4-(Dimethylthiocarbamoyloxy)benzoic acid methyl ester

Base Information

• Chemical Name: 4-(Dimethylthiocarbamoyloxy)benzoic acid methyl ester
• CAS No.: 13492-59-6
• Molecular Formula: C11H13NO3S
• Molecular Weight: 239.295
• NSC Number: 171479
• DSSTox Substance ID: DTXSID70305690
• Nikkaji Number: J1.628.046A
• Wikidata: Q82052412
• Mol file: 13492-59-6.mol

Synonyms:13492-59-6;4-(dimethylthiocarbamoyloxy)benzoic acid methyl ester;NSC171479;SCHEMBL11305905;DTXSID70305690;NSC-171479;methyl 4-[(dimethylcarbamothioyl)oxy]benzoate

Chemical Property of 4-(Dimethylthiocarbamoyloxy)benzoic acid methyl ester

Chemical Property:

• Vapor Pressure: 0.000325mmHg at 25°C
• Boiling Point: 320.1°C at 760 mmHg
• Flash Point: 147.4°C
• Density: 1.217g/cm³
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 239.06161445
• Heavy Atom Count: 16
• Complexity: 260

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C(=S)OC1=CC=C(C=C1)C(=O)OC

Technology Process of 4-(Dimethylthiocarbamoyloxy)benzoic acid methyl ester

There total 5 articles about 4-(Dimethylthiocarbamoyloxy)benzoic acid methyl ester 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: 98.0%

methyl 4-hydroxylbenzoate (99-76-3,156291-94-0) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-(4-carbomethoxyphenyl) N,N-dimethylthiocarbamate (13492-59-6)

Guidance literature:

With potassium fluoride on basic alumina; In acetonitrile; for 16h; Ambient temperature;

DOI:10.1080/00397919608004558

Reference yield:

4-hydroxy-benzoic acid (99-96-7) → O-(4-carbomethoxyphenyl) N,N-dimethylthiocarbamate (13492-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / NaY faujasite / 24 h / 165 °C

2: DABCO

With 1,4-diaza-bicyclo[2.2.2]octane; NaY faujasite;

DOI:10.1021/jo0520792

Reference yield:

Chlorthionameisensaeure-p-methoxycarbonylphenylester (10506-31-7) + dimethyl amine (124-40-3) → O-(4-carbomethoxyphenyl) N,N-dimethylthiocarbamate (13492-59-6)

Guidance literature:

In acetone;

DOI:10.1246/bcsj.44.1393

upstream raw materials:

Chlorthionameisensaeure-p-methoxycarbonylphenylester

dimethyl amine

methyl 4-hydroxylbenzoate

N,N-Dimethylthiocarbamoyl chloride

Downstream raw materials:

4-<(dimethylcarbamoyl)thio>benzoic acid

4--benzoesaeure

S-(4-carbomethoxyphenyl) N,N-dimethylthiocarbamate

Refernces

• 1、 Roesel, Arend F.,Ugandi, Mihkel,Huyen, Nguyen Thi Thu,Májek, Michal,Broese, Timo,Roemelt, Michael,Francke, Robert. "Electrochemically Catalyzed Newman-Kwart Rearrangement: Mechanism, Structure-Reactivity Relationship, and Parallels to Photoredox Catalysis". . p. 8029 - 8044. Retrieved 2020/07/25.
• 2、 Gilday, John P.,Lenden, Philip,Moseley, Jonathan D.,Cox, Brian G.. "The Newman-Kwart rearrangement: A microwave kinetic study". . p. 3130 - 3134. Retrieved 2008/09/19.