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

• 99-50-3 3,4-Dihydroxybenzoic acid 
• 75-11-6 diiodomethane 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 107-03-9 1-thiopropane 
• 32745-63-4 phenyl benzo[d][1,3]dioxole-5-carboxylate 
• 82461-58-3 benzo[1,3]dioxol-5-yl-glyoxylonitrile 
• 7732-18-5 water 
• 4720-66-5 Piperil 
• 120-57-0 piperonal 
• 4702-73-2 ((1E)-2-(2H-benzo[3,4-d]1,3-dioxolen-5-yl)-1-azavinyl)(4-nitrophenyl)amine 
• 90843-60-0 2-(3,4-dioxymethylenephenyl)propionaldehyde 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 108-24-7 acetic anhydride 
• 133-03-9 sesamin 

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 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 861079-54-1 3-hydroxy-4-methoxymethoxy-benzoic acid 
• 860596-42-5 4-hydroxy-3-methoxymethoxy-benzoic acid 

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).

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.

One-Pot Direct Oxidation of Primary Amines to Carboxylic Acids through Tandem ortho-Naphthoquinone-Catalyzed and TBHP-Promoted Oxidation Sequence

Biomimetic oxidation of primary amines to carboxylic acids has been developed where the copper-containing amine oxidase (CuAO)-like o-NQ-catalyzed aerobic oxidation was combined with the aldehyde dehydrogenase (ALDH)-like TBHP-mediated imine oxidation protocol. Notably, the current tandem oxidation strategy provides a new mechanistic insight into the imine intermediate and the seemingly simple TBHP-mediated oxidation pathways of imines. The developed metal-free amine oxidation protocol allows the use of molecular oxygen and TBHP, safe forms of oxidant that may appeal to the industrial application.