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5306-85-4

Basic Information
CAS No.: 5306-85-4
Name: ISOSORBIDE DIMETHYL ETHER
Article Data: 14
Molecular Structure:
Molecular Structure of 5306-85-4 (ISOSORBIDE DIMETHYL ETHER)
Formula: C8H14O4
Molecular Weight: 174.197
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;
EINECS: 226-159-8
Density: 1.15 g/cm3
Melting Point: -70 °C
Boiling Point: 236.4 °C at 760 mmHg
Flash Point: 108.3 °C
Solubility: Soluble in water.
Appearance: clear colorless to light yellow liquid
Safety: 23-24/25
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

C

5306-85-4

isosorbide dimethyl ether

Conditions
ConditionsYield
With triethylamine In biphenyl at 90 - 200℃; under 63756.4 Torr; for 48h; Reagent/catalyst; Autoclave; Inert atmosphere;A 14%
B 26%
C 60%
50-70-4

D-sorbitol

616-38-6

carbonic acid dimethyl ester

5306-85-4

isosorbide dimethyl ether

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With silicotungstic acid at 200℃; for 2h; Temperature; Reagent/catalyst; Overall yield = 75 %;A 14%
B 14%
C 47%
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
ConditionsYield
With Phosphotungstic acid at 100℃; for 3h; Time; Overall yield = 81 %;A 18%
B 18%
C 45%
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
ConditionsYield
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%
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
ConditionsYield
With Amberlyst-35 at 130℃; for 15h; Overall yield = 70 %;A 20%
B 15%
C 35%
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    MSDS/COA Download

    ISOSORBIDE DIMETHYL ETHER

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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 C8H14O4 and 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