121-05-1

Basic information

• Product Name: 2-Aminoethyldiisopropylamine
• Synonyms: 1,2-BIS-(ISOPROPYLAMINO)-ETHANE;n,n-diisopropyl-ethylenediamin;usafam-2;N,N-Diisoprylamino Ethylamine;N,N-Diisopropylamino;2-(Diisopropylamino)ethylamine;2-Aminoethyldiisopropylamine;N,N-Diisopropylamino ethylamine
• CAS NO: 121-05-1
• Molecular Formula: C₈H₂₀N₂
• Molecular Weight: 144.26
• EINECS: 204-447-4
• Product Categories: amine series;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Polyamines;Piperazines
• Mol File: 121-05-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 52°C (estimate)
• Boiling Point: 169-171 °C(lit.)
• Flash Point: 125 °F
• Appearance: /
• Density: 0.798 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.13mmHg at 25°C
• Refractive Index: n20/D 1.4289(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.18±0.28(Predicted)
• Water Solubility: Fully miscible in water.
• Sensitive: Air Sensitive
• BRN: 1734800
• CAS DataBase Reference: 2-Aminoethyldiisopropylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminoethyldiisopropylamine(121-05-1)
• EPA Substance Registry System: 2-Aminoethyldiisopropylamine(121-05-1)

Safety Data

• Hazard Codes: C,Xi
• Statements: 10-34-37/38
• Safety Statements: 16-26-27-36/37/39-45-28-23
• RIDADR: UN 2733 3/PG 3
• WGK Germany: 3
• RTECS: KV4200000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 121-05-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liquid

Uses

N,N-Diisopropylethylenediamine is used as a reactant in the preparation of 1,?4-?bis[(aminoalkyl)?amino]?-?9,?10-?anthracenediones for antitumor activity.

Flammability and Explosibility

Flammable

InChI:InChI=1/C8H20N2/c1-7(2)10(6-5-9)8(3)4/h7-8H,5-6,9H2,1-4H3

Synthetic route

N,N-(diisopropylamino)acetonitrile (54714-49-7) → N',N'-diisopropyl-ethane-1,2-diamine (121-05-1)

Conditions	Yield
With lithium aluminium tetrahydride; nickel dichloride In tetrahydrofuran at 5 - 65℃; for 5h; Solvent; Reagent/catalyst; Temperature;	83.7%

C9H21N3O (1211469-53-2) → N',N'-diisopropyl-ethane-1,2-diamine (121-05-1)

Conditions	Yield
With hydrogenchloride; sodium nitrate In water at 0 - 80℃; for 7h; Curtius rearrangement;	82%

2-(diisopropylamino)ethyl chloride hydrochloride → N',N'-diisopropyl-ethane-1,2-diamine (121-05-1)

Conditions	Yield
With ammonium hydroxide In water at 5 - 10℃; for 8h; Autoclave; Large scale;	51.7%

N-(2-diisopropylaminoethyl)phthalimide (85262-27-7) → N',N'-diisopropyl-ethane-1,2-diamine (121-05-1)

Conditions	Yield
With hydrogen bromide
With hydrogenchloride
With hydrazine

methyl (3-diisopropylamino)-propionate (27453-38-9) → N',N'-diisopropyl-ethane-1,2-diamine (121-05-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 12 h / 20 °C / Reflux 2: hydrogenchloride; sodium nitrate / water / 7 h / 0 - 80 °C View Scheme

diisopropylamine (108-18-9) → N',N'-diisopropyl-ethane-1,2-diamine (121-05-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: iron(III) chloride hexahydrate / water / 15 h / 20 °C 2: hydrazine hydrate / ethanol / 12 h / 20 °C / Reflux 3: hydrogenchloride; sodium nitrate / water / 7 h / 0 - 80 °C View Scheme

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + ethyl 2-isothiocyanatoacetate (24066-82-8) → 3-(2-diisopropylamino-ethyl)-2-thioxo-imidazolidin-4-one

Conditions	Yield
In chloroform for 4h;	99.8%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + 2-methylthio-2-imidazoline hydroiodide (5464-11-9) → 2-(2-(diisopropylamino)ethylamino)-4,5-dihydro-1H-imidazole

Conditions	Yield
Stage #1: N',N'-diisopropyl-ethane-1,2-diamine; 2-methylthio-2-imidazoline hydroiodide In tetrahydrofuran at 40℃; for 24h; Stage #2: With sodium hydroxide In water at 20℃;	99%

furfural (98-01-1) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → N1-(furan-2-ylmethylene)-N2,N2-diisopropylethane-1,2-diamine

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere; Darkness;	99%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + 5-norbornene-exo-2,3-dicarboxylic anhydride → N-(2-aminoethyldiisopropylamine)-5-norbornene-exo-2,3-dicarboxylic acid imide

Conditions	Yield
With triethylamine Reflux;	99%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + oxalic acid diethyl ester (95-92-1) → N1,N2-bis(2-(diisopropylamino)ethyl)oxalamide (25148-95-2)

Conditions	Yield
at 130℃;	99%

Isophthalaldehyde (626-19-7) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → bis[diisopropylaminoethyl]-N,N‘-m-xylylenediimine

Conditions	Yield
In ethanol	99%

2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid methyl ester (877997-99-4) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → 2-[N-(4,5-dimethoxy-2-hydroxybenzoyl)amino]-4-[(2-diisopropyl-aminoethyl)aminocarbonyl]-1,3-thiazole hydrochloride

Conditions	Yield
Stage #1: 2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid methyl ester; N',N'-diisopropyl-ethane-1,2-diamine In toluene at 100℃; for 5h; Stage #2: With hydrogenchloride In water; isopropyl alcohol	97%
Stage #1: 2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid methyl ester; N',N'-diisopropyl-ethane-1,2-diamine In 1,4-dioxane at 75℃; for 6h; Inert atmosphere; Stage #2: With hydrogenchloride In methanol; water	96.3%

2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid methyl ester (877997-99-4) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → N-[2-(diisopropylamino)ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxamide hydrochloride

Conditions	Yield
Stage #1: 2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid methyl ester; N',N'-diisopropyl-ethane-1,2-diamine In toluene at 70 - 100℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In water	97%

2-[N-(3-cyanobenzoyl)amino]-4-methoxycarbonyl-1,3-thiazole.hydrochloride (206882-11-3) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + trimethylaluminum (75-24-1) + 1,2-dichloro-ethane (107-06-2) → 2-[N-(3-Cyanobenzoyl)amino]-4-[(2-diisopropylaminoethyl)aminocarbonyl]-1,3-thiazolehydrochloride (206881-85-8)

Conditions	Yield
With hydrogenchloride In toluene	95.4%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + mono-6-deoxy-6-(p-tolylsulphonyl)-β-cyclodextrin (67217-55-4) → 6-deoxy-6-N,N'-diisopropyl-aminoethylamino-bcyclodextrin (1393337-75-1)

Conditions	Yield
at 85℃; for 0.5h; Microwave irradiation;	95%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + purpurin-18-methyl ester (5111-07-9, 51744-55-9) → purpurin-18-N-(N-isopropylamino)ethylimide

Conditions	Yield
In toluene for 2h; Inert atmosphere; Reflux;	94%

Methyltrichlorosilane (75-79-6) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → C25H60N6Si

Conditions	Yield
With triethylamine In hexane at 20℃; for 24h;	93%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + C16H20N2O6S → N-[2-(diisopropylamino)ethyl]-2-[(2,4,5-trimethoxybenzoyl)amino]-1,3-thiazole-4-carboxamide hydrochloride

Conditions	Yield
Stage #1: N',N'-diisopropyl-ethane-1,2-diamine; C16H20N2O6S In N,N-dimethyl acetamide at 120℃; for 8h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 20℃; for 4h; pH=1 - 2; Inert atmosphere;	93%

indole-3-acetic acid (87-51-4) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → N-(2-(diisopropylamino)ethyl)-2-(1H-indol-3-yl)acetamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h;	92.2%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + 2-N-phthalimide-4-methoxycarbonyl-1,3-thiazole → C20H24N4O3S

Conditions	Yield
at 100℃; for 6h;	91.5%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + 2,4-dichloro-1,3-di-tert-butyl-1,3,2,4-diazadiphosphetidine (24335-35-1) → C24H56N6P2 (1343408-39-8)

Conditions	Yield
With triethylamine In tetrahydrofuran for 24h; Inert atmosphere; Reflux;	91%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + benzaldehyde (100-52-7) → N1-benzylidene-N2,N2-diisopropylethane-1,2-diamine

Conditions	Yield
With sodium sulfate In diethyl ether at 20℃; for 2h; Reflux;	91%
With magnesium sulfate In diethyl ether at 20℃;	76%
In ethanol for 24h;

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + 1-chloro-7-hydroxy-4-nitro-9(10H)-acridinone (99009-49-1) → 1-(2-Diisopropylamino-ethylamino)-7-hydroxy-4-nitro-10H-acridin-9-one (174275-52-6)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 0.5h;	90%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + heptadecafluorononanic acid chloride (52447-23-1) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-octanoic acid (2-diisopropylamino-ethyl)-amide

Conditions	Yield
With triethylamine In dichloromethane for 0.5h;	90%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + 2,5-dihydroxyterephthaldeyde (1951-36-6) → 2,5-bis-[(2-diisopropylamino-ethylimino)-methyl]-benzene-1,4-diol

Conditions	Yield
In dichloromethane for 1h; Heating;	90%

pyridine-2-carbaldehyde (1121-60-4) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → PyCH2NH(CH2)2N(iPr)2

Conditions	Yield
Stage #1: pyridine-2-carbaldehyde; N',N'-diisopropyl-ethane-1,2-diamine for 1h; Inert atmosphere; Stage #2: With methanol; sodium tetrahydroborate for 1h; Inert atmosphere;	90%

2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid ethyl ester + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → Acotiamide

Conditions	Yield
at 120℃; for 3h; Inert atmosphere;	89.1%
at 70 - 105℃; for 13h; Temperature; Inert atmosphere; Large scale;

4-chloro-2-oxo-1-phenyl-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester (220866-33-1) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → ethyl 4-(2-diisopropylaminoethylamino)-2-oxo-1-phenyl-1,2-dihydroquinoline-3-carboxylate

Conditions	Yield
In tetrahydrofuran; water	87.3%

BARBITURIC ACID (67-52-7) + D-glucose (50-99-7) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → C22H34N6O9

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 50℃; for 12h;	87%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + N,N,N',N'-tetramethylchlorformamidinium chloride (56043-45-9, 13829-06-6) → 2-[2-(diisopropylamino)ethyl]-1,1,3,3-tetramethylguanidine (428514-99-2)

Conditions	Yield
Stage #1: N',N'-diisopropyl-ethane-1,2-diamine; N,N,N',N'-tetramethylchlorformamidinium chloride With triethylamine In acetonitrile for 3h; Inert atmosphere; Reflux; Stage #2: With sodium hydroxide In water; acetonitrile Inert atmosphere; Stage #3: With potassium hydroxide In water Inert atmosphere;	86%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + cyclohexanecarbaldehyde (2043-61-0) → 2-cyclohexylmethylene-N,N-diisopropylethylen-1-amine

Conditions	Yield
With sodium sulfate In diethyl ether at 20℃; for 2h; Reflux;	86%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + 2-chloro-1,3-dimethylimidazolinium chloride (37091-73-9) → N1-(1,3-dimethylimidazolidin-2-yliden)-N2,N2-diisopropylethan-1,2-diamine (1309596-51-7)

Conditions	Yield
Stage #1: N',N'-diisopropyl-ethane-1,2-diamine; 2-chloro-1,3-dimethylimidazolinium chloride With triethylamine In acetonitrile for 3h; Inert atmosphere; Reflux; Stage #2: With sodium hydroxide In water; acetonitrile Inert atmosphere; Stage #3: With potassium hydroxide In water Inert atmosphere;	85%

N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) + salicylaldehyde (90-02-8) → 2-(((2-(di-isopropylamino)ethyl)imino)methyl)phenol

Conditions	Yield
In methanol for 3h; Reflux;	85%

ethyl 2-[N-(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylate acetate + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → Acotiamide

Conditions	Yield
With dicyclohexyl-carbodiimide In neat (no solvent) at 20 - 120℃; for 1h; Solvent; Temperature; Inert atmosphere; Large scale;	83%
In toluene at 70 - 110℃; for 4h; Large scale;	82%

Upstream product

• 4261-68-1 1-chloro-2-diisopropylaminoethane hydrochloride 
• 54714-49-7 N-cyanomethyl-N,N-diisopropylamine 
• 108-18-9 diisopropylamine 
• 27453-38-9 methyl (3-diisopropylamino)-propionate 
• 1211469-53-2 C₉H₂₁N₃O 
• 85262-27-7 N-(2-phthalimidoethyl)diisopropylamine 

Downstream Products

• 70945-56-1 1,4-Bis-(2-diisopropylamino-ethylamino)-5,8-dihydroxy-anthraquinone 
• 758698-79-2 2-amino-N-(2-diisopropylamino-ethyl)-3-phenyl-propionamide 
• 110042-61-0 N-[2-[bis(1-methylethyl)amino]ethyl]-4-nitrobenzene sulfonamide 
• 401817-04-7 N-{4-[2-(3-chlorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-yl)-N-[2-(diisopropylamino)ethyl]amine 
• 1387639-38-4 HOtBu₂C₆H₂CHNCH₂CH₂N(iPr)2 
• 185106-16-5 Acotiamide 
• 1601472-87-0 3-bromo-N-(4-chloro-2-((2-(diisopropylamino)ethyl)carbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 

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