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

Uses

1,4-Dioxane-2,3-diol is used as a pharmaceutical intermediate and an intermediate in organic synthesis.

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 
• 7732-18-5 water 
• 107-21-1 ethylene glycol 
• 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 
• 6498-02-8 ethyl 1,2,4-triazine-3-carboxylate 
• 473895-87-3 ethyl ester of quinoxalin-6-ylacetic acid 

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