628-90-0

Basic information

• Product Name: 2,4,6-Trioxaheptane
• Synonyms: 2,4,6-Trioxaheptane;Methoxy(MethoxyMethoxy)Methane
• CAS NO: 628-90-0
• Molecular Formula: C₄H₁₀O₃
• Molecular Weight: 106.1204
• Mol File: 628-90-0.mol
• Article Data: 25

Chemical Properties

• Melting Point: -65 °C
• Boiling Point: 96℃
• Flash Point: 7.3°C
• Appearance: /
• Density: 0.933g/cm³
• Vapor Pressure: 179mmHg at 25°C
• Refractive Index: 1.371
• CAS DataBase Reference: 2,4,6-Trioxaheptane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trioxaheptane(628-90-0)
• EPA Substance Registry System: 2,4,6-Trioxaheptane(628-90-0)

Safety Data

• Hazardous Substances Data: 628-90-0(Hazardous Substances Data)

Usage

General Description

2,4,6-Trioxaheptane, also known as Diethylene glycol dimethyl ether and Diglyme, is a colorless, organic liquid with the molecular formula C6H14O3. It is a polar aprotic solvent commonly used in organic reactions and can act as a coordinating ligand for some metals. It is also useful in the preparation of certain batteries due to its ability to dissolve electrolytes. It is often used in the production of heat transfer fluids and dielectric fluids. However, it poses potential health hazards such as skin and eye irritation upon direct exposure. It also has potential environmental hazards as it is harmful to aquatic life.

InChI:InChI=1/C4H10O3/c1-5-3-7-4-6-2/h3-4H2,1-2H3

Synthetic route

methanol (67-56-1) + formaldehyd (50-00-0) → bis(methoxymethyl)ether (628-90-0)

Conditions	Yield
With sulfonic acid resin at 80 - 95℃; Temperature; Reagent/catalyst;	95.5%
With ZrO2#dotLa2O3 at 80℃; for 4h;	6.1%
With C16H36NO3S(1+)*CH3O4S(1-) at 125 - 130℃; under 26252.6 - 30003 Torr; Reagent/catalyst; Inert atmosphere;

methanol (67-56-1) + diethyl ether (60-29-7) + bromomethylmethyl ether (89125-42-8) → bis(methoxymethyl)ether (628-90-0)

Conditions	Yield
In ethyl acetate; N,N-dimethyl-formamide; mineral oil	90%

formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0)

Conditions	Yield
With sulfuric acid at 109.99℃; under 7500.75 Torr;	A n/a B 26%

methanol (67-56-1) + formaldehyd (50-00-0) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5)

Conditions	Yield
With ZrO2#dotLa2O3 at 130℃; under 6000.6 Torr; for 4h; Pressure; Reagent/catalyst;	A 23% B 23.3% C 14.9%

formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5)

Conditions	Yield
With La2O3 doped titania at 130℃; under 4500.45 Torr; for 4h; Reagent/catalyst; Pressure; Autoclave;	A 22.4% B 17.5% C 8.4%
With macroporous strong acidic styrene type cation exchange resin catalyst at 100℃; under 15001.5 Torr; for 10h; Temperature; Time; Overall yield = 51.66 %;
With Cl -/TiO2-La2O3/SBA-15 (Si/Al=38) at 130℃; under 4500.45 Torr; for 4h; Reagent/catalyst; Temperature; Pressure;

17beta-acetoxy-3,3-ethylenedioxy-16alpha,17alpha-methylene-estra-5(10),9(11)-diene + chloromethyl methyl ether (107-30-2) → 3,3-ethylenedioxy-17beta-methoxymethylene-oxy-16alpha,17alpha-methylene-estra-5(10),9(11)-diene + bis(methoxymethyl)ether (628-90-0)

Conditions	Yield
With naphthalene; lithium In tetrahydrofuran; water

1,3,5-Trioxan (110-88-3) + 1,1-dimethoxyethane (534-15-6) → C11H24O10 + C13H28O12 + bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5) + CH3-(OCH2)8-OCH3 (13352-78-8) + Methoxymethoxymethoxymethoxymethoxy-methoxymethoxymethoxymethoxymethoxymethoxy-methane (54261-86-8) + POMM5 (13352-76-6) + CH3-(OCH2)7-OCH3 (13353-04-3) + CH3-(OCH2)6-OCH3 (13352-77-7)

Conditions	Yield
Amberlite IR 120 at 100℃; for 24h; Product distribution / selectivity;
trifluorormethanesulfonic acid at 100℃; for 40h; Product distribution / selectivity;
sulfuric acid In water at 100℃; for 12h; Product distribution / selectivity;

...Expand

1,3,5-Trioxan (110-88-3) + 1,1-dimethoxyethane (534-15-6) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5)

Conditions	Yield
sulfuric acid In water at 100℃; for 16h; Product distribution / selectivity;

formaldehyd (50-00-0) + 1,1-dimethoxyethane (534-15-6) → C11H24O10 + C13H28O12 + bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5) + CH3-(OCH2)8-OCH3 (13352-78-8) + Methoxymethoxymethoxymethoxymethoxy-methoxymethoxymethoxymethoxymethoxymethoxy-methane (54261-86-8) + POMM5 (13352-76-6) + CH3-(OCH2)7-OCH3 (13353-04-3) + CH3-(OCH2)6-OCH3 (13352-77-7)

Conditions	Yield
Amberlite IR 120 at 100℃; for 8h; Product distribution / selectivity;

...Expand

formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) → 1,3,5-Trioxan (110-88-3) + C11H24O10 + C13H28O12 + bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5) + CH3-(OCH2)8-OCH3 (13352-78-8) + Methoxymethoxymethoxymethoxymethoxy-methoxymethoxymethoxymethoxymethoxymethoxy-methane (54261-86-8) + CH3-(OCH2)7-OCH3 (13353-04-3) + C14H30O13 + C15H32O14 + CH3-(OCH2)6-OCH3 (13352-77-7)

Conditions	Yield
With sulfuric acid at 55 - 115℃; Inert atmosphere;

...Expand

3-methylbut-2-enal, pyridinium trifluoromethanesulfonate + 2-methylpropan-1-amine, p-toluenesulfonic acid monohydrate + chloromethyl methyl ether (107-30-2) → bis(methoxymethyl)ether (628-90-0)

Conditions	Yield
With pyridine; hydrogenchloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane; toluene

Dimethyl ether (115-10-6) → methanol (67-56-1) + formaldehyd (50-00-0) + methane (34557-54-5) + bis(methoxymethyl)ether (628-90-0) + carbon monoxide (201230-82-2)

Conditions	Yield
With oxygen at 19.84℃; Flow reactor; Green chemistry;

Dimethyl ether (115-10-6) → methanol (67-56-1) + formaldehyd (50-00-0) + bis(methoxymethyl)ether (628-90-0) + carbon monoxide (201230-82-2)

Conditions	Yield
With oxygen at 19.84℃; Flow reactor; Green chemistry;

Dimethoxymethane (109-87-5) → methanol (67-56-1) + formaldehyd (50-00-0) + methane (34557-54-5) + bis(methoxymethyl)ether (628-90-0) + carbon monoxide (201230-82-2)

Conditions	Yield
With oxygen at 19.84℃; Flow reactor; Green chemistry;

Dimethoxymethane (109-87-5) → methanol (67-56-1) + formaldehyd (50-00-0) + bis(methoxymethyl)ether (628-90-0) + carbon monoxide (201230-82-2)

Conditions	Yield
With oxygen at 19.84℃; Flow reactor; Green chemistry;

1,3,5-Trioxan (110-88-3) + formaldehyd (50-00-0) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0)

Conditions	Yield
With strong acidic styrene type cation exchange resin catalyst at 100℃; under 15001.5 Torr; for 3h; Temperature; Time; Overall yield = 43.26 %;

1,3,5-Trioxan (110-88-3) + formaldehyd (50-00-0) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5)

Conditions	Yield
With strong acidic styrene type cation exchange resin catalyst at 80 - 100℃; under 15001.5 Torr; for 3h; Temperature; Time; Overall yield = 47.55 %;

methanol (67-56-1) + formaldehyd (50-00-0) → Dimethoxymethane (109-87-5) + bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0)

Conditions	Yield
With C16H36NO3S(1+)*CH3O4S(1-) at 125 - 130℃; under 26252.6 - 30003 Torr; Reagent/catalyst; Inert atmosphere;

methanol (67-56-1) + formaldehyd (50-00-0) → Dimethoxymethane (109-87-5) + bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5)

Conditions	Yield
With C16H36NO3S(1+)*CH3O4S(1-) at 125 - 130℃; under 26252.6 - 30003 Torr; Reagent/catalyst; Inert atmosphere;

methanol (67-56-1) + formaldehyd (50-00-0) → Dimethoxymethane (109-87-5) + bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5) + POMM5 (13352-76-6)

Conditions	Yield
With C16H36NO3S(1+)*CH3O4S(1-) In water at 125 - 130℃; under 26252.6 - 30003 Torr; Reagent/catalyst;

Upstream product

• 67-56-1 methanol 
• 4497-29-4 bis(bromomethyl) ether 
• 107-30-2 chloromethyl methyl ether 
• 50-00-0 formaldehyd 
• 109-87-5 Dimethoxymethane 
• 7664-93-9 sulfuric acid 
• 60-29-7 diethyl ether 
• 89125-42-8 bromomethylmethyl ether 
• 37559-64-1 methoxymethyl benzenesulfenate 
• 162927-72-2 1-(5-Methoxy-2-nitro-phenyl)-prop-2-en-1-ol 
• 110-88-3 1,3,5-Trioxan 
• 115-10-6 Dimethyl ether 
• 534-15-6 1,1-dimethoxyethane 
• 124-41-4 sodium methylate 

Downstream Products

• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 151166-05-1 3-[(3,5-Diisopropyl-4-hydroxy)benzoyl]-1-(3,4-dimethoxyphenyl)-4-hydroxy-2-methoxycarbonyl-6,7,8-trimethoxynaphthalene 
• 13353-03-2 bis-methoxymethoxy-methane 
• 13352-75-5 POMM₄ 
• 13352-78-8 CH₃-(OCH₂)8-OCH₃ 
• 54261-86-8 Methoxymethoxymethoxymethoxymethoxy-methoxymethoxymethoxymethoxymethoxymethoxy-methane 
• 13352-76-6 POMM₅ 
• 13353-04-3 CH₃-(OCH₂)7-OCH₃ 
• 13352-77-7 CH₃-(OCH₂)6-OCH₃ 
• 534-15-6 1,1-dimethoxyethane 
• 108-95-2 phenol 
• 2467-02-9 Bis(2-hydroxyphenyl)methane 
• 2467-03-0 2-[(4-hydroxyphenyl)methyl]phenol 

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