Benzoyl isocyanate

Base Information

• Chemical Name: Benzoyl isocyanate
• CAS No.: 4461-33-0
• Molecular Formula: C8H5NO2
• Molecular Weight: 147.133
• Hs Code.: 29291000
• European Community (EC) Number: 224-717-5
• NSC Number: 246191
• UNII: RW47ZKR2X7
• DSSTox Substance ID: DTXSID90196249
• Nikkaji Number: J80.842C
• Mol file: 4461-33-0.mol

Synonyms:Benzoicacid, anhydride with HNCO (6CI,7CI);Benzoic acid, anhydride with isocyanicacid (8CI);Isocyanic acid, anhydride with benzoic acid;NSC 246191;

Chemical Property of Benzoyl isocyanate

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 0.335mmHg at 25°C
• Melting Point: 25.9°C
• Refractive Index: n20/D 1.5514(lit.)
• Boiling Point: 199.8 °C at 760 mmHg
• Flash Point: 72.2 °C
• PSA: 46.50000
• Density: 1.11 g/cm³
• LogP: 1.16260
• Storage Temp.: -20°C
• Sensitive.: Moisture Sensitive
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 147.032028402
• Heavy Atom Count: 11
• Complexity: 188

Purity/Quality:

97% ^*data from raw suppliers

Benzoyl Isocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-27-28-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)N=C=O
• General Description: Benzoyl isocyanate is identified as a product formed during the reaction of benzoylcyanate oxide (BZNO) with pyridine, where a fragile zwitterionic intermediate decomposes to yield benzoyl isocyanate among other products. The formation of benzoyl isocyanate is influenced by solvent polarity and reaction conditions, highlighting its role as a reactive intermediate in these transformations.

Technology Process of Benzoyl isocyanate

There total 30 articles about Benzoyl isocyanate 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: 92.8%

sodium isocyanate (917-61-3) + benzoyl chloride (98-88-4) → benzoyl isocyanate (4461-33-0)

Guidance literature:

With toluene-4-sulfonic acid; zinc(II) chloride; In diethylene glycol dimethyl ether; at 40 - 60 ℃; for 6.5h;

Reference yield: 89.89%

bis(trichloromethyl) carbonate (32315-10-9) + benzamide (55-21-0,27208-38-4) → benzoyl isocyanate (4461-33-0)

Guidance literature:

In ethyl acetate; at -5 - 80 ℃; for 2.5h; Temperature; Solvent;

Reference yield: 60.0%

oxalyl dichloride (79-37-8) + N-trimethylsilylbenzamide (1011-57-0) → benzoyl isocyanate (4461-33-0)

Guidance literature:

upstream raw materials:

tetraisocyanatosilane

benzoyl chloride

silver cyanate

oxalyl dichloride

Downstream raw materials:

2-phenyl-2-oxazolin-4-one

N,N'-dibenzoylurea

2,6-diphenyl-[1,3,5]oxadiazin-4-one

N-phenyl-N'-benzoylurea

Refernces

ADDITION OF PYRIDINE AND ISOQUINOLINE TO BENZOYLCARBONITRILE OXIDE

10.1016/S0040-4020(01)86196-2

The study investigates the reactions of benzoylcyanate oxide (BZNO) with pyridine and isoquinoline. Pyridine reacts with BZNO to form a fragile zwitterionic adduct, which slowly reverts to the reactants and ultimately leads to benzoyl isocyanate and related products. In polar solvents, pyridine catalyzes the dimerization of BZNO to form the “abnormal” 1,4,2,3-dioxadiazine dimer, while in apolar solvents, site-specific biscycloadducts are obtained. The proposed mechanism involves two labile intermediates, a zwitterion and a monocycloadduct. The study also explores the stability of these intermediates through modifications of the reactants. The reaction of BZNO with isoquinoline yields a moderately stable cycloadduct, which can be converted to an isocarbostyril derivative through isomerization. The study provides insights into the solvent effects on product distribution and the stability of the intermediates involved in these reactions.