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240877

Sigma-Aldrich

p-Toluenesulfonyl chloride

ReagentPlus®, ≥99%

Synonym(s):

TsCl, Tosyl chloride

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5 G
$81.40
100 G
$202.00
500 G
$625.00

About This Item

Linear Formula:
CH3C6H4SO2Cl
CAS Number:
98-59-9
Molecular Weight:
190.65
Beilstein:
607898
EC Number:
202-684-8
MDL number:
MFCD00007450
UNSPSC Code:
12352100
PubChem Substance ID:
57648053
NACRES:
NA.21
form:
solid
Assay:
≥99%

$81.40

In StockDetails

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vapor pressure

1 mmHg ( 88 °C)

Quality Level

200

product line

ReagentPlus®

Assay

≥99%

form

solid

bp

134 °C/10 mmHg (lit.)

mp

65-69 °C (lit.)

solubility

benzene: freely soluble(lit.)
chloroform: freely soluble(lit.)
ethanol: freely soluble(lit.)
water: insoluble(lit.)

SMILES string

Cc1ccc(cc1)S(Cl)(=O)=O

InChI

1S/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3

InChI key

YYROPELSRYBVMQ-UHFFFAOYSA-N

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General description

p-Toluenesulfonyl chloride is an organic sulfonyl chloride mainly used to convert hydroxyl groups into good leaving group by forming sulfonates.[1]

Application

p-Toluenesulfonyl chloride may be used in the following processes:
  • In combination with N-methylimidazole for the esterification or thioesterification of carboxylic acids and alcohols or thiols.[2]
  • As an additive to enhance the yield of symmetrical biaryls via palladium chloride catalyzed homo-coupling of arylboronic acids in the absence of ligands.[3]
  • As a positive chlorine source for the ?-chlorination of ketones.[4]
  • Solvent-free tosylation of alcohols and phenols in the presence of heterodoxy acids.[5]
  • As an activator for reaction between 2-alkynylbenzaldoxime and phenols to form 1-aroxyisoquinolines in the presence of silver triflate.[6]
  • As a catalyst for the solvent-free preparation of symmetrical bis(benzhydryl)ethers from benzhydrols.[7]

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H290,H315,H317,H318

Hazard Classifications

Eye Dam. 1 - Met. Corr. 1 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

8B - Non-combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

262.4 °F - closed cup

Flash Point(C)

128 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2067
BCCM0124
MKCT4267
BCCK4643
MKCQ9876

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Immobilization of ligands with organic sulfonyl chlorides
Nilsson K & Mosbach K
Methods in Enzymology, 104, 56-69 (1984)
Solvent-free and selective tosylation of alcohols and phenols with p-toluenesulfonyl chloride by heteropolyacids as highly efficient catalysts
Fazaeli R, et al.
Canadian Journal of Chemistry, 84(5), 812-818 (2006)
Ligandless palladium chloride-catalyzed homo-coupling of arylboronic acids in aqueous media
Kabalka GW & Wang L.
Tetrahedron Letters, 43(16), 3067-3068 (2002)
Facile synthesis of symmetrical bis (benzhydryl) ethers using p-toluenesulfonyl chloride under solvent-free conditions
Brahmachari G & Banerjee B
Organic and Medicinal Chemistry Letters, 3(1), 1-1 (2013)
Generation of 1-aroxyisoquinolines via a silver-catalyzed reaction of 2-alkynylbenzaldoxime with phenol in the presence of p-toluenesulfonyl chloride
Xiao Q, et al.
Tetrahedron, 69(25), 5119-5122 (2013)
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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