3756-41-0

Basic information

• Product Name: (S)-1-Phenyl-1-chloroethane
• Synonyms: (-)-[(S)-1-Chloroethyl]benzene;(S)-1-Phenyl-1-chloroethane;[(S)-1-Chloroethyl]benzene
• CAS NO: 3756-41-0
• Molecular Formula: C₈H₉Cl
• Molecular Weight: 140.61006
• Mol File: 3756-41-0.mol
• Article Data: 20

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-1-Phenyl-1-chloroethane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-Phenyl-1-chloroethane(3756-41-0)
• EPA Substance Registry System: (S)-1-Phenyl-1-chloroethane(3756-41-0)

Safety Data

• Hazardous Substances Data: 3756-41-0(Hazardous Substances Data)

Usage

Description

(S)-1-Phenyl-1-chloroethane, also known as (S)-alpha-Methylbenzyl chloride, is an organic compound characterized by its chemical formula C8H9Cl. As a chiral compound, it possesses a non-superimposable mirror image, which is significant in the context of its applications. This colorless liquid exhibits a sweet, floral odor and is insoluble in water, yet it is soluble in many organic solvents. Its properties and reactivity make it a valuable building block in the synthesis of other organic compounds, particularly within the pharmaceutical and chemical industries.

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

• 1517-69-7 (R)-1-phenylethanol 
• 1445-91-6 (S)-1-phenylethanol 
• 7647-01-0 hydrogenchloride 
• 29002-72-0 tris{(+)-1-phenylethoxy}borane 
• 98-85-1 1-Phenylethanol 
• 75-36-5 acetyl chloride 
• 10035-10-6 hydrogen bromide 
• 672-65-1 (1-chloroethyl)benzene 
• 98-88-4 benzoyl chloride 
• 16197-92-5 (R)-1-phenethyl acetate 
• 257298-92-3 (R)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane 
• 40434-87-5 (R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate 
• 40435-14-1 (S)-1-phenyl-2-(tosyloxy)ethanol 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 

Downstream Products

• 779-54-4 (R)-phenyl-(1-phenylethyl)amine 
• 7529-63-7 (1'S)-(-)-1-(1'-phenylethyl)piperidine 
• 1861-02-5 (-)deuteriophenylethane 
• 1369514-84-0 2-((3,4-trans)-4-methyl-1-((R)-1-phenylethyl)pyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one 
• 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 
• 911715-89-4 (2R)-2-[(2-methoxy-5-{[(1R)-1-phenylethyl]sulfanyl}-[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol 
• 911715-92-9 (2R)-2-[(2-methoxy-5-{[(1S)-1-phenylethyl]sulfanyl}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol 
• 911715-88-3 (2R)-2-[(2-chloro-5-{[(1R)-1-phenylethyl]sulfanyl}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol 
• 911715-91-8 (2R)-2-[(2-chloro-5-{[(1S)-1-phenylethyl]sulfanyl}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol 
• 911715-90-7 (2R)-2-[(2-amino-5-{[(1R)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol 
• 911715-90-7 (2R)-2-[(2-amino-5-{[(1S)-1-phenylethyl]sulfanyl}- [1,3] thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 1028800-73-8 2-chloro-3-(1-phenyl-ethoxy)-cyclohex-2-enone 
• 1028800-74-9 2-chloro-5,5-dimethyl-3-(1-phenyl-ethoxy)-cyclohex-2-enone 

Relevant articles and documents

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.

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.

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.