2538-34-3

Basic information

• Product Name: C-(4-METHOXY-PHENYL)-C-PHENYL-METHYLAMINE
• Synonyms: AKOS BC-0992;(4-METHOXYPHENYL)(PHENYL)METHYLAMINE;C-(4-METHOXY-PHENYL)-C-PHENYL-METHYLAMINE;P-METHOXYBENZHYDRYLAMINE;TIMTEC-BB SBB007370;Nsc505711
• CAS NO: 2538-34-3
• Molecular Formula: C₁₄H₁₅NO
• Molecular Weight: 213.27
• Mol File: 2538-34-3.mol

Chemical Properties

• Boiling Point: 348.3°Cat760mmHg
• Flash Point: 167.1°C
• Appearance: /
• Density: 1.181
• Vapor Pressure: 5.07E-05mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: C-(4-METHOXY-PHENYL)-C-PHENYL-METHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: C-(4-METHOXY-PHENYL)-C-PHENYL-METHYLAMINE(2538-34-3)
• EPA Substance Registry System: C-(4-METHOXY-PHENYL)-C-PHENYL-METHYLAMINE(2538-34-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 2538-34-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
C-(4-METHOXY-PHENYL)-C-PHENYL-METHYLAMINE is used as a precursor in the synthesis of psychoactive compounds for research and medicinal purposes. It plays a crucial role in the development of new drugs and therapies for various medical conditions.
Used in Research and Development:
C-(4-METHOXY-PHENYL)-C-PHENYL-METHYLAMINE is used as a research chemical for studying the effects of psychoactive substances on the central nervous system. It helps scientists understand the mechanisms of action and potential therapeutic applications of these compounds.
Used in Illicit Substances Production:
C-(4-METHOXY-PHENYL)-C-PHENYL-METHYLAMINE is used as a precursor in the production of designer drugs and illicit substances, such as MDMA (ecstasy) and other related compounds. However, its use in this context is highly regulated and often illegal due to the potential for abuse and harm to human health.

InChI:InChI=1/C14H15NO/c1-16-13-9-7-12(8-10-13)14(15)11-5-3-2-4-6-11/h2-10,14H,15H2,1H3

Upstream product

• 611-94-9 4-Methoxybenzophenone 
• 540-69-2 ammonium formate 
• 64-17-5 ethanol 
• 10147-60-1 (4-methoxyphenyl)phenylmethanone oxime 
• 123-11-5 4-methoxy-benzaldehyde 
• 623-12-1 4-chloromethoxybenzene 
• 6229-07-8 N-benzylxanthone imine 
• 100-58-3 phenylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 1309244-68-5 C₂₂H₂₁NO₃ 
• 64187-51-5 N-trimethylsilyl(4-methoxy)benzaldimine 
• 24316-60-7 (4-methoxyphenyl)(phenyl)methanone oxime 
• 100-66-3 methoxybenzene 
• 100-47-0 benzonitrile 

Downstream Products

• 138768-32-8 N-((4-methoxyphenyl)(phenyl)methyl)benzamide 
• 611-94-9 4-Methoxybenzophenone 
• 1380114-32-8 N-benzylidine-1-(4-methoxyphenyl)-1-phenylmethanamine 
• 133175-59-4 (R)-2-Fluoro-N-[(R)-(4-methoxy-phenyl)-phenyl-methyl]-2-phenyl-acetamide 
• 133175-67-4 (R)-2-Fluoro-N-[(S)-(4-methoxy-phenyl)-phenyl-methyl]-2-phenyl-acetamide 

Relevant articles and documents

New imino-methoxy derivatives: design, synthesis, characterization, antimicrobial activity, DNA interaction and molecular docking studies

Four new diarylmethylamine imine compounds (5a-5d) were prepared in order to examine their DNA binding properties, antimicrobial activity and molecular docking. The compounds were characterized by the common spectroscopic and analytic methods. Furthermore

Sequential Selective C?H and C(sp3)?+P Bond Functionalizations: An Entry to Bioactive Arylated Scaffolds

Organophosphonium salts containing C(sp3)?+P bonds are among the most utilized reagents in organic synthesis for constructing C?C double bonds. However, their use as C-selective electrophilic groups is rare. Here, we explore an efficient and general transition-metal-free method for sequential chemo- and regioselective C?H and C(sp3)?+P bond functionalizations. In the present study, C?H alkylation resulting in the synthesis of benzhydryl triarylphosphonium salts was achieved by one-pot, four-component cross-coupling reactions of simple and commercially available starting materials. The utility of the resulting phosphonium salt building blocks was demonstrated by the chemoselective post-functionalization of benzylic C(sp3)?+PPh3 groups to achieve aminations, thiolations, and arylations. In this way, benzhydrylamines, benzhydrylthioethers, and triarylmethanes, structural motifs that are present in many pharmaceuticals and agrochemicals, are readily accessed. These include the synthesis of two anticancer agents from simple materials in only two to three steps. Additionally, a protocol for late-stage functionalization of bioactive drugs has been developed using benzhydrylphosphonium salts. This new approach should provide novel transformations for application in both academic and pharmaceutical research.

Hydrogen bond directed aerobic oxidation of amines via photoredox catalysis

An application of H-bonding interactions for directing the α-C-H oxidation of amines to amides and amino-ketones catalyzed by an organic photocatalyst is reported. The high efficiency of this method is demonstrated by the aerobic oxidation of pyrrolidines, diarylamines and benzylamines bearing urea groups with high yields and a wide substrate scope.

Direct Conversion of Aldehydes and Ketones into Azides by Sequential Nucleophilic Addition and Substitution

This report describes the direct conversion of aldehydes and ketones into alkyl azides by the addition of common organometallic reagents and tandem conversion of the resulting alkoxides without isolation of the intermediate alcohols. A wide range of aldehydes and organometallic reagents (R–Li or R–MgX) are suitable participants in this process. Additional reaction telescoping beyond azide formation is demonstrated.

Solvent-free amination of secondary benzylic alcohols with N-nucleophiles catalyzed by FeCl3

A general, simple, and environmentally friendly method for the direct amination of secondary benzyl alcohols with amides or 4-nitroaniline is described. This method has been applied to a variety of substrates, and the reaction proceeded smoothly at room temperature under solvent-free conditions. CbzNH2 was proved to be very useful in the direct preparation of the benzylic amines from corresponding alcohols.

Carbon-carbon bond formations at the benzylic positions of N-benzylxanthone imines and N-benzyldi-1-naphthyl ketone imine

Two N-benzyl imines are designed to allow for carbon-carbon bond formations at the aminated benzylic positions. Direct benzylic arylation reactions of N-benzylxanthone imine with aryl chlorides proceed under palladium catalysis in the presence of cesium hydroxide, yielding the corresponding benzhydrylamine derivatives. Alkylation reactions of N-benzyldi-1-naphthyl ketone imine with alkyl halides in the presence of potassium tert-butoxide afford the corresponding 1-phenylalkylamines in high yields. Conjugate addition of N-benzyldi-1-naphthyl ketone imine is also described.

Palladium-catalyzed benzylic arylation of N-benzylxanthone imine

(Chemical Equation Presented) The direct benzylic arylation of N-benzylxanthone imine with aryl chloride proceeds under palladium catalysis, yielding the corresponding coupling product. The product is readily transformed to benzhydrylamine. Taking into consideration that the imine is readily available from benzylic amine, the overall transformation represents a formal cross-coupling reaction of aryl halide with α-aminobenzyl metal.

METHODS OF PREPARING PRIMARY, SECONDARY AND TERTIARY CARBINAMINE COMPOUNDS IN THE PRESENCE OF AMMONIA

The present application relates to novel methods for the preparation of primary, secondary and tertiary carbinamine compounds, particularly the preparation of compounds of formulae I, IV and VI, from a carbonyl compound of formula II in the presence of ammonia or an ammonium equivalent of the formula NH4+X-, by way of allylation, crotylation, arylation, reductive amination and catalytic hydrogenation.

A practical synthesis of para di- and mono-substituted benzhydrylamines from benzhydrol precursors

A series of para-substituted benzhydrylamines 6 were obtained by substitution of the corresponding benzhydrol precursors 1 with phenyl carbamate 2 under acidic conditions, followed by basic hydrolysis of the carbamate intermediates 3. One unsymmetrical intermediate 3i has been resolved by preparative chiral chromatography. Subsequent deprotection of the carbamate function led to the recovery of enantiomerically pure (+)- and (-)- 4-chlorobenzhydryl amines.

Preparation of Primary Amines and 2-Azetidinones via N-Trimethylsilyl Imines

Nonenolizable aldehydes react with lithium bis(trimethylsilyl)amide at ambient temperatures to afford solutions of N-trimethylsilyl aldimines.Treatment of these solutions with Grignard reagents or alkyllithiums followed by an aqueous workup gives primary amines in moderate to excellent yields.Treatment of N-trimethylsilyl aldimines with ester enolates provides an expedient route to 1-unsubstituted 2-azetidinones.