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378895

Sigma-Aldrich

Piperonyloyl chloride

99%

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About This Item

Formule empirique (notation de Hill):
C8H5ClO3
Numéro CAS:
25054-53-9
Poids moléculaire :
184.58
Numéro MDL:
MFCD00016904
Code UNSPSC :
12352100
ID de substance PubChem :
24863592
Nomenclature NACRES :
NA.22

Pureté

99%

Point d'ébullition

155 °C/25 mmHg (lit.)

Pf

78-79 °C (lit.)

Chaîne SMILES 

ClC(=O)c1ccc2OCOc2c1

InChI

1S/C8H5ClO3/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2

Clé InChI

ZRSGZIMDIHBXIN-UHFFFAOYSA-N

Description générale

Piperonyloyl chloride is an acyl halide. It participates in the preparation of starting reagent (N-acyl indole), required for the synthesis of pyrrolophenanthridone alkaloids. Kinetic study of the solvolysis of piperonyloyl chloride in various pure and binary solvent mixtures has been proposed. Solvolysis reaction has been reported to proceed via electron-rich acyl transfer mechanism.

Application

Piperonyloyl chloride is suitable for use in a kinetic study to evaluate the solvolysis rate constants of piperonyloyl chloride in 27 different solvents. It may be used in the synthesis of the following compounds:
  • 2-phenylbenzimidazoles
  • (Z)-3-hydroxy-1-(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-phenylprop-2-en-1-one
  • pongapinone A
  • 2-((1-(2-(N-(4-chlorophenyl)benzo[d][1,3]dioxole-5-carboxamido)ethyl)piperidin-4-yl)oxy)acetic acid phosphoric acid salt, inhibitor of platelet aggregation
  • justicidin B, the piscicidal components of Justicia Hayatai var. decumbens
  • piperazine derivatives

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H314

Classification des risques

Eye Dam. 1 - Skin Corr. 1B

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

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Serena Scapecchi et al.
Bioorganic & medicinal chemistry, 12(1), 71-85 (2003-12-31)
Structure-activity relationships on two novel potent cognition enhancing drugs, unifiram (DM232, 1) and sunifiram (DM235, 2), are reported. Although none of the compounds synthesised reached the potency of the parent drugs, some fairly active compounds have been identified that may
Pelletier SW.
Alkaloids: Chemical and Biological Perspectives, Volume 14, 14, 441-442 (2000)
Hachemi Kadri et al.
Journal of enzyme inhibition and medicinal chemistry, 23(5), 641-647 (2008-09-30)
A new series of fluorinated and non-fluorinated 2-phenylbenzimidazoles bearing oxygenated substituents on the phenyl ring has been synthesized. Synthesis of the new series was based on our previous discovery of 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610) as a potent and selective antitumour agent
Concise Synthetic Approaches to Naturally Occurring ?-Hydroxypyranochalcones: First Total Synthesis of Purpurenone, Its Derivative, and Praecansone B.
Wang X, et al.
Bull. Korean Chem. Soc., 33(8), 2647-2650 (2012)
Correlation of the Rates of Solvolysis of Electron-Rich Benzoyl Chloride Using the Extended Grunwald-Wistein Equation.
Oh H, et al.
Bull. Korean Chem. Soc., 34(9), 2697-2697 (2013)
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