p-Toluenesulfonyl Isocyanate Property

Melting point:

5°C

Boiling point:

144 °C10 mm Hg(lit.)

Density 

1.291 g/mL at 25 °C(lit.)

vapor pressure 

1 mm Hg ( 100 °C)

refractive index 

n20/D 1.534(lit.)

Flash point:

>230 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Liquid

color 

Clear colorless to yellow

Specific Gravity

1.291.291

Odor

acrid odor

Water Solubility 

reacts

Sensitive 

Moisture Sensitive

BRN 

391287

InChIKey

VLJQDHDVZJXNQL-UHFFFAOYSA-N

LogP

0.6 at 30℃

CAS DataBase Reference

4083-64-1(CAS DataBase Reference)

NIST Chemistry Reference

4-Methylbenzenesulfonyl isocyanate(4083-64-1)

EPA Substance Registry System

Benzenesulfonyl isocyanate, 4-methyl- (4083-64-1)

Safety

Hazard Codes 

Xn

Risk Statements 

14-36/37/38-42

Safety Statements 

26-28-30-28A

RIDADR 

UN 2206 6.1/PG 3

WGK Germany 

1

RTECS 

DB9032000

F 

10

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29309090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

p-Toluenesulfonyl Isocyanate Chemical Properties,Usage,Production

Chemical Properties

clear liquid

Uses

It is a reagent used to prepare acetylated syn-1,2-diols,oxazolidin-2-ones, 2,3-diamino acids, and N-tosylcarbonamides. -Toluenesulfonyl isocyanate has been used as derivatization reagent in determination of 3-α-hydroxy tibolone in human plasma by LC-MS/MS. It is also employed in the derivatization reagent in simultaneous quantitative analysis of diethylene glycol and propylene glycol in pharmaceutical products by HPLC and as reagent in the preparation of acetylated syn-1,2-diols, oxazolidin-2-ones, 2,3-diamino acids and N-tosylcarbonamides.

Uses

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

Synthesis Reference(s)

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

General Description

p-Toluenesulfonyl isocyanate undergoes palladium-catalyzed bis-allylation reaction with allylstannanes and allyl chlorides.

Reactivity Profile

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.

Hazard

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

Safety

Danger! Harmful if swallowed, inhaled or absorbed through the skin. Causes skin and severe eye irritation. It may cause an allergic respiratory response. Reacts spontaneously and violently with water, alcohols, amines, acids and alkaline solutions. These substances should not be poured into a vessel containing PTSI. Prolonged exposure of PTSI to elevated temperatures can result in violent decomposition. Temperatures above 170?C are to be avoided. Reaction with water results in the generation of carbon dioxide. Reaction vessels should be vented to avoid pressure build‐up. Vent through a calcium chloride tube to prevent moisture from entering vessels. Do not get in the eyes, on the skin, or clothing. Avoid breathing vapour or mist. Keep the container closed. Use with adequate ventilation. Wash thoroughly after handling. If handled indoors, provide adequate mechanical exhaust ventilation or wear NIOSH/MSHA approved air ‐line respirator or SCBA. Wear impervious PVC or rubber gloves, goggles, and protective clothing. PTSI must be stored in air‐tight containers.

Synthesis

Add the organic azide 4-methylbenzenesulfonyl 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 ℃ for 4 h under the CO atmosphere (balloon). Concentrate the mixture under reduced pressure. Purify the residue by column chromatography (petroleum ether/EtOAc 3:1.-.1:1) to afford p-Toluenesulfonyl Isocyanate.