20637-49-4

Basic information

• Product Name: 1,2,3-Trimethoxypropane
• Synonyms: 1,2,3-Trimethoxypropane;PROPANE, 1,2,3-TRIMETHOXY-
• CAS NO: 20637-49-4
• Molecular Formula: C₆H₁₄O₃
• Molecular Weight: 134.1736
• Mol File: 20637-49-4.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 148°C (estimate)
• Flash Point: 42.7°C
• Appearance: /
• Density: 0.9460
• Vapor Pressure: 6.8mmHg at 25°C
• Refractive Index: 1.4055
• CAS DataBase Reference: 1,2,3-Trimethoxypropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-Trimethoxypropane(20637-49-4)
• EPA Substance Registry System: 1,2,3-Trimethoxypropane(20637-49-4)

Safety Data

• Hazardous Substances Data: 20637-49-4(Hazardous Substances Data)

Usage

General Description

1,2,3-Trimethoxypropane, also known as TMP, is a clear, colorless liquid that is commonly used as a solvent and a chemical intermediate in various industries. It is derived from the reaction of acetone with methanol and sulfuric acid. With a high boiling point and low evaporation rate, TMP is often used as a solvent for cellulose acetate, resins, and dyes. It is also utilized in the production of pharmaceuticals and pesticides, as well as in the synthesis of other organic compounds. Additionally, TMP can be used as an additive in fuel to improve combustion properties. It is important to handle TMP with care, as it is flammable and can cause irritation to the skin, eyes, and respiratory system upon exposure.

InChI:InChI=1/C6H14O3/c1-7-4-6(9-3)5-8-2/h6H,4-5H2,1-3H3

Synthetic route

methyl p-toluene sulfonate (80-48-8) + glycerol (56-81-5) → 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
With sodium hydroxide In water at 100℃; for 3h;	100%

methanol (67-56-1) + glycerol (56-81-5) → 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
amberlyst-15 at 90℃; under 750.075 Torr; Product distribution / selectivity;	90%

glycerol (56-81-5) + dimethyl sulfate (77-78-1) → 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
Stage #1: glycerol With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide at 20℃; for 0.5h; Stage #2: dimethyl sulfate With potassium hydroxide at 15 - 20℃;	79%
Stage #1: glycerol With sodium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.75h; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide at 0 - 20℃; for 48h;	20%
With sodium hydroxide at 60 - 70℃; dann bei 100grad;
Stage #1: glycerol With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In neat (no solvent) at 20℃; for 0.5h; Stage #2: dimethyl sulfate In neat (no solvent) at 15 - 20℃; for 24h;	95 %Spectr.

epichlorohydrin (106-89-8) + methyl iodide (74-88-4) + dimethoxy glycerol → 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
Stage #1: epichlorohydrin With sodium In methanol for 1h; Inert atmosphere; Reflux; Stage #2: dimethoxy glycerol In tetrahydrofuran; methanol; mineral oil for 1h; Inert atmosphere; Reflux; Stage #3: methyl iodide In tetrahydrofuran; methanol; mineral oil at 20℃; Inert atmosphere;	71%

trimethyl phosphite (512-56-1) + glycerol (56-81-5) → 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
With iron(II) triflate In neat (no solvent) at 100℃; for 15h;	67%

diazomethane (186581-53-3, 908094-01-9) + glycerol (56-81-5) → 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
With diethyl ether; boron trifluoride

glycerol (56-81-5) + dimethyl sulfate (77-78-1) + alkaline solution → 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield

dimethyl sulfate (77-78-1) + sodium compound of/the/ glyceroldimethyl ether → 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield

dimethyl sulfate (77-78-1) + sodium compound of glycerol-2-methyl ether → 2,3-dimethoxypropan-1-ol (40453-77-8) + 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield

2-methylglycerol (761-06-8) → 1,2,3-trimethoxy glycerol ether (20637-49-4) + glycerol-1.2-dimethyl ether

Conditions	Yield
bei der Methylierung;

Dimethyl ether (115-10-6) → 1,2-dimethoxyethane (110-71-4) + 1,3-dimethoxy propane (17081-21-9) + 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
at 100℃; under 760 Torr; Electrolysis;	A 23.37 % Chromat. B 5.66 % Chromat. C 1.48 % Chromat.

methanol (67-56-1) + glycerol (56-81-5) → glycerol 1-monomethyl ether (623-39-2, 36887-04-4) + 2,3-dimethoxypropan-1-ol (40453-77-8) + 1,3-dimethyl glycerol ether (623-69-8) + 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
With trifluorormethanesulfonic acid; aqua(2,2'-bipyridine)(η5-pentamethylcyclopentadienyl)ruthenium(II) triflate; hydrogen In sulfolane at 200℃; under 25877.6 Torr; for 3.5h; Autoclave;

glycerol (56-81-5) + dimethyl sulfate (77-78-1) → glycerol 1-monomethyl ether (623-39-2, 36887-04-4) + 2,3-dimethoxypropan-1-ol (40453-77-8) + 1,3-dimethyl glycerol ether (623-69-8) + 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
Stage #1: glycerol With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: dimethyl sulfate In tetrahydrofuran at 15 - 20℃; for 24h; Solvent;	A 8 %Spectr. B 6 %Spectr. C 6 %Spectr. D 79 %Spectr.

glycerol (56-81-5) + methyl iodide (74-88-4) → 2,3-dimethoxypropan-1-ol (40453-77-8) + 1,3-dimethyl glycerol ether (623-69-8) + 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
Stage #1: glycerol With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In neat (no solvent) at 20℃; for 0.5h; Stage #2: methyl iodide In neat (no solvent) at 15 - 20℃; for 24h;	A 11 %Spectr. B 16 %Spectr. C 72 %Spectr.

glycerol 1-monomethyl ether (623-39-2, 36887-04-4) + methyl p-toluene sulfonate (80-48-8) → 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
With sodium hydroxide In water at 70℃; for 2h;

methanol (67-56-1) + glycerol (56-81-5) → glycerol 1-monomethyl ether (623-39-2, 36887-04-4) + 1,3-dimethyl glycerol ether (623-69-8) + 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
With Amberlyst 36 dry sulfogroup cation exchange resin at 95 - 135℃;

1,3-dimethyl glycerol ether (623-69-8) + methyl iodide (74-88-4) → 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
Stage #1: 1,3-dimethyl glycerol ether With sodium hydride In tetrahydrofuran Stage #2: methyl iodide In tetrahydrofuran at 40℃;

glycerol (56-81-5) → methanol (67-56-1) + 1-butylene (106-98-9) + (Z)-2-Butene (590-18-1) + propene (187737-37-7) + methane (34557-54-5) + trans-2-Butene (624-64-6) + ethane (74-84-0) + propane (74-98-6) + Isobutane (75-28-5) + ethene (74-85-1) + 1,2,3-trimethoxy glycerol ether (20637-49-4) + tri-tert-butyl glycerol ether (92867-55-5) + ethylbenzene (100-41-4) + toluene (108-88-3) + acrolein (107-02-8) + isobutene (115-11-7) + n-butane (106-97-8) + benzene (71-43-2)

Conditions	Yield
With zeolite HZSM-5 In water at 340℃; Catalytic behavior; Reagent/catalyst; Flow reactor;

...Expand

Dimethyl ether (115-10-6) → 1,2-dimethoxyethane (110-71-4) + diethylene glycol dimethyl ether (111-96-6) + 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
With di-tert-butyl peroxide at 150℃; for 4h; Temperature; Autoclave;

Dimethyl ether (115-10-6) → 1,2-dimethoxyethane (110-71-4) + 1,2,3-trimethoxy glycerol ether (20637-49-4)

Conditions	Yield
With di-tert-butyl peroxide at 135℃; Autoclave;

Upstream product

• 186581-53-3 diazomethane 
• 56-81-5 glycerol 
• 77-78-1 dimethyl sulfate 
• 761-06-8 2-methylglycerol 
• 115-10-6 Dimethyl ether 
• 67-56-1 methanol 
• 106-89-8 epichlorohydrin 
• 74-88-4 methyl iodide 
• 80-48-8 methyl p-toluene sulfonate 
• 623-39-2 glycerol 1-monomethyl ether 
• 623-69-8 1,3-dimethyl glycerol ether 
• 512-56-1 trimethyl phosphite 

Relevant articles and documents

PROCESSES FOR FORMING GLYCOLS

This disclosure provides processes for forming glycols by upgrading hydrocarbons. In one embodiment, a process for forming a glycol includes introducing a first ether to a dihydrocarbyl peroxide to form a diether and a first alcohol. The process includes introducing the diether to water to form a glycol and a second alcohol. Processes of this disclosure may include one or more of: introducing a hydrocarbyl hydroperoxide to a third alcohol to form the dihydrocarbyl peroxide; oxidizing a first feed stream comprising a branched hydrocarbon to form the hydrocarbyl hydroperoxide and the first alcohol; and/or introducing the second alcohol to a catalyst to form a second ether.

Methylation of Polyols with Trimethylphosphate in the Presence of a Lewis or Br?nsted Acid Catalyst

The alkylation of alcohols and polyols has been investigated with alkylphosphates in the presence of a Lewis or Br?nsted acid catalyst. The permethylation of polyols was developed under solvent-free conditions at 100 °C with either iron triflate or Aquivion PW98, affording the isolated products in yields between 52 and 95 %. The methodology was also adjusted to carry out peralkylation with longer alkyl chains.

Thermodynamic characteristics of the sorption of glycerol ethers on stationary phase OV-101

Retention characteristics, temperature dependences of the retention characteristics, and thermodynamic characteristics of sorption on the nonpolar OV-101 phase are determined for 33 glycerol mono-, di-, and triethers with linear and branched monobasic alc