Methyl 4-isocyanatobenzoate

Base Information

• Chemical Name: Methyl 4-isocyanatobenzoate
• CAS No.: 23138-53-6
• Molecular Formula: C9H7NO3
• Molecular Weight: 177.159
• Hs Code.: 2929109000
• European Community (EC) Number: 627-644-0
• NSC Number: 132096
• DSSTox Substance ID: DTXSID30299687
• Nikkaji Number: J529.554H
• Mol file: 23138-53-6.mol

Synonyms:Methyl 4-isocyanatobenzoate;23138-53-6;4-Methoxycarbonyphenyl isocyanate;Benzoic acid, 4-isocyanato-, methyl ester;MFCD01863690;NSC132096;Methyl4-isocyanatobenzoate;methyl-4-isocyanatobenzoate;SCHEMBL445414;4-carbomethoxy-phenylisocyanate;AMY118;DTXSID30299687;FQDDBYGPHUUTRN-UHFFFAOYSA-N;Methyl 4-isocyanatobenzoate, 98%;BBL037643;STK502536;METHYL 4-ISOCYANATOBENZOATE98;4-isocyanato-benzoic acid methyl ester;AKOS005171064;NSC-132096;SY019627;VS-14340;BB 0255294;FT-0678561;EN300-201177;J-015000;InChI=1/C9H7NO3/c1-13-9(12)7-2-4-8(5-3-7)10-6-11/h2-5H,1H

Chemical Property of Methyl 4-isocyanatobenzoate

Chemical Property:

• Vapor Pressure: 0.00943mmHg at 25°C
• Melting Point: 50-52 °C(lit.)
• Refractive Index: 1.528
• Boiling Point: 264.9 °C at 760 mmHg
• Flash Point: 123.2 °C
• PSA: 55.73000
• Density: 1.15 g/cm³
• LogP: 1.44050
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 177.042593085
• Heavy Atom Count: 13
• Complexity: 225

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 4-isocyanatobenzoate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(C=C1)N=C=O
• Uses: Methyl 4-isocyanatobenzoate may be used in the preparation of benzimidazole-1-carboxamide-[N-(4-methylbenzoate)] 2-methylcarbamate. This compound shows significant antitumor potency against the prostate cancer cells.

Technology Process of Methyl 4-isocyanatobenzoate

There total 9 articles about Methyl 4-isocyanatobenzoate 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%

4-methoxycarbonyl aniline (619-45-4) + trichloromethyl chloroformate (503-38-8) → methyl 4-isocyanatobenzoate (23138-53-6)

Guidance literature:

In 1,4-dioxane; for 8h; Reflux;

DOI:10.1016/j.bmc.2012.04.055

Reference yield: 94.0%

phosgene (75-44-5) + methyl 4-[(trimethylsilyl)amino]benzoate → methyl 4-isocyanatobenzoate (23138-53-6)

Guidance literature:

In toluene; at 0 ℃;

DOI:10.1134/S1070363206070115

Reference yield: 63.0%

bis(trichloromethyl) carbonate (32315-10-9) + 4-methoxycarbonyl aniline (619-45-4) → methyl 4-isocyanatobenzoate (23138-53-6)

Guidance literature:

With triethylamine; In benzene; Heating;

DOI:10.1002/ps.2780420406

upstream raw materials:

phosgene

4-methoxycarbonyl aniline

4-azidocarbonyl-benzoic acid methyl ester

bis(trichloromethyl) carbonate

Downstream raw materials:

4-allyloxycarbonylamino-benzoic acid methyl ester

C₁₅H₁₄N₄O₄

methyl 4-(isoindoline-2-carboxamido)benzoate

N-{4-[(3-phenylpropyl)carbamoyl]phenyl}-1,3-dihydro-2H-isoindole-2-carboxamide

Refernces

• 1、 Hong, Wan Pyo,Tran, Van Hieu,Kim, Hee-Kwon. "Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions". . p. 15890 - 15895. Retrieved 2021/05/19.
• 2、 Rawling, Tristan,McDonagh, Andrew M.,Tattam, Bruce,Murray, Michael. "Synthesis of unsymmetrical biaryl ureas from N-carbamoylimidazoles: Kinetics and application". . p. 6065 - 6070. Retrieved 2012/09/22.