23243-68-7

Basic information

• Product Name: 3,6-DIOXAOCTANEDIOIC ACID
• Synonyms: 3,6-Dioxasuberic acid;Acetic acid, 2,2'-[1,2-ethanediylbis(oxy)]bis- (Triglycolic acid);Acetic acid, 2,2‘-[1,2-ethanediylbis(oxy)]bis-;(2-CARBOXYMETHOXYETHOXY)ACETIC ACID;2,2'-(Ethane-1,2-diylbis(oxy))diacetic acid;3,6-dioxoctanedioic acid;PEG2-(CH2CO2H)2;2-[2-(Carboxymethyloxy)ethoxy]acetic acid
• CAS NO: 23243-68-7
• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.14
• EINECS: 245-516-9
• Mol File: 23243-68-7.mol

Chemical Properties

• Melting Point: 68-71℃
• Boiling Point: 429.2 °C at 760 mmHg
• Flash Point: 182.6 °C
• Appearance: /
• Density: 1.375
• Vapor Pressure: 1.43E-08mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: Store below +30°C.
• PKA: 3.09±0.10(Predicted)
• CAS DataBase Reference: 3,6-DIOXAOCTANEDIOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-DIOXAOCTANEDIOIC ACID(23243-68-7)
• EPA Substance Registry System: 3,6-DIOXAOCTANEDIOIC ACID(23243-68-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-27-22
• RIDADR: 3261
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 23243-68-7(Hazardous Substances Data)

Usage

Uses

Used in Research and Development:
3,6-Dioxaoctanedioic Acid is used as a research chemical for various laboratory research and development processes. Its unique structure and properties make it a valuable compound for scientific investigations.
Used in Chemical Production:
3,6-Dioxaoctanedioic Acid is used as a reagent in the preparation of degradation agents for cyclin-dependent kinase. This application is crucial for the development of new drugs and therapies targeting specific cellular processes.
Used as an Organic Synthesis Intermediate:
3,6-Dioxaoctanedioic Acid serves as an organic synthesis intermediate, mainly used in the chemical production process. Its versatile structure allows for the creation of various compounds and materials with different applications across various industries.
Used in Pharmaceutical Intermediates:
3,6-Dioxaoctanedioic Acid is used as a pharmaceutical intermediate, playing a vital role in the development of new drugs and therapies. Its unique properties and reactivity contribute to the advancement of pharmaceutical research and drug discovery.

Flammability and Explosibility

Notclassified

Synthesis

To 15 ml (0.33 mol) of nitric acid was added at 45°C while stirring 1 g of diethylene glycol from the overall amount of 5.9 g (0.06 mol), and the mixture was heated to 65°C. After the end of nitrogen oxides evolution and cooling the mixture to 45-50°C another portion of diethylene glycol was added. Overall time of the reagent addition to the reaction mixture was 1 h. The mixture was kept at 45°C for 40 min and then it was heated at 80°C for 30 min. The solvent was removed in a vacuum at 70°C, the residue was dried by azeotropic distillation with benzene using Dean-Stark trap, then the product was fi ltered off and recrystallized from acetone-benzene mixture. 3,6-Dioxaoctanedioic acid (VIII) was similarly obtained. Yield 7.3 g (89%), colorless crystals. Rf 0.20 (E), mp 76-77°C (mp 75-76°C [13]). IR spectrum, ν, cm-1: 3167 (OH), 2914 (CH), 1733 (C=O acid), 1410, 1229 (C-O), 1121 (C-O). Mass spectrum, m/z (Irel, %): 178.5 [M]+ (76), 200.9 (55), 216.8 (46).

InChI:InChI=1/C6H10O6/c7-5(8)3-11-1-2-12-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)

Upstream product

• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 79-11-8 chloroacetic acid 
• 107-21-1 ethylene glycol 
• 79-08-3 bromoacetic acid 
• 112-60-7 Tetraethylene glycol 

Downstream Products

• 139360-39-7 (ethylenedioxy)diacetic acid pentafluorophenyl ester 
• 75953-77-4 7,19-dibenzyl-7,19-diaza-1,4,10,13,16-pentaoxacycloheneicosane-6,20-dione 
• 446061-85-4 (2-benzyloxycarbonylmethoxyethoxy)acetic acid 
• 446061-82-1 {2-[2-(trimethylsilyl)-ethoxycarbonylmethoxy]-ethoxy}-acetic acid benzyl ester 
• 84293-34-5 (S)-2-(2-{2-[((S)-1-Ethoxycarbonyl-2-phenyl-ethylcarbamoyl)-methoxy]-ethoxy}-acetylamino)-3-phenyl-propionic acid ethyl ester 
• 84308-19-0 (S)-2-(2-{2-[((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-methoxy]-ethoxy}-acetylamino)-3-phenyl-propionic acid benzyl ester 
• 84293-31-2 (S)-2-(2-{2-[((S)-1-Carboxy-2-phenyl-ethylcarbamoyl)-methoxy]-ethoxy}-acetylamino)-3-phenyl-propionic acid 
• 139338-68-4 (1S,12R)-24-(4-Chloro-benzyloxy)-24-oxo-5,8,14,17,20,23,25-heptaoxa-2,11-diaza-24λ⁵-phospha-bicyclo[10.9.5]hexacosane-3,10,13,21-tetraone 
• 139405-49-5 (9R,20S)-9,20-Bis-benzyloxymethyl-1,4,7,13,16-pentaoxa-10,19-diaza-cyclohenicosane-8,11,18,21-tetraone 
• 72469-41-1 2-(2-Dipropylcarbamoylmethoxy-ethoxy)-N,N-dioctadecyl-acetamide 
• 911384-73-1 (10R)-10-((1S)-1-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-2-{4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl}ethyl)-12-(1,3-benzodioxol-5-ylsulfonyl)-14-methyl-8-oxo-3,6,9-trioxa-12-azapentadecan-1-oic acid 
• 927881-75-2 C₂₃H₂₄N₂O₁₄S₃ 
• 328267-56-7 5-[2-(2-methoxy-ethoxy)-phenyl]-11,28-dimethyl-2,8,18,21-tetraoxa-5,15,24-triaza-tricyclo[23.4.0.0^9,14]nonacosa-1⁽²⁹⁾,9⁽¹⁴⁾,10,12,25,27-hexaene-16,23-dione 
• 328267-51-2 C₃₉H₅₅N₃O₈ 

Relevant articles and documents

MACROHETEROCYCLES. 12. SYNTHESIS AND PROPERTIES OF MACROCYCLIC TETRAAMIDES

The N,N'-bis(methoxycarbonylmethyl)diamides of the corresponding acids were obtained by the reaction of glycine methyl ester hydrochloride with oxalic, succinic, adipic, diglycolic, and triglycolic acid dichlorides.Fourteen new macrocyclic tetraamides were obtained by the reaction of these diamides with various diamines.The structures of the synthesized compounds were proved by means of their IR, PMR, and mass spectra.

Effective stabilisation of α-helical structures in short peptides with acetylenic cross-linking agents

The peptides cross-linked by the acetylenic cross-linking agents showed high α-helical contents, and the α-helices thus formed survived up to substantially elevated temperature.

Reactions of peroxide products of ozonolysis of allyl ethers/esters in the AcOH-CH2Cl2 system on treatment with semicarbazide hydrochloride

Background: A one-pot method for the preparation of the corresponding alkoxy acetic acids by low-temperature ozonolysis of allyl ethers/esters followed by treatment with semicarbazide hydrochloride has been suggested. The reaction occurs via formation of acetoxyhydroperoxide, subsequent reduction of which depends on the process temperature and the nature of the starting substrate. Objective: The article is aimed at the development of one-pot method for obtaining practically important alkoxy acetic acids, because the ozonolytic cleavage of a ?=? double bond is the key step in full syntheses of many biologically active compounds. Methods: We used a low temperature ozonolysis of functionally substituted olefins in the system acetic acid-methylene dichloride followed by reduction of semicarbazide hydrochloride. To create a method we have used available allyl ethers/esters as starting materials. Results: We investigated reaction of the peroxide products of ozonolysis of monoallyl ethers, ester and diallyl ethers in an AcOH/CH2Cl2 mixture on treatment with semicarbazide hydrochloride at various temperatures. We have discovered that the selectivity of reduction of acetoxyhydroperoxide formed at the first stage depends both on the process temperature and on the nature of the starting substrate. A decrease in temperature favors acid hydrolysis and formation of a carboxylic acid. Conclusion: We have proposed a simple and highly efficient one-pot method for the preparation alkoxy acetic acids without isolation of intermediate peroxides.

Ether acid copper complex monocrystal, and preparation method and application thereof

The invention discloses an ether acid copper complex monocrystal. The structure of the monocrystal is [Cu(L)(H2O)2], wherein L is ethyldioxydiacetic acid. The invention also discloses a preparation method of the monocrystal. The method adopts a normal temperature volatilization technology, and concretely comprises the following steps: stirring the L and Cu(Ac)2.H2O in water for 0.5h, filtering the obtained solution, and volatilizing the obtained filtrate at normal temperature for 2 weeks in order to obtain the blue block crystal suitable for X-ray single crystal diffraction, wherein a molar ratio of the L to Cu(Ac)2.H2O is 1:1. The invention further discloses an application of the ether acid copper complex monocrystal in detection of the adsorption quantity of a dye or a luminescence agent as a potential fluorescent material.

Selective recovery of rare earth elements using chelating ligands grafted on mesoporous surfaces

Nowadays, rare earth elements (REEs) and their compounds are critical for the rapidly growing advanced technology sectors and clean energy demands. However, their separation and purification still remain challenging. Among different extracting agents used for REE separation, the diglycolamide (DGA)-based materials have attracted increasing attention as one of the most effective extracting agents. In this contribution, a series of new and element-selective sorbents were generated through derivatisation of the diglycolamide ligand (DGA), grafted to mesoporous silica and tested for the separation of rare earth elements. It is shown that, by tuning the ligand bite angle and its environment, it is possible to improve the selectivity towards specific rare earth elements.

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Provided are a near-infrared-ray-absorbing composition having strong near-infrared shielding properties when a cured film is produced, a near-infrared-ray cut filter, a manufacturing method therefor, a camera module, and a manufacturing method therefor. The near-infrared-ray-absorbing composition includes a copper complex obtained by reacting a compound (A) having at least two coordination sites with a copper component.

Basic N-interlinked imipramines show apoptotic activity against malignant cells including Burkitt's lymphoma

We here report the synthesis of ethylene glycol N-interlinked imipramine dimers of various lengths from the tricyclic antidepressant desipramine via an amide coupling reaction followed by reduction with lithium aluminium hydride. The target molecules were found to be potent inhibitors of cellular viability while inducing cell type specific death mechanisms in three cancer cell lines including a highly chemoresistant Burkitt's lymphoma cell line. Basic amine analogues were found to be important for increased potency. Imipramine and desipramine were also tested for apoptotic activity and were found to be much less active than the novel dimeric compounds. Imipramine dimers were only found to be moderate inhibitors of the human serotonin transporter (hSERT) having IC50 values in the micromolar region whilst the induction of cell death occurred independently of hSERT expression. These results demonstrate the potential of newly designed and synthesised imipramines derivatives for use against malignant cells, including those resistant to standard chemotherapy.

Design, synthesis, and properties of neoglycolipids based on ethylene glycoles conjugated with lactose as components of targeted delivery systems of biologically active compounds

Synthesis has been developed of a series of new aliphatic lactose derivatives as components of liposomal targeted delivery systems distinguished by the length and the number of aliphatic chains and also by the length of the spacer fragment. The structure of compounds synthesized has been established by means of 1H NMR spectroscopy. Pleiades Publishing, Ltd., 2012.

CYTOSOLIC FLUORESCENT ION INDICATORS

Novel fluorophores for fluorescent ion indicators incorporate water-solubilizing functional groups. These fluorophores enable visible-wavelength analysis of ion concentrations with chelators that are insoluble or poorly soluble in water. A green version of the fluorophore comprises a putative fluorescein with carboxylate appendages. An orange version of the fluorophore comprises a putative rhodamine, also with carboxylate appendages. Attaching the fluorophore to a 12-crown-4, a 15-crown-5, a 18-crown-6, a 21-crown-7, or a 24-crown-8 produces lithium, sodium, potassium, rubidium, and cesium indicator families, respectively. Attaching the fluorophore to diaza [1,1,1], [1,1,2], [1,2,2], [2,2,2], [2,2,3], [2,3,3], or [3,3,3] cryptands produces more selective lithium, sodium, potassium, rubidium, and cesium indicator families, respectively. Attaching the fluorophore to BAPTA, APTRA, or half- BAPTA or their analogs produces new calcium, magnesium, and other metal ions indicator families that strongly resist leakage from the cell.

Electroorganic synthesis in oil-in-water (O/W) nanoemulsion: TEMPO-mediated electrooxidation of amphiphilic alcohols in water

Oil-in-water nanoemulsion which consisted of TEMPO, amphiphilic alcohols, and water offered unique reaction environments for electrooxidation of the alcohols to give the corresponding carboxylic acids in good to excellent yields.