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240877

Sigma-Aldrich

p-Toluenesulfonyl chloride

ReagentPlus®, ≥99%

Sinônimo(s):

TsCl, Tosyl chloride

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About This Item

Fórmula linear:
CH3C6H4SO2Cl
Número CAS:
98-59-9
Peso molecular:
190.65
Beilstein:
607898
Número CE:
202-684-8
Número MDL:
MFCD00007450
Código UNSPSC:
12352100
ID de substância PubChem:
57648053
NACRES:
NA.21

pressão de vapor

1 mmHg ( 88 °C)

Nível de qualidade

200

linha de produto

ReagentPlus®

Ensaio

≥99%

forma

solid

pb

134 °C/10 mmHg (lit.)

pf

65-69 °C (lit.)

solubilidade

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

cadeia de caracteres SMILES

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

InChI

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

chave InChI

YYROPELSRYBVMQ-UHFFFAOYSA-N

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Descrição geral

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

Aplicação

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.
  • As an additive to enhance the yield of symmetrical biaryls via palladium chloride catalyzed homo-coupling of arylboronic acids in the absence of ligands.
  • As a positive chlorine source for the ?-chlorination of ketones.
  • Solvent-free tosylation of alcohols and phenols in the presence of heterodoxy acids.
  • As an activator for reaction between 2-alkynylbenzaldoxime and phenols to form 1-aroxyisoquinolines in the presence of silver triflate.
  • As a catalyst for the solvent-free preparation of symmetrical bis(benzhydryl)ethers from benzhydrols.

Informações legais

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

Pictogramas

CorrosionExclamation mark
GHS05,GHS07

Palavra indicadora

Danger

Frases de perigo

H290,H315,H317,H318

Classificações de perigo

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

Código de classe de armazenamento

8B - Non-combustible corrosive hazardous materials

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

262.4 °F - closed cup

Ponto de fulgor (°C)

128 °C - closed cup

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
BCCM2067
BCCM0124
MKCT4267
BCCK4643
MKCQ9876

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Trietilamina ≥99.5%

Sigma-Aldrich

471283

Trietilamina

p-Toluenesulfonic acid monohydrate ACS reagent, ≥98.5%

Sigma-Aldrich

402885

p-Toluenesulfonic acid monohydrate

Methanesulfonyl chloride purum, ≥98.0% (AT)

Sigma-Aldrich

64270

Methanesulfonyl chloride

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)
Immobilization of ligands with organic sulfonyl chlorides
Nilsson K & Mosbach K
Methods in Enzymology, 104, 56-69 (1984)
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)
Haibo Mu et al.
Nature communications, 10(1), 4039-4039 (2019-09-08)
Antibiotic therapy is usually not recommended for salmonellosis, as it is associated with prolonged fecal carriage without reducing symptom duration or severity. Here we show that antibiotics encapsulated in hydrogen sulfide (H2S)-responsive glycovesicles may be potentially useful for the treatment
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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