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378895

Sigma-Aldrich

Piperonyloyl chloride

99%

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About This Item

Fórmula empírica (notación de Hill):
C8H5ClO3
Número de CAS:
25054-53-9
Peso molecular:
184.58
MDL number:
MFCD00016904
UNSPSC Code:
12352100
PubChem Substance ID:
24863592
NACRES:
NA.22

assay

99%

bp

155 °C/25 mmHg (lit.)

mp

78-79 °C (lit.)

SMILES string

ClC(=O)c1ccc2OCOc2c1

InChI

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

InChI key

ZRSGZIMDIHBXIN-UHFFFAOYSA-N

General description

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

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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)
Studies on the Piscicidal Components of Justicia Hayatai var. decumbens.
OHTA K, et al.
Agricultural and Biological Chemistry, 33(4), 610-614 (1969)
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)
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