20850-43-5

Basic information

• Product Name: Piperonyl chloride
• Synonyms: Piperonyl Chloride (~75% by weight in CH2Cl2);Piperonyl chloride(50% by weight in dichloromethane or dichloroethane);TIMTEC-BB SBB005588;PIPERONYL CHLORIDE;3,4-METHYLENEDIOXYBENZYL CHLORIDE;1,3-BENZODIOXOLE, 5-(CHLOROMETHYL)-;5-(CHLOROMETHYL)-1,3-BENZODIOXOLE;4-Chloromethyl-1,2-methylenedioxybenzene
• CAS NO: 20850-43-5
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• EINECS: 244-081-2
• Mol File: 20850-43-5.mol

Chemical Properties

• Melting Point: 20.5°C
• Boiling Point: 97-100°C 1mm
• Flash Point: 115.921 °C
• Appearance: /
• Density: 1.32
• Vapor Pressure: 0.931mmHg at 25°C
• Refractive Index: 1.5660 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform, Methanol
• Sensitive: Moisture Sensitive/Lachrymatory
• CAS DataBase Reference: Piperonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Piperonyl chloride(20850-43-5)
• EPA Substance Registry System: Piperonyl chloride(20850-43-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT, MOISTURE SENSITIVE, LA
• Hazardous Substances Data: 20850-43-5(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
Piperonyl chloride is used as a reagent for the synthesis of anti-proliferative hydroxyguanidine compounds. These compounds have significant applications in the development of pharmaceuticals that can inhibit the growth of cells, particularly cancer cells. The use of piperonyl chloride in this context is due to its ability to facilitate the formation of these bioactive compounds.
2. Used in Chemical Synthesis:
Due to its unique chemical structure, piperonyl chloride is also used as an intermediate in the synthesis of various organic compounds. Its reactivity and stability make it a valuable component in the production of a wide range of chemicals, from pharmaceuticals to agrochemicals.
3. Used in Insecticide Formulation:
Piperonyl chloride is also used in the formulation of certain insecticides. It acts as a synergist, enhancing the effectiveness of the primary insecticide by inhibiting the insects' ability to metabolize the compound, thereby increasing its toxicity to the target pests.
4. Used in Flavor and Fragrance Industry:
Given its distinct chemical properties, piperonyl chloride is also utilized in the flavor and fragrance industry. It is used to create specific scents and flavors in a variety of products, from perfumes to food items.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 16, p. 869, 1973 DOI: 10.1021/jm00266a001

InChI:InChI=1/C7H5ClO2/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3H,4H2

Upstream product

• 274-09-9 Methylenedioxybenzene 
• 495-76-1 piperonol 
• 7647-01-0 hydrogenchloride 
• 71-43-2 benzene 
• 50-00-0 formaldehyd 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 120-57-0 piperonal 
• 120-80-9 benzene-1,2-diol 
• 326-61-4 piperonyl acetate 
• 91-14-5 1,2-divinylbenzene 
• 7145-99-5 5-methyl-1,3-benzodioxole 

Downstream Products

• 57420-27-6 2-piperonylsuccinic acid 
• 802884-12-4 benzo[1,3]dioxol-5-ylmethyl-(2-methoxy-benzyl)-methyl-amine 
• 4439-02-5 3,4-methylenedioxyphenylacetonitrile 
• 869943-99-7 3-piperonylamino-propan-1-ol 
• 101169-24-8 3,5-Dimethyl-4-piperonyl-phenol 
• 120-57-0 piperonal 
• 109219-42-3 4-Piperonyl-phenol 
• 30609-33-7 1-(3,4-Methylendioxybenzyl)-1-cyan-2-benzoyl-1,2-dihydroisochinolin 
• 25186-59-8 1-benzo[1,3]dioxol-5-ylmethyl-2-benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-1-carbonitrile 
• 16658-48-3 Escholamin 
• 55436-41-4 1,4-bis-(3,4-methylenedioxybenzyl) piperazine 
• 40918-96-5 methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate 
• 82895-48-5 1,2-methylenedioxy-4-(phenylsulfonylmethyl)benzene 
• 77853-40-8 5-(tosylmethyl)benzo[d][1,3]dioxole 

Relevant articles and documents

Density functional theory calculations, vibration spectral analysis and molecular docking of the antimicrobial agent 6-(1,3-benzodioxol-5-ylmethyl)-5-ethyl-2-{[2-(morpholin-4-yl)ethyl] sulfanyl}pyrimidin-4(3H)-one

Vibrational spectral analysis and quantum chemical computations based on density functional theory have been performed on the antimicrobial agent 6-(1,3-benzodioxol-5-ylmethyl)-5-ethyl-2-{[2-(morpholin-4-yl)ethyl]sulfanyl}pyrimidin-4-(3H)-one. The equilibrium structural geometry, various bonding features and harmonic vibrational wavenumbers of the title compound have been investigated using DFT-B3LYP function at 6-311++G(d,p) basis set. The detailed interpretations of the vibrational spectra have been carried out with the aid of VEDA 4 program. The various intramolecular interactions of the title compound have been exposed by natural bond orbital analysis. The FT-IR and FT-Raman spectra of the title molecule have been recorded and analyzed. Blue-shifting of the C-H wavenumber along with a decrease in the C-H bond length attribute for the formation of the C-H...O hydrogen bonding provide an evidence for a charge transfer interaction. Also, the distribution of natural atomic charges reflects the presence of intramolecular hydrogen bonding. The analysis of the electron density of HOMO and LUMO gives an idea of the delocalization and the low value of energy gap indicates electron transfer within the molecule. Moreover, molecular docking studies revealed the possible binding of the title molecule to different antimicrobial target proteins.

Total Synthesis of [14C]-Labelled Homoharringtonine

A total synthesis of enantiomerically pure [14C]-labelled (-)-homoharringtonine in 17 steps is reported. This synthetic process enabled the production of Good Manufacturing Practice (GMP) compliant (-)-[14C]homoharringtonine that was used in a human mass balance study that was a post-approval commitment to the U.S. Food and Drug Administration. (-)-Homoharringtonine, also called omacetaxine mepesuccinate, is approved to treat adult patients with chronic myeloid leukemia (CML), a blood and bone marrow disease. In November 2012, the product was commercialised as Synribo in the U.S., marketed by Teva Pharmaceuticals. The total synthesis of (-)-[14C]homoharringtonine, for use in clinical studies, was achieved 17-steps, starting from 14C-labelled potassium cyanide.

Studies on Pyrrolidones. An Improved Synthesis of N-Arylmethyl Pyroglutamic Acids

Low solubility of the aromatic aldehyde in a water/ethanol medium can prevent the sodium borohydride reductive alkylation of the sodium salt of glutamic acid. In that case, the reductive alkylation can be realized in methanol by using a triethylammonium salt. The uses of 2 molar equivalent of triethylammonium salt of glutamic acid for one molar equivalent of aldehyde strongly raise the yields. Cyclization of the N-substituted glutamic acids obtained gives then N-arylmethyl pyroglutamic acids in good yields.

Method for synthesizing piperonyl chloride through continuous flow reaction

The invention provides a method for synthesizing piperonyl chloride through continuous flow reaction, which comprises the following steps: enabling 1,3-Benzodioxole and a chloromethylation reagent to pass through a continuous flow reactor through a metering pump, preheating, mixing, reacting, and carrying out after-treatment to obtain the piperonyl chloride. The method for synthesizing piperonyl chloride through continuous flow reaction is stable and feasible in process, capable of accurately controlling conditions, high in yield, high in reaction rate, good in selectivity, simple and convenient to operate, safe and environment-friendly, has an enlarged production prospect, and has a huge practical value in the aspect of improving the production efficiency.

AN EFFICIENT AND ENVIRONMENT FRIENDLY PROCESS FOR CHLOROMETHYLATION OF SUBSTITUTED BENZENES

Disclosed herein is an efficient, environment friendly and commercially viable process for preparation of chloromethylated compound of formula I in substantially pure form and high yield, from the compound of formula II. The process includes contacting the compound of formula II with a chloromethylating agent generated in-situ by reaction of a formaldehyde precursor and hydrogen chloride, in a suitable solvent/contacting medium and in the presence of a catalytic amount of a short chain/low molecular weight carboxylic acid of formula III. I II III wherein, R1, R2, R3 and R4 are as defined in the description.

Synthesis of 1,2,3-triazole derivatives of hydnocarpic acid isolated from carpotroche brasiliensis seed oil and evaluation of antiproliferative activity

Carpotroche brasiliensis is a tree native to Brazil, belonging to the family Flacurtiaceae, whose seeds contain a group of cyclopentenyl fatty acids: Gorlic (12%), chaulmugric (27%), and hydnocarpic (48.7%). These compounds are considered the main therapeutic agents in the treatment of leprosy. In the present study, a series of novel triazole compounds were obtained by conjugation between hydnocarpic acid and functionalized azides via copper(I)-catalyzed azidealkyne cycloaddition reaction (CuAAC). Hydnocarpic acid and its derivatives were tested against estrogen-positive breast carcinoma (MCF-7), hepatocellular carcinoma (HepG2), and non-small cell lung cancer (A549) cell lines. The (R)-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl-11-(cyclopent-2-en-1-yl)undecanoate (8) displayed promising antiproliferative activity against A549 cells. We demonstrated that this compound selectively inhibited the viability of A549 cell cultures. Furthermore, compound 8 inhibited the clonogenic capacity of A549 cells, and this effect was associated to its ability to inhibit cell cycle progression at G1 phase. These findings indicate that 8 is a promising antitumor agent on A549 cells and support further studies to evaluate the molecular mechanisms underlying its antiproliferative activity. In addition, hydnocarpic acid should be considered as a promising chemical prototype to obtain novel antineoplastic agents.

2-Amino-purine derivative compound, preparing method and use thereof

According to one aspect, provided are a purine compound, a stereoisomer, a derivative, a solvate, or a pharmaceutically acceptable salt thereof, a manufacturing method thereof and uses thereof. According to the same, the compound, and the stereoisomer, derivative, solvate, or pharmaceutically acceptable salt thereof have low cytotoxicity, and exhibit high selective inhibitory activity against HSP90, and antiproliferative effect of cancer cells, thereby being useful for preventing or treating cancer.(AA) Density(BB) Compound(CC) andbeta;- tubulinCOPYRIGHT KIPO 2018

Preparation method of piribedil

The invention provides a preparation method of piribedil. The preparation method comprises the following steps of: preparing piperonyl chloride; preparing piperazinyl pyrimidine; and preparing piribedil. The preparation method of piribedil is simple, low in production cost, high in integral yield of reaction and convenient for industrial production, and has huge promotional meaning.

Synthetic method of piribedil

The invention relates to a synthetic method of piribedil. The synthetic method is a brand new process comprising the steps of synthesizing piperonyl piperazine in one step under the effects of pentamethyleneamine, piperazine pyrimidine and paraformaldehyde, and reacting by virtue of piperonyl piperazine and dichloropyrimidine so as to synthesize piribedil. Piperonyl piperazine has not been synthesized by virtue of the synthetic method before. Compared with a traditional synthetic method of piribedil, the synthetic method has the advantages that synthetic steps are simplified, the three wastes are reduced, the utilization ratio of pentamethyleneamine is remarkably increased, and the after-treatment is relatively environment-friendly.

A heliotropin synthetic method

The invention relates to the technical field of the medical intermediate fine chemical industry and in particular relates to a synthetic method of piperonal. The synthetic method comprises the following steps: 1 uniformly mixing benzodioxole, formaldehyde with concentration of 40% and a primary catalyst dodecyl trimethyl ammonium bromide with a solvent, then adding hydrochloric acid with concentration of 35-37% and standing for layering after reaction, thus obtaining a piperonyl chloride solution, wherein the solvent is trichloromethane, tetrachloromethane or methylbenzene; 2 preparing a sodium bicarbonate or sodium carbonate water solution with concentration less than or equal to that of a saturated solution, adding the sodium bicarbonate or sodium carbonate water solution to the piperonyl chloride solution and reacting to obtain a piperonyl alcohol solution; 3 introducing air into the piperonyl alcohol solution to oxidize the piperonyl alcohol solution to generate a piperonal solution by using both ferric nitrate and 4-hydroxy-2,2,4,4-methylpiperidine nitroxyl free radical as final catalysts. The synthetic method provided by the invention has the advantages of accessible raw materials, mild reaction conditions, stable and high yield, few byproducts and low cost.