13114-22-2

Basic information

• Product Name: N-[(4-CHLOROPHENYL)METHYLENE]METHANAMINE
• Synonyms: N-[(4-CHLOROPHENYL)METHYLENE]METHANAMINE;p-Chlorobenzylidene methylamine
• CAS NO: 13114-22-2
• Molecular Formula: C₈H₈ClN
• Molecular Weight: 153.60882
• Mol File: 13114-22-2.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 266.2°C at 760 mmHg
• Flash Point: 114.8°C
• Appearance: /
• Density: 1.185g/cm³
• Vapor Pressure: 0.00879mmHg at 25°C
• Refractive Index: 1.627
• CAS DataBase Reference: N-[(4-CHLOROPHENYL)METHYLENE]METHANAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(4-CHLOROPHENYL)METHYLENE]METHANAMINE(13114-22-2)
• EPA Substance Registry System: N-[(4-CHLOROPHENYL)METHYLENE]METHANAMINE(13114-22-2)

Safety Data

• Hazardous Substances Data: 13114-22-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H8ClN/c9-8-3-1-7(2-4-8)5-6-10/h1-6H,10H2/b6-5+

Upstream product

• 593-51-1 methylamine hydrochloride 
• 104-88-1 4-chlorobenzaldehyde 
• 74-89-5 methylamine 
• 111323-52-5 C₁₅H₁₃ClF₃NO₃S 
• 82044-38-0 2-methyl-3-p-chlorooxaziridine 
• 104-11-0 N-methyl-4-chlorobenzylamine 
• 96-31-1 N,N'-Dimethylurea 
• 75-52-5 nitromethane 
• 65398-48-3 methylammonium N-methylcarbamate 

Downstream Products

• 100865-58-5 N-[4-chloro-α-(4-chloro-benzylidenamino)-benzyl]-formamide 
• 16486-29-6 4,6-bis-(4-chloro-phenyl)-3,5-dimethyl-[1,3,5]thiadiazinane-2-thione 
• 66172-21-2 4-(4-chloro-phenyl)-5-methyl-2,6-bis-(2,2,2-trifluoro-1-trifluoromethyl-ethylidene)-[1,3,5]dithiazinane 
• 51834-47-0 3-(4-chloro-phenyl)-2-methyl-2,3-dihydro-9H-indeno[2,1-e][1,4,3]oxathiazine 1,1-dioxide 
• 51874-97-6 2-(4-chloro-phenyl)-3-methyl-2,3,5,6-tetrahydro-naphtho[2,1-e][1,4,3]oxathiazine 4,4-dioxide 
• 39214-20-5 C₁₀H₈Cl₂N₂O₂ 
• 55881-66-8 3r-(4-chloro-phenyl)-2-methyl-4c-phenyl-[1,2]thiazetidine 1,1-dioxide 
• 55881-66-8 3r-(4-chloro-phenyl)-2-methyl-4t-phenyl-[1,2]thiazetidine 1,1-dioxide 
• 132907-12-1 (+/-)-trans-2-(4-chlorophenyl)-3,5-dimethylthiazolidin-4-one 
• 132907-12-1 (+/-)-cis-2-(4-chlorophenyl)-3,5-dimethylthiazolidin-4-one 
• 41555-47-9 1-(4-chlorobenzylidene)-2-methylhydrazine 
• 104-11-0 N-methyl-4-chlorobenzylamine 
• 106711-77-7 cis-N-methyl-3-(p-chlorophenyl)-4-carboxy-3,4-dihydro-1(2H)-isoquinolone 
• 106711-77-7 trans-N-methyl-3-(p-chlorophenyl)-4-carboxy-3,4-dihydro-1(2H)-isoquinolone 

Relevant articles and documents

4,4′-Trimethylenedipiperidine, a safe and greener alternative for piperidine, catalyzed the synthesis of N-methyl imines

A practical and facile synthesis of various N-methyl imines, versatile scaffolds, was conducted at 85?°C using 4,4′-trimethylenedipiperidine as a safe and green catalyst. This reagent is a commercially available solid and can be handled easily. It has high thermal stability, low toxicity, and good solubility in green solvents such as water and ethanol. The regenerated catalyst demonstrated stable activity after several recycle runs, and any changes were detected in its chemical structure by 1H NMR monitoring. The novelty of the current work is that the 4,4′-trimethylenedipiperidine can act as a promising alternative for piperidine in organic reaction at higher temperatures due to its broad liquid range temperature, thermal stability, acceptor/donor hydrogen bond property, and other unique merits. Furthermore, the current protocol avoids waste generation in the workup process, which is a drawback in most previous reported procedures.

Stable carbamate pathway towards organic-inorganic hybrid perovskites and aromatic imines

Methyl ammonium methyl carbamate (MAC), formulated as CH3NH3+CH3NHCO2-, was synthesized by reacting liquid methylamine with supercritical CO2, and its structure was refined by single-crystal X-ray diffraction. MAC is a white crystalline salt and is as reactive as methylamine, and is a very efficient alternative to toxic methylamine. We were able to produce hybrid perovskite MAPbI3 (MA = methyl ammonium) by grinding MAC with PbI2 and I2 at room temperature, followed by storing the mixed powder. Moreover, this one-pot method is easily scalable for the large-scale synthesis of MAPbI3 in a small vessel. We have also investigated the reactivity of MAC towards aromatic aldehydes in the absence of solvent. The solventless reactions afforded imines as exclusive products with over 97% yield, which show higher selectivity than the methylamine-based synthesis. Complete conversions were typically accomplished within 3 h at 25 °C. The results of this study emphasize the importance of solid carbamates such as MAC to develop an environmentally friendly process for the synthesis of various amine-based materials on the industrial scale.

Epoxide-Mediated Stevens Rearrangements of α-Amino-Acid-Derived Tertiary Allylic, Propargylic, and Benzylic Amines: Convenient Access to Polysubstituted Morpholin-2-ones

A new strategy has been established for the synthesis of polysubstituted morpholin-2-ones through Stevens rearrangements of tertiary amines via in situ activation with epoxides. A range of α-amino acid-derived tertiary allylic, propargylic, and benzylic amines reacted with epoxides in the presence of zinc halide catalysts to afford structurally diverse allyl-, allenyl-, and benzyl-substituted morpholin-2-ones, respectively, in moderate-to-good yields with high regioselectivity. The process involves [2,3]- and [1,2]-Stevens rearrangements of quaternary ammonium ylide intermediates and constitutes a very convenient method to prepare polysubstituted morpholin-2-ones through tandem formation of C?N, C?O, and C?C bonds. Moreover, replacing epoxides with aziridines permitted the synthesis of polysubstituted piperazin-2-ones.