94-53-1

Basic information

• Product Name: Piperonylic acid
• Synonyms: 1,3-BENZODIOXOLE-5-CARBOXYLIC ACID;3,4-METHYLENDIOXYBENZOIC ACID;3,4-(METHYLENEDIOXY)BENZOIC ACID;AKOS 213-90;TIMTEC-BB SBB003897;3,4-dioxymethylenebenzoicacid;5-benzodioxolecarboxylicacid;Benzoic acid, 3,4-(methylenedioxy)-
• CAS NO: 94-53-1
• Molecular Formula: C₈H₆O₄
• Molecular Weight: 166.13
• EINECS: 202-342-8
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzodiozoles, Benzodioxines & Benzodioxepines;Carboxylic Acids;Benzodiozoles, Benzodioxines & Benzodioxepines;Carboxylic Acids;Building Blocks;C8;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Quinoxalines ,Quinazolines ,Quinaldines
• Mol File: 94-53-1.mol
• Article Data: 92

Chemical Properties

• Melting Point: 229-231 °C(lit.)
• Boiling Point: 254.32°C (rough estimate)
• Flash Point: 139.6 °C
• Appearance: Off-white to beige/Powder
• Density: 1.3579 (rough estimate)
• Vapor Pressure: 9.95E-05mmHg at 25°C
• Refractive Index: 1.5090 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.35±0.20(Predicted)
• Water Solubility: slightly soluble
• Merck: 14,7477
• BRN: 150206
• CAS DataBase Reference: Piperonylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Piperonylic acid(94-53-1)
• EPA Substance Registry System: Piperonylic acid(94-53-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-36/37/39-37/39
• WGK Germany: 3
• RTECS: DF4912765
• TSCA: Yes
• Hazardous Substances Data: 94-53-1(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Piperonylic Acid is a compound closely mimicking the structure of transcinnamic acid involved in the phenylpropanoid pathway in plant physiology.

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 3803, 1975 DOI: 10.1021/jo00913a051

Purification Methods

Crystallise the acid from EtOH or water. [Beilstein 19/7 V 300.]

InChI:InChI=1/C8H6O4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H,9,10)

Upstream product

• 120-57-0 piperonal 
• 98-95-3 nitrobenzene 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 110029-53-3 1,1-bis-(6-methyl-benzo[1,3]dioxol-5-yl)-ethane 
• 97116-16-0 1,1-bis-(6-propyl-benzo[1,3]dioxol-5-yl)-ethane 
• 120-58-1 isosafrole 
• 17627-76-8 (Z)-5-(prop-1-en-1-yl)benzo[d][1,3]dioxole 
• 4043-71-4 isosafrole 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 124-38-9 carbon dioxide 
• 107-03-9 1-thiopropane 
• 32745-63-4 phenyl benzo[d][1,3]dioxole-5-carboxylate 

Downstream Products

• 74828-34-5 N-(2,3,4-trimethoxyphenethyl)(3',4'-methylenedioxyphenyl)acetamide 
• 81581-27-3 ethyl 3-(benzo[d][1,3]dioxol-5-yl)-3-oxopropanoate 
• 93743-61-4 6,7-methylendioxy-3,4-diphenylisocoumarin 
• 139557-86-1 Benzo[1,3]dioxole-5-carboxylic acid 2-iodo-4,5-dimethoxy-benzyl ester 
• 172974-34-4 phenacyl(3,4-methylenedioxyphenyl)benzoate 
• 153165-94-7 <1R-(1α,4β,5β,6β)> N-<5,6-bis-<(4-methoxyphenyl)methoxy>-4-hydroxy-2-cyclohexen-1-yl>-1,3 benzodioxole-5-carboxamide 
• 153221-62-6 <1R-(1α,4α,5β,6β)> N-<5,6-bis-<(4-methoxyphenyl)methoxy>-4-hydroxy-2-cyclohexen-1-yl>-1,3 benzodioxole-5-carboxamide 
• 15777-84-1 N-methylbenzo[d][1,3]dioxole-5-carboxamide 
• 326-56-7 methyl 3,4-methylenedioxybenzoate 
• 716-32-5 6-nitrobenzo[d][1,3]dioxole-5-carboxylic acid 
• 7748-59-6 5,6-dinitro-benzo[1,3]dioxole 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 259149-65-0 4-(2-chloroethoxy)-3,4-methylenedioxybenzophenone 

Relevant articles and documents

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Destructible Surfactants Based on a Silicon-Oxygen Bond

A "destructible" surfactant based on the lability of a silicon-oxygen bond, trimethylammonium nitrate (1b), has been prepared and characterized along with the corresponding chloride (1a) and tetraphenylborate (1c).

An efficient chromium(iii)-catalyzed aerobic oxidation of methylarenes in water for the green preparation of corresponding acids

A highly efficient method to oxidize methylarenes to their corresponding acids with a reusable Cr catalyst was developed. The reaction can be carried out in water with 1 atm oxygen and K2S2O8as cooxidants, proceeds under green and mild conditions, and is suitable for the oxidation of both electron-deficient and electron-rich methylarenes, including heteroaryl methylarenes, even at the gram level. The excellent result, together with its simplicity of operation and the ability to continuously reuse the catalyst, makes this new methodology environmentally benign and cost-effective. The generality of this methodology gives it the potential for use on an industrial scale. Differing from the accepted oxidation mechanism of toluene, GC-MS studies and DFT calculations have revealed that the key benzyl alcohol intermediate is formed under the synergetic effect of the chromium and molybdenum in the Cr catalyst, which can be further oxidized to afford benzaldehyde and finally benzoic acid.

Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics

Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.