3-Dimethylaminobenzoyl chloride

Base Information

• Chemical Name: 3-Dimethylaminobenzoyl chloride
• CAS No.: 54263-82-0
• Molecular Formula: C9H10ClNO
• Molecular Weight: 183.637
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID30426633
• Wikidata: Q82239495
• Mol file: 54263-82-0.mol

Synonyms:3-DIMETHYLAMINOBENZOYL CHLORIDE;54263-82-0;3-(dimethylamino)benzoyl chloride;Benzoyl chloride, 3-(dimethylamino)-;3-DIMETHYLAMINOBENZOYL CHLORIDE, 95;m-dimethylaminobenzoyl chloride;SCHEMBL220517;3-dimethylamino-benzoyl chloride;DTXSID30426633;CUECQYFYMGJLJD-UHFFFAOYSA-N;AKOS009159301;BP-10206;FT-0615606

Chemical Property of 3-Dimethylaminobenzoyl chloride

Chemical Property:

• Vapor Pressure: 0.00495mmHg at 25°C
• Refractive Index: 1.574
• Boiling Point: 275.9 °C at 760 mmHg
• Flash Point: 120.7 °C
• PSA: 20.31000
• Density: 1.193 g/cm³
• LogP: 2.13160
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 183.0450916
• Heavy Atom Count: 12
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

3-Dimethylaminobenzoyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R34:Causes burns.
• Hazard Codes: R34:Causes burns.
• Statements: R34:Causes burns.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36/37/39:Wear suitabl

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=CC(=C1)C(=O)Cl

Technology Process of 3-Dimethylaminobenzoyl chloride

There total 4 articles about 3-Dimethylaminobenzoyl chloride 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: 100.0%

3-(dimethylamino)benzoic acid (99-64-9) → 3-(dimethylamino)benzoyl chloride (54263-82-0)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 6h;

DOI:10.1002/adsc.201601108

Reference yield:

butyryl chloride (141-75-3) + 3-(dimethylamino)phenyl trifluoromethanesulfonate (365427-36-7) → 3-(dimethylamino)benzoyl chloride (54263-82-0)

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 100 ℃; for 16h; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.202005891

Reference yield:

3-Dimethylaminophenol (99-07-0) → 3-(dimethylamino)benzoyl chloride (54263-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 °C

2: bis(η3-allyl-μ-chloropalladium(II)); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine / toluene / 16 h / 100 °C / Sealed tube; Inert atmosphere

With bis(η3-allyl-μ-chloropalladium(II)); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In dichloromethane; toluene;

DOI:10.1002/anie.202005891

upstream raw materials:

3-(dimethylamino)benzoic acid

butyryl chloride

3-(dimethylamino)phenyl trifluoromethanesulfonate

3-Dimethylaminophenol

Downstream raw materials:

2-(3-dimethylamino-phenyl)-3-methyl-benzothiazolium; iodide

3-(dimethylamino)benzoic anhydride

2-chloro-10-(3-dimethylamino-benzoyl)-10H-phenothiazine

3-(dimethylamino)benzoic acid methyl ester

Refernces

• 1、 Bismuto, Alessandro,Boehm, Philip,Morandi, Bill,Roediger, Sven. "Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide". supporting information. p. 17887 - 17896. Retrieved 2020/08/19.
• 2、 Sijm, Maarten,Siciliano de Araújo, Julianna,Ramos Llorca, Alba,Orrling, Kristina,Stiny, Lydia,Matheeussen, An,Maes, Louis,de Esch, Iwan J. P.,de Nazaré Correia Soeiro, Maria,Sterk, Geert Jan,Leurs, Rob. "Identification of Phenylpyrazolone Dimers as a New Class of Anti-Trypanosoma cruzi Agents". supporting information. p. 1662 - 1668. Retrieved 2019/08/30.