5306-85-4

Basic information

• Product Name: ISOSORBIDE DIMETHYL ETHER
• Synonyms: ISOSORBIDE DIMETHYL ETHER;DIMETHYL ISOBORBIDE;DIMETHYL ISOSORBIDE;2,5-DI-O-METHYL-1,4:3,6-DIANHYDRO-D-GLUCITOL;1,4:3,6-DIANHYDRO-2,5-DI-O-METHYL-D-GLUCITOL;1,4:3,6-DIANHYDRO-2,5-O-DIMETHYL-D-GLUCITOL;1,4:3,6-DIANHYDROSORBITOL 2,5-DIMETHYL ETHER;O,O-DIMETHYLISOSORBIDE
• CAS NO: 5306-85-4
• Molecular Formula: C₈H₁₄O₄
• Molecular Weight: 174.19
• EINECS: 226-159-8
• Product Categories: Cosmetic
• Mol File: 5306-85-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: -70°C
• Boiling Point: 93-95 °C0.1 mm Hg(lit.)
• Flash Point: 227 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.15 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.073mmHg at 25°C
• Refractive Index: n20/D 1.461(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Soluble in water.
• BRN: 80854
• CAS DataBase Reference: ISOSORBIDE DIMETHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: ISOSORBIDE DIMETHYL ETHER(5306-85-4)
• EPA Substance Registry System: ISOSORBIDE DIMETHYL ETHER(5306-85-4)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 5306-85-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid. very stable under neutral conditions, hygroscopic and miscible with most organic solvents.

Uses

Different sources of media describe the Uses of 5306-85-4 differently. You can refer to the following data:
1. dimethyl isosorbide is a carrier, solvent, and viscosity controller. Its particular skin-penetrating ability opens the possibility of enhancing active substance efficacy in optical products. Its physical characteristics and solubility properties are superior to those of propylene glycol, glycerin, or ethyl alcohol.
2. Isosorbide dimethyl ether (DMI), a sustainable solvent, is widely used in various cosmetic and pharmaceutical formulations.General applications:DMI can be used as an alternative green solvent for epoxidation of cyclooctene, Baylis–Hillman reaction of isomaltulose-derived aldehydes with α,β-unsaturated ketones and also in solid-phase synthesis.It can be used as a coalescent for water-borne paints, where it acts as a co-solvent during the water loss phase and as a coalescing agent during the film formation.

Preparation

Isosorbide dimethyl ether is synthesized from isosorbide by methylation.Isosorbide dimethyl ether is obtained from stock like D-sorbitol, which is mainly derived from the hydrogenation of D-glucose.Isosorbide dimethyl has a low level of toxicity and is referred to as a green solvent due to its production from renewable/raw material.The boiling point of this solvent is high.lt is used as a substitute to dimethyl sulfoxide,and dimethylformamide-like solvents.

General Description

Dimethyl isosorbide (DMI) is a biobased greener solvent and thus aligns with "Use of Renewable Feedstocks" and "Safer Solvents and Auxiliaries".

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C8H14O4/c1-9-5-3-11-8-6(10-2)4-12-7(5)8/h5-8H,3-4H2,1-2H3

Synthetic route

carbonic acid dimethyl ester (616-38-6) + Isosorbide (652-67-5) → isosorbide dimethyl ether (5306-85-4)

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;

dimethyl sulfate (77-78-1) + Isosorbide (652-67-5) → isosorbide dimethyl ether (5306-85-4)

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

methylene chloride (74-87-3) + Isosorbide (652-67-5) → isosorbide dimethyl ether (5306-85-4)

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%

D-sorbitol (50-70-4) + carbonic acid dimethyl ester (616-38-6) → 1,4:3,6-dianhydro-D-mannitol (641-74-7) + 1,4:3,6-dianhydro-L-iditol (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) + isosorbide dimethyl ether (5306-85-4)

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%

D-sorbitol (50-70-4) + carbonic acid dimethyl ester (616-38-6) → isosorbide dimethyl ether (5306-85-4)

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%

trimethyl phosphite (512-56-1) + Isosorbide (652-67-5) → isosorbide dimethyl ether (5306-85-4)

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

diethylene glycol dimethyl ether (111-96-6) + Isosorbide (652-67-5) → (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

Dimethoxymethane (109-87-5) + diethylene glycol dimethyl ether (111-96-6) + Isosorbide (652-67-5) → (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

1,2-dimethoxyethane (110-71-4) + Isosorbide (652-67-5) → (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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%

Dimethoxymethane (109-87-5) + Isosorbide (652-67-5) → (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

carbonic acid dimethyl ester (616-38-6) + Isosorbide (652-67-5) → C9H14O6 (1235553-26-0) + C9H14O6 (1235553-25-9) + isosorbide di(methyl carbonate) (1235553-24-8) + isosorbide dimethyl ether (5306-85-4)

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%

Triethylene glycol dimethyl ether (112-49-2) + Isosorbide (652-67-5) → (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

methoxybenzene (100-66-3) + Isosorbide (652-67-5) → (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

1,4-dimethoxybezene (150-78-7) + Isosorbide (652-67-5) → (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

carbonic acid dimethyl ester (616-38-6) + Isosorbide (652-67-5) → C9H14O6 (1235553-26-0) + C9H14O6 (1235553-25-9) + isosorbide di(methyl carbonate) (1235553-24-8) + (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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%

D-sorbitol (50-70-4) + sodium carbonate → isosorbide dimethyl ether (5306-85-4)

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

3,6-anhydro-D-glucitol (53648-56-9) → isosorbide dimethyl ether (5306-85-4)

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

3,6-anhydro-D-glucose (7625-23-2) → isosorbide dimethyl ether (5306-85-4)

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

carbonic acid dimethyl ester (616-38-6) + Isosorbide (652-67-5) → C9H14O6 (1235553-26-0) + C9H14O6 (1235553-25-9) + isosorbide dimethyl ether (5306-85-4)

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;

isosorbide di(methyl carbonate) (1235553-24-8) → (3S,3aR,6aR)hexahydro-3,6-epoxyfuro[3,2-b]furan + isosorbide dimethyl ether (5306-85-4)

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

methanol (67-56-1) + Isosorbide (652-67-5) → isosorbide dimethyl ether (5306-85-4)

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

methanol (67-56-1) + Isosorbide (652-67-5) → (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

isosorbide di(methyl carbonate) (1235553-24-8) → (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

isosorbide di(methyl carbonate) (1235553-24-8) → (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

Isosorbide (652-67-5) → (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

Isosorbide (652-67-5) → (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + isosorbide dimethyl ether (5306-85-4)

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

carbonic acid dimethyl ester (616-38-6) + Isosorbide (652-67-5) → C9H14O6 (1235553-26-0) + C9H14O6 (1235553-25-9) + (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

carbonic acid dimethyl ester (616-38-6) + Isosorbide (652-67-5) → C9H14O6 (1235553-26-0) + C9H14O6 (1235553-25-9) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

carbonic acid dimethyl ester (616-38-6) + Isosorbide (652-67-5) → (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

D-sorbitol (50-70-4) + carbonic acid dimethyl ester (616-38-6) → isosorbide di(methyl carbonate) (1235553-24-8) + (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol (162426-86-0) + (1R,4S,5R,8R)-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol (6941-54-4) + isosorbide dimethyl ether (5306-85-4)

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

isosorbide dimethyl ether (5306-85-4) → di-O-methyl-1,4:3,6-dianhydro-D-mannitol (121693-37-6) + di-O-methyl-1,4:3,6-dianhydro-L-iditol

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;

isosorbide dimethyl ether (5306-85-4) → C6H10O4 + C7H12O4 + C8H14O4

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

isosorbide dimethyl ether (5306-85-4) → C6(2)H10O4 + C7(2)H12O4 + C8(2)H14O4

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

Upstream product

• 53648-56-9 3,6-anhydro-D-glucitol 
• 1235553-24-8 isosorbide di(methyl carbonate) 
• 652-67-5 Isosorbide 
• 616-38-6 carbonic acid dimethyl ester 
• 50-70-4 D-sorbitol 
• 74-87-3 methylene chloride 
• 67-56-1 methanol 
• 110-71-4 1,2-dimethoxyethane 
• 7625-23-2 3,6-anhydro-D-glucose 
• 77-78-1 dimethyl sulfate 
• 512-56-1 trimethyl phosphite 
• 100-66-3 methoxybenzene 
• 112-49-2 Triethylene glycol dimethyl ether 
• 111-96-6 diethylene glycol dimethyl ether 

Downstream Products

• 121693-37-6 dimethyl isomannide 

Relevant articles and documents

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