3424-21-3

Basic information

• Product Name: TRIISOPROPYL-AMINE
• Synonyms: SALOR-INT L308803-1EA;TRIISOPROPYL-AMINE;N,N-Bis(1-methylethyl)-2-propanamine;N,N-Diisopropyl-1-methylethanamine;Tris(1-methylethyl)amine;N,N-di(propan-2-yl)propan-2-amine
• CAS NO: 3424-21-3
• Molecular Formula: C₉H₂₁N
• Molecular Weight: 143.27
• EINECS: 222-317-5
• Mol File: 3424-21-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 131.8 °C at 760 mmHg
• Flash Point: 21.9 °C
• Appearance: /
• Density: 0.772 g/cm³
• Vapor Pressure: 9.12mmHg at 25°C
• Refractive Index: 1.424
• PKA: 11.06±0.50(Predicted)
• CAS DataBase Reference: TRIISOPROPYL-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIISOPROPYL-AMINE(3424-21-3)
• EPA Substance Registry System: TRIISOPROPYL-AMINE(3424-21-3)

Safety Data

• Hazardous Substances Data: 3424-21-3(Hazardous Substances Data)

Usage

Uses

Tris(isopropylamine) acts as a base for the synthesis of cyclodextrin, an additive.

InChI:InChI=1/C9H21N/c1-7(2)10(8(3)4)9(5)6/h7-9H,1-6H3

Synthetic route

diisopropylamine (108-18-9) + isopropyl alcohol (67-63-0) → triisopropylamine (3424-21-3)

Conditions	Yield
With iron(III) oxide; (triphenylphosphine)ruthenium acetate at 78℃; for 36h; Molecular sieve;	95.6%

methyllithium (917-54-4) + N-(Chlormethylen)-N-isopropyl-2-propanaminium-chlorid (54485-04-0) → triisopropylamine (3424-21-3)

Conditions	Yield
In diethyl ether for 12h; Ambient temperature;	74%

α-(diisopropylamino)propionitrile (91086-11-2) + methylmagnesium chloride (676-58-4) → triisopropylamine (3424-21-3)

Conditions	Yield
In diethyl ether for 4h; Heating;	49%
In diethyl ether for 0.5h; Heating;	45%

diisopropylamine (108-18-9) + acetone (67-64-1) → triisopropylamine (3424-21-3)

Conditions	Yield
With formic acid In water at 0℃; for 1h; Reflux;	5%

chloro-diisopropyl-amine (24948-81-0) + i-propylpotassium (4867-40-7) → triisopropylamine (3424-21-3)

Conditions	Yield
With Petroleum ether

diisopropyl sulfate (2973-10-6) + diisopropylamine (108-18-9) → triisopropylamine (3424-21-3)

N-(Chlormethylen)-N-isopropyl-2-propanaminium-chlorid (54485-04-0) + methyl iodide (74-88-4) → triisopropylamine (3424-21-3) + N,N,N',N'-tetraisopropyl-1,2-dimethylethylenediamine (99692-09-8)

Conditions	Yield
With magnesium 1.) ether 2.) 12 h, RT; Yield given. Multistep reaction. Yields of byproduct given;
With magnesium 1.) ether, 2.) 12 h, room temperature; Yield given. Multistep reaction. Yields of byproduct given;

isopropylamine (75-31-0) + aluminium oxide-molybdenum (III)-oxide catalyst → triisopropylamine (3424-21-3) + diisopropylamine (108-18-9)

Conditions	Yield
at 400℃;

chloro-diisopropyl-amine (24948-81-0) + i-propylpotassium (4867-40-7) + petroleum ether → triisopropylamine (3424-21-3) + tetraisopropylhydrazine (172909-37-4)

diisopropylamine hydrochloride (819-79-4) → triisopropylamine (3424-21-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 39 percent / H2O / 4 h / -0.1 °C 2: 49 percent / diethyl ether / 4 h / Heating View Scheme

diisopropylamine (108-18-9) → triisopropylamine (3424-21-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 37.6 percent / HCl 2: 45 percent / diethyl ether / 0.5 h / Heating View Scheme

tri-isopropylamine hydrochloride → triisopropylamine (3424-21-3)

Conditions	Yield
With sodium hydroxide In methanol at 40 - 50℃; pH=7;

1,3-propanesultone (1120-71-4) + triisopropylamine (3424-21-3) → C12H27NO3S

Conditions	Yield
In 1,2-dichloro-ethane at 40℃; for 4h;	99%

triisopropylamine (3424-21-3) + benzenediazonium tetrafluoroborate (369-57-3) → 1-phenyl-3,3-diisopropyltriaz-1-ene (36719-40-1) + N,N-diisopropylammonium tetrafluoroborate

Conditions	Yield
In acetonitrile at 0 - 20℃; for 1.08333h;	A 72% B 92%

Isopropyl 2-(ethylthiocarbonyloxy)-2-iodoethanoate (352320-96-8) + triisopropylamine (3424-21-3) + ibuprofen (15687-27-1) → 2-[4-(2-Methylpropyl)phenyl]propanoic acid (chlorocarbonyloxy)(isopropoxy-carbonyl)methyl ester (352540-95-5)

Conditions	Yield
With sulfuryl dichloride In dichloromethane	84%

triisopropylamine (3424-21-3) + anthranilic acid amide (28144-70-9) → 2,2-dimethyl-2,3-dihydro-1H-quinazolin-4-one (77726-78-4)

Conditions	Yield
With diphenyl-phosphinic acid; oxygen In 1,4-dioxane at 130℃; under 760.051 Torr; for 18h; Schlenk technique;	82%

triisopropylamine (3424-21-3) + 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid (70458-96-7) + 2-butoxy-1-[(chlorocarbonyl)oxy]-2-oxyethyl isobutyrate (352540-92-2) → 7-(4-[(Butoxycarbonyl)(2-methylpropanoyloxy)methoxycarbonyl]-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (352540-97-7)

Conditions	Yield
In dichloromethane	77%

triisopropylamine (3424-21-3) + p-toluenesulfonyl chloride (98-59-9) → N,N-diisopropyl-N′-tosylformimidamide (1209499-73-9)

Conditions	Yield
With sodium azide; copper(ll) bromide In 1,2-dichloro-ethane at 70℃; for 3h;	76%

morpholine (110-91-8) + triisopropylamine (3424-21-3) + 2,2,2-trichloroethyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate + sodium hydrogencarbonate (144-55-8) → N-[6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]morpholine-4-carboxamide (1005787-03-0)

Conditions	Yield
With dimethyl sulfoxide	73%

triisopropylamine (3424-21-3) + benzenesulfonyl chloride (98-09-9) → N,N-diisopropyl-N'-(phenylsulfonyl)formimidamide (91904-99-3)

Conditions	Yield
With sodium azide; copper(ll) bromide In 1,2-dichloro-ethane at 70℃; for 3h;	72%

triisopropylamine (3424-21-3) + 4-chlorobenzenesulfonyl chloride (98-60-2) → N'-((4-chlorophenyl)sulfonyl)-N,N-diisopropylformimidamide

Conditions	Yield
With sodium azide; copper(ll) bromide In 1,2-dichloro-ethane at 70℃; for 3h;	68%

triisopropylamine (3424-21-3) + 2,2,2-trichloroethyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate + 2-(2-Aminoethoxy)ethanol (929-06-6) → N-(3-{[2-({[2-(2-hydroxyethoxy)ethyl]carbamoyl}amino)imidazo[1,2-b]pyridazin-6-yl]oxy}phenyl)-3-(trifluoromethyl)benzamide

Conditions	Yield
With dimethyl sulfoxide	62%

rhodium(III) tetrakis(4-tolyl)porphyrin chloride (205259-72-9) + triisopropylamine (3424-21-3) → [rhodium(III)(diisobutylamine)(5,10,15,20-tetratolylporphyrin)]

Conditions	Yield
In further solvent(s) mixt. of Rh complex (0.014 mmol) and (iBu)3N degassed (3 freeze-pump-thaw cycles), heated under N2 at 120°C for 1 d; solvent evapd. in vac., residue chromd. (silica gel, hexane/CH2Cl2 eluent (1:1), then ethyl acetate/CH2Cl2 (1:2) eluent);	57%

1-methyl-piperazine (109-01-3) + triisopropylamine (3424-21-3) + 2,2,2-trichloroethyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate → 4-methyl-N-[6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]piperazine-1-carboxamide (1005787-05-2)

Conditions	Yield
With dimethyl sulfoxide	50%

Methyl fluorosulfonate (421-20-5) + triisopropylamine (3424-21-3) → N,N,N-Triisopropyl-N-methylammonium-fluorsulfonat

Conditions	Yield
In dichloromethane at 25℃; for 9h; Product distribution; alkylation of other amines, relative alkylation possibility;	31%
In dichloromethane at 20℃; for 0.5h;	31%

triisopropylamine (3424-21-3) → N,N-Bis(5-chloro-3-oxo-1,2-dithiol-4-yl)amine + N,N-Bis(5-chloro-3-oxo-1,2-dithiol-4-yl)isopropylamine

Conditions	Yield
Stage #1: triisopropylamine With 1,4-diaza-bicyclo[2.2.2]octane; disulfur dichloride In 1,2-dichloro-ethane at -40 - 20℃; for 72h; Cyclization; Stage #2: With formic acid In 1,2-dichloro-ethane for 1.5h; Substitution; Heating;	A 6% B 12%

triisopropylamine (3424-21-3) + 2-butoxy-1-[(chlorocarbonyl)oxy]-2-oxyethyl isobutyrate (352540-92-2) → 4-([(Butoxycarbonyl)(2-methylpropanoyloxy)methoxycarbonyl]amino)-N-(5-methyl-3-isoxazolyl)benzenesulfonamide (352541-02-7)

Conditions	Yield
In diethyl ether; dichloromethane; sulfamethoxazole	7.3%

triisopropylamine (3424-21-3) → isopropylphosphoric acid (1623-24-1)

Conditions	Yield
With phosphonic Acid; iodine In ethanol

triisopropylamine (3424-21-3) → N-chloro-tri-isopropylammonium perchlorate

Conditions	Yield
With silver perchlorate; chlorine 1.) CCl4, -20 deg C; 2.) TFA, -20 deg C; Multistep reaction;

triisopropylamine (3424-21-3) + p-benzoquinone (106-51-4) → hydroquinone radical (3225-30-7) + C9H20N

Conditions	Yield
In acetonitrile Quantum yield; flash photolysis study;

triisopropylamine (3424-21-3) → triisopropylamine radical cation

Conditions	Yield
With antimony pentafluoride In dichloromethane at -78.15℃; Oxidation;

Upstream product

• 2973-10-6 diisopropyl sulfate 
• 108-18-9 diisopropylamine 
• 917-54-4 methyllithium 
• 54485-04-0 N-(Chlormethylen)-N-isopropyl-2-propanaminium-chlorid 
• 75-31-0 isopropylamine 
• 24948-81-0 chloro-diisopropyl-amine 
• 4867-40-7 i-propylpotassium 
• 819-79-4 diisopropylamine hydrochloride 
• 91086-11-2 α-(diisopropylamino)propionitrile 
• 676-58-4 methylmagnesium chloride 
• 67-63-0 isopropyl alcohol 
• 67-64-1 acetone 
• 74-88-4 methyl iodide 

Downstream Products

• 1623-24-1 isopropylphosphoric acid 
• 815-24-7 Di-t-butyl ketone 
• 352540-95-5 2-[4-(2-Methylpropyl)phenyl]propanoic acid (chlorocarbonyloxy)(isopropoxy-carbonyl)methyl ester 
• 1209499-73-9 N,N-diisopropyl-N′-tosylformimidamide 
• 91904-99-3 N,N-diisopropyl-N'-(phenylsulfonyl)formimidamide 
• 2700-30-3 N,N-diisorpopylformamide 
• 77726-78-4 2,2-dimethyl-2,3-dihydro-1H-quinazolin-4-one 
• 1005787-03-0 N-[6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]morpholine-4-carboxamide 
• 352541-02-7 4-([(Butoxycarbonyl)(2-methylpropanoyloxy)methoxycarbonyl]amino)-N-(5-methyl-3-isoxazolyl)benzenesulfonamide 
• 3225-30-7 hydroquinone radical 

Relevant articles and documents

Photophysics of a Sterically Crowded Tertiary-Saturated Amine: Triisopropylamine

The spectroscopic and photophysical properties of triisopropylamine (TIPA), a sterically overcrowded amine, are reported in the vapor phase and in n-hexane and tetrahydrofuran solution.On the basis of available experimental data and several semiempirical

Aryldiazonium Salts as Nitrogen-Based Lewis Acids: Facile Synthesis of Tuneable Azophosphonium Salts

Inspired by the commercially available azoimidazolium dyes (e.g., Basic Red 51) that can be obtained from aryldiazonium salts and N-heterocyclic carbenes, we developed the synthesis of a unique set of arylazophosphonium salts. A range of colours were obtained by applying readily tuneable phosphine donor ligands and para-substituted aryldiazonium salts as nitrogen-based Lewis acids. With cyclic voltammetry, a general procedure was designed to establish whether the reaction between a Lewis acid and a Lewis base occurs by single-electron transfer or electron-pair transfer.

Triisopropylamin, ein sterisch ueberfuelltes Molekuel mit eingeebneter NC3-Pyramide und einem p-Typ-Stickstoffelektronenpaar

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