1014-98-8

Usage

Safety Profile

A poison. A flammable liquid. When heated to decomposition it emits toxic vapors of CN-.

InChI:InChI=1/C10H8N2O2/c13-7-11-5-9-1-2-10(4-3-9)6-12-8-14/h1-4H,5-6H2

Upstream product

• 623-24-5 1,4-bis(bromomethyl)benzene 
• 20236-50-4 silver (I) nitro cyanamide 
• 119027-95-1 p-xylene-α,α'-diylbisnitrocyanamide 
• 75-44-5 phosgene 
• 539-48-0 p-xylylidenediamine 

Downstream Products

• 27959-91-7 dimethyl (1,4-phenylenebis(methylene))dicarbamate 
• 117688-77-4 C₄₄H₇₀N₈O₄ 
• 124887-67-8 1,4-Bis<(1-carboxymethyl-3-hydantoinyl)methyl>benzene 
• 15571-22-9 1,4-bis-[(aziridine-1-carbonylamino)-methyl]-benzene 

Relevant academic research and scientific papers

Storage-stable biuret polyisocyanates

Storage-stable biuret polyisocyanates useful, e.g., for the production of paints and adhesives, are prepared by reacting at least one aliphatic, alicyclic or arylaliphatic diisocyanate with a biuret-forming reactant, in the presence of an effective amount of at least one organic carboxylic acid and/or anhydride thereof.

Preparation of biureto polyisocyanates

Clear, precipitate-free, storage-stable biureto polyisocyanates, well adopted for paint applications, are prepared by reacting at least one aliphatic, alicyclic or arylaliphatic monomeric diisocyanate with water, at a temperature of at least 70° C. and under an absolute pressure of at least 1.2 bar, including a partial pressure of carbon dioxide of at least 0.2 bar.

Alkylation of Nitrocyanamide. A New Synthesis of Isocyanates

Thirteen alkyl halides (primary, secondary, and tertiary aliphatic including alicyclic, aralkyl, and heteroalkyl systems) and certain non-vicinal dihalides on treatment with silver nitrocyanamide are converted into the corresponding isocyanates (63-95percent).Intermediate alkylnitrocyanamides, spectroscopically detected, thermolysed (-20-80 deg C) to the expected isocyanates.In certain examples silver nitrocyanamide is generated in situ from sodium nitrocyanamide and silver nitrate.Silver nitrocyanamide does not react with cyclopropyl bromide, acetyl chloride, toluene-p-sulphonyl chloride, phenacyl bromide and 2-bromomethyldioxolane (27), and the ethylene acetal (28) of 1-bromo-4-iodopentacyclo-nonan-9-one.Silver nitrocyanamide reacts with 4,6-bis(bromomethyl)-3,7-dimethyl-1,5-diazabicyclo3.3.0)octane-2,8-dione (26), to give an intractable mixture.Vicinal dihalides give erratic results without detectable formation of vicinal di-isocyanates: unisolated 2-bromoethyl isocyanate (tentative assignment) has been detected in a product mixture from ethylene dibromide; an expected rearrangement during the reaction with 1,2-dibromocyclobutane, brought about the formation of 4-bromobut-3-enyl isocyanate isolated as ethyl 4-bromobut-3-enylcarbamate in low yield; and 1,2-dibromocyclohexane gives 2-bromocyclohexyl isocyanate isolated as ethyl N-(2-bromocyclohexyl)-carbamate in low yield.