21062-20-4

Basic information

• Product Name: 2,2'-OXYDIACETYL CHLORIDE
• Synonyms: Oxybisacetic acid dichloride;Oxydi(acetic acid chloride);2,2'-Oxydiacetylchloride ,95%;Diglycolyl chloride,2,2′-Oxydiacetyl chloride;Diglycolyl chloride 95%;2,2'-OXYDIACETYL CHLORIDE;DIGLYCOLYL CHLORIDE;oxydiacetyl dichloride
• CAS NO: 21062-20-4
• Molecular Formula: C₄H₄Cl₂O₃
• Molecular Weight: 170.98
• EINECS: 244-186-3
• Mol File: 21062-20-4.mol
• Article Data: 23

Chemical Properties

• Melting Point: 121-123 °C
• Boiling Point: 84-87 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.439 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0277mmHg at 25°C
• Refractive Index: n20/D 1.473(lit.)
• CAS DataBase Reference: 2,2'-OXYDIACETYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-OXYDIACETYL CHLORIDE(21062-20-4)
• EPA Substance Registry System: 2,2'-OXYDIACETYL CHLORIDE(21062-20-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 21062-20-4(Hazardous Substances Data)

Usage

Description

2,2'-OXYDIACETYL CHLORIDE, also known as Diglycolyl chloride, is an acid halide that serves as a versatile reagent in the synthesis of various chemical compounds. It is characterized by its ability to react with other molecules, particularly in the formation of ester and amide bonds, making it a valuable component in the production of polymers and other specialty chemicals.

Uses

Used in Polymer Synthesis:
2,2'-OXYDIACETYL CHLORIDE is used as a reagent for the synthesis of poly(ether ester) compounds, which are known for their unique properties such as high thermal stability, mechanical strength, and chemical resistance. These polymers find applications in various industries, including automotive, aerospace, and electronics.
Used in Chiral Compounds Synthesis:
In the pharmaceutical industry, 2,2'-OXYDIACETYL CHLORIDE is used as a key intermediate in the synthesis of chiral diphenyl substituted polyether-diester compounds. These chiral compounds are essential in the development of drugs with improved efficacy and reduced side effects, as they can exhibit different biological activities based on their stereochemistry.
Used in Morpholine Dione Analog (IMDNQ) Synthesis:
2,2'-OXYDIACETYL CHLORIDE is utilized as a starting material in the synthesis of morpholine dione analog (IMDNQ), a compound with potential applications in the development of new pharmaceuticals and agrochemicals. The versatility of this acid halide allows for the creation of diverse structural variations, which can be crucial in optimizing the properties and activities of the final products.
Used in Salicylic Acid (SA)-based Diacids Synthesis:
In the chemical industry, 2,2'-OXYDIACETYL CHLORIDE is used as a reactant in the synthesis of salicylic acid (SA)-based diacids. These diacids are important building blocks for the production of various specialty chemicals, including additives, coatings, and adhesives. The use of 2,2'-OXYDIACETYL CHLORIDE in this process enables the creation of a wide range of products with tailored properties to meet specific application requirements.

InChI:InChI=1/C4H4Cl2O3/c5-3(7)1-9-2-4(6)8/h1-2H2

Upstream product

• 110-99-6 2,2'-oxybis-acetic acid 
• 111-46-6 diethylene glycol 

Downstream Products

• 56173-23-0 oxydi-acetic acid bis-(4-nitro-phenyl ester) 
• 124119-07-9 oxydi-acetic acid bis-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylamide) 
• 2618-25-9 2,4,6,2',4',6'-hexaiodo-3,3'-(3-oxa-pentanedioyldiamino)-di-benzoic acid 
• 83936-42-9 diglycolic acid dianilide 
• 846589-01-3 2,2'-(3-oxa-pentanedioyldioxy)-di-benzoic acid 
• 71190-05-1 oxydi-acetic acid bis-(2-nitro-phenyl ester) 
• 42031-80-1 16,16'-(3-oxa-pentanedioyl)-bis-(1,4,10,13-tetraoxa-7,16-diaza-cyclooctadecane-7-carboxylic acid) dibenzyl ester 
• 110514-12-0 4-(4-methyl-thiobenzoyl)-morpholine-3,5-dione 
• 71190-09-5 [2-(2-Methoxy-ethoxy)-ethoxycarbonylmethoxy]-acetic acid 2-(2-methoxy-ethoxy)-ethyl ester 
• 71190-04-0 (2,4-Di-tert-butyl-phenoxycarbonylmethoxy)-acetic acid 2,4-di-tert-butyl-phenyl ester 
• 118726-66-2 4-thiobenzoyl-morpholine-3,5-dione 
• 20638-02-2 oxydi-acetic acid diphenyl ester 
• 74267-28-0 4,4'-[Oxybis(1-oxoethan-2,1-diyl)]bis[morpholin] 
• 105399-90-4 1,7-bis(2-methoxybenzyl)-2,6-dioxo-4-oxa-1,7-diazaheptane 

Relevant articles and documents

Solubilities of diglycolic acid esters in supercritical carbon dioxide

A series of new CO2-soluble diglycolic acid esters were designed and synthesized, and their structures were confirmed by IR, NMR, and elemental analysis. The solubilities of compounds were measured at temperatures ranging from (313 to 333) K and pressures from (8.5 to 19.3) MPa in supercritical carbon dioxide. AU of the newly synthesized esters showed good to high solubility (as high as 1.25 mol % for compound 1) in supercritical CO2 at easily accessible temperatures and pressures. The measured solubility data were correlated using a semiempirical model. Consequently, the calculated results showed satisfactory agreement with the experimental data and differed from the measured values by between (3.18 and 19.58) %.

Host-Guest Complexation. 38. Cryptahemispherands and Their Complexes

Syntheses and crystal structures are reported for a new class of hosts, their complexes, and their precursors.The cryptahemispherands 5-8 are composed of molecular modules that are half spherand 1 and half cryptand 3.They were synthesized by the reactions of diacid chloride 20 with cyclic diamines 21-23 to produce diamides 13-16, reduction of which gave the desired hosts 5-8.These diamines were best purified, stored, and handled through their respective hydroborane complexes, 9-12.Hosts 6 and 7 are diastereomeric, as are diamides 14 and 15 and hydroborane complexes 10 and 11.Diamines 6 and 7 equilibrate rapidly at 25 deg C probably by ring inversion of the methoxyl groups to give a 5:1 ratio of 6 over 7.Diamides 14 and 15 equilibrate readily at 90 deg C to give only 14 in detectable amounts.Hydroborane complexes 10 and 11 do not equilibrate at 90 deg C.Cryptahemispherands 5, 6 and 8 formed a variety of complexes with the alkali metal cations, diamides 14 and 16 exhibited a low level of binding power, and hydroborane complexes 10 and 12 had no detectable affinity for the alkali metal cations.Hemispherand 17 was synthesized for comparison purposes.Crystal structures were determined for the isomeric diamides 14 and 15, for hydroborane complex 9, and for alkali cation complexes 5.NaB(Ph)4, 6.KSCN, 8.NaSCN, 8.KSCN, and 8.CsClO4.The trisanisyl modules of all eight compounds possess the same preorganized conformation, with the unshared electron pairs of the three methoxyl groups turned inward and the methyl groups outward.The potential cavities of 9, 14, and 15 are filled inward-turned hydrogens of the ethylene bridges.In the alkali metal ion complexes, the unshared electron pairs of the heteroatoms are all turned inward toward the quest metal ion.The use of CPK molecular models in predicting the structures of complexes is evaluated.

Solubilities of amide compounds in supercritical carbon dioxide

2,2′-Oxybis(N,N-diethylacetamide), 2,2′-oxybis(N,N- dibutylacetamide), and 2,2′-oxybis(N,N-dihexylacetamide) were synthesized, and their structures were confirmed by IR, NMR, and elemental analysis. The solubilities of compounds were measured at temperatures ranging from (313 to 333) K and pressures from (8.7 to 16.4) MPa in supercritical carbon dioxide. The measured solubilities were correlated using a semiempirical model. The calculated results showed satisfactory agreement with the experimental data and differed from the measured values by between (4.54 and 30.84) %.

Novel process for synthesizing N,N,N',N'-tetraoctyl-3-oxyglutaramide

The invention provides a novel process for synthesizing N,N,N',N'-tetraoctyl-3-oxyglutaramide (TODGA). The novel process includes the steps of firstly, allowing diglycolic acid to have reaction with SOCl2 to generate diglycolic acyl chloride, and allowing the diglycolic acyl chloride to have reaction with amine to generate part of TODGA; secondly, removing components, which can be easily dissolvedin water, in the byproducts, and separating to obtain monooxaamide carboxylic acid; thirdly, allowing the monooxaamide carboxylic acid to have reaction with amine to generate part of TODGA again. Bythe novel process with the features of an existing process, high yield is achieved.

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.