110-99-6

Basic information

• Product Name: Diglycolic acid
• Synonyms: DIGLYCOLIC ACID;DIGLYCOLLIC ACID;2,2'-OXYDIACETIC ACID;A,A'-OXYDIACETIC ACID;2,2’-oxybis-aceticaci;2,2’-oxybisaceticacid;2,2’-oxybis-Aceticacid;3-Oxapentanedioic acid
• CAS NO: 110-99-6
• Molecular Formula: C₄H₆O₅
• Molecular Weight: 134.09
• EINECS: 203-823-5
• Product Categories: Heterocyclic Compounds
• Mol File: 110-99-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: 140-144 °C(lit.)
• Boiling Point: 167.16°C (rough estimate)
• Flash Point: 201.7°C
• Appearance: White to light beige/Crystalline Powder
• Density: 1.486
• Vapor Pressure: 3.63E-09mmHg at 25°C
• Refractive Index: 1.4000 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: ethanol: soluble5%, clear to slightly hazy, colorless to greenis
• PKA: pK1:2.96 (25°C)
• Water Solubility: Soluble
• BRN: 1072117
• CAS DataBase Reference: Diglycolic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Diglycolic acid(110-99-6)
• EPA Substance Registry System: Diglycolic acid(110-99-6)

Safety Data

• Hazard Codes: Xn,C
• Statements: 22-36/37/38-34
• Safety Statements: 26-36-45-36/37/39
• RIDADR: 2811
• WGK Germany: 3
• RTECS: AJ1530000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 110-99-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light beige crystalline powder

Uses

Diglycolic acid was used in the preparation of needle-like aragonite particles from calcium nitrate aqueous solutions.

General Description

Diglycolic acid is a toxic metabolite of diethylene glycol (DEG) responsible for DEG-induced proximal tubular necrosis.

Biochem/physiol Actions

Diglycolic acid has antithrombogenic properties and induces vasodilation. It inhibits succinate dehydrogenase activity in human proximal tubule cells.

Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.

Purification Methods

Crystallise diglycolic acid from water. [Beilstein 3 IV 577.]

InChI:InChI=1/C4H6O5/c5-3(6)1-9-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)/p-2

Synthetic route

diethylene glycol (111-46-6) → 2,2'-oxybis-acetic acid (110-99-6)

Conditions	Yield
With nitric acid at 45 - 80℃; for 2.16667h;	92%
With nitric acid	90%
With C24H33IrN4O3; water; sodium hydroxide for 18h; Reflux;	90%

p-dioxanone (3041-16-5) → 2,2'-oxybis-acetic acid (110-99-6)

Conditions	Yield
With dinitrogen tetraoxide In chloroform	75%

Tetraethylene glycol (112-60-7) → 2,2'-oxybis-acetic acid (110-99-6) + 3,6-dioxasuberic acid (23243-68-7) + tetraglycolic acid (13887-98-4)

Conditions	Yield
at 5℃; for 8h; electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 1M NaOH/H2O; Title compound not separated from byproducts;	A 3% B 16% C 50%

cis-1,4-anhydroerythritol (4358-64-9) → 2,2'-oxybis-acetic acid (110-99-6) + 2-(formyloxymethoxy)acetic acid

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 0.75h; Time; Inert atmosphere;	A n/a B 29%

glycolic Acid (79-14-1) → 2,2'-oxybis-acetic acid (110-99-6)

Conditions	Yield
at 200 - 240℃;

bromoacetic acid (79-08-3) → 2,2'-oxybis-acetic acid (110-99-6) + glycolic Acid (79-14-1)

Conditions	Yield
With water quantitativer Verlauf der Bildung mit verschiedenen Basen;

chloroacetic acid (79-11-8) → 2,2'-oxybis-acetic acid (110-99-6)

Conditions	Yield
With calcium hydroxide; water
With barium dihydroxide; water
With strontium hydroxide; water
With barium dihydroxide Darstellung; ueber mehrere Stufen;

chloroacetic acid (79-11-8) → 2,2'-oxybis-acetic acid (110-99-6) + glycolic Acid (79-14-1)

Conditions	Yield
With water; lead(II) oxide
With water; magnesium oxide

1,4-dioxane (123-91-1) → 2,2'-oxybis-acetic acid (110-99-6)

Conditions	Yield
With hydrogenchloride; sodium hypochlorite

diethylene glycol dimethyl ether (111-96-6) → 2,2'-oxybis-acetic acid (110-99-6)

Conditions	Yield
With hydrogenchloride; sodium hypochlorite

1,4-dioxane-2,6-dione (4480-83-5) + water (7732-18-5) → 2,2'-oxybis-acetic acid (110-99-6)

morpholine-3,5-dione (4430-05-1) + KOH-solution → 2,2'-oxybis-acetic acid (110-99-6)

4-ethyltetrahydro-1,4-oxazine-3,5-dione (462110-57-2) + water (7732-18-5) → 2,2'-oxybis-acetic acid (110-99-6) + ethylamine (75-04-7)

4-methyltetrahydro-1,4-oxazine-3,5-dione (57503-67-0) + water (7732-18-5) → 2,2'-oxybis-acetic acid (110-99-6) + methylamine (74-89-5)

water (7732-18-5) + bromoacetic acid (79-08-3) → 2,2'-oxybis-acetic acid (110-99-6) + glycolic Acid (79-14-1)

Conditions	Yield
Geschwindigkeit und Verlauf der Reaktionen;

bromoacetic acid (79-08-3) + -base → 2,2'-oxybis-acetic acid (110-99-6) + glycolic Acid (79-14-1)

Conditions	Yield
Geschwindigkeit und Verlauf der Reaktionen;

chloroacetic acid (79-11-8) + -base → 2,2'-oxybis-acetic acid (110-99-6) + glycolic Acid (79-14-1)

dimethyl ester of/the/ diglycolic acid → 2,2'-oxybis-acetic acid (110-99-6)

Conditions	Yield
With sulfuric acid; water
With water
With phosphoric acid; water

chloroacetic acid (79-11-8) + lithium hydroxide → 2,2'-oxybis-acetic acid (110-99-6)

Conditions	Yield
With water

chloroacetic acid ethyl ester (105-39-5) + sodium glycolic acid ester → 2,2'-oxybis-acetic acid (110-99-6)

Conditions	Yield
und Verseifung des entstehenden Diaethylesters;

nitric acid (7697-37-2) + diethylene glycol (111-46-6) → 2,2'-oxybis-acetic acid (110-99-6) + glycolic Acid (79-14-1) + oxalic acid (144-62-7)

diethylene glycol (111-46-6) → 2,2'-oxybis-acetic acid (110-99-6) + glycolic acid and oxalic acid

Conditions	Yield
With nitric acid

glycolic Acid (79-14-1) → 2,2'-oxybis-acetic acid (110-99-6) + poly glycolide + polyoxymethylene

Conditions	Yield
at 200 - 240℃;

hydrogenchloride (7647-01-0) + diglycolamide (22064-41-1) → 2,2'-oxybis-acetic acid (110-99-6) + ammonium chloride

Conditions	Yield
und Behandeln mit Wasser;

diglycolamide (22064-41-1) + alkali → 2,2'-oxybis-acetic acid (110-99-6) + ammonia (7664-41-7)

1,4-dioxane-2,6-dione (4480-83-5) + (4,4'-isopropylidenedithio)bis[2,6-di-tert-butylphenol] (23288-49-5) → 2,2'-oxybis-acetic acid (110-99-6) + diglycolic acid, mono[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenyl]ester

Conditions	Yield
In tetrahydrofuran

dipotassium salt of diglycolic acid → 2,2'-oxybis-acetic acid (110-99-6)

Conditions	Yield
In carbon dioxide
In carbon dioxide

1,4-dioxane-2,6-dione (4480-83-5) + diethyl ether (60-29-7) → 2,2'-oxybis-acetic acid (110-99-6)

Conditions	Yield
With dmap In pyridine

2,2'-oxybis-acetic acid (110-99-6) + methanol (67-56-1) → dimethyl diglycolate (7040-23-5)

Conditions	Yield
With thionyl chloride at 0 - 20℃;	100%
Stage #1: 2,2'-oxybis-acetic acid With thionyl chloride at 20℃; for 8h; Stage #2: methanol	98%
With sulfuric acid for 24h; Heating;	90%

2,2'-oxybis-acetic acid (110-99-6) → diglycolyl chloride (21062-20-4)

Conditions	Yield
With oxalyl dichloride In benzene	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Cooling with ice;	88%
With thionyl chloride for 5h; Reflux;	86.2%

2,2'-oxybis-acetic acid (110-99-6) + thorium(IV) nitrate hexahydrate → [Th(oxydiacetate)2]n

Conditions	Yield
In methanol stoich. amts. (pptn.);	99%
In not given addn. of >= 2 equiv. of ligand to Th salt; crystn. (several days), filtration, washing (H2O, MeOH); elem. anal.;

2,2'-oxybis-acetic acid (110-99-6) + (2R)-2-aminobutan-1-ol (5856-63-3) → (-)-bis{[4-(R)-ethyloxazolin-2-yl]methyl} ether (850410-75-2)

Conditions	Yield
In toluene for 23h; Reflux;	98%

PD 0332991 (571190-30-2) + 2,2'-oxybis-acetic acid (110-99-6) → 2-(2-(4-(6-((6-acetyl-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazin-1-yl)-2-oxoethoxy)acetic acid

Conditions	Yield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; dimethyl sulfoxide at 20℃;	96%

2,2'-oxybis-acetic acid (110-99-6) + terbium(III) perchlorate hexahydrate + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Tb2(oxydiacetate)6Cd3(H2O)6]·6H2O}n

Conditions	Yield
Stage #1: 2,2'-oxybis-acetic acid; terbium(III) perchlorate hexahydrate; water With sodium hydroxide at 20℃; for 1h; pH=6.0; Stage #2: cadmium(II) perchlorate dihydrate With sodium hydroxide at 60℃; for 4h; pH=6.5;	95%

2,2'-oxybis-acetic acid (110-99-6) + praseodymium perchlorate hexahydrate + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Pr2((oxydiacetate))6Cd3(H2O)6]·9H2O}n

Conditions	Yield
Stage #1: 2,2'-oxybis-acetic acid; praseodymium perchlorate hexahydrate; water With sodium hydroxide at 20℃; for 1h; pH=6; Stage #2: cadmium(II) perchlorate dihydrate With sodium hydroxide at 60℃; for 4h; pH=6.5;	95%

2,2'-oxybis-acetic acid (110-99-6) + neodymium(III) perchlorate hexahydrate + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Nd2((oxydiacetate))6Cd3(H2O)6]·6H2O}n

Conditions	Yield
Stage #1: 2,2'-oxybis-acetic acid; neodymium(III) perchlorate hexahydrate; water With sodium hydroxide at 20℃; for 1h; pH=6; Stage #2: cadmium(II) perchlorate dihydrate With sodium hydroxide at 60℃; for 4h; pH=6.5;	95%

2,2'-oxybis-acetic acid (110-99-6) + samarium(III) perchlorate hexahydrate + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Sm2((oxydiacetate))6Cd3(H2O)6]·6H2O}n

Conditions	Yield
Stage #1: 2,2'-oxybis-acetic acid; samarium(III) perchlorate hexahydrate; water With sodium hydroxide at 20℃; for 1h; pH=6; Stage #2: cadmium(II) perchlorate dihydrate With sodium hydroxide at 60℃; for 4h; pH=6.5;	95%

2,2'-oxybis-acetic acid (110-99-6) + europium(III) perchlorate hexahydrate + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Eu2((oxydiacetate))6Cd3(H2O)6]·6H2O}n

Conditions	Yield
Stage #1: 2,2'-oxybis-acetic acid; europium(III) perchlorate hexahydrate; water With sodium hydroxide at 20℃; for 1h; pH=6; Stage #2: cadmium(II) perchlorate dihydrate With sodium hydroxide at 60℃; for 4h; pH=6.5;	95%

2,2'-oxybis-acetic acid (110-99-6) + dysprosium(III) perchlorate hexahydrate + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Dy2((oxydiacetate))6Cd3(H2O)6]·3H2O}n

Conditions	Yield
Stage #1: 2,2'-oxybis-acetic acid; dysprosium(III) perchlorate hexahydrate; water With sodium hydroxide at 20℃; for 1h; pH=6; Stage #2: cadmium(II) perchlorate dihydrate With sodium hydroxide at 60℃; for 4h; pH=6.5;	95%

2,2'-oxybis-acetic acid (110-99-6) + diethylamine (109-89-7) → N,N,N′,N′-tetraethyl diglycolamide (77077-06-6)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In chloroform at 20℃; for 18h;	95%

2,2'-oxybis-acetic acid (110-99-6) + (3S,4S)-N3,N4-bis(((1S,2R)-2-phenylcyclopropyl)carbamoyl)pyrrolidine-3,4-dicarboxamide hydrochloride → (3S,3’S,4S,4’S)-1,1’-(2,2’-oxybis(acetyl))bis-(N3,N4-bis((1S,2R)-2-phenylcyclopropyl)pyrrolidine-3,4-dicarboxamide)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 18h;	94%

2,2'-oxybis-acetic acid (110-99-6) → 1,4-dioxane-2,6-dione (4480-83-5)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In toluene for 3h; Inert atmosphere; Reflux;	93%
With phosphoric acid; acetic anhydride at 145℃; for 2h; Temperature;	90%
With niobium(V) oxide hydrate In o-xylene at 160℃; for 72h; Inert atmosphere; Molecular sieve;	86%

2,2'-oxybis-acetic acid (110-99-6) + gadolinium(III) perchlorate hexahydrate + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Gd2(oxydiacetate)6Cd3(H2O)6]·6H2O}n

Conditions	Yield
Stage #1: 2,2'-oxybis-acetic acid; gadolinium(III) perchlorate hexahydrate; water With sodium hydroxide at 20℃; for 1h; pH=6.0; Stage #2: cadmium(II) perchlorate dihydrate With sodium hydroxide at 60℃; for 4h; pH=6.5;	92%

2,2'-oxybis-acetic acid (110-99-6) + 5-[2-([3-(2-amino-ethoxy)-5-([(4-benzyloxycarbonyl-butylcarbamoyl)-methyl]-{[2-(4-fluoro-phenyl)-ethylcarbamoyl]-methyl}-carbamoyl)-benzoyl]-{[2-(4-fluoro-phenyl)-ethylcarbamoyl]-methyl}-amino)-acetylamino]-pentanoic acid benzyl ester; hydrochloride → C120H136F4N14O25

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 12h; Condensation;	90%

2,2'-oxybis-acetic acid (110-99-6) + cobalt(II) nitrate hexahydrate + hydrazine hydrate (7803-57-8) → Co(2+)*CO2CH2OCH2CO2(2-)*2N2H4=Co(CO2CH2OCH2CO2)*2N2H4

Conditions	Yield
In water oxiacetic acid and hydrazine hydrate in water were added to the aq. soln. of metal nitrate hydrate; ppt. was washed with water, alcohol and ther and dried in air; elem. anal.;	90%

2,2'-oxybis-acetic acid (110-99-6) + nickel(II) nitrate hydrate + hydrazine hydrate (7803-57-8) → Ni(2+)*CO2CH2OCH2CO2(2-)*2N2H4=Ni(CO2CH2OCH2CO2)*2N2H4

Conditions	Yield
In water oxiacetic acid and hydrazine hydrate in water were added to the aq. soln. of metal nitrate hydrate; ppt. was washed with water, alcohol and ther and dried in air; elem. anal.;	90%

2,2'-oxybis-acetic acid (110-99-6) + zinc(II) nitrate hydrate + hydrazine hydrate (7803-57-8) → Zn(2+)*CO2CH2OCH2CO2(2-)*N2H4*H2O=Zn(CO2CH2OCH2CO2)*N2H4*H2O (332397-36-1)

Conditions	Yield
In water oxiacetic acid and hydrazine hydrate in water were added to the aq. soln. of metal nitrate hydrate; ppt. was washed with water, alcohol and ther and dried in air; elem. anal.;	90%

2,2'-oxybis-acetic acid (110-99-6) + dysprosium hydroxide + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Cd(H2O)6]·[Dy2(oxydiacetate)6Cd2]·6H2O}n

Conditions	Yield
at 170℃; for 168h; High pressure;	90%

2,2'-oxybis-acetic acid (110-99-6) + erbium hydroxide + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Cd(H2O)6]·[Er2(oxydiacetate)6Cd2]·12H2O}n

Conditions	Yield
at 170℃; for 168h; High pressure;	90%

2,2'-oxybis-acetic acid (110-99-6) + holmium(III) hydroxide + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Cd(H2O)6]·[Ho2(oxydiacetate)6Cd2]·12H2O}n

Conditions	Yield
at 170℃; for 168h; High pressure;	90%

2,2'-oxybis-acetic acid (110-99-6) + thulium(III) hydroxide + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Cd(H2O)6]·[Tm2(oxydiacetate)6Cd2]·12H2O}n

Conditions	Yield
at 170℃; for 168h; High pressure;	90%

2,2'-oxybis-acetic acid (110-99-6) + lutetium(III) hydroxide + cadmium(II) perchlorate dihydrate + water (7732-18-5) → {[Cd(H2O)6]·[Lu2(oxydiacetate)6Cd2]·12H2O}n

Conditions	Yield
at 170℃; for 168h; High pressure;	90%

2,2'-oxybis-acetic acid (110-99-6) + azido-PEG24-CO[N(PN)2][Lys]4[(α-NH2*TFA)(ε-NHPEG1100)]4 + (8S,10S)-10-(4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxy-acetyl)-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione → azido-PEG24-CO[N(PN)2][Lys]4[(α-NH-DGA-3'-NH-dox)(ε-NH-COPEG1100)]4

Conditions

Yield

Stage #1: (8S,10S)-10-(4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxy-acetyl)-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione With dmap In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 2,2'-oxybis-acetic acid In N,N-dimethyl-formamide for 3h; Stage #3: azido-PEG24-CO[N(PN)2][Lys]4[(α-NH2*TFA)(ε-NHPEG1100)]4 With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

89%

2,2'-oxybis-acetic acid (110-99-6) + azido-PEG24-CO[N(PN)2][Lys]4[(α-NH2*TFA)(ε-NHPEG1100)]4 + Nemorubicin → azido-PEG24CO-[N(PN)2][Lys]4[(α-NH-DGA-14-O-nemo)(ε-NH-COPEG1100) ]4

Conditions	Yield
Stage #1: Nemorubicin With dmap In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 2,2'-oxybis-acetic acid In N,N-dimethyl-formamide for 3h; Stage #3: azido-PEG24-CO[N(PN)2][Lys]4[(α-NH2*TFA)(ε-NHPEG1100)]4 With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	89%

2,2'-oxybis-acetic acid (110-99-6) + carbazitaxel (183133-96-2) → diglycolyl-cabazitaxel (1375468-21-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1.5h;	88.5%

2,2'-oxybis-acetic acid (110-99-6) + 1,2-diamino-benzene (95-54-5) → 1,3-bis(1H-benzimidazol-2-yl)-2-oxapropane (94665-42-6)

Conditions	Yield
With silphox [POCl3-n(SiO2)n, silica phosphinoxide] In N,N-dimethyl-formamide for 0.25h; Microwave irradiation;	87%
With hydrogenchloride; water for 14h; Heating;	72%
With polyphosphoric acid at 180℃;	70%

2,2'-oxybis-acetic acid (110-99-6) + uranyl nirate hexahydrate → oxydiacetatodioxouranium(VI) (45979-40-6, 48122-12-9)

Conditions	Yield
With sodium bicarbonate In water diglycolic acid and sodium bicarbonate dissolved in H2O, uranyl nitrate hexahydrate in H2O added, heated to reflux, cooled to ambient temp.; filtered, washed with H2O and acetone, dried by suction;	87%

Upstream product

• 79-14-1 glycolic Acid 
• 112-60-7 Tetraethylene glycol 
• 111-46-6 diethylene glycol 
• 123-91-1 1,4-dioxane 
• 111-96-6 diethylene glycol dimethyl ether 
• 4480-83-5 1,4-dioxane-2,6-dione 
• 7732-18-5 water 
• 4430-05-1 morpholine-3,5-dione 
• 462110-57-2 4-ethyltetrahydro-1,4-oxazine-3,5-dione 
• 57503-67-0 4-methyltetrahydro-1,4-oxazine-3,5-dione 
• 7697-37-2 nitric acid 
• 7647-01-0 hydrogenchloride 
• 22064-41-1 diglycolamide 
• 76-25-5 triamcinolone acetonide 

Downstream Products

• 71190-03-9 oxydi-acetic acid di-o-tolyl ester 
• 5441-63-4 3-oxa-glutaric acid diallyl ester 
• 99513-52-7 benzothiazol-2-ylmethoxy-acetic acid 
• 33051-25-1 1,7-dibenzyl-2,6-dioxo-4-oxa-1,7-diazaheptane 
• 333-36-8 1,1,1-trifluoro-2-(2,2,2-trifluoroethoxy)ethane 
• 57503-67-0 4-methyltetrahydro-1,4-oxazine-3,5-dione 
• 64571-78-4 4-(2-benzoyl-phenyl)-10-phenyl-4H-[1,4]oxazino[3,2-b]quinolin-3-one 
• 56173-23-0 oxydi-acetic acid bis-(4-nitro-phenyl ester) 
• 79-14-1 glycolic Acid 
• 64-19-7 acetic acid 
• 15719-64-9 methylammonium carbonate 
• 57503-73-8 4-phenyltetrahydro-1,4-oxazine-3,5-dione 
• 20978-91-0 4-benzyltetrahydro-1,4-oxazine-3,5-dione 
• 852212-62-5 [Ph₂Sn(oxydiacetate)(H₂O)]2 

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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.

Synthesis of Dicarboxylic Acids from Aqueous Solutions of Diols with Hydrogen Evolution Catalyzed by an Iridium Complex

A catalytic system for the synthesis of dicarboxylic acids from aqueous solutions of diols accompanied by the evolution of hydrogen was developed. An iridium complex bearing a functional bipyridonate ligand with N,N-dimethylamino substituents exhibited a high catalytic performance for this type of dehydrogenative reaction. For example, adipic acid was synthesized from an aqueous solution of 1,6-hexanediol in 97 % yield accompanied by the evolution of four equivalents of hydrogen by the present catalytic system. It should be noted that the simultaneous production of industrially important dicarboxylic acids and hydrogen, which is useful as an energy carrier, was achieved. In addition, the selective dehydrogenative oxidation of vicinal diols to give α-hydroxycarboxylic acids was also accomplished.

Oxidative Cleavage of Vicinal Diols with the Combination of Platinum and Vanadium Catalysts and Molecular Oxygen

The combination of Pt/C and V2O5 catalysts gave good performance for the oxidative cleavage of trans-1,2-cyclohexanediol into adipic acid via 2-hydroxycyclohexanone. The yield of adipic acid reached 90 % in the one-pot oxidative cleavage of trans-1,2-cyclohexanediol. The yield was higher than that obtained in the oxidation of 2-hydroxycyclohexanone with V catalyst, and the higher yield was due to the low 2-hydroxycyclohexanone concentration during the one-pot oxidation of trans-1,2-cyclohexanediol. Cyclic vicinal diols having a six-membered ring and linear vicinal diols having two secondary OH groups were converted into dicarboxylic acids and two carboxylic acids, respectively. The activity of the Pt catalyst decreased during the reaction, and the activity was partially restored by treating the used catalyst with H2 at 573K. Even without regeneration, the turnover number based on total Pt could reach ≈1000 in a long reaction with an increased amount of trans-1,2-cyclohexanediol.