Piperonyl chloride

• CAS: 20850-43-5
• Catalog Number: ACM20850435
• Category: Main Products
• Molecular Weight: 170.59
• Molecular Formula: C₈H₇ClO₂
• Synonyms: TIMTEC-BB SBB005588;PIPERONYL CHLORIDE;3,4-METHYLENEDIOXYBENZYL CHLORIDE;1,3-BENZODIOXOLE, 5-(CHLOROMETHYL)-;5-(CHLOROMETHYL)-1,3-BENZODIOXOLE;4-Chloromethyl-1,2-methylenedioxybenzene;5-(chloromethyl)-3-benzodioxole;Toluene, alpha-chloro-3,4-(methylenedioxy)-
• IUPAC Name: 5-(chloromethyl)-1,3-benzodioxole
• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)CCl
• InChI Key: DWSUJONSJJTODA-UHFFFAOYSA-N
• Boiling Point: 97-100°C1mm
• Melting Point: 20.5ºC
• Flash Point: 115.9ºC
• Density: 1.32
• Appearance: liquid
• Exact Mass: 170.01300
• Hazard Statements: Xi
• Safety Description: 26-36/37/39

Case Study

Piperonyl Chloride Utilized in the Synthesis of Heterocyclic Lactam Derivatives Featuring a Piperonyl Structure

Wang, Shuangshuang, et al. Bioorganic & Medicinal Chemistry Letters, 2019, 29(20), 126661.

In this study, two series of piperonyl-containing heterocyclic lactam derivatives (I1-14) were designed and synthesized, and their potential in vitro antibacterial activity against 12 different plant pathogenic fungi was evaluated. Initial biological activity assessments indicated that all synthesized compounds I1-14 demonstrated broad-spectrum and moderate antibacterial effects. Further investigations revealed that compounds I5 (IC50 = 19.13 µM) and I12 (IC50 = 9.12 µM) showed significant antibacterial activity against Phytophthora capsici, outperforming the commercial agricultural fungicide hymexazol (IC50 = 325.45 µM).
Synthesis Strategy
The key intermediate 5 was synthesized from readily available starting materials, including proline, pipecolinic acid, and substituted phenylacetic acid, through a four-step process involving esterification, acylation, N-acylation, and intramolecular heterocyclization. Following this, the key intermediate 5 was etherified with piperonyl chloride in a potassium carbonate solution in dry acetonitrile to yield the desired products I1-7. Meanwhile, the target molecules I8-14 were produced from intermediate 5 using piperonyloyl chloride in the presence of Et3N in CH2Cl2. All newly synthesized tetramic acid derivatives were reported for the first time, achieved in good yields and thoroughly characterized using satisfactory spectroscopic techniques, including 1H NMR, 13C NMR, and ESI-MS.

Application of Piperonyl Chloride in the Synthesis of Kingianin Bicyclo[4.2.0]Octane System

Taib, Mohamad Nurul Azmi Mohamad, et al. Organic Communications, 2024, 1, 56-62.

Kingianin exhibits good activity in inhibiting anti-apoptotic proteins and anti-diabetic proteins (α-glucosidase). This work proposed a non-biomimetic synthesis strategy, using the [2+2] enone cycloaddition reaction as a key step to synthesize the bicyclo[4.2.0]octane system of Kingianin. It involves the use of piperonyl chloride to synthesize 2-chlorocarboxylic acid 19 intermediate compounds as one of the key steps.
Synthesis Strategy
The process of 2-chlorocarboxylic acid 19 involved two key components: piperonyl chloride 20 and ethyl-2-chloro-3-oxobutanoate 21. Using sulfuryl chloride researchers synthesized compound 21 from ethyl-3-oxobutanoate 23 through a single-step process. The nucleophilic substitution between 20 and 21 produced chloroketone 24 which transformed into acid 19 with a 90% yield when treated with NaOH in ethanol.
After preparing 2-chlorocarboxylic acid 19 research efforts turned to the [2+2] cycloaddition reaction between ketene and 1,3-cyclohexadiene 15. 15 and chloro piperonyl ketene 14 underwent the reaction while the latter compound was produced in situ from its acyl chloride with triethylamine (Et3N) in diethyl ether at room temperature. The production of bicyclic cyclobutanone 25 resulted in a 7% yield. The yield of the reaction increased to 25% after testing different solvents under reflux conditions when cyclohexane was used as the solvent.

Custom Q&A

What is the molecular formula of piperonyl chloride?

The molecular formula of piperonyl chloride is C8H7ClO2.

What are some synonyms for piperonyl chloride?

Some synonyms for piperonyl chloride include 5-(Chloromethyl)benzo[d][1,3]dioxole, 3,4-Methylenedioxybenzyl chloride, and 1,3-Benzodioxole, 5-(chloromethyl)-.

What is the CAS number of piperonyl chloride?

The CAS number of piperonyl chloride is 20850-43-5.

What is the IUPAC name of piperonyl chloride?

The IUPAC name of piperonyl chloride is 5-(chloromethyl)-1,3-benzodioxole.

What is the InChIKey of piperonyl chloride?

The InChIKey of piperonyl chloride is DWSUJONSJJTODA-UHFFFAOYSA-N.

What is the molecular weight of piperonyl chloride?

The molecular weight of piperonyl chloride is 170.59g/mol.

How many hydrogen bond donor counts does piperonyl chloride have?

Piperonyl chloride has no hydrogen bond donor counts.

How many hydrogen bond acceptor counts does piperonyl chloride have?

Piperonyl chloride has two hydrogen bond acceptor counts.

How many rotatable bond counts does piperonyl chloride have?

Piperonyl chloride has one rotatable bond count.

What is the topological polar surface area of piperonyl chloride?

The topological polar surface area of piperonyl chloride is 18.5Ų.