Product Name

  • Name

    TRIETHYLENE GLYCOL MONOMETHYL ETHER

  • EINECS 203-962-1
  • CAS No. 112-35-6
  • Article Data19
  • CAS DataBase
  • Density 1.021 g/cm3
  • Solubility Completely miscible in water
  • Melting Point -44oC
  • Formula C7H16O4
  • Boiling Point 233.9 °C at 760 mmHg
  • Molecular Weight 164.202
  • Flash Point 95.3 °C
  • Transport Information
  • Appearance Colorless odorless liquid
  • Safety 24/25-22
  • Risk Codes
  • Molecular Structure Molecular Structure of 112-35-6 (TRIETHYLENE GLYCOL MONOMETHYL ETHER)
  • Hazard Symbols
  • Synonyms 2-[2-(2-Methoxyethoxy)ethoxy]ethanol;3,6,9-Trioxa-1-decanol;3,6,9-Trioxadecanol;Bikanol M 3;Dowanol TMAT;HymolTM;Methyltriglycol;Methyltrioxitol;NSC 97395;Triglycol monomethyl ether;
  • PSA 47.92000
  • LogP -0.34170

Synthetic route

3-Hydroxybenzyl alcohol
620-24-6

3-Hydroxybenzyl alcohol

A

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

B

3-Phenoxybenzyl alcohol
13826-35-2

3-Phenoxybenzyl alcohol

Conditions
ConditionsYield
A n/a
B 87%
dimethyl sulfate
77-78-1

dimethyl sulfate

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

Conditions
ConditionsYield
With sodium hydroxide at 120℃; for 4h;59%
With sodium hydroxide at 120℃;
triethylene glycol benzyl methyl ether
249508-40-5

triethylene glycol benzyl methyl ether

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

Conditions
ConditionsYield
With hydrogen; palladium97%
2-[2-(2-methoxyethoxy)etoxy]acetic acid
16024-58-1

2-[2-(2-methoxyethoxy)etoxy]acetic acid

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

Conditions
ConditionsYield
Stage #1: 2-[2-(2-methoxyethoxy)etoxy]acetic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 22℃; for 0.333333h;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h;
Stage #3: With potassium hydrogensulfate In tetrahydrofuran; ethyl acetate at 22℃; for 24h;
17%
triethylene glycol monomethyl ether and lithium picrate complex

triethylene glycol monomethyl ether and lithium picrate complex

A

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

B

lithium picrate-RG7

lithium picrate-RG7

Conditions
ConditionsYield
With RG7 In toluene at 25℃; Equilibrium constant;
dimethyl sulfate
77-78-1

dimethyl sulfate

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

A

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

B

Triethylene glycol dimethyl ether
112-49-2

Triethylene glycol dimethyl ether

Conditions
ConditionsYield
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With sodium hydroxide at 55 - 60℃; for 0.166667h;
Stage #2: dimethyl sulfate at 55 - 60℃; for 6h;
A 33%
B n/a
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

methyl halide

methyl halide

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

Conditions
ConditionsYield
With solid alkali In 1,4-dioxane; water15%
oxirane
75-21-8

oxirane

methanol
67-56-1

methanol

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

Conditions
ConditionsYield
With phosphoric acid at 60 - 70℃;
With sodium methylate at 60 - 140℃;
triethylene glycol monobenzyl ether
55489-58-2

triethylene glycol monobenzyl ether

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH
2: 97 percent / H2 / Pd
View Scheme
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. NaOH
2: aq. NaOH
3: 97 percent / H2 / Pd
View Scheme
methyl iodide
74-88-4

methyl iodide

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 2h;
C27H40O8
81194-71-0

C27H40O8

A

benzophenone
119-61-9

benzophenone

B

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water at 30℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), var. temp.;
triethylene glycol bromide

triethylene glycol bromide

2,5-dihydroxy-4-nitrobenzoic acid methyl ester
1447497-17-7

2,5-dihydroxy-4-nitrobenzoic acid methyl ester

A

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

B

methyl 2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoate
1447497-18-8

methyl 2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone Inert atmosphere; Reflux;
oxirane
75-21-8

oxirane

methanol
67-56-1

methanol

A

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

B

2-methoxy-ethanol,O-methyl-diethylene glycol

2-methoxy-ethanol,O-methyl-diethylene glycol

Conditions
ConditionsYield
With sodium methylate
bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 2-(2-[2-methoxyethoxy]ethoxy)ethyl ester
157874-64-1

bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 2-(2-[2-methoxyethoxy]ethoxy)ethyl ester

A

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

B

bicyclo[2.2.1]hept-2-ene-5-carbonyl chloride
27063-48-5, 34733-86-3, 37750-50-8, 117835-14-0, 143916-13-6

bicyclo[2.2.1]hept-2-ene-5-carbonyl chloride

Conditions
ConditionsYield
With Citric acid buffer; phosphoric acid at 80℃; pH=3.1; Kinetics; Further Variations:; pH-values; Temperatures;
oxirane
75-21-8

oxirane

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

3,6,9-trioxadecyl iodide
62999-96-6

3,6,9-trioxadecyl iodide

Conditions
ConditionsYield
Stage #1: triethylene glucol monomethyl ether With 1H-imidazole; triphenylphosphine In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
77%
With 1H-imidazole; iodine; triphenylphosphine In toluene for 4h; Heating;53%
Multi-step reaction with 2 steps
1: pyridine / CH2Cl2
2: NaI / acetone / 5 h / Heating
View Scheme
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

1-chloro-3,6,9-trioxadecane
52995-76-3

1-chloro-3,6,9-trioxadecane

Conditions
ConditionsYield
With pyridine; thionyl chloride In chloroform for 3h; Heating;94%
With pyridine; thionyl chloride In toluene at 60 - 80℃; for 3h; Cooling with ice;92%
With pyridine; thionyl chloride In tetrahydrofuran90%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

4-Nitrophthalonitrile
31643-49-9

4-Nitrophthalonitrile

4-phthalonitrile
172599-63-2

4-phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;82%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;81%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;75%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

8-methoxy-1-(methylsulfonyl)oxy-3,6-dioxaoctane
74654-05-0

8-methoxy-1-(methylsulfonyl)oxy-3,6-dioxaoctane

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1.5h;100%
With triethylamine In dichloromethane100%
With triethylamine In dichloromethane at 0 - 20℃; for 2h;97%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

carbonochloridic acid, chloromethyl ester
22128-62-7

carbonochloridic acid, chloromethyl ester

chloromethyl (2-(2-(2-methoxyethoxy)ethoxy)ethyl) carbonate
209551-63-3

chloromethyl (2-(2-(2-methoxyethoxy)ethoxy)ethyl) carbonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 22h; Inert atmosphere;99%
With pyridine In dichloromethane at 0 - 20℃;99%
With pyridine In dichloromethane
With pyridine In dichloromethane at 20℃;
With pyridine In dichloromethane at -78℃; for 3h;
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

cyanoacetic acid
372-09-8

cyanoacetic acid

2-(2-(2-methoxyethoxy)ethoxy)ethyl 2-cyanoacetate

2-(2-(2-methoxyethoxy)ethoxy)ethyl 2-cyanoacetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 110℃; for 4h; Dean-Stark; Inert atmosphere;90%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 2h;86%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 6h;86%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

4-Nitrophenyl chloroformate
7693-46-1

4-Nitrophenyl chloroformate

2-(2-(2-methoxyethoxy)ethoxy)ethyl (4-nitrophenyl) carbonate

2-(2-(2-methoxyethoxy)ethoxy)ethyl (4-nitrophenyl) carbonate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 5h;99%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 5h;99%
In dichloromethane at 0 - 20℃; for 16.5h;67%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

propargyl bromide
106-96-7

propargyl bromide

3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)prop-1-yne
89635-82-5

3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)prop-1-yne

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 168h; Inert atmosphere;99%
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere;
Stage #2: propargyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;
91%
With sodium hydride; sodium iodide In tetrahydrofuran; toluene; mineral oil at 20℃; for 16h; Inert atmosphere;85%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

epichlorohydrin
106-89-8

epichlorohydrin

2-((2-(2-(2-methoxyethoxy)ethoxy)ethoxy)methyl)oxirane
73692-54-3

2-((2-(2-(2-methoxyethoxy)ethoxy)ethoxy)methyl)oxirane

Conditions
ConditionsYield
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 2h;
Stage #2: epichlorohydrin In tetrahydrofuran; mineral oil at 20℃; for 20h; Reflux;
91%
With sodium hydride In tetrahydrofuran 1.) 2h, 2.) RT, 16h; 4h, reflux;86.6%
With tetra(n-butyl)ammonium hydroxide; sodium hydroxide In water at 0 - 20℃; for 16h; Cooling with ice;79%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

tert-butyl (monomethoxy)triethylene glycol acetate
331992-12-2

tert-butyl (monomethoxy)triethylene glycol acetate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 12h;98%
Stage #1: triethylene glucol monomethyl ether With potassium tert-butylate In tert-butyl alcohol at 20℃; for 2h;
Stage #2: bromoacetic acid tert-butyl ester In tert-butyl alcohol at 20℃; for 12h;
75%
With sodium hydride In tetrahydrofuran at 20 - 25℃; Cooling with ice;59.6%
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: bromoacetic acid tert-butyl ester In tetrahydrofuran; hexane at 0 - 20℃; for 15h; Inert atmosphere;
50%
With sodium hydride In tetrahydrofuran
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

2-bromoacetic acid-2-[2-(2-methoxyethoxy)ethoxy]ethyl ester
56521-80-3

2-bromoacetic acid-2-[2-(2-methoxyethoxy)ethoxy]ethyl ester

Conditions
ConditionsYield
With triethylamine In diethyl ether at 0 - 20℃; for 0.683333h; Inert atmosphere;73%
With triethylamine In dichloromethane at -78℃; Inert atmosphere;58%
With triethylamine In dichloromethane at -78 - -20℃; Inert atmosphere;
With sodium hydrogencarbonate In acetonitrile at 0℃; for 0.166667h; Inert atmosphere;
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

3,6,9-trioxadecyl bromide
72593-77-2

3,6,9-trioxadecyl bromide

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0℃; for 5h; Inert atmosphere;84%
With phosphorus tribromide In methanol; diethyl ether 1.) 0 deg C, 10 min, 2.) RT, 30 min;75%
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 50℃; for 12h; Inert atmosphere;70%
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

2,5-dioxopyrrolidin-1-yl (2-(2-(2-methoxyethoxy)ethoxy)ethyl)carbonate
477775-77-2

2,5-dioxopyrrolidin-1-yl (2-(2-(2-methoxyethoxy)ethoxy)ethyl)carbonate

Conditions
ConditionsYield
Stage #1: triethylene glucol monomethyl ether With triethylamine In dichloromethane at 0℃; for 0.25h;
Stage #2: di(succinimido) carbonate In dichloromethane at 20℃; for 18h;
75%
With triethylamine In acetonitrile at 20℃; for 16.1667h;55%
With triethylamine In acetonitrile at 20℃;20%
With triethylamine In acetonitrile
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

D-glucal triacetate
2873-29-2

D-glucal triacetate

A

2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
1400767-53-4

2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

B

2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
1400767-54-5

2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside

Conditions
ConditionsYield
With tellurium tetrachloride In dichloromethane at 0 - 20℃; for 0.25h; Ferrier Carbohydrate Rearrangement; Inert atmosphere; diastereoselective reaction;A 86%
B n/a
With toluene-4-sulfonic acid In acetonitrile at 25℃; for 0.333333h; Sonication;A 82%
B n/a
With tellurium tetrachloride In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Overall yield = 86%; Overall yield = 0.32g;A n/a
B n/a
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

3,5-dinitrobenoyl chloride
99-33-2

3,5-dinitrobenoyl chloride

2‐[2‐(2‐methoxyethoxy)ethoxy]ethyl 3,5‐dinitrobenzoate
93310-27-1

2‐[2‐(2‐methoxyethoxy)ethoxy]ethyl 3,5‐dinitrobenzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;89.3%
In N,N-dimethyl acetamide for 8h; cooling;69%
With triethylamine In dichloromethane at 0 - 20℃;
3-Bromothiophene
872-31-1

3-Bromothiophene

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)thiophene
282540-12-9

3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)thiophene

Conditions
ConditionsYield
Stage #1: triethylene glucol monomethyl ether With pyridine; copper(l) iodide; potassium tert-butylate In toluene at 20℃; for 0.5h;
Stage #2: 3-Bromothiophene In toluene at 110℃; for 24h;
68%
Stage #1: triethylene glucol monomethyl ether With copper(l) iodide; potassium tert-butylate at 20℃; for 1h; Inert atmosphere;
Stage #2: 3-Bromothiophene at 100℃; for 24h; Inert atmosphere;
63%
With sodium hydride; copper(I) bromide In N,N-dimethyl-formamide23%
Stage #1: triethylene glucol monomethyl ether With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere;
Stage #2: 3-Bromothiophene With copper(I) bromide In N,N-dimethyl-formamide at 110℃; for 12h; Inert atmosphere;
11.6 g
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide

1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide

3,6,9,12,15,18,21-heptaoxadocosan-1-ol
4437-01-8

3,6,9,12,15,18,21-heptaoxadocosan-1-ol

Conditions
ConditionsYield
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: 1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide In tetrahydrofuran; mineral oil at 20℃; for 12h; Inert atmosphere;
Stage #3: With sulfuric acid In tetrahydrofuran; water for 3h; Reflux;
98%
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: 1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide In tetrahydrofuran; mineral oil at 20℃; for 12h; Inert atmosphere;
Stage #3: With sulfuric acid; water In tetrahydrofuran for 3h; Inert atmosphere; Reflux;
89%
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere;
Stage #2: 1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide With sulfuric acid In tetrahydrofuran; water; mineral oil at 20℃; pH=3; Inert atmosphere;
84%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

ethyl bromoacetate
105-36-2

ethyl bromoacetate

methoxytriethyleneglycol carboxylic acid ethyl ester
66664-66-2

methoxytriethyleneglycol carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: triethylene glucol monomethyl ether With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: ethyl bromoacetate In tetrahydrofuran at 0 - 20℃;
78.74%
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Williamson Ether Synthesis;
Stage #2: ethyl bromoacetate In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Williamson Ether Synthesis;
56%
With sodium hydride In 1,2-dimethoxyethane for 1h;42%
C17H12O3
696661-26-4

C17H12O3

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

2-[2-(2-methoxyethoxy)ethoxy]ethyl 3-(4-methylphenyl)-1-oxo-1H-indene-2-carboxylate
1016567-36-4

2-[2-(2-methoxyethoxy)ethoxy]ethyl 3-(4-methylphenyl)-1-oxo-1H-indene-2-carboxylate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In dichloromethane at 20℃;67%
2-chloromethyl-3-chloroprop-1-ene
1871-57-4

2-chloromethyl-3-chloroprop-1-ene

triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-2-({2-[2-(2-methoxyethoxy)ethoxy]ethoxy}methyl)propene
1240167-42-3

3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-2-({2-[2-(2-methoxyethoxy)ethoxy]ethoxy}methyl)propene

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20 - 65℃; for 12.25h; Inert atmosphere;81%
With sodium hydride In tetrahydrofuran at 65℃;35%
With sodium hydride In tetrahydrofuran at 65℃; for 24h;
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 60℃; for 0.5h; Inert atmosphere;
Stage #2: 2-chloromethyl-3-chloroprop-1-ene In tetrahydrofuran; mineral oil at 20 - 65℃; Inert atmosphere;
With sodium hydride In tetrahydrofuran at 65℃; for 12h; Inert atmosphere;
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

4,4'-(5,5-difluoro-1,9-diphenyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,5,2]triazaborinine-3,7-diyl)diphenol
1195110-34-9

4,4'-(5,5-difluoro-1,9-diphenyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,5,2]triazaborinine-3,7-diyl)diphenol

2-(N-tert-butoxycarbonylamino)ethanol
26690-80-2

2-(N-tert-butoxycarbonylamino)ethanol

C46H49BF2N4O7
1234293-52-7

C46H49BF2N4O7

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16.33h;39%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h;39%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Mitsunobu reaction;33%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate
62921-74-8

2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 3h;99%
With triethylamine In tetrahydrofuran; dichloromethane at 20℃; for 24h; Inert atmosphere;81.6%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

tert-Butyl acrylate
1663-39-4

tert-Butyl acrylate

tert-butyl 2,5,8,11-tetraoxatetradecan-14-oate
883554-11-8

tert-butyl 2,5,8,11-tetraoxatetradecan-14-oate

Conditions
ConditionsYield
With sodium methylate at 20℃;75.3%
Stage #1: triethylene glucol monomethyl ether With sodium In tetrahydrofuran at 20 - 50℃; Inert atmosphere;
Stage #2: tert-Butyl acrylate In tetrahydrofuran at 20 - 40℃;
65%
With hydrogenchloride In tetrahydrofuran
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

phthalocyanine silicon(IV) dichloride
19333-10-9

phthalocyanine silicon(IV) dichloride

bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)silicon phthalocyanine
916428-71-2

bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)silicon phthalocyanine

Conditions
ConditionsYield
With sodium hydride In toluene at 120℃; for 24h; Inert atmosphere;54%
With sodium hydride In toluene Inert atmosphere; Reflux;32.91%
With sodium hydride In toluene at 125℃; for 16h;25%
With potassium carbonate In toluene for 14h; Inert atmosphere; Reflux;15.6%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

2-chloro-4-(6-(piperidin-1-yl)naphthalen-2-yl)nicotinonitrile

2-chloro-4-(6-(piperidin-1-yl)naphthalen-2-yl)nicotinonitrile

2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-(6-(piperidin-1-yl)naphthalen-2-yl)nicotinonitrile

2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-(6-(piperidin-1-yl)naphthalen-2-yl)nicotinonitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 60℃; for 12h;70%
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 12h;70%
Stage #1: triethylene glucol monomethyl ether With sodium hydride In N,N-dimethyl-formamide at 0℃;
Stage #2: 2-chloro-4-(6-(piperidin-1-yl)naphthalen-2-yl)nicotinonitrile In N,N-dimethyl-formamide at 0 - 60℃; for 12h;
70%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

C35H75ClN3O20P3

C35H75ClN3O20P3

Conditions
ConditionsYield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; sodium hydride In tetrahydrofuran at 20℃; for 5.5h; Inert atmosphere; Cooling with ice;75%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

10,12-docosadiynedioic acid
28393-02-4

10,12-docosadiynedioic acid

bis(triethylene glycol methyl ether) docosa-10,12-diynedioate

bis(triethylene glycol methyl ether) docosa-10,12-diynedioate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 18h;84%

Triethylene glycol monomethyl ether Chemical Properties

MF: C7H16O4
MW: 164.2
Fp: >230 °F
EINECS: 203-962-1
bp: 122 °C10 mm Hg(lit.)
density: 1.026 g/mL at 25 °C(lit.)
vapor density: 5.66 (vs air)
vapor pressure:  <0.01 mm Hg ( 20 °C)
refractive index:  n20/D 1.439(lit.)

Triethylene glycol monomethyl ether Uses

TRIETHYLENE GLYCOLMONOMETHYL ETHER  is used as the brake fluid and chemical raw materials.

Triethylene glycol monomethyl ether Toxicity Data With Reference

1.   

skn-rbt 10 mg/24H open MLD

   AIHAAP    American Industrial Hygiene Association Journal. 23 (1962),95.
2.   

eye-rbt 500 mg/24H MLD

   85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,634.
3.   

orl-rat LD50:11,300 mg/kg

   AIHAAP    American Industrial Hygiene Association Journal. 23 (1962),95.
4.   

skn-rbt LD50:7100 mg/kg

   AIHAAP    American Industrial Hygiene Association Journal. 23 (1962),95.
5.   RTECS  KL6390000

Triethylene glycol monomethyl ether Consensus Reports

Glycol ether compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

Triethylene glycol monomethyl ether Safety Profile

Mildly toxic by ingestion and skin contact. A skin and eye irritant. Many glycol ether compounds have dangerous human reproductive effects. Combustible when exposed to heat or flame. To fight fire, use alcohol foam, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.
Safety Statements  24/25-22
WGK Germany  1
F  10-23
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