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T35955

Sigma-Aldrich

p-Toluenesulfonyl chloride

reagent grade, ≥98%

Synonym(s):

Tosyl chloride

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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:
57654666
NACRES:
NA.21
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grade

reagent grade

Quality Level

200

vapor pressure

1 mmHg ( 88 °C)

Assay

≥98%

bp

134 °C/10 mmHg (lit.)

mp

65-69 °C (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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Application

p-toluenesulfonyl chloride may be used along with N-methylimidazole for the esterification or thioesterification of carboxylic acids and alcohols or thiols.[1] It may also be used as a chlorine source for α-chlorination of ketones in the presence of lithium diisopropylamide.[2]

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

8A - 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
BCCL3037
BCCL9805
BCCK3676
BCCJ4756
BCCJ4755

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Maxim V Khrolenko et al.
Journal of chromatography. A, 1093(1-2), 111-117 (2005-10-20)
The application of supported-liquid membrane (SLM) technique for effective extraction of N-(phosphonomethyl)glycine (glyphosate) and its primary metabolite aminomethylphosphonic acid (AMPA) from juices (orange, grapefruit, apple and blackcurrant) in combination with HPLC-UV detection after derivatization with p-toluenesulphonyl chloride (TsCl) is presented.
α-Chlorination of ketones using p-toluenesulfonyl chloride.
Brummond KM and Gesenberg KD.
Tetrahedron Letters, 40(12), 2231-2234 (1999)
Rince Wong et al.
The Journal of organic chemistry, 72(10), 3969-3971 (2007-04-21)
A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines is reported. This method relies on a tosyl chloride mediated decomposition of a dithiocarbamate salt that is generated in situ by treatment of an amine
Y Tabata et al.
Biomaterials, 7(3), 234-238 (1986-05-01)
The cyanogen bromide (CNBr) activation method was adopted to link collagen molecules onto the surface of cellulose and poly(vinyl alcohol) (PVA) films via covalent bonding. The amount of bound protein was determined by the ninhydrin method and found to be
I M Kung et al.
Biomaterials, 16(8), 649-655 (1995-05-01)
Three different surface modifications were conducted on the membranes of double-layer alginate/poly(L-lysine) microcapsules with tosyl chloride-activated poly(ethylene glycol), cyanuric chloride-activated poly(ethylene glycol) and tosyl chloride-activated poly(vinyl alcohol), separately. All these surface modifications strengthen the microcapsular membranes. Of the three surface-modified
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    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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