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CAS RN: 98-59-9 | Product Number: T0272

p-Toluenesulfonyl Chloride


Purity: >99.0%(GC)
Synonyms:
  • Tosyl Chloride
Documents:
25G
$30.00
4   6   ≥40 
500G
$61.00
30   16   ≥100 

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Product Number T0272
Purity / Analysis Method >99.0%(GC)
Molecular Formula / Molecular Weight C__7H__7ClO__2S = 190.64 
Physical State (20 deg.C) Solid
Store Under Inert Gas Store under inert gas
Condition to Avoid Moisture Sensitive
CAS RN 98-59-9
Reaxys Registry Number 607898
PubChem Substance ID 87576251
SDBS (AIST Spectral DB) 3090
Merck Index (14) 9534
MDL Number

MFCD00007450

Specifications
Appearance White to Light yellow powder to crystal
Purity(GC) min. 99.0 %
Purity(Argentometric Titration) min. 98.0 %
Melting point 67.0 to 71.0 °C
NMR confirm to structure
Properties (reference)
Melting Point 68 °C
Boiling Point 146 °C/15 mmHg
GHS
Pictogram Pictogram
Signal Word Danger
Hazard Statements H314 : Causes severe skin burns and eye damage.
H402 : Harmful to aquatic life.
H290 : May be corrosive to metals.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P273 : Avoid release to the environment.
P260 : Do not breathe dusts or mists.
P234 : Keep only in original container.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P390 : Absorb spillage to prevent material damage.
P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower.
P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P363 : Wash contaminated clothing before reuse.
P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
P406 : Store in corrosive resistant container with a resistant inner liner.
P405 : Store locked up.
Related Laws:
Transport Information:
UN Number (DOT-AIR) UN3261
Class (DOT-AIR) 8
Packing Group (TCI-A) III
HS Number 2904.10.3700
Application
TCI Practical Example: Tosylation of Hydroxy Group Using TsCl

TCI Practical Example: Tosylation of Hydroxy Group Using TsCl

Used Chemicals

Procedure

Triethylamine (1.23 mL, 7.64 mmol, 1.5 eq.), DMAP (23.1 mg, 0.19 mmol, 0.04 eq.), and TsCl (1.17 g, 6.11 mmol, 1.2 eq.) were added to a solution of diethylene glycol monobenzyl ether (1.00 g, 5.10 mmol) in dichloromethane (12.1 mL) at room temperature. The reaction mixture was stirred for overnight. The reaction mixture was quenched with 1 mol/L HCl (10 mL) and extracted with dichloromethane (3 x 10 mL). The organic layer washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane = 10:90 – 25:75 on silica gel), giving 1 as a colorless liquid (1.58 g, 89% yield).

Experimenter’s Comments

The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:1, Rf = 0.55).

Analytical Data

Tosylate 1

1H NMR (270 MHz, CDCl3); δ 7.80 (d, J = 8.4 Hz, 2H), 7.39-7.29 (m, 7H), 4.54 (s, 2H), 4.17 (t, J = 4.6 Hz, 2H), 3.70 (brt, J = 4.9 Hz, 2H), 3.62 (m, 2H), 3.56 (m, 2H), 2.43 (s, 3H).

Other Reference


Application
Stereocomplementary Enol Tosylation

Typical Procedure (Enol Tosylation of α-Formyl Esters) Method A: An α-formyl ester (1.00 mmol) in toluene (1 mL) and TsCl (228 mg, 1.20 mmol) in toluene (1 mL) are successively added dropwise to a stirred solution of N-methylimidazole (NMI) (99 mg, 1.20 mmol) and Et3N (121 mg, 1.20 mmol) in toluene (1 mL) at 0-5 °C under an Ar atmosphere, and the mixture is stirred at the same temperature for 1 h. Water is added to the mixture, which is extracted twice with AcOEt. The combined organic phase is washed with brine, dried (Na2SO4), and concentrated. The residue is purified by SiO2 column chromatography (hexane : AcOEt = 25 : 1-5 : 1) to give the desired (E)-enol tosylates. Method B: An α-formyl ester (1.00 mmol) in toluene (1 mL), TsCl (228 mg, 1.20 mmol) in toluene (1 mL), and NMI (99 mg, 1.20 mmol) are successively added dropwise to a stirred suspension of LiOH powder (anhydrous; 29 mg, 1.20 mmol) in toluene (1 mL) at 0-5 °C under an Ar atmosphere, and the mixture is stirred at the same temperature for 1 h. A workup similar to that of method A gives the desired (Z)-enol tosylates.

References


PubMed Literature


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