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p-Toluenesulfonyl Isocyanate

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p-Toluenesulfonyl Isocyanate Basic information
Product Name:p-Toluenesulfonyl Isocyanate
Synonyms:4-Isocyanatosulphonyltoluene,;p-Toluenesulfonyl isocyanate, 96%, AcroSeal;Isocyanicacid, anhydride with p-toluenesulfonic acid (6CI);p-Toluenesulfonyl isocyanate 96%;p-Toluenesulfonyl isocyanate, 96%, SpcSeal;p-Toluenesulfonylisocyanate,95%;Benzenesulfonyl isocyanate, 4-methyl-;Benzenesulfonylisocyanate,4-methyl-
CAS:4083-64-1
MF:C8H7NO3S
MW:197.21
EINECS:223-810-8
Product Categories:Building Blocks;Chemical Synthesis;Isocyanates;Nitrogen Compounds;Organic Building Blocks;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Benzene derivates;organic chemical;Benzene derivatives;4083-64-1
Mol File:4083-64-1.mol
p-Toluenesulfonyl Isocyanate Structure
p-Toluenesulfonyl Isocyanate Chemical Properties
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.)
Fp >230 °F
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
form Liquid
color Clear colorless to yellow
Specific Gravity1.291.291
Odoracrid odor
Water Solubility reacts
Sensitive Moisture Sensitive
BRN 391287
InChIKeyVLJQDHDVZJXNQL-UHFFFAOYSA-N
LogP0.6 at 30℃
CAS DataBase Reference4083-64-1(CAS DataBase Reference)
NIST Chemistry Reference4-Methylbenzenesulfonyl isocyanate(4083-64-1)
EPA Substance Registry SystemBenzenesulfonyl isocyanate, 4-methyl- (4083-64-1)
Safety Information
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
10
TSCA Yes
HazardClass 6.1
PackingGroup III
HS Code 29309090
MSDS Information
ProviderLanguage
Tosyl isocyanate English
SigmaAldrich English
ACROS English
ALFA English
p-Toluenesulfonyl Isocyanate Usage And Synthesis
Chemical Propertiesclear liquid
UsesIt 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.
Usesp-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 Descriptionp-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.
p-Toluenesulfonyl Isocyanate
HazardModerately toxic by ingestion. Low toxicity by inhalation. A mild skin and moderate eye irritant.
SafetyDanger! 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.
SynthesisAdd 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.Synthesis_4083-64-1
p-Toluenesulfonyl Isocyanate Preparation Products And Raw materials
Preparation Products4-Methylphenylsulfonylurea-->Tosular
Tag:p-Toluenesulfonyl Isocyanate(4083-64-1) Related Product Information
Chloral hydrate Sulfosulfuron Chlorosulfonyl isocyanate Tosyl cyanide Dimethyl sulfone p-Toluenesulfonamide Sodium p-toluenesulfinate p-Tolyl isocyanate P-Toluenesulfonic anhydride Tosyl chloride Sodium p-toluenesulfonate p-Toluenesulfonic acid p-Toluenesulfonic acid monohydrate p-Toluenesulfonyl semicarbazide Tosyl azide 4-Methylbenzenesulfonhydrazide Ethyl p-toluenesulfonate Diethyl (tosyloxy)methylphosphonate

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