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Merck
CN

09954

Propargyl p-toluenesulfonate

≥97.0% (GC)

Synonym(s):

Propargyl tosylate

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About This Item

Empirical Formula (Hill Notation):
C10H10O3S
CAS Number:
6165-76-0
Molecular Weight:
210.25
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
329748867
MDL number:
MFCD01462194
Beilstein/REAXYS Number:
1912957

Key Documents

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Product Name

Propargyl p-toluenesulfonate, ≥97.0% (GC)

InChI

1S/C10H10O3S/c1-3-8-13-14(11,12)10-6-4-9(2)5-7-10/h1,4-7H,8H2,2H3

SMILES string

Cc1ccc(cc1)S(=O)(=O)OCC#C

InChI key

LMBVCSFXFFROTA-UHFFFAOYSA-N

assay

≥97.0% (GC)

refractive index

n20/D 1.530

density

1.215 g/mL at 20 °C (lit.)

functional group

tosylate

storage temp.

2-8°C

Quality Level

200

Related Categories

Application

Propargyl p-toluenesulfonate can be used as an initiator in the synthesis of linear and cyclic poly(2-isopropyl-2-oxazoline)s by cationic ring-opening polymerization of 2-isopropyl-2-oxazoline.
It can also be used as a reagent to synthesize:
  • 2-hydroxy-4-pentynoic acid by an alkylation reaction with diethyl 2-acetamidomalonate followed by subsequent hydrolysis, decarboxylation, diazotization, and hydroxylation reactions.
  • Furan derivatives by Pd-catalyzed reaction with acylchromates.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

212.0 °F - closed cup

flash_point_c

100 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000468950
0000468950
0000297950
0000276889
0000255271

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Preparation of furans by palladium-catalyzed reaction of acylchromates and propargylic tosylates
Nakamura M, et al.
Heterocycles, 59(1), 333-345 (2003)
An economical and safe procedure to synthesize 2-hydroxy-4-pentynoic acid: A precursor towards `clickable?biodegradable polylactide
Zhang Quanxuan, et al.
Beilstein Journal of Organic Chemistry, 10(1), 1365-1371 (2014)
Linear and cyclic poly (2-isopropyl-2-oxazoline) s for fine control of thermoresponsiveness
Jung Yongseok, et al.
European Polymer Journal, 88, 605-612 (2017)
Lucca Trachsel et al.
ACS nano, 14(8), 10054-10067 (2020-07-07)
The physicochemical properties of cyclic polymer adsorbates are significantly influenced by the steric and conformational constraints introduced during their cyclization. These translate into a marked difference in interfacial properties between cyclic polymers and their linear counterparts when they are grafted
Yuji Odagaki et al.
Journal of pharmacological sciences, 125(2), 157-168 (2014-05-23)
The functional activation of Gi/o proteins coupled to muscarinic acetylcholine receptors (mAChRs) was investigated with the conventional guanosine-5'-O-(3-[(35)S]thio) triphosphate ([(35)S]GTPγS) binding assay in rat brain membranes. The most efficacious stimulation elicited by acetylcholine or carbachol (CCh) was obtained in striatal

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