4845-50-5

Basic information

• Product Name: 1,4-DIOXANE-2,3-DIOL
• Synonyms: TRANS-2,3-DIHYDROXY-1,4-DIOXANE;1,4-DIOXANE-2,3-DIOL;2,3-DIHYDROXY-1,4-DIOXANE;GLYOXAL MONOETHYLENE ACETAL;2,3-Dihydroxy-1,4-dioxane~Glyoxal monoethylene acetal;Dioxanediol;trans-1,4-Dioxane-2,3-diol;1,4-Dioxane-2,3-diol,97%
• CAS NO: 4845-50-5
• Molecular Formula: C₄H₈O₄
• Molecular Weight: 120.1
• EINECS: 225-431-3
• Product Categories: Dioxanes;Dioxanes & Dioxolanes
• Mol File: 4845-50-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 91-95 °C(lit.)
• Boiling Point: 259.4 °C at 760 mmHg
• Flash Point: 110.7 °C
• Appearance: White to off-white/Powder or Crystalline Powder
• Density: 1.455 g/cm³
• Vapor Pressure: 0.00189mmHg at 25°C
• Refractive Index: 1.513
• PKA: 11.72±0.40(Predicted)
• Water Solubility: It is soluble in water.
• BRN: 104209
• CAS DataBase Reference: 1,4-DIOXANE-2,3-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIOXANE-2,3-DIOL(4845-50-5)
• EPA Substance Registry System: 1,4-DIOXANE-2,3-DIOL(4845-50-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36-36/37/38
• Safety Statements: 22-24/25-36/37/39-26
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 4845-50-5(Hazardous Substances Data)

Usage

Description

1,4-Dioxane-2,3-diol, also known as Glycerol, is a simple polyol compound with a hydroxyl group attached to each of its three carbon atoms. It is a colorless, odorless, viscous liquid that is hygroscopic in nature. Glycerol is widely used in various industries due to its versatile properties and ability to act as a solvent, sweetener, and humectant.

Uses

Used in Pharmaceutical Industry:
1,4-Dioxane-2,3-diol is used as a pharmaceutical intermediate for the production of various drugs and medications. Its properties make it suitable for use in the synthesis of antibiotics, antifreeze, and other pharmaceutical compounds.
Used in Organic Synthesis:
1,4-Dioxane-2,3-diol serves as an intermediate in organic synthesis, where it is utilized in the production of various chemicals, including cosmetics, lubricants, and polymers. Its versatility as a solvent and its ability to form esters make it a valuable component in the synthesis of a wide range of organic compounds.

Purification Methods

Recrystallise it from Me2CO. With phenylhydrazine it gives glyoxal phenylhydrazone m 175o (from Me2CO/pet ether). The diacetyl derivative has m 105-106o [Head J Chem Soc 1036 1955, Raudnitz Chem Ind (London) 166 1956]. [Beilstein 1 IV 3627.]

InChI:InChI=1/C4H8O4/c5-3-4(6)8-2-1-7-3/h3-6H,1-2H2

Synthetic route

Glyoxal (131543-46-9) + ethylene glycol (107-21-1) → 2,3-dihydroxy-1,4-dioxane (4845-50-5)

Conditions	Yield
In water; benzene for 10h; Heating;	45%
With sodium hydroxide; water; sodium carbonate unter vermindertem Druck;
With phosphorus pentoxide unter vermindertem Druck;

Glyoxal (131543-46-9) + water (7732-18-5) + ethylene glycol (107-21-1) → 2,3-dihydroxy-1,4-dioxane (4845-50-5)

Glyoxal (131543-46-9) + water (7732-18-5) + ethylene glycol (107-21-1) + sodium carbonate → 2,3-dihydroxy-1,4-dioxane (4845-50-5)

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 2-deoxy-2-amino glucose (90-76-6, 90-77-7, 530-23-4, 579-32-8, 579-33-9, 643-68-5, 2596-19-2, 6490-68-2, 6490-70-6, 6490-72-8, 6490-73-9, 6490-74-0, 14196-84-0, 14196-86-2, 14257-69-3, 58381-21-8) → C14H24N2O10

Conditions	Yield
With formic acid In ethanol at 65℃; for 48h; Sonication; Inert atmosphere; Schlenk technique;	98%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 6-chloro-2-methylpyrimidine -4,5-diamine (933-80-2) → 4-chloro-2-methylpteridine (827031-79-8)

Conditions	Yield
In ethanol at 20℃; for 2h;	97%
In ethanol
In ethanol at 25℃; for 1h;

2,3-dihydroxy-1,4-dioxane (4845-50-5) + tert-Butyl-2-(4-amino-3-nitrophenoxy)ethylcarbamate (1392489-02-9) → tert-Butyl-2-(quinoxalin-6-yloxy)ethylcarbamate (1392489-03-0)

Conditions	Yield
Stage #1: tert-Butyl-2-(4-amino-3-nitrophenoxy)ethylcarbamate With hydrogen; palladium 10% on activated carbon In ethanol at 20℃; for 6h; Stage #2: 2,3-dihydroxy-1,4-dioxane In ethanol at 20℃;	97%
In ethanol; water

2,3-dihydroxy-1,4-dioxane (4845-50-5) + Methyl 3,4-diaminobenzoate (36692-49-6) → methyl quinoxaline-6-carboxylate (23088-23-5)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 8h; Temperature;	96.7%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 5,6-diamino-2-(4,5-bis(propylthio)-1,3-dithiol-2-ylidene)-benzo[d]-1,3-dithiole (892505-53-2) → C18H18N2S6 (1602762-36-6)

Conditions	Yield
With acetic acid In ethanol Reflux;	96%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 1,2-diamino-benzene (95-54-5) → 2,3-diethynylquinoxaline (91-19-0)

Conditions	Yield
In ethanol for 0.5h; Ambient temperature;	95%
In ethanol	95%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 4-methyl-4H-bis[1,2,5]oxadiazolo[3,4-b:3',4'-f]azepine-8,9-diamine → 8-methyl-8H-bis[1,2,5]oxadiazolo[3,4-b:3',4'-f]pyrazino[2,3-d]azepine

Conditions	Yield
With boron trifluoride diethyl etherate In isopropyl alcohol for 5h; Reflux;	94%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 2,2'-thiobis[1-(4-bromophenyl)ethanone] (58881-56-4) → 2,5-bis-(4-bromo-benzoyl)-thiophene (72612-50-1)

Conditions	Yield
With sodium methylate In 1,4-dioxane; methanol for 0.5h; Ambient temperature;	93%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 4-amino-3,5-diisopropylphenol → N,N’-bis(4-hydroxy-2,6-diisopropylphenyl)-1,4-diazabutadiene (1620922-72-6)

Conditions	Yield
With formic acid In ethanol for 8h; Inert atmosphere; Schlenk technique; Heating;	93%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + tert-butyl 7,8-diamino-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (1241840-58-3) → tert-butyl 6,7,9,10-tetrahydro-8H-azepino[4,5-g]quinoxaline-8-carboxylate (1241841-16-6)

Conditions	Yield
In water; isopropyl alcohol at 20 - 32℃;	92%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 1,2-diamino-5-bromo-3-chlorobenzene (16429-44-0) → 7-bromo-5-chloroquinoxaline

Conditions	Yield
In ethanol at 20℃; for 28h;	92%
In ethanol at 20℃; for 28h;	92%
In ethanol at 20℃; for 24h;	4.7 g

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 3-bromo-5-chloro-1,2-diaminobenzene → 7-bromo-5-chloroquinoxaline

Conditions	Yield
In ethanol at 20℃; for 28h;	92%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 3-amino-1,2-dimethyl-1H-benzo[d]imidazole-3-ium 2,4,6-trimethylbenzenesulfonate (51073-43-9) → 1-amino-2,3-dimethylbenzimidazolium mesitylenesulfonate

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 70℃; for 1h; Condensation;	90%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + C11H11N5 (10495-77-9) → 6-[1,2,4]Triazin-3-yl-[2,2']bipyridinyl (220525-54-2)

Conditions	Yield
In methanol for 3h; Reflux;	90%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 3,5-dimethyl-4-aminophenol (3096-70-6) → 4,4'-(ethane-1,2-diylidenebis(azanylylidene))bis(3,5-dimethylphenol) (1313430-56-6)

Conditions	Yield
With formic acid In ethanol for 8h; Inert atmosphere; Schlenk technique; Heating;	90%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 1-(7,8-diamino-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone → 1-(9,10-dihydro-6H-6,10-methanoazepino[4,5-g]quinoxaline-8(7H)-yl)-2,2,2,-trifluoroethanone

Conditions	Yield
In water; isopropyl alcohol at 20 - 25℃; for 15h;	89%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 2-(isopropylamino)-2-methylpropan-1-ol (90434-44-9) → 4,9-diisopropyl-3,3,8,8-tetramethyloctahydro-4H,9H-<1,4>dioxano<2,3-b:5,6-b'>bis<1,4>oxazine (136503-81-6)

Conditions	Yield
In water at 70 - 80℃; for 2h;	88%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 2,3-Diaminopyridine (452-58-4) → 5-azaquinoxaline (322-46-3)

Conditions	Yield
In ethanol for 0.5h; Ambient temperature;	87%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 2-(ethylamino)-2-methylpropanol hydrochloride (82922-13-2) → 4,9-diethyl-3,3,8,8-tetramethyloctahydro-4H,9H-<1,4>dioxano<2,3-b:5,6-b'>bis<1,4>oxazine (136503-80-5)

Conditions	Yield
In water	85%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + (dimethylamino)dimethylarsine (30880-19-4) → Dimethylarsinigsaeure-(1,4)dioxan-2,3-diyl-ester

Conditions	Yield
In diethyl ether Heating;	85%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 2,3-diamino-5-bromobenzoic acid methyl ester (1248541-63-0) → methyl 7-bromoquinoxaline-5-carboxylate

Conditions	Yield
In ethanol at 110℃; for 0.166667h; Microwave irradiation;	85%
In ethanol	74.2%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 4-[(3-bromophenyl)amino]-6,7-diaminoquinazoline (169205-87-2) → 4-(3-bromoanilino)pyrazino[2,3-g]quinazoline

Conditions	Yield
In methanol Ambient temperature;	83%
In methanol	83%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 6-chloronicotinonitrile (33252-28-7) → 2-chloro-5-(2'-pyridyl)pyridine (93297-75-7)

Conditions	Yield
	82.5%
	82.5%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 5-bromo-3-fluoro-1,2-phenylenediamine (517920-69-3) → 7-bromo-5-fluoroquinoxaline (1210048-05-7)

Conditions	Yield
In ethanol at 20℃; for 28h;	80%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 2,3-Diaminonaphthalene (771-97-1) → 6,7-benzoquinoxaline (260-50-4)

Conditions	Yield
In ethanol	77%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 4,7-bis(4-(2,2-bis(4-methoxyphenyl)-1-phenylvinyl)phenyl)benzo[c][1,2,5]thiadiazole-5,6-diamine (1378502-44-3) → 4,9-bis{4-[2,2-bis(4-methoxyphenyl)-1-phenylvinyl]phenyl}[1,2,5]thiadiazolo-[3,4-g]quinoxaline (1378502-48-7)

Conditions	Yield
In chloroform; acetic acid at 80℃; for 24h; Inert atmosphere;	77%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 4,7-diphenyl-2,1,3-benzothiadiazole-5,6-diamine (165617-58-3) → 4,9-Diphenyl-2-thia-1,3,5,8-tetraaza-cyclopenta[b]naphthalene

Conditions	Yield
In nitromethane for 2h; Heating;	76%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 3,5-diisopropyl sulfanilic acid sodium salt → C26H34N2S2O6(2-)*2Na(1+)

Conditions	Yield
With formic acid In ethanol at 20℃; for 48h;	76%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 2,5-bis(4-(2,2-bis(4-methoxyphenyl)-1-phenylvinyl)phenyl)thiophene-3,4-diamine → 5,7-bis(4-(2,2-bis(4-methoxyphenyl)-1-phenylvinyl)phenyl)thieno[3,4-b]pyrazine

Conditions	Yield
With acetic acid In chloroform at 60℃; for 12h;	76%

2,3-dihydroxy-1,4-dioxane (4845-50-5) + 2,3,6,7,14,15-hexaammoniumtriptycene hexahydrochloride → C26H14N6

Conditions	Yield
With potassium acetate In tetrahydrofuran at 20℃; for 19h;	75%

Upstream product

• 131543-46-9 Glyoxal 
• 107-21-1 ethylene glycol 
• 7732-18-5 water 
• 44307-07-5 glyoxal bis-hydrate 

Downstream Products

• 322-46-3 5-azaquinoxaline 
• 6966-78-5 4-methylthiopteridine 
• 72612-50-1 2,5-bis-(4-bromo-benzoyl)-thiophene 
• 111336-65-3 3-(3-nitrophenyl)-1,2,4-triazine 
• 111336-64-2 3-(p-hydroxyphenyl)asym-triazine 
• 57446-74-9 3-(4-nitrophenyl)-1,2,4-triazine 
• 91-19-0 2,3-diethynylquinoxaline 
• 124782-25-8 9,10-Dibenzyl-1,4,5,8-tetraoxa-9,10-diazaperhydroanthracene 
• 124782-15-6 2,4,6,8,10,12-hexabenzyl-2,4,5,8,10,12-hexaazatetracyclo[5.5.0.0^3,11.0^5,9]dodecane 
• 497-26-7 2-methyl-1,3-dioxolane 
• 543-75-9 1,4-dioxene 
• 244090-18-4 Ethyl 6-phenylpyrido[2,3-b]pyrazine-8-carboxylate 
• 230615-70-0 1-(9,10-dihydro-6H-6,10-methanoazepino[4,5-g]quinoxaline-8(7H)-yl)-2,2,2,-trifluoroethanone 
• 827031-79-8 4-chloro-2-methylpteridine 

Relevant articles and documents

DERMATOLOGICAL COMPOSITIONS AND METHODS

Disclosed are methods and compositions for regulating the melanin content of mammalian melanocytes; regulating pigmentation in mammalian skin, hair, wool or fur; treating or preventing various skin and proliferative disorders; by administration of various compounds, including alcohols, diols and/or triols and their analogues.

Treatment of diseases mediated by the nitric oxide/cGMP/protein kinase G pathway

Disclosed are methods and compositions for stimulating cellular nitric oxide (NO) synthesis, cyclic guanosine monophosphate levels (cGMP), and protein kinase G (PKG) activity for purposes of treating diseases mediated by deficiencies in the NO/cGMP/PKG signal transduction pathway, by administration of various compounds including alcohols, diols and/or triols and their analogues.

2,3-Dihydroxy-1,4-dioxane: A Stable Synthetic Equivalent of Anhydrous Glyoxal

-