96-80-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Diisopropylaminoethanol is used as a catalyst in the preparation of Fluvastatin, a cholesterol-lowering drug, through a method catalyzed by carbonyl reductase. This application is significant in the pharmaceutical industry as it aids in the synthesis of an essential medication for managing hypercholesterolemia and reducing the risk of cardiovascular diseases.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

N,N-DIISOPROPYL ETHANOLAMINE is an amino alcohol. Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Safety Profile

Moderately toxic by ingestion and skin contact. A skin and severe eye irritant.

InChI:InChI=1/C8H19NO/c1-6(2)9(7(3)4)8(5)10/h6-8,10H,1-5H3

Synthetic route

oxirane (75-21-8) + diisopropylamine (108-18-9) → 2-(diisopropylamino)ethanol (96-80-0)

Conditions	Yield
at 200℃;
at 200℃;

diisopropylamine (108-18-9) + 2-chloro-ethanol (107-07-3) → 2-(diisopropylamino)ethanol (96-80-0)

Conditions	Yield
at 120℃;
In toluene for 3h; Reflux;

Iodoethanol (624-76-0) + diisopropylamine (108-18-9) → 2-(diisopropylamino)ethanol (96-80-0)

oxirane (75-21-8) + diisopropylamine (108-18-9) → 2-(diisopropylamino)ethanol (96-80-0) + 4-methylene-hex-5-en-1-ol (17844-23-4)

Conditions	Yield
With n-butyllithium; potassium tert-butylate; isoprene 1.) THF/hexane, -70 deg C, 1 min 2.) THF/hexane, -70 deg C to -20 deg C; Yield given. Multistep reaction. Yields of byproduct given;

2-(diisopropylamino)ethanol (96-80-0) + 1,1'-carbonyldiimidazole (530-62-1) → C12H21N3O2

Conditions	Yield
In dichloromethane at 20℃; for 2h; Inert atmosphere;	100%

2-(diisopropylamino)ethanol (96-80-0) → 2-(diisopropylamino)ethyl chloride hydrochloride

Conditions	Yield
With thionyl chloride at 0 - 80℃; for 10h; Large scale;	93%

2-(diisopropylamino)ethanol (96-80-0) + diisopropylamine (108-18-9) + acetylene (74-86-2) → bis(2-diisopropylaminoethyl) ether (52183-40-1)

Conditions	Yield
With potassium hydroxide In 1,3-dioxane at 120℃; for 3h;	85.6%

2-(diisopropylamino)ethanol (96-80-0) + (11-hydroxyundecyl)carbamic acid tert-butyl ester (144191-92-4) → C25H53N2O4PS

Conditions	Yield
Stage #1: (11-hydroxyundecyl)carbamic acid tert-butyl ester With dmap; triethylamine; methylphosphonothioic dichloride In chloroform at 20℃; for 3h; Inert atmosphere; Stage #2: 2-(diisopropylamino)ethanol With triethylamine In chloroform at 20℃; for 16h; Inert atmosphere;	82%

2-(diisopropylamino)ethanol (96-80-0) + (2-chloroethyl)-diisopropylamine (96-79-7) → bis(2-diisopropylaminoethyl) ether (52183-40-1)

Conditions	Yield
With sodium hydroxide; adogen 464 In tetrahydrofuran for 6h; Heating;	74%

4-(benzyloxy)-1-(4-hydroxyphenyl)pyridin-2(1H)-one (864757-74-4) + 2-(diisopropylamino)ethanol (96-80-0) → 4-(benzyloxy)-1-(4-[2-(diisopropylamino)ethoxy]-phenyl)pyridin-2(1H)-one

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 4h; Mitsunobu reaction;	73%

2-(diisopropylamino)ethanol (96-80-0) + 4-chlorobenzonitrile (100-00-5) → Diisopropyl-[2-(4-nitro-phenoxy)-ethyl]-amine (85002-94-4)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 70℃; for 0.5h;	67.2%

2-(diisopropylamino)ethanol (96-80-0) + 4-fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone (193966-49-3) → (4-[2-(diisopropylamino)ethoxy]phenyl)-(2-[4-[2-(1-pyrrolidinyl)ethoxy]-phenyl]benzo[b]thiophen-3-yl)ketone (193966-53-9)

Conditions	Yield
Stage #1: 2-(diisopropylamino)ethanol With sodium hydride In N,N-dimethyl-formamide for 0.25h; deprotonation; Stage #2: 4-fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone In N,N-dimethyl-formamide at 20℃; for 5h; Condensation; Further stages.;	62%

2-(diisopropylamino)ethanol (96-80-0) + methyl iodide (74-88-4) → N,N-diisopropyl-N-(2-methoxyethyl)amine (139709-38-9)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 40℃; for 0.5h;	58%

2-(diisopropylamino)ethanol (96-80-0) + lead thiocyanate → N,N-diisopropyl-(2-thiocyanatoethyl)amine (167940-05-8)

Conditions	Yield
Stage #1: lead thiocyanate With bromine In acetonitrile at -40℃; for 0.5h; Stage #2: With triphenylphosphine In acetonitrile at -40℃; for 0.5h; Stage #3: 2-(diisopropylamino)ethanol In acetonitrile at -40℃; for 2h; Further stages.;	56%

2-(diisopropylamino)ethanol (96-80-0) + trifluoroacetic acid (76-05-1) + 8-(4-bromo-benzyl)-3-isobutyl-3,7-dihydro-purine-2,6-dione (480445-51-0) → 8-(4-bromo-benzyl)-1-(2-diisopropylamino-ethyl)-3-isobutyl-3,7-dihydro-purine-2,6-dione

Conditions

Yield

Stage #1: 8-(4-bromo-benzyl)-3-isobutyl-3,7-dihydro-purine-2,6-dione With {4-[(2,4-dimethoxyphenyl)chloromethyl]phenoxy}-Rink resin; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: 2-(diisopropylamino)ethanol With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Mitsunobu reaction; Stage #3: trifluoroacetic acid In dichloromethane at 20℃; for 0.5h;

45%

2-(diisopropylamino)ethanol (96-80-0) + 1,3-bis-(bromomethyl)benzene (626-15-3) → N-(2-(3-(bromomethyl)benzyloxy)ethyl)-N-isopropylpropan-2-amine (1246680-25-0)

Conditions	Yield
Stage #1: 2-(diisopropylamino)ethanol With n-butyllithium; potassium iodide In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: 1,3-bis-(bromomethyl)benzene In tetrahydrofuran; hexane at -78 - 75℃; Inert atmosphere;	45%

7-bromo-1-cyclohexyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (179942-97-3) + 2-(diisopropylamino)ethanol (96-80-0) → 2-diisopropylamino-ethyl 7-bromo-1-cyclohexyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate

Conditions	Yield
	38%

4,6-dichloropyrimidine (1193-21-1) + 2-(diisopropylamino)ethanol (96-80-0) → N-{2-[(6-chloropyrimidin-4-yl)oxy]ethyl}-N-isopropylpropan-2-amine (848472-41-3)

Conditions	Yield
With caesium carbonate In propyl cyanide at 180℃; for 0.333333h; microwave irradiation;	20%

2-(diisopropylamino)ethanol (96-80-0) → 4-(2-chloroethyl)bis[1,2]dithiolo[3,4-b:4',3'-e][1,4]thiazine-3,5-dione (204758-33-8)

Conditions	Yield
Stage #1: 2-(diisopropylamino)ethanol With 1,4-diaza-bicyclo[2.2.2]octane; disulfur dichloride In 1,2-dichloro-ethane at -40 - 20℃; Addition; Stage #2: With formic acid In 1,2-dichloro-ethane for 1h; Cyclization; Heating;	13%

2-(diisopropylamino)ethanol (96-80-0) + copper(II) acetate monohydrate (6046-93-1) → Cu(2+)*((CH3)2CH)2NCH2CH2O(1-)*NCS(1-) = Cu((CH3)2CH)2NC2H4O(NCS)

Conditions	Yield
With NH4SCN In methanol NH4SCN in MeOH added to 2-diisopropylaminoethanol and Cu(II) in MeOH, standed (5°C, several days); filtered, dried (in vac. over P2O5); elem. anal.;	8%

2-(diisopropylamino)ethanol (96-80-0) → 5,6-dihydro-4-(3-thiono[1,2]dithiol-4-yl)-[1,2]dithiolo[3,4-b][1,4]thiazine-3-thione (204758-35-0)

Conditions	Yield
Stage #1: 2-(diisopropylamino)ethanol With disulfur dichloride In tetrahydrofuran at -40 - 20℃; Addition; Stage #2: With diphosphorus pentasulfide In tetrahydrofuran for 5.5h; Cyclization; Heating;	7%

methyl bromide (74-83-9) + 2-(diisopropylamino)ethanol (96-80-0) → (2-hydroxy-ethyl)-diisopropyl-methyl-ammonium; bromide (866-67-1)

Conditions	Yield
With butanone

tetraethoxy orthosilicate (78-10-4) + 2-(diisopropylamino)ethanol (96-80-0) → silicic acid diethyl ester-bis-(2-diisopropylamino-ethyl ester) (18642-90-5)

2-(diisopropylamino)ethanol (96-80-0) + N,N-dicyclohexylcarbamoyl chloride (6292-88-2) → dicyclohexyl-carbamic acid-(2-diisopropylamino-ethyl ester) (102444-91-7)

Conditions	Yield
With toluene

2-(diisopropylamino)ethanol (96-80-0) → 1-chloro-2-diisopropylaminoethane hydrochloride (4261-68-1)

Conditions	Yield
With thionyl chloride; chloroform
With thionyl chloride; benzene
With thionyl chloride Chlorination; Vogel method;
With thionyl chloride In chloroform Reflux; Cooling with ice;

2-(diisopropylamino)ethanol (96-80-0) → (2-chloroethyl)-diisopropylamine (96-79-7)

Conditions	Yield
With thionyl chloride; benzene
With thionyl chloride for 3h; Heating;
With thionyl chloride In toluene for 2h; Reflux;
With thionyl chloride In chloroform at 0℃; for 4h; Reflux;

2-(diisopropylamino)ethanol (96-80-0) + 4-phenyltetrahydropyran-4-carbonyl chloride (100119-45-7) → 4-phenyl-tetrahydro-pyran-4-carboxylic acid-(2-diisopropylamino-ethyl ester) (102371-15-3)

Conditions	Yield
With benzene

2-(diisopropylamino)ethanol (96-80-0) + cyclohex-2-enyl-[2]thienyl-acetyl chloride (853919-58-1) → cyclohex-2-enyl-[2]thienyl-acetic acid-(2-diisopropylamino-ethyl ester) (102370-98-9)

Conditions	Yield
With triethylamine; benzene

2-(diisopropylamino)ethanol (96-80-0) + 9H-Thioxanthene-9-acetic acid (1503-19-1) → thioxanthen-9-yl-acetic acid-(2-diisopropylamino-ethyl ester); hydrochloride (113649-39-1)

Conditions	Yield
With thionyl chloride; benzene

2-(diisopropylamino)ethanol (96-80-0) + xanthen-9-yl-acetyl chloride (100954-91-4) → xanthen-9-yl-acetic acid-(2-diisopropylamino-ethyl ester)

Conditions	Yield
With benzene

2-(diisopropylamino)ethanol (96-80-0) + 9H-Thioxanthene-9-acetic acid 10,10-dioxide (40020-65-3) → (10,10-dioxo-10λ6-thioxanthen-9-yl)-acetic acid-(2-diisopropylamino-ethyl ester); hydrochloride (102762-88-9)

Conditions	Yield
With thionyl chloride; benzene

2-(diisopropylamino)ethanol (96-80-0) + 4-nitro-benzoyl chloride (122-04-3) → 4-nitro-benzoic acid-(2-diisopropylamino-ethyl ester); hydrochloride

Conditions	Yield
With benzene

2-(diisopropylamino)ethanol (96-80-0) + ethyl iodide (75-03-6) → ethyl-(2-hydroxy-ethyl)-diisopropyl-ammonium; chloride

Conditions	Yield
mit Hilfe von Silberchlorid;

Upstream product

• 75-21-8 oxirane 
• 108-18-9 diisopropylamine 
• 107-07-3 2-chloro-ethanol 
• 624-76-0 Iodoethanol 

Downstream Products

• 102444-91-7 dicyclohexyl-carbamic acid-(2-diisopropylamino-ethyl ester) 
• 4261-68-1 1-chloro-2-diisopropylaminoethane hydrochloride 
• 96-79-7 (2-chloroethyl)-diisopropylamine 
• 102371-15-3 4-phenyl-tetrahydro-pyran-4-carboxylic acid-(2-diisopropylamino-ethyl ester) 
• 102370-98-9 cyclohex-2-enyl-[2]thienyl-acetic acid-(2-diisopropylamino-ethyl ester) 
• 95160-54-6 AL₃₈₈₈₉ 
• 16715-83-6 2-(diisopropylamino)ethyl methacrylate 
• 85002-94-4 Diisopropyl-[2-(4-nitro-phenoxy)-ethyl]-amine 
• 5710-40-7 5-Fluor-2-methoxy-benzoesaeure-<2-diisopropylamino-aethylester> 
• 94166-25-3 α-(4-Chlorphenoxy)-isobuttersaeure-(2-diisopropylaminoethyl)-ester 
• 5710-48-5 4-Aethoxy-3-fluor-benzoesaeure-<2-diisopropylamino-aethylester> 
• 5710-37-2 3-Fluor-4-methoxy-benzoesaeure-<2-diisopropylamino-aethylester> 
• 5750-16-3 2-Aethoxy-5-fluor-benzoesaeure-<2-diisopropylamino-aethylester> 
• 193966-53-9 (4-[2-(diisopropylamino)ethoxy]phenyl)-(2-[4-[2-(1-pyrrolidinyl)ethoxy]-phenyl]benzo[b]thiophen-3-yl)ketone 

Relevant academic research and scientific papers

Design, Synthesis, and Biological Evaluation of Scutellarein Derivatives Based on Scutellarin Metabolic Mechanism in Vivo

Three series of scutellarein derivatives have been designed and synthesized based on metabolic mechanism of scutellarin (1) in vivo. Their thrombin inhibition activities were tested through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT), and fibrinogen (FIB). The antioxidant activities of these target products were assessed by 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) assay and the ability to protect PC12 cells against H2O2-induced cytotoxicity, and their solubilities were evaluated by ultraviolet (UV) spectrophotometer. The results showed that the two isopropyl groups substituted derivative (18c) demonstrated stronger anticoagulant activity, better water solubility, and good antioxidant activity compared with scutellarein (2), which warrants further development of 18c as a promising agent for ischemic cerebrovascular disease treatment. Three series of scutellarein derivatives have been designed and synthesized based on metabolic mechanism of scutellarin (1) in vivo. The results of the biological evaluation showed that the two isopropyl groups substituted derivative (18c) demonstrated stronger anticoagulant activity, better water solubility, and good antioxidant activity compared with scutellarein (2), which warrants further development of 18c as a promising agent for ischemic cerebrovascular disease treatment.

Compounds for the treatment of urinary incontinence

The invention concerns compounds having the formula I STR1 wherein Ar is a phenyl or benzyl group which is optionally substituted with hydroxy or alkoxy;R 1 is hydrogen, lower alkyl, lower alkoxy, hydroxy;R 2 is hydrogen, lower alkyl;R 3 is NR 4 R 5, whereinR 4 and R 5 which can be the same or different, are lower alkyl, or wherein R 4 and R 5, when taken together, form a ring with the nitrogen atom, whereby said ring optionally is substituted with lower alkyl;n is 0 or 1;m is 2 or 3 andtheir salts with physiologically acceptable acids and when the compounds can be in form of optical isomers, the racemic mixture and the individual isomers, for the treatment of disorders of the urinary bladder.

ON THE DIRECT METALATION OF ISOPRENE

Isoprene has been metalated in tetrahydrofuran with an excess of sterically hindered potassium dialkylamides, prepared by combining equimolar amounts of the corresponding lithium amide and potassium tert-butoxide.Subsequent reaction with oxirane, alkyl bromides, and pivaldehyde gave the expected coupling products in reasonable yields.Coupling with (CH3)2CHCH2CH=O and (CH3)2C=CHCH=O afforded the bark beetle pheromones (+/-)-ipsenol and (+/-)-ipsdienol in low yields.