3756-41-0

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-Phenyl-1-chloroethane is used as a synthetic building block for the creation of various pharmaceutical compounds. Its unique chiral nature allows for the development of enantiomerically pure drugs, which can have different biological activities and reduce potential side effects associated with racemic mixtures.
Used in Chemical Industry:
In the chemical industry, (S)-1-Phenyl-1-chloroethane serves as a key intermediate in the synthesis of a range of organic compounds. Its versatility in reactions and compatibility with organic solvents make it a valuable component in the production of specialty chemicals.
Used in Perfumery:
(S)-1-Phenyl-1-chloroethane is used as a component in the manufacture of perfumes, capitalizing on its sweet, floral odor to contribute to the overall scent profile of fragrances.
Used in Flavorings:
(S)-1-Phenyl-1-chloroethane is also utilized in the production of flavorings, where its distinct odor can enhance or create unique taste experiences in the food and beverage industry.
Safety Precautions:
It is crucial to handle (S)-1-Phenyl-1-chloroethane with care due to its toxicity. Exposure can lead to skin and eye irritation, and respiratory issues may arise if the compound is inhaled. Proper safety measures, including the use of personal protective equipment and ventilation, should be implemented during its use and storage.

Upstream product

• 75-44-5 phosgene 
• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 
• 102761-62-6 phosphoric acid tris-((R)-1-phenyl-ethyl ester) 
• 98-85-1 1-Phenylethanol 
• 17199-29-0 (S)-Mandelic acid 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 611-71-2 (R)-Mandelic Acid 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 40435-14-1 (S)-1-phenyl-2-(tosyloxy)ethanol 
• 40434-87-5 (R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate 
• 257298-92-3 (R)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane 
• 16197-92-5 (R)-1-phenethyl acetate 
• 98-88-4 benzoyl chloride 

Downstream Products

• 61587-06-2 ethyl-((R)-1-phenyl-ethyl)-ether 
• 7214-60-0 (S)-1-nitrosyloxy-1-phenyl-ethane 
• 129575-56-0 (R)-α-methylbenzyl azide 
• 71698-86-7 (R)-(-)-1-deuterioethylbenzene 
• 57793-28-9 (R)-(+)-(1-methylsulfanylethyl)benzene 
• 4593-90-2 (S)-2-phenylbutanoic acid 
• 139914-70-8 C₃₂H₂₈ 
• 779-54-4 (R)-phenyl-(1-phenylethyl)amine 
• 1028800-74-9 2-chloro-5,5-dimethyl-3-(1-phenyl-ethoxy)-cyclohex-2-enone 
• 1028800-73-8 2-chloro-3-(1-phenyl-ethoxy)-cyclohex-2-enone 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 1369514-85-1 2-((3,4-trans)-4-methyl-1-((S)-1-phenylethyl)pyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one 
• 7529-63-7 (1'S)-(-)-1-(1'-phenylethyl)piperidine 
• 1861-02-5 (-)deuteriophenylethane 

Relevant academic research and scientific papers

Formamide-Catalyzed Nucleophilic Substitutions: Mechanistic Insight and Rationalization of Catalytic Activity

Herein, detailed mechanistic investigations into formamide-catalyzed nucleophilic substitution (SN) of alcohols are reported. Alkoxyiminium chlorides and hexafluorophosphates were synthesized and characterized as a key intermediate of the catalytic cycle. The determination of reaction orders and control experiments indicated that the nucleophilic attack of the formamide catalyst onto the reagent BzCl is the rate-determining step. Linear free energy relationship revealed a correlation between the quantified Lewis basicity strength of formamides by means of 11B NMR spectroscopy and their catalytic activity in SN-transformations. The observed difference in catalytic ability was attributed to the natural bond order charge, dipole moment, and Sterimol parameter B5. Importantly, this rationalization enables the prediction of the capacity of formamides to promote SN-type transformations in general.

Optically Active 1-Deuterio-1-phenylethane – Preparation and Proof of Enantiopurity

Enantiopure (S)-(1-2H)ethylbenzene was prepared in two steps from optically active (S)-1-phenylethanol via (R)-(1-chloroethyl)benzene (two inversions of configuration). Since the value for the specific rotation [α] is very low for the enantiomers of (1-2H)ethylbenzene, the enantiopurity of the synthetic product could not be determined with certainty by polarimetry. Therefore, bis-sulfonamides were prepared by twofold chlorosulfonation (para and ortho) of (S)-(1-2H)ethylbenzene and subsequent amidation with (R)- and (S)-α-phenethylamine. For both diastereoisomers, the (R,R,S)- and the (S,S,S)-sulfonamides, 92 % de was determined by 1H NMR spectroscopy. Therefore, it could be concluded, that (S)-(1-2H)ethylbenzene had been obtained with 92 % ee.

Systematic Evaluation of Sulfoxides as Catalysts in Nucleophilic Substitutions of Alcohols

Herein, a method for the nucleophilic substitution (SN) of benzyl alcohols yielding chloro alkanes is introduced that relies on aromatic sulfoxides as Lewis base catalysts (down to 1.5 mol-%) and benzoyl chloride (BzCl) as reagent. A systematic screening of various sulfoxides and other sulfinyl containing Lewis bases afforded (2-methoxyphenyl)methyl sulfoxide as optimal catalyst. In contrast to reported formamide catalysts, sulfoxides also enable the application of plain acetyl chloride (AcCl) as reagent. In addition, it was demonstrated that weakly electrophilic carboxylic acid chlorides like BzCl promote Pummerer rearrangement of sulfoxides already at room temperature. This side-reaction also provided the explanation, why sulfoxide catalyzed SN-reactions of alcohols do not allow the effective production of aliphatic and electron deficient chloro alkanes. Comparison experiments provided further insight into the reaction mechanism.

A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions

A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Nucleophilic substitution catalyzed by a supramolecular cavity proceeds with retention of absolute stereochemistry

While the reactive pocket of many enzymes has been shown to modify reactions of substrates by changing their chemical properties, examples of reactions whose stereochemical course is completely reversed are exceedingly rare. We report herein a class of wa

IMIDAZOTRIAZINONE COMPOUNDS

The present invention provides imidazotriazinone compounds which are inhibitors of phosphodiesterase 9 and pharmaceutically acceptable salt thereof. The present invention further provides processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of PDE9 associated diseases or disorders in mammals, including humans.

Supercritical carbon dioxide: A promoter of carbon-halogen bond heterolysis

Amazing reaction medium: Supercritical carbon dioxide, with zero dipole moment, lower dielectric constant than pentane, and non-hydrogen-bonding behavior, ionizes carbon-halogen bonds, dissociates the resulting ion pairs, and escapes from capture by the carbocation intermediates at temperatures above 40 °C. These properties allow the observation of carbocation chemistry in the absence of acids.

DMSO-catalyzed chlorination of alcohols using N-phenylbenzimidoyl chloride

N-phenylbenzimidoyl chloride has been demonstrated as an efficient chlorination reagent catalyzed by dimethyl sulfoxide (DMSO) in conversion of alcohols to corresponding chlorides. The reaction conditions were mild, and most of the substrates gave satisfactory yields. The configuration inversion of the chlorination was proved using optically active phenyl alcohols. The amount of DMSO can be as low as 0.001 eq without reducing the efficiency of the chlorination. A plausible mechanism for the reaction was proposed and proved by experiments. The reaction is stereoselective and potentially chemoselective among primary benzyl alcohols, secondary benzyl alcohols, and unactivated aliphatic alcohols.

IMIDAZOTRIAZINONE COMPOUNDS

The present invention provides imidazotriazinone compounds which are inhibitors of phosphodiesterase 9. The present invention further provides processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of PDE9 associated diseases or disorders in mammals, including CNS or neurodegeneration disorder.