Isosorbide dimethyl ether supplier

Name
ISOSORBIDE DIMETHYL ETHER
EINECS 226-159-8
CAS No. 5306-85-4
Article Data14
CAS DataBase
Density 1.15 g/cm³
Solubility Soluble in water.
Melting Point -70 °C
Formula C₈H₁₄O₄
Boiling Point 236.4 °C at 760 mmHg
Molecular Weight 174.197
Flash Point 108.3 °C
Transport Information
Appearance clear colorless to light yellow liquid
Safety 23-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Glucitol,1,4:3,6-dianhydro-2,5-di-O-methyl-, D- (7CI,8CI);Sorbitol,1,4:3,6-dianhydro-2,5-di-O-methyl- (6CI);1,4:3,6-Dianhydro-2,5-di-O-methyl-D-glucitol;2,5-Di-O-methyl-1,4:3,6-dianhydro-D-glucitol;Arlasolve DMI;Dimethylisosorbide;NSC 40727;NSC 44695;
PSA 36.92000
LogP -0.18600

Synthetic route

: 616-38-6
carbonic acid dimethyl ester

: 652-67-5
Isosorbide

: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With sodium methylate at 90℃; under 750.075 Torr; for 20h; Inert atmosphere;	98%
With 1-Methylpyrrolidine at 200℃; under 15001.5 Torr; for 12h; Pressure; Reagent/catalyst; Temperature; Autoclave; chemoselective reaction;	85%
CBV8014 zeolite at 200℃; for 2h;
With dmap at 20 - 150℃; for 0.283333h;

: 77-78-1
dimethyl sulfate

: 652-67-5
Isosorbide

: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
Stage #1: Isosorbide With sodium hydroxide In water at 60 - 90℃; Stage #2: dimethyl sulfate In water at 60 - 130℃;	92.4%
Stage #1: Isosorbide With sodium hydroxide In water at 60 - 90℃; for 1h; Large scale; Stage #2: dimethyl sulfate In water at 60 - 130℃; Large scale;	59.5%
With sodium hydroxide

: 74-87-3
methylene chloride

: 652-67-5
Isosorbide

: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
Stage #1: Isosorbide With sodium hydroxide In water at 60 - 90℃; Stage #2: methylene chloride In water at 80 - 90℃; under 3000.3 Torr;	89.5%
Stage #1: Isosorbide With sodium hydroxide In water at 60 - 90℃; Large scale; Stage #2: methylene chloride In water at 80 - 90℃; under 3000.3 Torr; Large scale;	74%

: 50-70-4
D-sorbitol

: 616-38-6
carbonic acid dimethyl ester

A: 641-74-7
1,4:3,6-dianhydro-D-mannitol

B: 641-74-7, 652-67-5, 5627-19-0, 24332-71-6, 28218-68-0, 28948-16-5, 28980-83-8, 89825-36-5, 124508-14-1, 151380-60-8
1,4:3,6-dianhydro-L-iditol

C: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With triethylamine In biphenyl at 90 - 200℃; under 63756.4 Torr; for 48h; Reagent/catalyst; Autoclave; Inert atmosphere;	A 14% B 26% C 60%

...Expand

: 50-70-4
D-sorbitol

: 616-38-6
carbonic acid dimethyl ester

: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With 1-Methylpyrrolidine at 90 - 200℃; under 22502.3 Torr; for 72h; Pressure; Autoclave; chemoselective reaction;	55%
With triethylamine In biphenyl at 200℃; under 37503.8 Torr; for 24h; Reagent/catalyst; Autoclave; Inert atmosphere;	24%

: 512-56-1
trimethyl phosphite

: 652-67-5
Isosorbide

: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With iron(II) triflate In neat (no solvent) at 100℃; for 15h;	54%

: 111-96-6
diethylene glycol dimethyl ether

: 652-67-5
Isosorbide

A: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

C: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With silicotungstic acid at 200℃; for 2h; Temperature; Reagent/catalyst; Overall yield = 75 %;	A 14% B 14% C 47%

...Expand

: 109-87-5
Dimethoxymethane

: 111-96-6
diethylene glycol dimethyl ether

: 652-67-5
Isosorbide

A: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

C: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With Phosphotungstic acid at 100℃; for 3h; Time; Overall yield = 81 %;	A 18% B 18% C 45%

...Expand

: 110-71-4
1,2-dimethoxyethane

: 652-67-5
Isosorbide

A: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

C: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With Silicotungstic acid at 150℃; for 5h; Reagent/catalyst; Temperature; Overall yield = 82 %;	A 18% B 21% C 43%
With phosphotungstic acid at 150℃; for 1h; Reagent/catalyst; Autoclave;	A 28% B 18% C 20%

...Expand

: 109-87-5
Dimethoxymethane

: 652-67-5
Isosorbide

A: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

C: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With Amberlyst-35 at 130℃; for 15h; Overall yield = 70 %;	A 20% B 15% C 35%

...Expand

: 616-38-6
carbonic acid dimethyl ester

: 652-67-5
Isosorbide

A: 1235553-26-0
C9H14O6

B: 1235553-25-9
C9H14O6

C: 1235553-24-8
isosorbide di(methyl carbonate)

D: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With sodium methylate at 90℃; under 750.075 Torr; for 20h; Inert atmosphere;	A n/a B n/a C n/a D 32%

...Expand

: 112-49-2
Triethylene glycol dimethyl ether

: 652-67-5
Isosorbide

A: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

C: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With Amberlyst-35 Overall yield = 52 %;	A 29% B 12% C 11%

...Expand

: 100-66-3
methoxybenzene

: 652-67-5
Isosorbide

A: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

C: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With Amberlyst-35 at 130℃; for 15h; Overall yield = 66 %;	A 20% B 18% C 28%

...Expand

: 150-78-7
1,4-dimethoxybezene

: 652-67-5
Isosorbide

A: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

C: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With Amberlyst-35 at 130℃; for 15h; Overall yield = 63 %;	A 22% B 17% C 24%

...Expand

: 616-38-6
carbonic acid dimethyl ester

: 652-67-5
Isosorbide

A: 1235553-26-0
C9H14O6

B: 1235553-25-9
C9H14O6

C: 1235553-24-8
isosorbide di(methyl carbonate)

D: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

E: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

F: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With sodium methylate at 90℃; under 750.075 Torr; for 20h; Inert atmosphere;	A n/a B n/a C n/a D 8% E n/a F 20%

...Expand

: 50-70-4
D-sorbitol

sodium carbonate: sodium carbonate

: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl; water 2: aq. NaOH solution View Scheme

: 53648-56-9
3,6-anhydro-D-glucitol

: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 / 280 °C 2: aq. NaOH solution View Scheme

: 7625-23-2
3,6-anhydro-D-glucose

: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Raney nickel; water / 110 - 120 °C / 73550.8 Torr / Hydrogenation 2: H2SO4 / 280 °C 3: aq. NaOH solution View Scheme

: 616-38-6
carbonic acid dimethyl ester

: 652-67-5
Isosorbide

A: 1235553-26-0
C9H14O6

B: 1235553-25-9
C9H14O6

C: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With potassium tert-butylate at 90℃; under 750.075 Torr; for 20h; Inert atmosphere;
With 1-Methylpyrrolidine at 200℃; under 9750.98 - 12751.3 Torr; for 6h; Time; Autoclave; chemoselective reaction;

...Expand

: 1235553-24-8
isosorbide di(methyl carbonate)

A: (3S,3aR,6aR)hexahydro-3,6-epoxyfuro[3,2-b]furan

B: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With Hydrotalcite KW200 In hexane; toluene at 240℃;	A 54 %Chromat. B 38 %Chromat.

: 67-56-1
methanol

: 652-67-5
Isosorbide

: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With potassium 12-tungstophosphoric acid at 225℃; for 4h; Temperature; Time; Reagent/catalyst; Inert atmosphere;

: 67-56-1
methanol

: 652-67-5
Isosorbide

A: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

C: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With MCM-22 at 205℃; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Inert atmosphere;

...Expand

: 1235553-24-8
isosorbide di(methyl carbonate)

A: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

C: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With N,N-dimethyl pyrrolidinium methylcarbonate In acetonitrile at 200℃; under 11251.1 - 12751.3 Torr;

...Expand

: 1235553-24-8
isosorbide di(methyl carbonate)

A: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With 1-Methylpyrrolidine; carbonic acid dimethyl ester at 200℃; under 11251.1 - 12751.3 Torr;

: 652-67-5
Isosorbide

A: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / 6 h / 90 °C / Dean-Stark 2: carbonic acid dimethyl ester; 1-Methylpyrrolidine / 200 °C / 11251.1 - 12751.3 Torr View Scheme
Multi-step reaction with 2 steps 1: 200 °C / 9750.98 - 12751.3 Torr / Autoclave 2: carbonic acid dimethyl ester; 1-Methylpyrrolidine / 200 °C / 11251.1 - 12751.3 Torr View Scheme

: 652-67-5
Isosorbide

A: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / 6 h / 90 °C / Dean-Stark 2: N,N-dimethyl pyrrolidinium methylcarbonate / acetonitrile / 200 °C / 11251.1 - 12751.3 Torr View Scheme
Multi-step reaction with 2 steps 1: 200 °C / 9750.98 - 12751.3 Torr / Autoclave 2: N,N-dimethyl pyrrolidinium methylcarbonate / acetonitrile / 200 °C / 11251.1 - 12751.3 Torr View Scheme

: 616-38-6
carbonic acid dimethyl ester

: 652-67-5
Isosorbide

A: 1235553-26-0
C9H14O6

B: 1235553-25-9
C9H14O6

C: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

D: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

E: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With pyridine at 200℃; under 9750.98 - 12751.3 Torr; Autoclave; chemoselective reaction;

...Expand

: 616-38-6
carbonic acid dimethyl ester

: 652-67-5
Isosorbide

A: 1235553-26-0
C9H14O6

B: 1235553-25-9
C9H14O6

C: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

D: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With 1-Methylpyrrolidine at 200℃; under 9750.98 - 12751.3 Torr; for 12h; Reagent/catalyst; Autoclave; chemoselective reaction;

...Expand

: 616-38-6
carbonic acid dimethyl ester

: 652-67-5
Isosorbide

A: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

B: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With dmap at 200℃; under 9750.98 - 12751.3 Torr; Reagent/catalyst; Autoclave; chemoselective reaction;

...Expand

: 50-70-4
D-sorbitol

: 616-38-6
carbonic acid dimethyl ester

A: 1235553-24-8
isosorbide di(methyl carbonate)

B: 162426-86-0
(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol

C: 6941-54-4
(1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol

D: 5306-85-4
isosorbide dimethyl ether

Conditions

Conditions	Yield
With 1-Methylpyrrolidine at 200℃; under 15001.5 Torr; for 20h; Autoclave; chemoselective reaction;

...Expand

: 5306-85-4
isosorbide dimethyl ether

A: 121693-37-6
di-O-methyl-1,4:3,6-dianhydro-D-mannitol

B: di-O-methyl-1,4:3,6-dianhydro-L-iditol

Conditions

Conditions	Yield
With 2,3,5-trimethyl-pyridine; 2,2-bis(tert-butylperoxy)butane; tri-tert-butoxysilanethiol In octane at 125℃; for 5h;
With 1-(2,4,6-triisopropylphenylsulfonyl)-1H-1,2,4-triazole In octane at 125℃; for 4h; Product distribution; Further Variations:; Reagents;

: 5306-85-4
isosorbide dimethyl ether

A: C6H10O4

B: C7H12O4

C: C8H14O4

Conditions

Conditions	Yield
With 5 wt% ruthenium/carbon; hydrogen In water at 160℃; under 18751.9 Torr; for 3h; Autoclave;

...Expand

: 5306-85-4
isosorbide dimethyl ether

A: C6(2)H10O4

B: C7(2)H12O4

C: C8(2)H14O4

Conditions

Conditions	Yield
With 5 wt% ruthenium/carbon; hydrogen; water-d2 at 160℃; under 18751.9 Torr; for 3h; Autoclave;

...Expand

Isosorbide dimethyl ether Specification

The CAS register number of Isosorbide dimethyl ether is 5306-85-4. It also can be called as 1,4:3,6-Dianhydro-2,5-di-O-methyl-D-glucitol and the IUPAC name about this chemical is 3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan. The molecular formula about this chemical is C₈H₁₄O₄and the molecular weight is 174.19. When you are using it, please do not breathe vapour and avoid contact with skin and eyes. This chemical can be used as raw material of cosmetics.

Physical properties about Isosorbide dimethyl ether are: (1)ACD/LogP: -0.65; (2)ACD/LogD (pH 5.5): -0.65; (3)ACD/LogD (pH 7.4): -0.65; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 10.53; (7)ACD/KOC (pH 7.4): 10.53; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 36.92Å²; (11)Index of Refraction: 1.465; (12)Molar Refractivity: 41.87 cm³; (13)Molar Volume: 151.2 cm³; (14)Polarizability: 16.59x10^-24cm³; (15)Surface Tension: 33.7 dyne/cm; (16)Enthalpy of Vaporization: 45.4 kJ/mol; (17)Boiling Point: 236.4 °C at 760 mmHg; (18)Vapour Pressure: 0.073 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O([C@@H]1[C@H]2OC[C@@H](OC)[C@H]2OC1)C
(2)InChI: InChI=1/C8H14O4/c1-9-5-3-11-8-6(10-2)4-12-7(5)8/h5-8H,3-4H2,1-2H3/t5-,6+,7-,8-/m1/s1
(3)InChIKey: MEJYDZQQVZJMPP-ULAWRXDQBG
(4)Std. InChI: InChI=1S/C8H14O4/c1-9-5-3-11-8-6(10-2)4-12-7(5)8/h5-8H,3-4H2,1-2H3/t5-,6+,7-,8-/m1/s1
(5)Std. InChIKey: MEJYDZQQVZJMPP-ULAWRXDQSA-N

Product Name

ISOSORBIDE DIMETHYL ETHER

Synthetic route

Isosorbide dimethyl ether Specification

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