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

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

Uses

Used in Pharmaceutical Industry:
Ethylene Glycol Mono-tert-butyl Ether is used as a key compound in the preparation of potent and selective NPY5 receptor antagonists for the pharmaceutical industry. These antagonists are crucial in the development of treatments for various medical conditions, as they help regulate the activity of the NPY5 receptor, which is involved in several physiological processes.
Used in the Synthesis of PDE5 Inhibitors:
In the pharmaceutical industry, Ethylene Glycol Mono-tert-butyl Ether is also used in the synthesis of PDE5 inhibitors. These inhibitors are essential in blocking the degradative action of phosphodiesterase 5, an enzyme that breaks down cyclic guanosine monophosphate (cGMP). By inhibiting PDE5, cGMP levels can be increased, leading to vasodilation and improved blood flow, which is particularly beneficial in treating conditions like erectile dysfunction and pulmonary arterial hypertension.

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 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 
• 67-63-0 isopropyl alcohol 
• 1343-93-7 phosphotungestic acid 
• 109-65-9 1-bromo-butane 
• 507-20-0 tertiary butyl chloride 
• 111-66-0 oct-1-ene 
• 83490-15-7 2-<2-(2-hydroxyethoxy)-ethyl>-1,3-dioxolane 

Downstream Products

• 108366-80-9 2-(tert-butoxy)ethyl 4-methylbenzenesulfonate 
• 570407-87-3 3,4,5-trifluorobenzoic acid 2-tert-butoxyethyl ester 
• 570408-11-6 4-(2-tert-butoxyethoxy)-3,5-difluorobenzoic acid 2-tert-butoxyethyl ester 
• 112853-59-5 4-nitro-benzoic acid-(2-tert-butoxy-ethyl ester) 
• 1403265-16-6 184B-43-1 

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.

Method for synthesizing ethylene glycol monobutyl ether in alkaline ionic liquid (by machine translation)

The invention relates to a method, for synthesizing ethylene glycol monobutyl ether from basic ionic liquid by using a basic ionic liquid as a catalyst and a solvent to catalyze tert-butyl alcohol to react with ethylene oxide to prepare ethylene glycol mont-butyl ether, and the preparation method has the yield of more than, purity greater than 93%, and the process simple 99%, suitable for industrial production . (by machine translation)

METHOD FOR PRODUCING ASYMMETRIC ALKYL ETHER HAVING TERTIARY ALKYL GROUP

PROBLEM TO BE SOLVED: To provide a method capable of obtaining an asymmetric alkyl ether having a tertiary alkyl group easily and industrially. SOLUTION: (1) There is provided a method for producing an asymmetric alkyl ether having a tertiary alkyl group by subjecting a tertiary alcohol and a primary alcohol or a secondary alcohol to a dehydration reaction using activated clay as a catalyst. (2) There is provided the method for producing an asymmetric alkyl ether having a tertiary alkyl group according to (1), where the tertiary alcohol is any one selected from the group consisting of tert-butanol, tert-amylalcohol and 1-adamantyl alcohol. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

PROCESS FOR PREPARING AN ALKOXYLATED ALCOHOL OR PHENOL

Process for preparing an alkoxylated alcohol comprising reacting a starting monohydroxy alcohol selected from secondary alcohols, tertiary alcohols and mixtures thereof with an alkylene oxide in the presence of hydrogen fluoride and a boron-containing compound comprising at least one B-O bond. The alcohol may also be a primary monohydroxy alcohol when the boron containing compound is boric acid or boric acid anhydride or a mixture thereof, or may be a primary mono hydroxy alcohol, except a C14/C15 alcohol when reacted with ethylene oxide in the presence of HF and trimethyl borate. A phenol may be alkoxylated in the same way instead of the mono-hydroxyalcohol.

Synthesis of low molecular weight glycol ethers from oxiranes plus olefins

Disclosed is a process for preparation of monoalkyl ethers by reacting low molecular weight olefins and the corresponding oxiranes, in the presence of a catalyst comprising an acidic heterogeneous or homogeneous catalyst, generally represented by the equation: STR1 where R, R', R may be hydrogen or an alkyl radical.

Synthesis of low molecular weight ethylene propylene glycol ethers via olefin addition to the corresponding glycol

A selective process for the synthesis of ethers of polyols involves reacting an olefin and a polyol in the presence of a heteropoly acid catalyst at a temperature of 25 to 200oC and a pressure of up to 7MPa.

Influence of the reaction temperature on some acid-catalized processes of 6-hydroxy-4-oxa-alkanal derivatives and related products. Ring contraction in 5-alkoxy-1,4-dioxepanes

The qualitative effect of the reaction temperature on some acid-catalized processes carried out on 6-hydroxy-4-oxa-alkanal derivatives may be rationalized by means of two simultaneous or competitive pathways which involve intermediates such as 5-alkoxy-1,4-dioxepane derivatives or vinyl dioxolanes.We describe herein an acid catalyzed contraction of the 5-isopropoxy-1,4-dioxepane ring in dioxane and different alcohol interchange reactions with 5-alkoxy-1,4-dioxepanes that also occur with ring contraction when the reaction temperature is 60 deg C or higher.The transacetalization reactions between 6-hydroxy-4-oxa-hexal ethylene acetal and 6-hydroxy-4-oxa-heptanal 1,2-propylene acetal and tert-butanol, carried out at the reflux of the reacting mixtures are also described.The results obtained suggest 2-vinyl-1,3-dioxolanes as reactive intermediates.In order to prove this hypothesis the reaction between 2-vinyl-1,3-dioxolane and tert-butanol at reflux has been stuied.It leads to the same reaction products.

The Kinetics of the Halcon Reaction

We have investigated the influence of all types of reaction products on the rate of the Halcon reaction.The experiments show that the retarding effect of epoxide is higher than that of the alcohol.Furthermore we have found that the consecutive products of the epoxide retard the Halcon reaction more than the primary reaction products.The reaction rate can be described by an equation of the Michaelis-Menten-type.We determined the initial reaction rate in dependence on the starting concentration of the reaction products.