37830-90-3

Basic information

• Product Name: 4,5-Dimethyl-1,3-dioxol-2-one
• Synonyms: 4,5-DIMETHYL-1,3-DIOXOL-2-ONE;1,3-DIOXOL-2-ONE, 4,5-DIMETHYL-;DIMETHYLDIOXOLONE;4,5-DIMETHYL-1,3-DIOXOLENE-2-ONE (DMDO);5-Dimethyl-1,3-dioxol-2-one;4,5-Dimethyl-1,3-dioxolen-3-one;4,5-Dimethyl-1,3-dioxolen-2-one;4,5-dimethyl-2-oxo-1,3-dioxolene
• CAS NO: 37830-90-3
• Molecular Formula: C₅H₆O₃
• Molecular Weight: 114.1
• EINECS: 1592732-453-0
• Product Categories: Oxygen cyclic compounds;Fluorobenzene;Agricultural chemicals(bactericide);Pharmaceutical Intermediates
• Mol File: 37830-90-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 78°C
• Boiling Point: 130 °C / 6mmHg
• Flash Point: 55.8 °C
• Appearance: white powder
• Density: 1.181 g/cm³
• Vapor Pressure: 17.8mmHg at 25°C
• Refractive Index: 1.454
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 4,5-Dimethyl-1,3-dioxol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dimethyl-1,3-dioxol-2-one(37830-90-3)
• EPA Substance Registry System: 4,5-Dimethyl-1,3-dioxol-2-one(37830-90-3)

Safety Data

• Statements: 36/37/38-37-36
• Safety Statements: 26-36/37/39-36
• Hazardous Substances Data: 37830-90-3(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

4,5-Dimethyl-1,3-dioxol-2-one is a dioxolanone derivative used in the preparation of synthetic chemotherapeutic antibiotics such as Prulifloxacin (P838885).

InChI:InChI=1/C5H6O3/c1-3-4(2)8-5(6)7-3/h1-2H3

Synthetic route

trans-4,5-dichloro-4,5-dimethyl-1,3-dioxolan-2-one → 4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3)

Conditions	Yield
With acetic anhydride; zinc In toluene at 30 - 80℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent;	83%

carbon dioxide (124-38-9) + 3-hydroxy-2-butanon (513-86-0, 52217-02-4) → 4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3)

Conditions	Yield
Stage #1: carbon dioxide; 3-hydroxy-2-butanon With sodium carbonate; potassium hydrogencarbonate at 28 - 32℃; for 5h; Autoclave; Large scale; Green chemistry; Stage #2: With potassium methanolate; sodium ethanolate at 38 - 42℃; under 26252.6 Torr; Temperature; Reagent/catalyst; Pressure; Large scale; Green chemistry;	80.7%

phosgene (75-44-5) + 3-hydroxy-2-butanon (513-86-0, 52217-02-4) → 4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3)

Conditions	Yield
In dichloromethane; N,N-dimethyl-aniline; toluene	55%
In dichloromethane; N,N-dimethyl-aniline	3.53 g (25%)

bis(trichloromethyl) carbonate (32315-10-9) + 3-hydroxy-2-butanon (513-86-0, 52217-02-4) → 4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3)

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; 3-hydroxy-2-butanon With N,N-dimethyl-aniline In dichloromethane at 20℃; for 2h; Stage #2: at 160℃; for 4h;	42%

C5H7ClO3 → 4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3)

Conditions	Yield
at 160℃; for 4h;

3-hydroxy-2-butanon (513-86-0, 52217-02-4) + methyl chloroformate (79-22-1) → 4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3)

Conditions	Yield
In N,N-dimethyl-aniline at 15℃; for 5.5h; Temperature;	450 g

3-hydroxy-2-butanon (513-86-0, 52217-02-4) + chloroformic acid ethyl ester (541-41-3) → 4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3)

Conditions	Yield
In dichloromethane; N,N-dimethyl-aniline at 12℃; for 6h; Temperature; Solvent;	850 g

3-hydroxy-2-butanon (513-86-0, 52217-02-4) + propoxycarbonyl chloride (109-61-5) → 4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3)

Conditions	Yield
In dichloromethane; N,N-dimethyl-aniline at 20℃; for 0.5h; Temperature; Solvent;	190 g

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one (80715-22-6)

Conditions	Yield
With N-Bromosuccinimide In chloroform Reflux; Large scale;	93.8%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 77℃; for 6h;	92%
With bromine; pyridine hydrochloride-aluminum trichloride In acetone for 1.66667h; Reagent/catalyst; Wavelength; Solvent; Microwave irradiation;	92%

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) + a,a-azobisisobutyronitrile (AIBN) → 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one (80715-22-6)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane	90%

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → 4-chloromethyl-5-methyl-1,3-dioxol-2-one (80841-78-7)

Conditions	Yield
With chlorine In 1,2-dichloro-ethane for 0.5h; Solvent; Reagent/catalyst; Reflux; Molecular sieve;	89.3%
With N-chloro-succinimide In tetrachloromethane for 80h; Ambient temperature; Irradiation;	9.2%
With chlorine; copper 1.) dichloromethane, 90 min, reflux, 2.) dichloromethane, 2 h, reflux; Yield given. Multistep reaction;
With sulfuryl dichloride In dichloromethane
With N-chloro-succinimide; dibenzoyl peroxide at 90℃; for 5.5h; Temperature; Solvent; Large scale;	326 g

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) + C19H11ClN2S → C23H15ClN2S

Conditions	Yield
With tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate In 1,2-dichloro-ethane at 80℃; for 20h; Inert atmosphere;	89.3%

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → 4-chloro-4-methyl-5-methylene-1,3-dioxolane-2-one (95579-71-8)

Conditions	Yield
With sulfuryl dichloride In dichloromethane for 0.5h; Heating;	75%
With sulfuryl dichloride In dichloromethane
With thionyl chloride In dichloromethane for 4.5h; Solvent; Reflux;
With sulfuryl dichloride In dichloromethane at 40℃; for 2h;

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → 4,5-di(bromomethyl)-2-oxo-1,3-dioxole (62458-19-9)

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene at 110℃; for 2h; Inert atmosphere;	66%
With N-Bromosuccinimide; azobisisobutyronitrile In tetrachloromethane
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene for 1h; Reflux;

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) + azobisisobutyronitrile (34241-39-9) → 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one (80715-22-6)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane	48%
With N-Bromosuccinimide In tetrachloromethane

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → 4-chloromethyl-5-methyl-1,3-dioxol-2-one (80841-78-7) + 4-chloro-4-methyl-5-methylene-1,3-dioxolane-2-one (95579-71-8) + 4,5-dimethyl-4,5-dichloro-1,3-dioxolan-2-one (129482-56-0)

Conditions	Yield
With chlorine In dichloromethane at 43 - 45℃; Product distribution; further solvents;	A 1.4 % Chromat. B 87.5 % Chromat. C n/a

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl trans-4-<<(tert-butoxycarbonyl)amino>methyl>cyclohexanecarboxylate (100165-57-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-bromosuccinimide, α,α-azobis(isobutyronitrile) / CCl4 2: 41 percent / K2CO3, (C4H9)4NBr (QBr) / trichloroethene / 20 h / 60 °C View Scheme

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl trans-4-(aminomethyl)cyclohexanecarboxylate hydrochloride (100165-54-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-bromosuccinimide, α,α-azobis(isobutyronitrile) / CCl4 2: 41 percent / K2CO3, (C4H9)4NBr (QBr) / trichloroethene / 20 h / 60 °C 3: 70 percent / HCl(g) / ethyl acetate / 2.5 h / 0 - 20 °C View Scheme

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → C21H32N2O7*2ClH (100165-55-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-bromosuccinimide, α,α-azobis(isobutyronitrile) / CCl4 2: K2CO3, (C4H9)4NBr (QBr) / trichloroethene / 20 h / 60 °C 3: HCl(g) / ethyl acetate / 2.5 h / 0 - 20 °C View Scheme

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → C31H48N2O11

Conditions	Yield
Multi-step reaction with 2 steps 1: N-bromosuccinimide, α,α-azobis(isobutyronitrile) / CCl4 2: K2CO3, (C4H9)4NBr (QBr) / trichloroethene / 20 h / 60 °C View Scheme

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl iodide (80841-79-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80.8 percent / sodium bicarbonate, α,α'-azobisisobutyronitrile, Br2 / CCl4 / 1.08 h / 70 °C 2: 92 percent / potassium iodide / acetone / Ambient temperature View Scheme

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 80.8 percent / sodium bicarbonate, α,α'-azobisisobutyronitrile, Br2 / CCl4 / 1.08 h / 70 °C 2: 1.) potassium bicarbonate / 1.) DMF, 0 deg C, 3 h; 2.) 0 deg C, 3 h View Scheme

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → ampicillin (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride (80734-02-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80.8 percent / sodium bicarbonate, α,α'-azobisisobutyronitrile, Br2 / CCl4 / 1.08 h / 70 °C 2: 1.) potassium bicarbonate / 1.) DMF, 0 deg C, 3 h; 2.) 0 deg C, 3 h 3: 60 percent / 1N HCl / acetonitrile / 0.5 h / 0 - 5 °C / pH=2.0 View Scheme

N-Bromosuccinimide (128-08-5) + 4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one (80715-22-6)

Conditions	Yield
2,2'-azobis(isobutyronitrile) In benzene at 20℃; for 0.5h; Heating / reflux;

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → 4-hydroxymethyl-5-methyl-[1,3]dioxol-2-one (91526-18-0)

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane
With selenium(IV) oxide In 1,4-dioxane
With selenium(IV) oxide In 1,4-dioxane for 1h; Heating / reflux;

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-{[(4,5-dichloro-2-thienyl)sulfonyl]amino}-2-hydroxybenzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: sodium hydrogencarbonate / N,N-dimethyl-formamide / 20 °C View Scheme

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → prulifloxacin (123447-62-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / chloroform / Reflux; Large scale 2: potassium hydrogencarbonate / N,N-dimethyl-formamide / 5 h / 0 °C / Large scale View Scheme

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / 80 °C 2: potassium carbonate / acetone / 24 h / 55 °C View Scheme

4,5-Dimethyl-1,3-dioxole-2-one (37830-90-3) → (S)-3-(tert-butoxycarbonylamino-methyl)-5-methyl-hexanoic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester (1026789-40-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / tetrachloromethane 2: caesium carbonate / methanol / 2 h / 20 °C View Scheme

Upstream product

• 75-44-5 phosgene 
• 513-86-0 3-hydroxy-2-butanon 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 102-09-0 bis(phenyl) carbonate 
• 513-85-9 2.3-butanediol 
• 116857-05-7 trans-4,5-dichloro-4,5-dimethyl-1,3-dioxolan-2-one 
• 109-61-5 propoxycarbonyl chloride 
• 541-41-3 chloroformic acid ethyl ester 
• 79-22-1 methyl chloroformate 
• 124-38-9 carbon dioxide 

Downstream Products

• 80715-22-6 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one 
• 91526-17-9 4-formyloxymethyl-5-methyl-1,3-dioxolen-2-one 
• 123447-62-1 prulifloxacin 
• 91526-18-0 4-hydroxymethyl-5-methyl-[1,3]dioxol-2-one 
• 80734-02-7 ampicillin (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride 
• 100165-55-7 C₂₁H₃₂N₂O₇*2ClH 
• 100165-54-6 (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl trans-4-(aminomethyl)cyclohexanecarboxylate hydrochloride 
• 100165-57-9 (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl trans-4-<<(tert-butoxycarbonyl)amino>methyl>cyclohexanecarboxylate 
• 95579-71-8 4-chloro-4-methyl-5-methylene-1,3-dioxolane-2-one 
• 80841-78-7 4-chloromethyl-5-methyl-1,3-dioxol-2-one 
• 129482-56-0 4,5-dimethyl-4,5-dichloro-1,3-dioxolan-2-one 

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