1669-70-1

Basic information

• Product Name: 2-(4-CHLOROPHENYL)-2-METHYLOXIRANE
• Synonyms: 2-(4-CHLOROPHENYL)-2-METHYLOXIRANE
• CAS NO: 1669-70-1
• Molecular Formula: C₉H₉ClO
• Molecular Weight: 168.6202
• Mol File: 1669-70-1.mol

Chemical Properties

• Boiling Point: 228.2°Cat760mmHg
• Flash Point: 96.9°C
• Appearance: /
• Density: 1.214g/cm³
• Vapor Pressure: 0.112mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: 2-(4-CHLOROPHENYL)-2-METHYLOXIRANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-CHLOROPHENYL)-2-METHYLOXIRANE(1669-70-1)
• EPA Substance Registry System: 2-(4-CHLOROPHENYL)-2-METHYLOXIRANE(1669-70-1)

Safety Data

• Hazardous Substances Data: 1669-70-1(Hazardous Substances Data)

Usage

Classification

Organic compound, belongs to the family of oxirane compounds.

Color

Colorless liquid.

Odor

Faint, sweet.

Solubility

Insoluble in water, soluble in most organic solvents.

Uses

Chemical intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds.
Building block in the production of polymers and resins.

Flammability

2-(4-chlorophenyl)-2-methyloxirane is flammable.

Skin and eye irritation

May cause skin and eye irritation.

Handling and storage

Should be handled and stored with proper safety precautions.

InChI:InChI=1/C9H9ClO/c1-9(6-11-9)7-2-4-8(10)5-3-7/h2-5H,6H2,1H3

Upstream product

• 1712-70-5 1-chloro-4-(1-methylethenyl)-benzene 
• 75-18-3 dimethylsulfide 
• 99-91-2 para-chloroacetophenone 
• 1774-47-6 trimethylsulfoxonium iodide 
• 2788-86-5 4-Chlorostyrene oxide 
• 74-88-4 methyl iodide 
• 333-27-7 methyl trifluoromethanesulfonate 
• 2181-42-2 trimethylsulphonium iodide 
• 6814-64-8 methylenedimethyl sulfurane 

Downstream Products

• 102877-35-0 2-(4-chlorophenyl)-propane-1,2-diol 
• 236408-50-7 (S)-p-chloro-α-methylstyrene oxide 
• 1225434-48-9 2-(4-chlorophenyl)-1-(2,3,4,5-tetrahydro-3,9-dimethylazepino[4,5-b]indol-6(1H)-yl)propan-2-ol 
• 1225434-42-3 1-(9-chloro-2,3,4,5-tetrahydro-3-methylazepino[4,5-b]indol-6(1H)-yl)-2-(4-chlorophenyl)propan-2-ol 
• 1239767-04-4 C₉H₁₀ClN₃O 
• 1213256-40-6 C₉H₁₀ClN₃O 
• 1239766-96-1 (R)-1-azido-2-(4-chlorophenyl)propan-2-ol 
• 1239766-86-9 1-azido-2-(4-chlorophenyl)propan-2-ol 
• 312304-85-1 (S)-2-(4-chlorophenyl)propanal 
• 286964-62-3 2-(4-chlorophenyl)propanal 
• 1283086-29-2 C₂₃H₂₅ClN₂O 
• 59667-21-9 p-Chloro-β-methylphenethyl alcohol 

Relevant articles and documents

Enantioselective hydrolysis of 2,2-disubstituted oxiranes mediated by microsomal epoxide hydrolase

2-Aryl-2-methyloxiranes are enantioselectively hydrolyzed with microsomal epoxide hydrolase from pig liver to provide 1,2-diols containing a tertiary benzylic alcohol stereogenic centre upto 34% enantiomeric purities.

An Asymmetric SN2 Dynamic Kinetic Resolution

The SN2 reaction exhibits the classic Walden inversion, indicative of the stereospecific backside attack of the nucleophile on the stereogenic center. Observation of the inversion of the stereocenter provides evidence for an SN2-type displacement. However, this maxim is contingent on substitution proceeding on a discrete stereocenter. Here we report an SN2 reaction that leads to enantioenrichment of product despite starting from a racemic mixture of starting material. The enantioconvergent reaction proceeds through a dynamic Walden cycle, involving an equilibrating mixture of enantiomers, initiated by a chiral aminocatalyst and terminated by a stereoselective SN2 reaction at a tertiary carbon to provide a quaternary carbon stereocenter. A combination of computational, kinetic, and empirical studies elucidates the multifaceted role of the chiral organocatalyst to provide a model example of the Curtin-Hammett principle. These examples challenge the notion of enantioenriched products exclusively arising from predefined stereocenters when operating through an SN2 mechanism. Based on these principles, examples are included to highlight the generality of the mechanism. We anticipate the asymmetric SN2 dynamic kinetic resolution to be used for a variety of future reactions.

Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines

The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one-pot reductive amination using pyrrolidine as imine-formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups. A DFT study of its mechanism is presented showing that the isomerization takes place via an iridium hydride mechanism with a low energy barrier, in agreement with the mild reaction conditions. (Figure presented.).

Isomerization of terminal epoxides by a [Pd-H] catalyst: A combined experimental and theoretical mechanistic study

An unusual palladium hydride complex has been shown to be a competent catalyst in the isomerization of a variety of terminal and internal epoxides. The reaction displayed broad scope and synthetic utility. Experimental and theoretical evidence are provided for an unprecedented hydride mechanism characterized by two distinct enantio-determining steps. These results hold promise for the development of an enantioselective variant of the reaction.

Catalytic hydrogen atom transfer (HAT) for sustainable and diastereoselective radical reduction

Going cyclic! A catalytic cycle and cyclic transition states enable a novel sustainable and catalytic hydrogen atom transfer (HAT) for highly diastereoselective radical reductions. Readily available nontoxic silanes are the terminal reductants for epoxides that are opened by bifunctional titanocene(III) hydride catalysts. Copyright

Generation and reactions of oxiranyllithiums by use of a flow microreactor system

A flow microreactor system consisting of micromixers and microtubes provides an effective reactor for the generation and reactions of aryloxiranyllithiums without decomposition by virtue of short residence time and efficient temperature control. The depro

Resolution of 2,2-disubstituted epoxides via biocatalytic azidolysis

A practical procedure for the enzymatic resolution of 2-alkyl-2-aryl- disubstituted epoxides using the Codex HHDH P2E2 enzyme and sodium azide is reported. This method allowed the synthesis of novel regio-and enantioselective 1-azido-2-arylpropan-2-ols in

Efficient catalytic Corey-Chaykovsky reactions involving ketone substrates

It has been demonstrated for the first time that a sulfide catalyst, utilised at 20 mol% loading, can promote methylene transfer to ketones in the presence of methyl triflate and an organic base. This metal-free methodology is of broad scope-both aliphatic and aromatic ketones (including trifluoromethyl ketones) can be converted to synthetically useful terminal epoxides in excellent yields at room temperature.

AZEPINO [4, 5-B] INDOLES AND METHODS OF USE

This disclosure relates to new azepino[4,5-b]indole compounds that may be used to modulate a histamine receptor in an individual. Novel compounds are described, including new 1, 2,3,4,5, 6-tetrahydroazepino[4,5-b]indoles. Pharmaceutical compositions are also provided.

PYRIDO (4,3-B) INDOLES CONTAINING RIGID MOIETIES

This disclosure is directed to pyrido[4,3-b]indoles having rigid moieties. The compounds in one embodiment are pyrido[4,3-b]indoles having an unsaturated hydrocarbon moiety. The compounds in another embodiment are pyrido[4,3-b]indoles having a cycloalkyl, cycloalkenyl or heterocyclyl moiety. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.