5768-39-8

Basic information

• Product Name: 1,3-BENZODIOXOLE-4-CARBOXYLIC ACID
• Synonyms: BUTTPARK 27\02-57;1,3-BENZODIOXOLE-4-CARBOXYLIC ACID;RARECHEM AL BE 0228;2,3-Methylene dioxy benzoic acid;benzo[d][1,3]dioxole-4-carboxylic acid;1,3-Benzodioxole-4-carboxylic acid 97+%;o-Piperonylic acid;4-Carboxy-1,3-benzodioxole, 2,3-(Methylenedioxy)benzoic acid
• CAS NO: 5768-39-8
• Molecular Formula: C₈H₆O₄
• Molecular Weight: 166.13
• Product Categories: Acids and Derivatives;Heterocycles
• Mol File: 5768-39-8.mol
• Article Data: 21

Chemical Properties

• Melting Point: 224 °C
• Boiling Point: 318.3 °C at 760 mmHg
• Flash Point: 136.6 °C
• Appearance: /
• Density: 1.468 g/cm³
• Vapor Pressure: 2.48E-12mmHg at 25°C
• Refractive Index: 1.682
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.97±0.20(Predicted)
• CAS DataBase Reference: 1,3-BENZODIOXOLE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BENZODIOXOLE-4-CARBOXYLIC ACID(5768-39-8)
• EPA Substance Registry System: 1,3-BENZODIOXOLE-4-CARBOXYLIC ACID(5768-39-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 5768-39-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 17, p. 3361, 1976 DOI: 10.1016/S0040-4039(00)93045-4

InChI:InChI=1/C17H14BrN3O2/c18-13-6-7-15-14(8-13)12(9-19-15)10-20-21-17(23)16(22)11-4-2-1-3-5-11/h1-10,16,20,22H,(H,21,23)/b12-10-

Upstream product

• 303-38-8 2,3-Dihydroxybenzoic acid 
• 769-30-2 benzo[1,3]dioxol-4-yl-methanol 
• 23158-06-7 benzo[1,3]dioxole-4-carboxylic acid ethyl ester 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 2411-83-8 methyl-2,3-dihydroxybenzoate 
• 33842-16-9 benzo[1,3]dioxole-4-carboxylic acid methyl ester 
• 274-09-9 Methylenedioxybenzene 
• 124-38-9 carbon dioxide 
• 75-11-6 diiodomethane 
• 254973-61-0 benzo[d][1,3]dioxol-5-yl(trimethylsilyl)methanone 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 

Downstream Products

• 111081-10-8 tert-butyl [2,3-(methylenedioxy)phenyl]carbamate 
• 1261963-95-4 C₂₁H₂₄N₂O₄ 
• 1137558-08-7 benzyl benzo[d][1,3]dioxol-4-ylcarbamate 
• 33842-16-9 benzo[1,3]dioxole-4-carboxylic acid methyl ester 
• 198554-04-0 4-[1-(1,3-benzodioxol-4-ylcarbonyl)piperidin-4-yl]-6-(4-methoxybenzyl)pyrimidin-2-amine 
• 112885-30-0 2,3-methylenedioxy-N-[(4-benzyl-2-morpholinyl)methyl]benzamide 
• 38489-70-2 2,3-(methylenedioxy)cinnamic acid 
• 161886-19-7 benzo[1,3]dioxole-4-carbonitrile 
• 769-30-2 benzo[1,3]dioxol-4-yl-methanol 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 
• 482-32-6 kokusagine 
• 1668-84-4 benzo[d][1,3]dioxol-4-amine 
• 69151-39-9 NU 1034 
• 97174-59-9 N,N'-di-(1,3-benzodioxol-4-yl)urea 

Relevant articles and documents

Synthesis of 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide and 3-oxo-3,4-dihydrobenzo[b][1,4]oxazine-8-carboxamide derivatives as PARP1 inhibitors

Poly(ADP-ribose) polymerase 1 (PARP1), a widely explored anticancer drug target, plays an important role in single-strand DNA break repair processes. High-throughput virtual screening (HTVS) of a Maybridge small molecule library using the PARP1-benzimidazole-4-carboxamide co-crystal structure and pharmacophore model led to the identification of eleven compounds. These compounds were evaluated using recombinant PARP1 enzyme assay that resulted in the acquisition of three PARP1 inhibitors: 3 (IC50 = 12 μM), 4 (IC50 = 5.8 μM), and 10 (IC50 = 0.88 μM). Compound 4 (2,3-dihydro-1,4-benzodioxine-5-carboxamide) was selected as a lead and was subjected to further chemical modifications, involving analogue synthesis and scaffold hopping. These efforts led to the identification of (Z)-2-(4-hydroxybenzylidene)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxamide (49, IC50 = 0.082 μM) as the most potent inhibitor of PARP1 from the series.

4-Alkyliden-azetidinones modified with plant derived polyphenols: Antibacterial and antioxidant properties

Antimicrobial resistance is one of the major and growing concerns in hospital- and community acquired infections, and new antimicrobial agents are therefore urgently required. It was reported that oxidative stress could contribute to the selection of resistant bacterial strains, since reactive oxygen species (ROS) revealed to be an essential driving force. In the present work 4-alkylidene-azetidinones, a new class of antibacterial agents, were functionalized with phytochemical polyphenolic acids such as protocatechuic, piperonyl, caffeic, ferulic, or sinapic acids and investigated as dual target antibacterial-antioxidant compounds. The best candidates showed good activities against multidrug resistant clinical isolates of MRSA (MICs 2–8 μg/mL). Among the new compounds, two revealed the best antioxidant capacity with TEAC-DPPH and TEAC-ABTS being significantly more active than Trolox.

SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME

ABSTRACT The present invention provides for certain sulfonyl ureas and related compounds which have advantageous properties and show useful activity in the inhibition of activation of the NLRP3 inflammasome. Such compounds are useful in the treatment of a wide range of disorders in which the inflammation process, or more specifically the NLRP3 inflammasome, have been implicated as being a key factor.