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791571

Sigma-Aldrich

Isopropyl p-toluenesulfonate

97%

Synonym(s):

Isopropyl p-tosylate

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About This Item

Empirical Formula (Hill Notation):
C10H14O3S
CAS Number:
2307-69-9
Molecular Weight:
214.28
EC Number:
218-989-4
MDL number:
MFCD00968877
UNSPSC Code:
12352100
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.503

density

1.142 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[S](=O)(=O)(Oc1ccc(cc1)C)C(C)C

InChI

1S/C10H14O3S/c1-8(2)14(11,12)13-10-6-4-9(3)5-7-10/h4-8H,1-3H3

InChI key

MUTOLSSCMLECRU-UHFFFAOYSA-N

Application

Isopropyl p-toluenesulfonate can be used as a reactant:
  • For the alkylation of amines in the presence of triethylamine[1].
  • For the O-alkylation of cyclic thiohydroxamic acids in the presence of tetrabutylammonium hydroxide[2].
  • To synthesize 3-methyl-2-phenyl-1-butanol by reacting with styrene in the presence of bromo(2-cyclohexylethyl)magnesium and zirconocene dichloride[3].
Isopropyl p-toluenesulfonate can be used:
  • as a thermal acid generator that synthesizes inherently stretchable p-conjugated polymer [4]
  • as a catalyst for the deprotection of PBHEMA [Poly(2-(tert-butoxycarbonyloxy)ethyl methacrylate)] on heating [5]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000314096
0000350006
0000216225
0000272013
0000245189

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J de Armas et al.
Organic letters, 3(13), 2097-2100 (2001-06-22)
[reaction: see structure] The first examples of efficient electrophilic Zr-catalyzed carbomagnesations are disclosed, where in contrast to previous catalytic carbomagnesations the alkyl moiety of the electrophile is transferred (vs that of the Grignard reagent). The identity of the Grignard reagent
Design, Synthesis and Antimicrobial Evaluation of Novel Tricyclic Benzoxazine Fluoroquinolones under Conventional and Microwave Methods
Guruswamy B, et al.
Journal of Heterocyclic Chemistry, 52, 532-538 (2015)
B Y P Tay et al.
International journal of cosmetic science, 38(6), 627-633 (2016-05-14)
Isopropyl p-toluenesulfonate (IPTS) is a potentially genotoxic by-product formed during the esterification of palm oil-based palmitic and palm kernel oil-based myristic acid with isopropanol to produce isopropyl palmitate or isopropyl myristate. There are no methods described for the analysis of
Spin trapping of alkoxyl radicals generated from 5-methyl and 5-aryl-3-alkoxy-4-methylthiazole-2 (3H)-thiones in photochemically induced and microwave-initiated reactions
Gross A, et al.
Tetrahedron, 64, 10882-10889 (2008)
Satsuki Chikura et al.
Mutation research, 811, 110-116 (2016-12-10)
As part of a collaborative study in the Mammalian Mutagenicity Study group of the Japanese Environmental Mutagen Society, we evaluated the in vivo mutagenicity of isopropyl p-toluenesulfonate (IPTS) using a peripheral blood Pig-a assay in rats. Pig-a mutant frequency (MF)

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