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378895

Sigma-Aldrich

Piperonyloyl chloride

99%

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About This Item

Empirical Formula (Hill Notation):
C8H5ClO3
CAS Number:
25054-53-9
Molecular Weight:
184.58
MDL number:
MFCD00016904
UNSPSC Code:
12352100
PubChem Substance ID:
24863592
NACRES:
NA.22

Quality Level

100

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

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

378895-1G:
378895-VAR:
378895-BULK:
378895-10G:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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)
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
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