4083-64-1

Moderately toxic by ingestion. Low toxicity by inhalation. A mild skin and moderate eye irritant.

clear liquid

p-Toluenesulfonyl isocyanate is a reagent used to prepare acetylated syn-1,2-diols,1 oxazolidin-2-ones,2 2,3-diamino acids,3 and N-tosylcarbonamides.4

Tetrahedron Letters, 35, p. 9609, 1994 DOI: 10.1016/0040-4039(94)88523-0

p‐Toluenesulfonyl Isocyanate (PTSI) is recommended especially for one‐component, low‐VOC polyurethane coatings. The reaction of PTSI with water introduced from pigments and solvents in the paint formulation generates carbon dioxide and soluble inert chemical products. Experience has demonstrated that 13 grams of PTSI effectively scavenges 1 gram of water. PTSI reacts with water in a 1 to 1 molar ratio, generating PTSA and carbon dioxide gas. This reaction occurs readily at room temperature and does not require heating. The PTSA generated in the process is essentially an inert material that does not further react with PTSI or other isocyanate groups, resulting in the formation of insoluble ureas. The hydroxyl group is reacted with excess p-toluenesulfonyl isocyanate (TSI) to form an acidic carbamate. Water is added to convert unreacted isocyanate to sulfonamide, followed by direct potentiometric titration of the acidic carbamate with tetrabutylammonium hydroxide (Bu4NOH) in nonaqueous medium.

Add the organic azide (0.75 mmol), Pd(OAc)2 (5.6 mg, 5 mol%) to an oven-dried Schlenk tube (10 mL). Purge the tube and backfill with CO (three cycles) from a balloon. Inject anhydrous MeCN (3.0 mL) into the tube. Stir at 80??C for 4 h under CO atmosphere (balloon). Concentrate the mixture under reduced pressure. Purify the residue by column chromatography (petroleum ether/EtOAc 3:1.-.1:1).