7580-85-0

Basic information

• Product Name: ETHYLENE GLYCOL MONO-TERT-BUTYL ETHER
• Synonyms: TERT-BUTYL CELLOSOLVE;ETHYLENE GLYCOL MONO-T-BUTYL ETHER;ETHYLENE GLYCOL MONO-TERT-BUTYL ETHER;2-TERT-BUTOXYETHANOL;2-(1,1-dimethylethoxy)-ethano;2-(1,1-dimethylethoxy)ethanol;2-tert-butoxy-ethano;swasolveetb
• CAS NO: 7580-85-0
• Molecular Formula: C₆H₁₄O₂
• Molecular Weight: 118.17
• EINECS: 242-826-6
• Product Categories: Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols
• Mol File: 7580-85-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 152 °C
• Flash Point: 55°C
• Appearance: /
• Density: 0,9 g/cm3
• Vapor Pressure: 2.08mmHg at 25°C
• Refractive Index: 1.4160 to 1.4190
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.44±0.10(Predicted)
• Water Solubility: Completely miscible in water
• CAS DataBase Reference: ETHYLENE GLYCOL MONO-TERT-BUTYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYLENE GLYCOL MONO-TERT-BUTYL ETHER(7580-85-0)
• EPA Substance Registry System: ETHYLENE GLYCOL MONO-TERT-BUTYL ETHER(7580-85-0)

Safety Data

• Statements: 10-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3271
• RTECS: KJ8750000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 7580-85-0(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

2-(1,1-Dimethylethoxy)ethanol is used in the preparation of potent and selective NPY5 receptor antagonists. Also used in the synthesis of PDE5 inhibitors, used to block the degradative action of phosphodiesterase 5.

InChI:InChI=1/C6H14O2/c1-6(2,3)8-5-4-7/h7H,4-5H2,1-3H3

Synthetic route

oxirane (75-21-8) + tert-butyl alcohol (75-65-0) → tert-butyl glycidyl ether (7580-85-0)

Conditions	Yield
With K-MgO/γ-alumina In tetrahydrofuran at 50℃; for 5h; Temperature;	97.3%
With hydro silicate
With hydro silicate

1-bromo-butane (109-65-9) + tert-butyl alcohol (75-65-0) → tert-butyl glycidyl ether (7580-85-0)

Conditions	Yield
Stage #1: 1-bromo-butane With 1-methyl-1H-imidazole at 80℃; for 3h; Stage #2: With imidazolyl sodium In methanol at 20℃; for 6h; Stage #3: tert-butyl alcohol at 30 - 50℃; Temperature;	94.2%

2-vinyl-1,3-dioxolane (3984-22-3) + tert-butyl alcohol (75-65-0) → tert-butyl glycidyl ether (7580-85-0) + Ethylene glycol di-tert-butyl diether (26547-47-7) + 2-(2-tert-butoxyethyl)-1,3-dioxolane (107378-68-7)

Conditions	Yield
With sulfuric acid for 5h; Heating;	A 8.5% B 2% C 6 g

t-butyl bromide (507-19-7) + ethylene glycol (107-21-1) → tert-butyl glycidyl ether (7580-85-0)

ethylene glycol (107-21-1) + isobutene (115-11-7) → tert-butyl glycidyl ether (7580-85-0) + Ethylene glycol di-tert-butyl diether (26547-47-7)

Conditions	Yield
With hydrogenchloride at 75℃;
With sulfuric acid at 75℃;
With hydrogenchloride at 75℃;
With sulfuric acid at 75℃;

2-ethoxy-1,3-dioxolane (4544-20-1) + tert-butoxytrimethylsilane (13058-24-7) → ethyl trimethylsilyl ether (1825-62-3) + tert-butyl glycidyl ether (7580-85-0) + 1-tert-butoxy-2-trimethylsiloxy ethane (129345-72-8) + 1-formyloxy-2-tert-butoxy ethane (129345-71-7)

Conditions	Yield
at 16 - 20℃; for 1h; Further byproducts given;

tert-butyl glycidyl ether (7580-85-0) + methanesulfonyl chloride (124-63-0) → 2-(tert-butoxy)ethyl methanesulfonate

Conditions	Yield
With triethylamine In tert-butyl methyl ether at 0 - 20℃; for 2h;	100%
With triethylamine In dichloromethane at 0℃; for 2h;
With sodium hydrogencarbonate; triethylamine In dichloromethane

maleic anhydride (108-31-6) + tert-butyl glycidyl ether (7580-85-0) → Bis-(2-t-butoxyethyl)-maleat (7580-82-7)

Conditions	Yield
With KC105A strong acid catalyst In toluene at 115℃; for 5h; Temperature; Inert atmosphere; Flow reactor;	99.5%

ethylene glycol diglycidyl ether (2224-15-9) + tert-butyl glycidyl ether (7580-85-0) → C14H28O6

Conditions	Yield
With boron trifluoride diethyl etherate at 80℃; for 3h;	99.3%

carbon disulfide (75-15-0) + tert-butyl glycidyl ether (7580-85-0) + benzyl chloride (100-44-7) → O-tert-butoxyethyl-S-benzylxanthate

Conditions	Yield
Stage #1: carbon disulfide; tert-butyl glycidyl ether With sodium hydroxide In water at 25℃; for 2h; Stage #2: benzyl chloride In water at 75℃; for 4h;	98.2%

tert-butyl glycidyl ether (7580-85-0) + methyl 3-fluoro-4-hydroxybenzoate (403-01-0) → C14H19FO4

Conditions	Yield
With di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 1h;	98%

2,3-dihydro-2H-furan (1191-99-7) + tert-butyl glycidyl ether (7580-85-0) → 2-(2-tert-butoxyethoxy)tetrahydrofuran

Conditions	Yield
With copper(I) triflate In Petroleum ether for 2h; Reagent/catalyst; Solvent; Time; Reflux;	96%

5-Chlorothiophene-2-carboxylic acid (24065-33-6) + tert-butyl glycidyl ether (7580-85-0) → (2-(2-methyl-2-propoxy)-ethyl) 5-chlorothiophene-2-carboxylate (91505-31-6)

Conditions	Yield
Stage #1: 5-Chlorothiophene-2-carboxylic acid With oxalyl dichloride In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #2: tert-butyl glycidyl ether With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h;	95.56%

tert-butyl glycidyl ether (7580-85-0) + 1,1,1-trimethylolpropane triglycidyl ether (3454-29-3) → C21H40O8

Conditions	Yield
With Amberlyst-15 resin at 80℃; for 4h;	95.5%

4-nitro-1H-pyrazole (2075-46-9) + tert-butyl glycidyl ether (7580-85-0) → 1-(2-(tert-butoxy)ethyl)-4-nitro-1H-pyrazole

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h;	95%

cyclohexane-1,4-dimethanole diglycidyl ether + tert-butyl glycidyl ether (7580-85-0) → C20H38O6

Conditions	Yield
With Amberlyst-15 resin at 80℃; for 4h;	94.3%

1,4-Butanediol diglycidyl ether (2425-79-8) + tert-butyl glycidyl ether (7580-85-0) → C16H32O6

Conditions	Yield
With tin(IV) chloride at 80℃; for 5h; Reagent/catalyst;	94.1%

[6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl](4-hydroxyphenyl)methanone (63676-19-7) + tert-butyl glycidyl ether (7580-85-0) + diethylazodicarboxylate (1972-28-7) → [6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl][(4-t-butoxyethoxy)phenyl]methanone (220655-20-9)

Conditions	Yield
With triphenylphosphine In tetrahydrofuran	94%

tert-butyl glycidyl ether (7580-85-0) + 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide potassium salt → N-[6-[2-(1,1-dimethylethoxy)ethoxy]-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)benzenesulfonamide

Conditions	Yield
With sodium hydroxide In toluene at 55℃;	91.8%
With sodium hydroxide

tert-butyl glycidyl ether (7580-85-0) + 4,6-dichloro-2-(methylsulfonyl)pyrimidine (4489-34-3) → 2-(2-(tert-butoxy)ethoxy)-4,6-dichloropyrimidine

Conditions	Yield
Stage #1: tert-butyl glycidyl ether With sodium hydride In tetrahydrofuran for 1h; Inert atmosphere; Cooling with ice; Stage #2: 4,6-dichloro-2-(methylsulfonyl)pyrimidine In tetrahydrofuran Inert atmosphere;	91%

tert-butyl glycidyl ether (7580-85-0) + p-toluenesulfonyl chloride (98-59-9) → 2-(tert-butoxy)ethyl 4-methylbenzenesulfonate (108366-80-9)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0 - 5℃; for 2h;	90%
With sodium hydroxide In tetrahydrofuran	90%
With triethylamine In dichloromethane at 0 - 20℃; for 0.5h;	61%
With triethylamine In dichloromethane at 0 - 20℃; for 17.5h;

tert-butyl glycidyl ether (7580-85-0) + 4,6-dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine (150728-13-5) → 4-(2-tert-butoxyethoxy)-5-(2-methoxyphenoxy)-6-chloro-2,2'-bipyrimidine (1177447-87-8)

Conditions	Yield
With sodium hydroxide In toluene at 55℃; for 2h;	90%
With potassium carbonate; tetrabutylammomium bromide In toluene at 100 - 110℃; for 9h;

6-chloronicotinonitrile (33252-28-7) + tert-butyl glycidyl ether (7580-85-0) → 6-(2-tert-butoxy-ethoxy)-nicotinonitrile

Conditions	Yield
Stage #1: tert-butyl glycidyl ether With lithium hexamethyldisilazane In tetrahydrofuran for 0.5h; Stage #2: 6-chloronicotinonitrile In tetrahydrofuran at 70℃; for 9h; Further stages.;	87%

tert-butyl glycidyl ether (7580-85-0) + N-5-(4-bromophenyl)-6-chloro-4-pyrimidinyl-N‘-propylsulfamide (1393813-42-7) → N‐[5‐(4‐bromophenyl)‐6‐[2‐hydroxyethoxy]‐4‐pyrimidinyl]‐N‐propylsulfamide (1393813-43-8)

Conditions	Yield
Stage #1: N-5-(4-bromophenyl)-6-chloro-4-pyrimidinyl-N‘-propylsulfamide With potassium tert-butylate In toluene at 20℃; for 0.0833333h; Stage #2: tert-butyl glycidyl ether In toluene at 85℃; for 2h; Stage #3: With titanium tetrachloride In toluene at 35℃; for 20h;	86%

tert-butyl glycidyl ether (7580-85-0) + 1,8-bis(benzyloxy)-9,10-anthraquinone-3-carbonyl chloride → 1,8-bis(benzyloxy)-9,10-anthraquinone-O-(2-(tert-butoxy)ethyl)-3-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere;	85%

5-chlorothiophene-2-carbonyl chloride (42518-98-9) + tert-butyl glycidyl ether (7580-85-0) → (2-(2-methyl-2-propoxy)-ethyl) 5-chlorothiophene-2-carboxylate (91505-31-6)

Conditions	Yield
With triethylamine In tetrahydrofuran 1) r.t., 1 h, 2) reflux, 10 min;	80%

tert-butyl glycidyl ether (7580-85-0) + tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (1173068-83-1) → tert-butyl 4-(3-(2-tert-butoxyethoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (1173068-84-2)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium fluoride on basic alumina In toluene at 120℃; for 40h;	68%

tert-butyl glycidyl ether (7580-85-0) + 5-bromo-1,3-dimethoxy-2-nitrobenzene (815632-47-4) → 5-(2-(tert-butoxy)ethoxy)-1,3-dimethoxy-2-nitrobenzene

Conditions	Yield
With 5-di(1-adamantylphosphino)-1-(1,3,5-triphenyl-1H-pyrazol-4-yl)-1H-pyrazole; palladium diacetate; caesium carbonate at 80℃; Inert atmosphere; Schlenk technique;	68%

tert-butyl glycidyl ether (7580-85-0) + methyl 7-(benzyloxy)-1H-indole-5-carboxylate → C16H21NO4

Conditions	Yield
With triphenylphosphine at 20℃; for 2h;	68%

tert-butyl glycidyl ether (7580-85-0) + (2-(2-methyl-2-propoxy)-ethyl) 5-chlorothiophene-2-carboxylate (91505-31-6) → (2-(2-methyl-2-propoxy)-ethyl) 5-(2-(2-methyl-2-propoxy)-ethoxy)-thiophene-2-carboxylate (91505-34-9)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 65℃; for 1h;	65%
With sodium hydride In N,N-dimethyl-formamide at 20 - 65℃; for 1.5h; Inert atmosphere;	62.27%

tert-butyl glycidyl ether (7580-85-0) + methyl 5-formyl-4-hydroxy-2-methoxybenzoate → methyl 4-(2-(tert-butoxy)ethoxy)-5-formyl-2-methoxybenzoate

Conditions	Yield
With 2-(diphenylphosphino)pyridine; di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 4h;	63%

tert-butyl glycidyl ether (7580-85-0) + methyl 5-(thiazol-2-yl)-2H-1,2,6-thiadiazine-3-carboxylate 1,1-dioxide → methyl 2-(2-(tert-butoxy)ethyl)-5-(thiazol-2-yl)-2H-1,2,6-thiadiazine-3-carboxylate 1,1-dioxide

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 60℃; for 16h; Mitsunobu Displacement; Inert atmosphere;	61%

formic acid (64-18-6) + tert-butyl glycidyl ether (7580-85-0) → 3-(tert-butoxy)propane-1,2-diol (74338-98-0)

Conditions	Yield
In water for 12h; Ambient temperature;	52%

tert-butyl glycidyl ether (7580-85-0) + 2-chloro-4,6-dimethoxy-5-nitro-pyrimidine (478010-54-7) → 2-(2-tert-butoxyethoxy)-4,6-dimethoxy-5-nitropyrimidine (918444-85-6)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃; for 0.25h;	50%
With sodium hydride In tetrahydrofuran at -41℃;

Upstream product

• 75-21-8 oxirane 
• 75-65-0 tert-butyl alcohol 
• 507-19-7 t-butyl bromide 
• 107-21-1 ethylene glycol 
• 115-11-7 isobutene 
• 4544-20-1 2-ethoxy-1,3-dioxolane 
• 13058-24-7 tert-butoxytrimethylsilane 
• 3984-22-3 2-vinyl-1,3-dioxolane 
• 83490-15-7 2-<2-(2-hydroxyethoxy)-ethyl>-1,3-dioxolane 
• 111-66-0 oct-1-ene 
• 507-20-0 tertiary butyl chloride 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 

Downstream Products

• 108366-80-9 2-(tert-butoxy)ethyl 4-methylbenzenesulfonate 
• 220655-20-9 [6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl][(4-t-butoxyethoxy)phenyl]methanone 
• 570408-11-6 4-(2-tert-butoxyethoxy)-3,5-difluorobenzoic acid 2-tert-butoxyethyl ester 
• 301646-60-6 N-[6-[2-(1,1-dimethylethoxy)ethoxy]-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)benzenesulfonamide 
• 570407-87-3 3,4,5-trifluorobenzoic acid 2-tert-butoxyethyl ester 
• 104743-21-7 N-(2-tert-butoxy-ethyl)-aniline 
• 235098-18-7 2-(tert-butoxy)ethyl methanesulfonate 
• 132734-53-3 C₆H₁₃⁽²⁾HO₂ 

Relevant articles and documents

Ethylene glycol mono-tert-butyl ether preparation method

The invention relates to an ethylene glycol mono-tert-butyl ether preparation method. According to the invention, K-MgO/gamma-aluminum oxide is selected as a catalyst, tert-butyl alcohol and ethyleneoxide are adopted as reaction raw materials, an ethylene glycol monotert-butyl ether preparation method suitable for industrial production is provided, the yield of the preparation method is larger than 95%, the purity of the product is larger than 99%, the process is simple, and the preparation method meets the requirement of industrial production.

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