89585-53-5

Basic information

• Product Name: 3-chloro-N-methyl-N-phenylpropanamide
• Synonyms: 3-chloro-N-methyl-N-phenylpropanamide;UKRORGSYN-BB BBV-036972;3-chloro-N-methyl-N-phenylpropanamide(SALTDATA: FREE)
• CAS NO: 89585-53-5
• Molecular Formula: C₁₀H₁₂ClNO
• Molecular Weight: 197.66
• Mol File: 89585-53-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 289°C at 760 mmHg
• Flash Point: 128.6°C
• Appearance: /
• Density: 1.169g/cm³
• Vapor Pressure: 0.00226mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: 3-chloro-N-methyl-N-phenylpropanamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-N-methyl-N-phenylpropanamide(89585-53-5)
• EPA Substance Registry System: 3-chloro-N-methyl-N-phenylpropanamide(89585-53-5)

Safety Data

• Hazardous Substances Data: 89585-53-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H12ClNO/c1-12(10(13)7-8-11)9-5-3-2-4-6-9/h2-6H,7-8H2,1H3

Upstream product

• 625-36-5 2-chloropropionyl chloride 
• 100-61-8 N-methylaniline 

Downstream Products

• 18859-20-6 N-methyl-N-phenyl-3-phenylpropanamide 
• 6273-94-5 N-methyl-N-phenylacrylamide 

Relevant articles and documents

Stereoelectronic and Resonance Effects on the Rate of Ring Opening of N-Cyclopropyl-Based Single Electron Transfer Probes

N-Cyclopropyl-N-methylaniline (5) is a poor probe for single electron transfer (SET) because the corresponding radical cation undergoes cyclopropane ring opening with a rate constant of only 4.1 × 104 s-1, too slow to compete with other processes such as radical cation deprotonation. The sluggish rate of ring opening can be attributed to either (i) a resonance effect in which the spin and charge of the radical cation in the ring-closed form is delocalized into the phenyl ring, and/or (ii) the lowest energy conformation of the SET product (5a￠+) does not meet the stereoelectronic requirements for cyclopropane ring opening. To resolve this issue, a new series of N-cyclopropylanilines were designed to lock the cyclopropyl group into the required bisected conformation for ring opening. The results reveal that the rate constant for ring opening of radical cations derived from 1′-methyl-3′,4′-dihydro-1′H-spiro[cyclopropane-1,2′-quinoline] (6) and 6′-chloro-1′-methyl-3′,4′-dihydro-1′H-spiro[cyclopropane-1,2′-quinoline] (7) are 3.5 × 102 s-1 and 4.1 × 102 s-1, effectively ruling out the stereoelectronic argument. In contrast, the radical cation derived from 4-chloro-N-methyl-N-(2-phenylcyclopropyl)aniline (8) undergoes cyclopropane ring opening with a rate constant of 1.7 × 108 s-1, demonstrating that loss of the resonance energy associated with the ring-closed form of these N-cyclopropylanilines can be amply compensated by incorporation of a radical-stabilizing phenyl substituent on the cyclopropyl group. Product studies were performed, including a unique application of EC-ESI/MS (Electrochemistry/ElectroSpray Ionization Mass Spectrometry) in the presence of 18O2 and H218O to elucidate the mechanism of ring opening of 7a￠+ and trapping of the resulting distonic radical cation.

4-[diaryl)hydroxymethyl]-1-piperidinealkylcarboxylic acids, salts and esters useful in the treatment of allergic disorders

Novel compounds useful in the treatment of allergic disorders and having the formula: STR1 where Ar and Ar1 are pyridinyl, phenyl, or substituted phenyl and where Y is --OH,--O? M≈ m,--O--loweralkyl, --O--Aryl, or NR1 R2 (R1, R2 =H, loweralkyl, aryl) are herein disclosed.