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378895

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

Key Documents

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assay

99%

bp

155 °C/25 mmHg (lit.)

mp

78-79 °C (lit.)

functional group

acyl chloride

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

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This Item
242705545694B12695
Piperonyloyl chloride 99%

Sigma-Aldrich

378895

Piperonyloyl chloride

2-Propanesulfonyl chloride 97%

Sigma-Aldrich

242705

2-Propanesulfonyl chloride

2,4-Dichlorobenzenesulfonyl chloride 97%

Sigma-Aldrich

545694

2,4-Dichlorobenzenesulfonyl chloride

Benzoyl chloride ReagentPlus®, ≥99%

Sigma-Aldrich

B12695

Benzoyl chloride

assay

99%

assay

97%

assay

97%

assay

≥99%

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

200

mp

78-79 °C (lit.)

mp

-

mp

55-58 °C (lit.)

mp

−1 °C (lit.)

bp

155 °C/25 mmHg (lit.)

bp

74-75 °C/19 mmHg (lit.)

bp

-

bp

198 °C (lit.)

functional group

acyl chloride

functional group

-

functional group

chloro

functional group

acyl chloride, phenyl

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.[1] 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.[2]

Application

Piperonyloyl chloride is suitable for use in a kinetic study to evaluate the solvolysis rate constants of piperonyloyl chloride in 27 different solvents.[2] It may be used in the synthesis of the following compounds:
  • 2-phenylbenzimidazoles[3]
  • (Z)-3-hydroxy-1-(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-phenylprop-2-en-1-one[4]
  • pongapinone A[4]
  • 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[5]
  • justicidin B, the piscicidal components of Justicia Hayatai var. decumbens[6]
  • piperazine derivatives[7]

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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Certificates of Analysis (COA)

Lot/Batch Number
MKBK3894V
MKBG4972V
02628CH
05214DE
16909KU

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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
Yasuhiro Morita et al.
Molecules (Basel, Switzerland), 17(2), 1233-1246 (2012-02-02)
An efficient synthesis of a highly potent and selective IP (PGI(2) receptor) agonist that is not structurally analogous to PGI(2) is described. This synthesis is accomplished through the following key steps: Nucleophilic ring-opening of 3-(4-chlorophenyl)-oxazolidin-2-one prepared by a one-pot procedure
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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