106690-33-9

Basic information

• Product Name: (1,3-BENZODIOXOL-5-YLOXY)ACETIC ACID
• Synonyms: TIMTEC-BB SBB004482;CHEMBRDG-BB 3013803;ART-CHEM-BB B013803;ASINEX-REAG BAS 13090906;(BENZO[1,3]DIOXOL-5-YLOXY)-ACETIC ACID;AKOS B013803;(1,3-BENZODIOXOL-5-YLOXY)ACETIC ACID;2-(2H-1,3-BENZODIOXOL-5-YLOXY)ACETIC ACID
• CAS NO: 106690-33-9
• Molecular Formula: C₉H₈O₅
• Molecular Weight: 196.16
• Mol File: 106690-33-9.mol

Chemical Properties

• Boiling Point: 345°C at 760 mmHg
• Flash Point: 142.5°C
• Appearance: /
• Density: 1.445g/cm³
• Vapor Pressure: 2.42E-05mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: (1,3-BENZODIOXOL-5-YLOXY)ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (1,3-BENZODIOXOL-5-YLOXY)ACETIC ACID(106690-33-9)
• EPA Substance Registry System: (1,3-BENZODIOXOL-5-YLOXY)ACETIC ACID(106690-33-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 106690-33-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1,3-Benzodioxol-5-yloxy)acetic acid is used as a building block for the synthesis of pharmaceuticals due to its ability to contribute to the development of biologically active molecules. Its presence in the molecular structure of various drugs aids in enhancing their therapeutic effects.
Used in Medicinal Chemistry:
As a key intermediate in medicinal chemistry, (1,3-benzodioxol-5-yloxy)acetic acid is utilized for the preparation of compounds with potential anti-inflammatory and analgesic properties, thereby contributing to the advancement of treatments for inflammatory conditions and pain management.
Used in Agrochemical Production:
(1,3-Benzodioxol-5-yloxy)acetic acid is used as an intermediate in the production of agrochemicals, where its benzodioxole ring serves as an important structural element in the development of effective and targeted crop protection agents.
Used in Flavor and Fragrance Industry:
(1,3-BENZODIOXOL-5-YLOXY)ACETIC ACID is also used as an intermediate in the creation of flavors and fragrances, capitalizing on its chemical properties to produce unique scents and tastes for various applications in the food, beverage, and cosmetic industries.
Used in Organic Synthesis:
(1,3-Benzodioxol-5-yloxy)acetic acid is employed as a versatile intermediate in organic synthesis, enabling the production of a wide range of chemical products, from specialty chemicals to high-value fine chemicals, due to its reactive functional groups and structural features.

InChI:InChI=1/C9H8O5/c10-9(11)4-12-6-1-2-7-8(3-6)14-5-13-7/h1-3H,4-5H2,(H,10,11)

Upstream product

• 533-31-3 Sesamol 
• 3926-62-3 sodium monochloroacetic acid 
• 179110-57-7 ethyl 2-(benzo[d][1,3]dioxol-5-yloxy)acetate 
• 105-36-2 ethyl bromoacetate 
• 96-32-2 bromoacetic acid methyl ester 
• 120-57-0 piperonal 
• 79-11-8 chloroacetic acid 

Downstream Products

• 1374762-27-2 2-(benzo[d][1,3]dioxol-5-yloxy)-N-phenyl-N-(thiophen-2-ylmethyl)acetamide 
• 124497-64-9 3-(Benzo[1,3]dioxol-5-yloxymethyl)-6-(4-bromo-phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 124497-62-7 3-(Benzo[1,3]dioxol-5-yloxymethyl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 115398-67-9 4-Amino-5-(benzo[1,3]dioxol-5-yloxymethyl)-4H-[1,2,4]triazole-3-thiol 
• 133748-70-6 ethyl 1-(3,4-methylenedioxyphenoxyacetyl)-piperidine-4-carboxylate 

Relevant articles and documents

1,3-Benzodioxole-based fibrate derivatives as potential hypolipidemic and hepatoprotective agents

A series of target compounds 1,3-benzodioxole-based fibrate derivatives were designed and synthesized. All the target compounds were preliminarily evaluated by hyperlipidemia mice induced by Triton WR-1339, in which compound 12 displayed a greater anti-hyperlipidemia activity than other compounds as well as positive drug fenofibrate (FF). 12 showed a significant reduction of plasma lipids, such as triglycerides (TG), total cholesterol (TC) and low-density lipoprotein cholesterin (LDL-C), in high fat diet (HFD) induced hyperlipidemic mice. In addition, hepatic transaminases (AST and ALT) were ameliorated after administration of 12, in particular the AST, and the histopathological examination showed that 12 improved the hepatic lipid accumulation. The expression of PPAR-α involved in lipids metabolism was up-regulated in the liver tissues of 12-treated group. Other significant activity such as antioxidant, and anti-inflammation was confirmed and reinforced the effects of 12 as a potential hypolipidemia and hepatoprotective agent.

Structural simplification and bioisostere principle lead to Bis-benzodioxole-fibrate derivatives as potential hypolipidemic and hepatoprotective agents

The bis-benzodioxole-fibrate hybrids were designed by structural simplification and bioisostere principle. Lipids lowering activity was preliminarily screened by Triton WR 1339 induced hyperlipidemia mice model, in which T3 showed the best hypolipidemia, decreasing plasma triglyceride (TG) and total cholesterol (TC), which were better than sesamin and fenofibrate (FF). T3 was also found to significantly reduce TG, TC and low density lipoprotein cholesterin (LDL-C) both in plasma and liver tissue of high fat diet (HFD) induced hyperlipidemic mice. In addition, T3 showed hepatoprotective activity, which the noteworthy amelioration in liver aminotransferases (AST and ALT) was evaluated and the histopathological observation exhibited that T3 inhibited lipids accumulation in the hepatic and alleviated liver damage. The expression of PPAR-α receptor involved lipids metabolism in liver tissue significantly increased after T3 supplementation. Other potent activity, such as antioxidation and anti-inflammation, was also observed. The molecular docking study revealed that T3 has good affinity activity toward to the active site of PPAR-α receptor. Based on these findings, T3 may serve as an effective hypolipidemic agent with hepatoprotection.

An efficient synthesis of benzofurans and their application in the preparation of natural products of the genus Calea

The intramolecular cyclization of the β-substituted olefins methyl 2-aryloxy-3-dimethylaminopropenoates 3a-3f catalyzed by Lewis acids leads to a short and novel synthesis of benzofurans 2a-2f. When the olefins 4-dimethylamino-3-aryloxy-3-buten-2-ones 4a-4f were used, the cyclization process was faster and provided the corresponding substituted 2-acetylbenzofurans 1a-1f. Among the latter, naturally occurring compounds calebertin (1a), caleprunin A (1b), and caleprunin B (1c) were prepared in good overall yields. These benzofurans were also obtained by direct treatment under MW irradiation of the precursors 1-aryloxypropan-2-ones 7a-7c with DMFDMA, followed by addition of the catalyst, resulting in a route that was one step shorter.

Captodative olefins: Methyl 2-aryloxy-3-dimethyl-aminopropenoates and their application in a new synthesis of benzofurans

The β-substituted captodative olefins methyl 2-aryloxy-3- dimethylaminopropenoates 4a-h were synthesized, via aminomethylenation of the corresponding 2-phenoxyacetic esters 9a-h. Lewis acid promoted intramolecular cyclization of alkenes 4 led to benzofurans 7a-h, in an efficient synthetic approach to the benzofuran frame.

N-aryl thienyl-, furyl-, and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin

Thienyl-, furyl- and pyrrolyl-sulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl)furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.

Camptothecin derivatives

(20S) esters of camptothecin analogs are provided. The compounds are (20S) esters of an oxyalkanoic acid and camptothecin, which is optionally substituted at the 7, 9, 10, 11, and 12 positions of the camptothecin ring. The compounds are useful for treatin

Synthesis and Growth Retardant Activities of Trialkylammonium Iodides from Piperonal and &β-Naphthol

N,N-dimethyl-2-(β-naphthoxy)ethanamine (4), N, N-dimethyl-2-(3',4'-methylenedioxyphenoxy)ethanamine (4b), N,N-diethyl-2-(β-naphthoxy)ethanamine (8a), N,N-diethyl-2-(3',4'-methylenedioxyphenoxy)ethanamine (8b) and N,N-dimethyl-3-(3',4'-methylenedioxyphenyl)prop-2-enamine (15) have been prepared and converted into the corresponding quaternary salts of ammonia by treating them with methyl and ethyl iodides.The compounds have been tested as plant growth inhibitors on Brasica juncea.