1,3-Dioxolan-2-one,4-(hydroxymethyl)- supplier

Name
4-HYDROXYMETHYL-1,3-DIOXOLAN-2-ONE
EINECS 213-235-0
CAS No. 931-40-8
Article Data178
CAS DataBase
Density 1.375 g/cm³
Solubility 1000g/L at 24℃
Melting Point
Formula C₄H₆O₄
Boiling Point 353.9 °C at 760 mmHg
Molecular Weight 118.089
Flash Point 165.9 °C
Transport Information
Appearance
Safety 23
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Carbonicacid, (hydroxymethyl)ethylene ester (6CI);Carbonic acid, cyclic(hydroxymethyl)ethylene ester (7CI,8CI);(2-Oxo-1,3-dioxolan-4-yl)methanol;3-Hydroxypropylene carbonate;4-Hydroxymethyl-1,3-dioxolan-2-one;Glycerincarbonate;Glycerol 1,2-carbonate;Glycerol carbonate;Glycerol cyclic1,2-carbonate;Jeffsol GC;NSC 60535;Racemic glycerol 1,2-carbonate;
PSA 55.76000
LogP -0.48590

Synthetic route

: 124-38-9
carbon dioxide

: 556-52-5
oxiranyl-methanol

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With C25H13O12Si(5-)3Ni(2+)HO(1-); tetrabutylammomium bromide In neat (no solvent) at 99.84℃; under 7500.75 Torr; for 3h; Catalytic behavior; Autoclave;	100%
With tetrabutylammomium bromide In neat (no solvent) at 60℃; under 7500.75 Torr; for 3h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave; Green chemistry;	99%
With Cu7(H1L)2(TPT)3(H2O)6; tetrabutylammomium bromide at 100℃; under 760.051 Torr; for 3h; Catalytic behavior; Kinetics; Autoclave;	99%

: 56-81-5
glycerol

: 616-38-6
carbonic acid dimethyl ester

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
Candida antarctica lipase B In tert-butyl alcohol at 70℃; for 10 - 24h; Enzyme kinetics; Enzymatic reaction; Molecular sieve;	100%
With N-methyl-N'-n-butylimidazolium-2-carboxylate at 74℃; for 0.5h; Inert atmosphere;	100%
With Mg-Al hydrotalcite In N,N-dimethyl-formamide at 99.84℃; for 2h; Inert atmosphere;	99%

: 864079-61-8
4-(((trimethylsilyl)oxy)methyl)-1,3-dioxolan-2-one

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 20℃; for 2h;	99.5%

: 4-(((tert-butyldimethylsilyl)oxy)methyl)-1,3-dioxolan-2-one

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 20℃; for 2h;	99.01%

: 4-(1-propenyloxymethyl)-1,3-dioxalan-2-one

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With water; dichloro bis(acetonitrile) palladium(II) In acetonitrile at 40℃; for 2h;	99%

: 4-(1-propenyloxymethyl)-1,3-dioxalan-2-one

A: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

B: 123-38-6
propionaldehyde

Conditions

Conditions	Yield
With water; dichloro bis(acetonitrile) palladium(II) at 40℃; for 2h;	A 99% B n/a

: 2238-07-5
Diglycidyl ether

: 124-38-9
carbon dioxide

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With N-methyl-N-tetradecylmorpholinium bromide; potassium iodide at 35℃; under 750.075 Torr; for 24h; Autoclave;	96.1%

: 56-81-5
glycerol

: 57-13-6
urea

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With bifunctional zinc-tin composite oxide at 155℃; for 4h; Reagent/catalyst; Temperature; Inert atmosphere; Green chemistry;	95.6%
With iron(II) bromide In 1,4-dioxane at 150℃; for 18h; Inert atmosphere; Sealed tube;	95%
With zeolite Zn-Y at 150℃; for 3h; Kinetics; Catalytic behavior; Reagent/catalyst; Temperature; Green chemistry;	92.7%

: 201230-82-2
carbon monoxide

: 56-81-5
glycerol

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
Stage #1: carbon monoxide; glycerol With sulfur; triethylamine In N,N-dimethyl-formamide at 80℃; under 7500.75 Torr; for 5h; Inert atmosphere; Autoclave; Stage #2: With copper(ll) bromide In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 16h;	94%
With N-chloro-succinimide; (neocuproine)Pd(OAc)2; sodium acetate In acetonitrile at 55℃; under 760.051 Torr; for 24h; Molecular sieve;	88%
With oxygen; potassium iodide; palladium(II) iodide In N,N-dimethyl acetamide at 100℃; under 15201 Torr; for 15h;	62%

: 56-81-5
glycerol

: 616-38-6
carbonic acid dimethyl ester

A: 67-56-1
methanol

B: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With calcium oxide at 75℃; for 0.5h; Activation energy; Kinetics; Reagent/catalyst; Temperature; Concentration; Inert atmosphere;	A n/a B 94%
With magnesium oxide at 90℃; for 0.5h; Overall yield = 16 %Chromat.;

...Expand

: 124-38-9
carbon dioxide

: 106-91-2
2,3-Epoxypropyl methacrylate

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With tetrabutylammomium bromide In acetonitrile at 50℃; under 760.051 Torr; for 6h; Electrochemical reaction;	94%

: 56-81-5
glycerol

: 105-58-8
Diethyl carbonate

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 130℃; for 0.5h;	93%
With Mg-Al hydrotalcite In N,N-dimethyl-formamide at 139.84℃; for 3h; Inert atmosphere;	77%
With sodium methylate at 110℃; for 3h;	11.9 g

: 80403-20-9
allyl ((2-oxo-1,3-dioxolan-4-yl)methyl) carbonate

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at -10℃;	88%

: 201230-82-2
carbon monoxide

: 556-52-5
oxiranyl-methanol

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With 1-carboxypropyl-imidazolium bromide at 120℃; under 11251.1 Torr; for 2h;	86.85%

: 4437-80-3
4,4-dimethyl-5-methylene-1,3-dioxolan-2-one

: 56-81-5
glycerol

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine In acetonitrile at 25℃; for 24h;	85%

: 826-29-9
4-allyloxymethyl-1,3-dioxolan-2-one

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; palladium on activated charcoal In methanol at 20℃; for 144h;	80%

: 2171-74-6
1,3-benzodioxol-2-one

: 56-81-5
glycerol

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With magnesium oxide In tetrahydrofuran at 60℃; under 760.051 Torr; for 1h; Catalytic behavior; Time; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;	77%
With sodium methylate at 60℃; for 1h; Reagent/catalyst; Temperature; Time; Inert atmosphere;	95.5 %Chromat.

: 56-81-5
glycerol

: 57-13-6
urea

A: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

B: 15546-08-4
4-Hydroxymethyl oxazolidin-2-one

Conditions

Conditions	Yield
With boiler ash at 110℃; for 4h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Inert atmosphere;	A 75.3% B n/a

...Expand

: 4540-44-7
1-bromo-3-chloro-propan-2-ol

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With potassium carbonate; 18-crown-6 ether at 80℃; for 24h;	75%

: 79-22-1
methyl chloroformate

: 56-81-5
glycerol

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With calcium hydroxide In toluene at 0℃; for 30h; Reflux; Dean-Stark;	72%

: 122012-52-6
diammine diisocyanatozinc(II)

: 56-81-5
glycerol

A: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

B: 16754-68-0
1,3-dioxa-2-zinc-4-cyclopentylmethanol

Conditions

Conditions	Yield
In neat (no solvent) at 140℃; under 30.003 Torr; for 6h; Schlenk technique;	A 67% B 250 mg

...Expand

: 56-81-5
glycerol

: 616-38-6
carbonic acid dimethyl ester

A: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

B: 76913-29-6
methyl ((2-oxo-1,3-dioxolan-4-yl)methyl)carbonate

C: 556-52-5
oxiranyl-methanol

Conditions

Conditions	Yield
With potassium fluoride at 80℃; for 1.5h; Catalytic behavior; Reagent/catalyst;	A 58.4% B n/a C n/a
With tetrabutylammomium bromide at 160℃; under 8250.83 Torr; for 0.05h; Flow reactor;

...Expand

: 56-81-5
glycerol

: 57-13-6
urea

A: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

B: 223754-90-3
2,3-dihydroxypropyl carbamate

C: 855687-99-9
(2-oxo-1,3-dioxolan-4-yl)-methyl urethane

Conditions

Conditions	Yield
With 3-(2-hydroxyethyl)-1-methyl-1H-imidazol-3-ium chloride at 140℃; for 4h;	A 58% B 22% C 14%
With metal-organic framework-templated porous Co3O4 nanocage catalyst at 150℃; for 3h; Catalytic behavior; Inert atmosphere;
With MoO3*SnO2 In neat (no solvent) at 149.84℃; for 4h; Catalytic behavior; Reagent/catalyst;

...Expand

: 56-81-5
glycerol

: 57-13-6
urea

A: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

B: 855687-99-9
(2-oxo-1,3-dioxolan-4-yl)-methyl urethane

C: 15546-08-4
4-Hydroxymethyl oxazolidin-2-one

Conditions

Conditions	Yield
With Zn2CrO at 140℃; under 22.5023 Torr; for 3h; Reagent/catalyst;	A 57% B n/a C n/a

...Expand

: 56-81-5
glycerol

: 57-13-6
urea

A: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

B: 223754-90-3
2,3-dihydroxypropyl carbamate

Conditions

Conditions	Yield
With 3-(2-hydroxyethyl)-1-methyl-1H-imidazol-3-ium tetrafluoroborate at 130℃; for 4h; Reagent/catalyst;	A 54% B 26%
With 1,3-dioxa-2-zinc-4-cyclopentylmethanol In neat (no solvent) at 130℃; under 30.003 Torr; for 7h; Temperature; Schlenk technique;	A 24 %Chromat. B n/a
With silicotungstate(30 percent SiW12) impregnated to MCM-41 In neat (no solvent) at 150℃; for 8h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Green chemistry;
With H2β at 149.84℃; for 8h; Reagent/catalyst; Green chemistry;
at 149.84℃; for 8h; Green chemistry;

...Expand

: 56-81-5
glycerol

: 57-13-6
urea

A: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

B: 223754-90-3
2,3-dihydroxypropyl carbamate

C: 855687-99-9
(2-oxo-1,3-dioxolan-4-yl)-methyl urethane

D: 15546-08-4
4-Hydroxymethyl oxazolidin-2-one

Conditions

Conditions	Yield
With Zn2CoO at 140℃; under 22.5023 Torr; for 3h; Reagent/catalyst;	A 52% B n/a C n/a D n/a
With 2.5wt%Au/ZnO at 150℃; for 4h;	A 49% B 17 %Chromat. C 20 %Chromat. D 7 %Chromat.
With 2.5wt%Au/C at 150℃; for 4h;	A 22% B 38 %Chromat. C 19 %Chromat. D 9 %Chromat.

...Expand

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: C36H62Cl2O2

: C44H72O10

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Inert atmosphere;	99.5%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 1263905-66-3
C4H5ClO5S

Conditions

Conditions	Yield
With thionyl chloride at 20℃; for 1h; Inert atmosphere;	99.1%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 556-52-5
oxiranyl-methanol

Conditions

Conditions	Yield
With zinc(II) nitrate; 1-butyl-3-methylimidazolium nitrate at 175℃; under 20.027 Torr; for 2.5h;	98.2%
With zinc-lanthanum mixed oxides at 180℃; under 375.038 Torr; Reagent/catalyst;	76.22%
With sodium sulfate at 140 - 180℃; for 3h; Green chemistry;	33%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 98-59-9
p-toluenesulfonyl chloride

: 949895-84-5
(2-oxo-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 16h;	98%
With dmap In dichloromethane at -10 - 20℃; for 3h;	92%
With triethylamine In tetrahydrofuran at 20℃; for 24h; Cooling with ice; Inert atmosphere;	83%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 75-36-5
acetyl chloride

: 1607-31-4
(2-oxo-1,3-dioxolan-4-yl)methyl acetate

Conditions

Conditions	Yield
In dichloromethane for 1.5h; Inert atmosphere; Reflux;	98%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 871835-30-2
2-oxo-1,3-dioxolane-4-carboxylic acid

Conditions

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sodium hydrogencarbonate; sodium bromide In water; acetone at 0 - 20℃; for 12h; Reagent/catalyst; Temperature; Solvent;	97%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sodium hydrogencarbonate; sodium bromide In water; acetone at 0 - 20℃; for 12h; Reagent/catalyst; Temperature; Solvent;	97%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sodium hydrogencarbonate; sodium bromide In water; acetone at 0 - 20℃; for 12h; Reagent/catalyst; Temperature; Solvent;	97%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sodium hydrogencarbonate; sodium bromide In water; acetone at 0 - 20℃; for 12h;	97%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; water; sodium hydrogencarbonate; sodium bromide In acetone at 0 - 20℃; for 12h;	97%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 1273-86-5
1-ferrocenylmethanol

: 1551616-24-0
4-[(ferrocenylmethyl)oxymethyl]-1,3-dioxolan-2-one

Conditions

Conditions	Yield
at 60℃; for 0.5h; Kinetics;	97%
at 60℃; for 0.5h; Kinetics;	97%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 57-10-3
1-hexadecylcarboxylic acid

: 305847-08-9
rac-1-monopalmitoylglycerol

Conditions

Conditions	Yield
With triethylamine at 143 - 145℃; for 9.5h;	93%

: 110-89-4
piperidine

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: C9H17NO4

Conditions

Conditions	Yield
In tetrachloromethane; acetone at 60℃; for 5h;	92.8%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 103-80-0
phenylacetyl chloride

: 125399-86-2
Phenyl-acetic acid 2-oxo-[1,3]dioxolan-4-ylmethyl ester

Conditions

Conditions	Yield
In dichloromethane for 3h; Inert atmosphere; Reflux;	92%
With pyridine In dichloromethane 1.) 0 deg C, 15 min, 2.) room temp., overnight; Yield given;

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 2463-45-8
4-chloromethyl-[1,3]dioxolan-2-one

Conditions

Conditions	Yield
With phosphorus trichloride In dichloromethane at 40℃; for 3h;	92%
With 1-pyrrolidinecarboxaldehyde; 1,3,5-trichloro-2,4,6-triazine In acetonitrile at 80℃; for 2.5h; Time; Sealed tube; Green chemistry;	84%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 98-88-4
benzoyl chloride

: 98760-26-0
(+/-)-4-<(benzoyloxy)methyl>-1,3-dioxolan-2-one

Conditions

Conditions	Yield
In dichloromethane for 3h; Inert atmosphere; Reflux;	92%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 3121-61-7
2-methoxyethyl acrylate

: 7528-90-7
acrylic acid 2-oxo-[1,3]dioxolan-4-ylmethyl ester

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; zinc diacrylate; oxygen; 4-methoxy-phenol at 105 - 120℃; under 90 - 760 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Pressure;	92%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 112-80-1
cis-Octadecenoic acid

: 111-03-5, 2716-53-2, 30836-40-9, 34487-30-4, 69483-90-5, 99297-71-9, 129784-87-8
1-monooleoyl glycerol

Conditions

Conditions	Yield
With triethylamine at 140℃; for 9h;	91.5%

: 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one

: 57-11-4
stearic acid

: 22610-63-5
octadecanoic acid 2,3-dihydroxypropyl ester

Conditions

Conditions	Yield
Stage #1: 4-hydroxymethyl-1,3-dioxolan-2-one; stearic acid With sodium hydroxide at 160℃; for 5h; Stage #2: With water; calcium carbonate at 85℃; for 3h; Temperature; Reagent/catalyst;	91.3%
With triethylamine at 143 - 145℃; for 10h;	90%
With tetra-(n-butyl)ammonium iodide at 140 - 142℃; for 24h; Reflux;	86%

1,3-Dioxolan-2-one,4-(hydroxymethyl)- Specification

The 1,3-Dioxolan-2-one,4-(hydroxymethyl)-, with the CAS registry number 931-40-8, is also known as AI3-22904. It belongs to the product categories of Dioxanes & Dioxolanes; Dioxolanes; Carbonates; Carbonyl Compounds; Organic Building Blocks. Its EINECS registry number is 213-235-0. This chemical's molecular formula is C₄H₆O₄ and molecular weight is 118.09. Its IUPAC name is called 4-(hydroxymethyl)-1,3-dioxolan-2-one. This chemical's classification code is TSCA Flag P [A commenced PMN (Premanufacture Notice) substance]. When you are using this chemical, please be cautious about it. You should not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer). The product should be sealed away from strong oxides.

Physical properties of 1,3-Dioxolan-2-one,4-(hydroxymethyl)-: (1)ACD/LogP: -1.64; (2)ACD/LogD (pH 5.5): -1.64; (3)ACD/LogD (pH 7.4): -1.64; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 3.06; (7)ACD/KOC (pH 7.4): 3.06; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.457; (12)Molar Refractivity: 23.4 cm³; (13)Molar Volume: 85.8 cm³; (14)Surface Tension: 44.1 dyne/cm; (15)Density: 1.375 g/cm³; (16)Flash Point: 165.9 °C; (17)Enthalpy of Vaporization: 69.34 kJ/mol; (18)Boiling Point: 353.9 °C at 760 mmHg; (19)Vapour Pressure: 2E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1C(OC(=O)O1)CO
(2)InChI: InChI=1S/C4H6O4/c5-1-3-2-7-4(6)8-3/h3,5H,1-2H2
(3)InChIKey: JFMGYULNQJPJCY-UHFFFAOYSA-N

Product Name

4-HYDROXYMETHYL-1,3-DIOXOLAN-2-ONE

Synthetic route

1,3-Dioxolan-2-one,4-(hydroxymethyl)- Specification

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