CID 518827

Base Information

• Chemical Name: CID 518827
• CAS No.: 138-24-9
• Molecular Formula: C9H14N^.Cl
• Molecular Weight: 171.67
• Hs Code.: 29239000
• Mol file: 138-24-9.mol

Synonyms:

Chemical Property of CID 518827

Chemical Property:

• Appearance/Colour: White or greyish-blue crystalline powder
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 246-248 °C (dec.)(lit.)
• Refractive Index: 1.6224 (estimate)
• Boiling Point: 283.2°C (rough estimate)
• PSA: 0.00000
• Density: 1.0683 (rough estimate)
• LogP: -1.11270
• Storage Temp.: Store below +30°C.
• Sensitive.: Hygroscopic
• Solubility.: H2O: 0.1 g/mL, clear
• Water Solubility.: soluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 171.0814771
• Heavy Atom Count: 11
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

Phenyltrimethylammonium chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 24/25
• Safety Statements: 53-25-39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+](C)(C)C1=CC=CC=C1.[Cl-]
• Uses: Phenyltrimethylammonium chloride is an effective phase transfer catalyst, methylating agent, also useful for alkaline depolymerizations, corrosion inhibitor for low carbon steel.

Technology Process of CID 518827

There total 8 articles about CID 518827 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

bis(chloromethyl)mercury (5293-94-7) + N,N-dimethyl-aniline (121-69-7,77733-26-7) → phenyltrimethylammonium chloride (138-24-9) + 4,4'-methylene-bis(N,N-dimethylaniline) (101-61-1)

Guidance literature:

In dibutyl ether; at 100 ℃; for 48h;

Reference yield:

aniline (62-53-3) + methyl trifluoromethanesulfonate (333-27-7) → N-methylaniline hydrochloride (2739-12-0) + phenyltrimethylammonium chloride (138-24-9) + aniline hydrochloride (142-04-1,36663-09-9) + N,N-dimethylaniline hydrochloride (5882-44-0)

Guidance literature:

aniline; methyl trifluoromethanesulfonate; With 1,1,1,3',3',3'-hexafluoro-propanol; In d⁽⁴⁾-methanol; at 20 ℃; for 1h;

With hydrogenchloride; In water; for 1h;

DOI:10.1039/c3cc48997c

Reference yield:

phenyltrimethylammonium iodide (98-04-4) → phenyltrimethylammonium chloride (138-24-9)

Guidance literature:

With silver(I) chloride;

upstream raw materials:

phenyltrimethylammonium iodide

methylene chloride

N,N-dimethyl-aniline

bis(chloromethyl)mercury

Downstream raw materials:

1-bromo-4-methoxy-benzene

N,N-dimethyl-aniline

4-tert-butylcyclohexyl methyl ether

3-methoxy-1-phenylpropene

Refernces

A simplified synthesis of (±)-4-hydroxy-N-methylmorphinan-6-one

10.1021/jo00147a039

The research presents a simplified synthesis of (±)-4-hydroxy-N-methylmorphinan-6-one (2) and its methyl ether (3), which exhibit morphine-like antinociceptive activity. The synthesis involves several key steps and chemicals. Initially, the ketone 5 is reduced with L-Selectride in DMF and THF to obtain the triol 6. Subsequently, 6 is O-alkylated with 5-chloro-1-phenyl-1H-tetrazole in the presence of potassium carbonate to yield ethers 7 and 8. Hydrogenolysis of 7 over Pd/C in acetic acid produces acetate 10 and diol 9. Hydrolysis of 9 and 10 with methanolic HCl affords amine 11, which is then reductively N-methylated to form diol 12. Oppenauer oxidation of 12 with benzophenone and potassium tert-butoxide yields ketone 2 and an interesting byproduct, diphenylmethylene ketone 13. Additionally, O-methylation of 12 with phenyltrimethylammonium chloride produces ether alcohol 14, which upon further reaction yields the desired methyl ether 3. Finally, demethylation of 3 with BBr3 in chloroform gives phenol 2. The synthesized compounds 2 and 3 show significant antinociceptive activity, making them valuable for further pharmacological studies.