1459-15-0

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-Phenyl-1-chloroethane is used as an intermediate in the production of pharmaceuticals for its ability to be chemically modified and incorporated into various drug molecules.
Used in Fragrance Industry:
(R)-1-Phenyl-1-chloroethane is used as a component in the synthesis of fragrances due to its sweet odor, contributing to the creation of various scent profiles.
Used in Organic Compounds Production:
(R)-1-Phenyl-1-chloroethane is used as an intermediate in the production of other organic compounds, highlighting its versatility in organic synthesis.
Used as a Solvent in Chemical Processes:
(R)-1-Phenyl-1-chloroethane is used as a solvent in various chemical processes, taking advantage of its ability to dissolve a range of substances and facilitate reactions.

Upstream product

• 7647-01-0 hydrogenchloride 
• 40435-14-1 (S)-1-phenyl-2-(tosyloxy)ethanol 
• 40434-87-5 (R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate 
• 1445-91-6 (S)-1-phenylethanol 
• 2570-00-5 3,3-dichloro-1,2-diphenylcyclopropene 
• 16197-92-5 (R)-1-phenethyl acetate 
• 98-85-1 1-Phenylethanol 
• 29002-72-0 tris{(+)-1-phenylethoxy}borane 
• 75-36-5 acetyl chloride 
• 672-65-1 (1-chloroethyl)benzene 
• 98-88-4 benzoyl chloride 
• 257298-92-3 (R)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane 
• 17279-31-1 (-)-(S)-N,N-dimethyl-1-phenylethylamine 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 

Downstream Products

• 53520-16-4 (4-chloro-phenyl)-((S)-1-phenyl-ethyl)-ether 
• 100975-85-7 1-methoxy-4-((S)-1-phenyl-ethoxy)-benzene 
• 89818-49-5 (S-)-(-) 1-phenylethyl 2-pyridyl sulfide 
• 111900-63-1 D-erythro-2,3-diphenyl-butyric acid 
• 1857-74-5 2,3-diphenylbutane 
• 100-41-4 ethylbenzene 
• 1861-02-5 1-deuterioethylbenzene 
• 4613-11-0 2,3-diphenylbutane 
• 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 
• 5789-35-5 (RR)/(SS)-2,3-diphenylbutane 
• 5789-35-5 RR,SS-2,3-diphenylbutane 
• 911820-07-0 2-amino-5-{[(1S)-1-phenylethyl]sulfanyl}[1,3]thiazolo[4,5-d]pyrimidin-7-ol 
• 911820-08-1 7-chloro-5-{[(1S)-1-phenylethyl]sulfanyl}[1,3]thiazolo[4,5-d]pyrimidin-2-amine 
• 1246182-86-4 C₈H₉⁽²⁾HO 

Relevant academic research and scientific papers

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.

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.

A PROCESS FOR THE STEREOSELECTIVE PREPARATION OF CHIRAL 2-[(HETERO)ARYLALKYLSULFANYL]PYRIMIDINES AND PRODUCTS OBTAINABLE THEREFROM

There is provided a process for the preparation of a compound of formula I, wherein R1 and R2 each have the meanings provided in the description. There is also provided a process for the preparation of pharmaceutically-active compoun

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.

Nucleophilic Substitutions of Alcohols in High Levels of Catalytic Efficiency

A practical method for the nucleophilic substitution (SN) of alcohols furnishing alkyl chlorides, bromides, and iodides under stereochemical inversion in high catalytic efficacy is introduced. The fusion of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent allows notable turnover numbers up to 100. Moreover, the use of plain acetyl chloride as a stoichiometric promotor in an invertive SN-type transformation is demonstrated for the first time. The operationally straightforward protocol exhibits high levels of stereoselectivity and scalability and tolerates a variety of functional groups.

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.

Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers

A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.

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

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.