted epoxides isomerize with complete regioselectivity to form a single carbonyl compound via cleavage of the benzylic C-O bond. The reactions are simple, fast, and high yielding. This procedure is very mild compared to those catalyzed with BF3 and other Lewis acids and compatible with several acid-sensitive functionalities. This protocol provides a highly selective synthesis of substituted benzylic aldehydes and ketones. However, rearrangement of alkyl- substituted epoxides is not very selective.

Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3- epoxybutane and 1-phenyl-1,2-epoxypropane

All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2- epoxypropane (β-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.