4421-09-4

Basic information

• Product Name: Piperonylonitrile
• Synonyms: 5-Cyano-1,3-benzodioxole;Piperonylonitrile, 97% 25GR;3,4-Methylenedioxy benzonitrile (Piperonyl Nitrile);Piperonylonitrile 97%;3,4-Methylenedioxy benzonitrile Piperonylonitrile;2H-1,3-benzodioxole-5-carbonitrile;AKOS B004105;AKOS 214-97
• CAS NO: 4421-09-4
• Molecular Formula: C₈H₅NO₂
• Molecular Weight: 147.13
• EINECS: 224-590-6
• Product Categories: Benzodiozoles, Benzodioxines & Benzodioxepines;Benzodiozoles, Benzodioxines & Benzodioxepines;Aromatic Esters
• Mol File: 4421-09-4.mol
• Article Data: 143

Chemical Properties

• Melting Point: 91-93 °C(lit.)
• Boiling Point: 267.22°C (rough estimate)
• Flash Point: 115.4 °C
• Appearance: White to beige/Crystalline Powder or Needles
• Density: 1.3067 (rough estimate)
• Vapor Pressure: 0.0146mmHg at 25°C
• Refractive Index: 1.5510 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• BRN: 6224
• CAS DataBase Reference: Piperonylonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Piperonylonitrile(4421-09-4)
• EPA Substance Registry System: Piperonylonitrile(4421-09-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-20/21
• Safety Statements: 36-23-24/25
• RIDADR: 3276
• WGK Germany: 3
• RTECS: TO2645000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 4421-09-4(Hazardous Substances Data)

Usage

Description

Piperonylonitrile, also known as a methylenedioxyphenyl (MDP) compound, is an organic compound with the chemical formula C11H9NO2. It is a white crystalline solid that is soluble in organic solvents and has a characteristic bitter taste. Piperonylonitrile is known for its ability to inhibit various enzymes and has been extensively studied for its potential applications in different industries.

Uses

Used in Pharmaceutical Industry:
Piperonylonitrile is used as an inhibitor of nasal P 450-dependent N-demethylase in rabbits. This property makes it a valuable compound in the development of drugs that target specific enzymes and pathways in the body.
Used in Agriculture:
Piperonylonitrile is used as a toxic agent against D. farinae, D. pteronyssinus, and T. putrescentiae, which are common pests in agricultural settings. Its ability to control these pests helps protect crops and improve overall agricultural productivity.
Used in Microbiology:
Piperonylonitrile has been used to alter the growth of Nif+ and Nifstrains of K.pneumoniae, which are bacteria involved in nitrogen fixation. This application can be useful in studying the effects of Piperonylonitrile on bacterial growth and metabolism, as well as in developing strategies for controlling bacterial populations in various environments.

InChI:InChI=1/C8H5NO2/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-3H,5H2

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 98-09-9 benzenesulfonyl chloride 
• 153968-40-2 (Benzo[1,3]dioxole-5-carbonyl)-phosphonic acid diethyl ester 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 7732-18-5 water 
• 871875-58-0 piperonal-chlorimin 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 110-86-1 pyridine 
• 151-50-8 potassium cyanide 
• 62396-98-9 benzo[1,3]dioxol-5-yl-oxo-acetic acid 
• 4720-72-3 (Z)-N'-hydroxy benzo[d][1,3]dioxole-5-carboximidamide 
• 7553-56-2 iodine 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 82-85-9 benzo[1,3]dioxol-5-yl-(2-hydroxy-4,6-dimethoxy-phenyl)-ketone 
• 861531-48-8 benzo[1,3]dioxol-5-yl-(2,4,6-trimethoxy-phenyl)-ketone 
• 28281-49-4 3,4-methylenedioxypropiophenone 
• 857550-36-8 benzo[d][1,3]dioxol-5-yl(phenyl)methanimine 
• 2620-50-0 1,3-benzodioxol-5-ylmethyl amine 
• 5423-17-6 2-benzo[1,3]dioxol-5-yl-4-methyl-thiazole 
• 145737-10-6 4-(2-benzo[1,3]dioxol-5-yl-thiazol-4-yl)-pyrocatechol 
• 862574-89-8 1-(2H-1,3-benzodioxol-5-yl)cyclopropane-1-carboxylic acid 
• 80531-15-3 benzo[1,3]dioxole-5-carboxamidine hydrochloride 
• 54225-86-4 (3,4-methylenedioxyphenyl) phenyl methanone 
• 63740-98-7 1-(benzo[d]-1,3-dioxol-5-yl)pentan-1-one 
• 146721-06-4 (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane 
• 248249-56-1 2-(benzo[3,4-d]1,3-dioxolan-5-yl)-4-hydroxymethyl-1,3-thiazole 
• 248249-53-8 ethyl 4-(benzo[3,4-d]1,3-dioxolan-5-yl)-3,5-thiazole carboxylate 

Relevant articles and documents

Imidazole hydrochloride promoted synthesis of 3,5-disubstituted-1,2,4-oxadiazoles

Imidazole hydrochloride as an additive promotes the reaction of amidoximes and DMA derivatives to generated 3,5-disubstituted-1,2,4-oxadiazoles in low to excellent yields without the use of coupling reagents, oxidants, strong acids or bases and other additives.

Revisiting the synthesis of aryl nitriles: a pivotal role of CAN

Facilitated by the dual role of Ceric Ammonium Nitrate (CAN), herein we report a cost-effective approach for the cyanation of aryl iodides/bromides with CAN-DMF as an addition to the existing pool of combined cyanation sources. In addition to being an oxidant, CAN acts as a source of nitrogen in our protocol. The reaction is catalyzed by a readily available Cu(ii) salt and the ability of CAN to generate ammonia in the reaction medium is utilized to eliminate the additional requirement of a nitrogen source, ligand, additive or toxic reagents. The mechanistic study suggests an evolution of CN?leading to the synthesis of a variety of aryl nitriles in moderate to good yields. The proposed mechanism is supported by a series of control reactions and labeling experiments.

Cu2O-Catalyzed Conversion of Benzyl Alcohols Into Aromatic Nitriles via the Complete Cleavage of the C≡N Triple Bond in the Cyanide Anion

Nitrogen transfer from cyanide anion to an aldehyde is emerging as a promising method for the synthesis of aromatic nitriles. However, this method still suffers from a disadvantage that a use of stoichiometric Cu(II) or Cu(I) salts is required to enable the reaction. As we report herein, we overcame this drawback and developed a catalytic method for nitrogen transfer from cyanide anion to an alcohol via the complete cleavage of the C≡N triple bond using phen/Cu2O as the catalyst. The present condition allowed a series of benzyl alcohols to be smoothly converted into aromatic nitriles in moderate to high yields. In addition, the present method could be extended to the conversion of cinnamic alcohol to 3-phenylacrylonitrile.