109-59-1

Basic information

• Product Name: 2-ISOPROPOXYETHANOL
• Synonyms: 2-(1-methylethoxy)-ethano;2-(1-methylethoxy)-Ethanol;2-isopropoxy-ethano;beta-Hydroxyethyl isopropyl ether;beta-hydroxyethylisopropylether;Dowanal EiPAT;dowanaleipat;Dowanol EiPAT
• CAS NO: 109-59-1
• Molecular Formula: C₅H₁₂O₂
• Molecular Weight: 104.15
• EINECS: 203-685-6
• Product Categories: Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols
• Mol File: 109-59-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: -60 °C
• Boiling Point: 42-44 °C13 mm Hg(lit.)
• Flash Point: 114 °F
• Appearance: clear colorless liquid
• Density: 0.903 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00467mmHg at 25°C
• Refractive Index: n20/D 1.41(lit.)
• Storage Temp.: Flammables area
• Solubility: >100g/l soluble
• PKA: 14.47±0.10(Predicted)
• Explosive Limit: 1.6-13.0%(V)
• Water Solubility: It is soluble in water.
• Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
• BRN: 1732184
• CAS DataBase Reference: 2-ISOPROPOXYETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ISOPROPOXYETHANOL(109-59-1)
• EPA Substance Registry System: 2-ISOPROPOXYETHANOL(109-59-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21-36
• Safety Statements: 24/25
• RIDADR: UN 2929 6.1/PG 2
• WGK Germany: 1
• RTECS: KL5075000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 109-59-1(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 109-59-1 differently. You can refer to the following data:
1. 2-Isopropoxyethanol was used to study the products of the gas-phase reactions of OH radical with n-butyl methyl ether and 2-isopropoxyethanol in the presence of NO. 2-Isopropoxyethanol was used to develop methodology for evaluating electromagnetic sensor performance in nonrelaxing and nonconducting (e.g., sandy soil) media
2. Ethylene glycol monoisopropyl ether (EGIE) is used as a solvent for resins, dyes, and cellulose esters, and in coatings..
3. Solvent in latex paints, lacquers, and other coatings, resins, coalescing aids, and coupling solvents

General Description

A clear liquid. Density 0.903 g / cm3. Flash point 114°F. An irritant.

Air & Water Reactions

Flammable. Oxidizes in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. Water soluble .

Reactivity Profile

2-ISOPROPOXYETHANOL acts both as an alcohol and ether. May react violently with strong oxidizing agents. May generate flammable and/or toxic gases with alkali metals, nitrides, and other strong reducing agents. May initiate the polymerization of isocyanates and epoxides.

Hazard

Combustible liquid with flash p 49C. Toxic by skin absorption.

Health Hazard

Different sources of media describe the Health Hazard of 109-59-1 differently. You can refer to the following data:
1. EGIE shows low toxicity from inhalation, ingestion, and skin absorption. The toxic symptomsaresimilartothoseproducedbythe butyl ether of the ethylene glycol. The effects noted in rats from exposure to 1000 ppm for 6 hours were hemoglobinuria, anemia, and lung congestion (Gage 1970). Other effectsobservedwereincreasesintheosmotic fragility of the red blood cells. Such effects were manifested at EGIE concentrations of >200 ppm. A 4-hour exposure to 4000 ppm was lethal to rats. In human exposure to this compound can result in anemiaLD50 value, oral (rats): 5660 mg/kgNo testicular toxicity was observed in rats from a single exposure to 3500 ppm of EGIE in air (Doe 1984)..
2. May be harmful by inhalation, ingestion or skin absorption. May cause skin and eye irritation.

Fire Hazard

Special Hazards of Combustion Products: Emits toxic fumes when heated upon decomposition.

Waste Disposal

Chemical incineration is the most suitable method of destruction. Drain disposal may be done for small amounts of EGIE.

InChI:InChI=1/C6H14O.C2H6O2/c1-5(2)7-6(3)4;3-1-2-4/h5-6H,1-4H3;3-4H,1-2H2

Synthetic route

oxirane (75-21-8) + isopropyl alcohol (67-63-0) → 2-(1-methylethoxy)-ethanol (109-59-1)

Conditions	Yield
With boron trifluoride at 80℃;
With hydro silicate bei Siedehitze;
With ortho-tungstic acid at 90 - 95℃; under 7355.08 - 8826.09 Torr;

ethylene glycol (107-21-1) + isopropyl bromide (75-26-3) → 2-(1-methylethoxy)-ethanol (109-59-1)

Conditions	Yield
With sodium carbonate

ethyl bromoacetate (105-36-2) + isopropyl alcohol (67-63-0) → 2-(1-methylethoxy)-ethanol (109-59-1)

Conditions	Yield
(i) Na, (ii) LiAlH4; Multistep reaction;

oxirane (75-21-8) + ethanol (64-17-5) + isopropyl alcohol (67-63-0) + tert-butyl alcohol (75-65-0) → 2-ethoxy-ethanol (110-80-5) + 2-(1-methylethoxy)-ethanol (109-59-1) + tert-butyl glycidyl ether (7580-85-0)

Conditions	Yield
Trimethyl borate; hydrogen fluoride In water at 30℃; for 0.166667h;

bisoprolol fumarate (66722-45-0, 103419-24-5, 104344-23-2, 105878-43-1, 112945-47-8) → 2-(1-methylethoxy)-ethanol (109-59-1) + C13H20ClNO2*ClH

Conditions	Yield
With hydrogenchloride In water at 70.04℃; Kinetics; Mechanism; Temperature; Concentration;

bisoprolol fumarate (66722-45-0, 103419-24-5, 104344-23-2, 105878-43-1, 112945-47-8) → 2-(1-methylethoxy)-ethanol (109-59-1) + C13H20BrNO2*BrH

Conditions	Yield
With hydrogen bromide; potassium bromide In water at 70.04℃; Kinetics; Mechanism; Temperature; Reagent/catalyst;

bisoprolol fumarate (66722-45-0, 103419-24-5, 104344-23-2, 105878-43-1, 112945-47-8) → 2-(1-methylethoxy)-ethanol (109-59-1) + C13H20INO2*HI

Conditions	Yield
With hydrogen iodide; potassium iodide In water at 70.04℃; Kinetics; Mechanism; Temperature; Reagent/catalyst;

2-(1-methylethoxy)-ethanol (109-59-1) + methanesulfonyl chloride (124-63-0) → methanesulfonic acid 2-isopropoxyethyl ester (235097-76-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1.5h; Cooling with ice;	100%
With triethylamine In dichloromethane at 20℃;	80%
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	80%

Y5(OiPr)13O + 2-(1-methylethoxy)-ethanol (109-59-1) → [Y4(μ3,η2-OC2H4OCH(CH3)2)3(μ,η2-OC2H4OCH(CH3)2)2(η1-OC2H4OCH(CH3)2)4(μ,η1-OC2H4OCH(CH3)2)3]2 (794521-39-4)

Conditions	Yield
In toluene reactions carried out under argon; Y5O(OCH(CH3)2)13 reacted with 2-isopropoxyethanol in toluene at room temp. for 12 h; elem. anal.;	99%

2-(1-methylethoxy)-ethanol (109-59-1) + 8-bromo-7-(4-chlorobenzyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione → 7-(4-chlorobenzyl)-8-(2-isopropoxyethoxy)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione

Conditions	Yield
Stage #1: 2-(1-methylethoxy)-ethanol With sodium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 8-bromo-7-(4-chlorobenzyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione In tetrahydrofuran at 20℃; for 16h;	95.2%

2-(1-methylethoxy)-ethanol (109-59-1) + vanadium(V) oxychloride (7727-18-6) → bis[μ-chloro-chloro(η2-2-isopropoxyethanolato)oxovanadium(V)]

Conditions	Yield
In pentane byproducts: HCl; Schlenk technique, protected from direct sun light; VOCl3 slowly added to soln. of alcohol in n-pentane at 0°C; HCl completely removed by heating at 30°C; crystd. at -30°C overnight; additional portion of crystals obtained by concg. the decanted soln. and storing at -30°C overnight; elem. anal.;	95%

2-(1-methylethoxy)-ethanol (109-59-1) + pivaloyl chloride (3282-30-2) → C5H12O2C5H8O

Conditions	Yield
With lanthanum(III) nitrate at 20℃; for 0.333333h;	91%

2-(1-methylethoxy)-ethanol (109-59-1) + boric acid (11113-50-1) → 3C5H11O2(1-)*B(3+)

Conditions	Yield
In toluene for 24h; Dean-Stark; Reflux;	91%

N-hydroxyphthalimide (524-38-9) + 2-(1-methylethoxy)-ethanol (109-59-1) → 2-(2-isopropoxyethoxy)isoindoline-1,3-dione (54149-22-3)

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; toluene at 20℃; Inert atmosphere;	90%

2-(1-methylethoxy)-ethanol (109-59-1) + Br(1-)*C15H22NO(1+) (1187956-07-5) → 2-(2'-isopropoxyethoxy)-2,3-dihydro-3-methylenebenzofuran (1187956-37-1)

Conditions	Yield
Stage #1: 2-(1-methylethoxy)-ethanol With sodium Inert atmosphere; Stage #2: Br(1-)*C15H22NO(1+) at 120℃; for 0.166667h; Inert atmosphere;	88%

2-(1-methylethoxy)-ethanol (109-59-1) + (4-hydroxyphenyl)methanol (623-05-2) → 4-(2-isopropoxy-ethoxymethyl)-phenol (177034-57-0)

Conditions	Yield
With indium(III) chloride at 80℃; for 3.25h; Neat (no solvent);	87%
With ytterbium(III) triflate at 80℃; for 1.5h;	67%
With cation exchange resin AG 50W-X8 Heating;
With polymer supported SO3H at 0 - 20℃; for 17h; Amberlyst-15 resin;

2-(1-methylethoxy)-ethanol (109-59-1) + ethylphosphonic acid (6779-09-5) → 2-(isopropoxy)ethyl hydrogen ethylphosphonate

Conditions	Yield
With phenylarsonic acid In toluene for 28h; Heating;	87%

2-(1-methylethoxy)-ethanol (109-59-1) + 2-fluoro-8-(3,4,5-trimethoxy-benzyl)-9H-purin-6-ylamine (422508-26-7) → PU29F

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In dichloromethane; toluene at 20℃;	86%

2-(1-methylethoxy)-ethanol (109-59-1) + 4-bromobenzenesulfonyl chloride (98-58-8) → 2-isopropoxyethyl 4-bromobenzenesulfonate (318958-62-2)

Conditions	Yield
With triethylamine In dichloromethane	86%

2-(1-methylethoxy)-ethanol (109-59-1) + (4-hydroxyphenyl)methanol (623-05-2) → 4,4’-dihydroxydibenzyl ether (76890-93-2) + 4-(2-isopropoxy-ethoxymethyl)-phenol (177034-57-0)

Conditions	Yield
With ytterbium(III) triflate In acetonitrile at 80℃; for 5h;	A 4% B 85%

2-(1-methylethoxy)-ethanol (109-59-1) + p-toluenesulfonyl chloride (98-59-9) → p-toluenesulfonic-acid-(2-isopropoxyethyl)-ester (51218-98-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	85%
With triethylamine In dichloromethane at 0 - 20℃; for 6h;	83%
With triethylamine In dichloromethane at 0 - 25℃; for 16h;	81%
With pyridine In dichloromethane at 20℃; for 3h;	60%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	57%

2-(1-methylethoxy)-ethanol (109-59-1) + diethylzinc → 2C5H11O2(1-)*Zn(2+)

Conditions	Yield
In hexane at 0 - 23℃; for 18.6667h;	85%

2-(1-methylethoxy)-ethanol (109-59-1) + indium (III) tris(hexamethyldisilyl) amide → 3C5H11O2(1-)*In(3+)

Conditions	Yield
In toluene at 23 - 70℃; for 18.0833h;	85%

2-(1-methylethoxy)-ethanol (109-59-1) + 4-Benzyloxyphenol (103-16-2) → 1-((4-(2-isopropyloxyethoxy)phenoxy)methyl)benzene (1354968-43-6)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane Inert atmosphere;	84%

2-(1-methylethoxy)-ethanol (109-59-1) + sorbinyl chloride (2614-88-2) → (2E,4E)-Hexa-2,4-dienoic acid 2-isopropoxy-ethyl ester (88973-72-2)

Conditions	Yield
	83%

2-(1-methylethoxy)-ethanol (109-59-1) + 4-hydroxy-benzaldehyde (123-08-0) → 4-(2-isopropoxyethoxy)benzaldehyde

Conditions	Yield
With diethylazodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 0 - 20℃; for 18h;	82%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 25℃;

2-(1-methylethoxy)-ethanol (109-59-1) + sodium isocyanate (917-61-3) → ethylene glycol monoisopropyl ether carbamate (67952-46-9)

Conditions	Yield
With perchloric acid on silica gel at 20℃; for 0.75h;	81%
With trichloroacetic acid

2-(1-methylethoxy)-ethanol (109-59-1) + [Cu2(trifluoroacetate)4(tetrahyrofuran)2] → [Cu2(trifluoroacetate)4(2-isopropoxyethanol)2] (861642-75-3)

Conditions	Yield
In toluene all manipulations under N2 atm.; org. compd. added to Cu compd. in toluene, stirred for 12 h at room temp.; concd.C; elem. anal.;	81%

2-(1-methylethoxy)-ethanol (109-59-1) + 3C5H11O2(1-)*In(3+) + 2C5H11O2(1-)*Zn(2+) → 0.1In(3+)*Zn(2+)*2.3C5H11O2(1-)

Conditions	Yield
In toluene at 23 - 50℃; for 18h;	80%

2-(1-methylethoxy)-ethanol (109-59-1) → 2-(2-iodoethoxy)propane (318958-37-1)

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In diethyl ether at 0℃; for 12h;	80%
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 16 h / 0 - 25 °C 2: sodium iodide / acetone / 16 h / 60 °C View Scheme

vinyl acetate (108-05-4) + 2-(1-methylethoxy)-ethanol (109-59-1) → hydroxy-functional oligo(vinyl acetate), DP = 10, Mn = 964; monomer(s): vinyl acetate; 2-isopropoxyethanol

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 90℃; for 24h;	79%

4-methyleneoxetan-2-one (674-82-8) + 2-(1-methylethoxy)-ethanol (109-59-1) → 3-Oxo-butyric acid 2-isopropoxy-ethyl ester (57792-07-1)

Conditions	Yield
With triethylamine at 50 - 60℃;	77.9%

2-(1-methylethoxy)-ethanol (109-59-1) + 2,2,2,4,4,4-hexafluoro-1,3-dimethyl-1,3,2λ5,4λ5-diazadiphosphetidine (3880-04-4) → 2,2,2,4,4,4,4-Octafluor-1,3-dimethyl-1,3,2λ6,4λ6-diazadiphosphetidin-HF-Addukt (70317-21-4) + 2,2,2,4,4-Pentafluoro-4-(2-isopropoxy-ethoxy)-1,3-dimethyl-2λ5,4λ5-[1,3,2,4]diazadiphosphetidine (94446-39-6)

Conditions	Yield
In dichloromethane for 12h; Ambient temperature; Yields of byproduct given;	A n/a B 77%

ethyl 3-(2-([3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy)-4-hydroxyphenyl)propanoate (888740-63-4) + 2-(1-methylethoxy)-ethanol (109-59-1) → 3-[2-{[3-chloro-5-(trifluoromethyl)pyridine-2-yl]oxy}-4-(2-isopropoxyethoxy)phenyl]propanoic acid ethyl ester (888740-64-5)

Conditions	Yield
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran for 1h;	75%

ethyl 3-(2-([3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy)-4-hydroxyphenyl)propanoate (888740-63-4) + 2-(1-methylethoxy)-ethanol (109-59-1) + 1,1'-(Azodicarbonyl)dipiperidin (10465-81-3) → 3-[2-{[3-chloro-5-(trifluoromethyl)pyridine-2-yl]oxy}-4-(2-isopropoxyethoxy)phenyl]propanoic acid ethyl ester (888740-64-5)

Conditions	Yield
With tributylphosphine In tetrahydrofuran; di-isopropyl ether	75%

2-(1-methylethoxy)-ethanol (109-59-1) + titanium tetrachloride (7550-45-0) → TiCl3(2-(i-propoxy)ethanol-H) (1378027-15-6)

Conditions	Yield
In toluene under an inert atm.; to a soln. of TiCl4 (9.10 mmol) in toluene was added a soln. of a ligand (9.10 mmol) in toluene; the mixt. was stirred for 4 d and allowed to settle; the supernatant was decanted and the resulting solid washed with tolueneand petroleum spirits; the solid was dried overnight under vac.; elem. anal.;	74%

2-(1-methylethoxy)-ethanol (109-59-1) + 2-phenyl-1-cyclopropanecarbonyl chloride (939-87-7, 5685-36-9, 37107-48-5, 42916-08-5, 42916-12-1, 42916-13-2, 62624-90-2, 78738-39-3) → (+/-)-trans-2-Phenyl-cyclopropanecarboxylic acid 2-isopropoxy-ethyl ester

Conditions	Yield
With pyridine; triethylamine In dichloromethane	65%

Upstream product

• 66722-45-0 bisoprolol fumarate 
• 75-21-8 oxirane 
• 64-17-5 ethanol 
• 67-63-0 isopropyl alcohol 
• 75-65-0 tert-butyl alcohol 
• 105-36-2 ethyl bromoacetate 
• 107-21-1 ethylene glycol 
• 75-26-3 isopropyl bromide 

Downstream Products

• 827302-39-6 C₃₅H₃₄N₅O₂PS 
• 827302-42-1 C₃₇H₃₈N₅O₄PS 
• 67952-46-9 ethylene glycol monoisopropyl ether carbamate 
• 66722-57-4 2-((4-((2-isopropoxyethoxy)methyl)phenoxy)methyl)oxirane 
• 333316-11-3 1-(p-2-isopropoxyethoxymethylphenoxy)-3-amino-propan-2-ol 
• 888740-64-5 3-[2-{[3-chloro-5-(trifluoromethyl)pyridine-2-yl]oxy}-4-(2-isopropoxyethoxy)phenyl]propanoic acid ethyl ester 
• 660851-13-8 N-[5-chloro-2-(2-isopropoxyethoxy)phenyl]-N'-(5-cyano-2-pyrazinyl)urea 
• 28383-11-1 C₁₄H₁₉N₂O₄PS 
• 28239-83-0 Thiophosphoric acid O-ethyl ester O'-(2-isopropoxy-ethyl) ester O''-(4-methanesulfonyl-phenyl) ester 
• 28248-87-5 Thiophosphoric acid O-(2-isopropoxy-ethyl) ester O'-isopropyl ester O''-(4-methanesulfinyl-phenyl) ester 
• 28253-65-8 Thiophosphoric acid O-ethyl ester O'-(2-isopropoxy-ethyl) ester O''-(4-methanesulfinyl-3-methyl-phenyl) ester 
• 28239-79-4 Thiophosphoric acid O-(2-isopropoxy-ethyl) ester O'-(4-methanesulfonyl-phenyl) ester O''-methyl ester 
• 28248-44-4 Thiophosphoric acid O-(2-isopropoxy-ethyl) ester O'-isopropyl ester O''-(4-methylsulfanyl-phenyl) ester 
• 926-65-8 vinyl isopropyl ether 

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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.