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

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

Uses

Used in Pharmaceutical Industry:
2-Aminoethyldiisopropylamine is used as a reactant for the synthesis of 1,4-bis[(aminoalkyl)amino]-9,10-anthracenediones, which are compounds with potential antitumor properties. This makes it a valuable component in the development of new cancer treatments.

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

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

Downstream Products

• 111240-60-9 2-methoxy-benzoic acid-(2-diisopropylamino-ethylamide); hydrochloride 
• 70945-56-1 1,4-Bis-(2-diisopropylamino-ethylamino)-5,8-dihydroxy-anthraquinone 
• 758698-76-9 [(S)-1-(2-diisopropylamino-ethyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 373633-77-3 1-[[[2-[Bis(1-methylethyl)amino]ethyl]amino]carbonyl]-3,4-dihydro-6-(phenylmethoxy)-2(1H)-isoquinoline-carboxylic acid,1,1-dimethylethyl ester 
• 853942-78-6 3-[2-(diisopropylamino)ethyl]-4-phenyl-4-(trichloromethyl)-3,4-dihydroquinazolin-2(1H)-one 
• 847573-82-4 N-(6,7-methylenedioxyquinolin-4-yl)-N-[2-(N,N-diisopropylamino)ethyl]-2-iodo-4,5-dimethoxybenzamide 

Relevant articles and documents

The preparation method of N, N - diisopropylethylenediamine. Preparation method of

N, N -isopropyl N chloroethylamine hydrochloride and the urotropine are reacted in an organic solvent to obtain N - and N diisopropyltripropylestamine quaternary ammonium salt; and the method comprises the following steps: N - reacting with the urotropine in an organic solvent to obtain the quaternary ammonium salt.2 - N - N. N, N - Diisopropyltriprolol quaternary ammonium salt and concentrated hydrochloric acid were reacted in an organic solvent to give N, N - diisopropylethylamine. To the preparation method, safety risks caused by high-pressure production routes are avoided, the quality risks caused by dimer impurities are avoided, environmental pollution is avoided, raw materials are economical and easy to obtain, production cost is low, and good economic benefits are achieved.

Synthesizing method of N,N-diisoprylamino ethylamine

The invention discloses a synthesizing method of N,N-diisoprylamino ethylamine. The synthesizing method comprises the following steps of using diisopropylamine and chloroacetonitrile as initial raw materials, and performing aminolysis reaction and reduction reaction, so as to synthesize the N,N-diisoprylamino ethylamine. The synthesizing method has the advantages that the technology route is advanced, the technology condition is reasonable, the cost of raw materials is low, the obtaining is easy, the reaction condition is mild, the operation is simple and safe, the atom economy is high, the production cost is low, the amount of three wastes (waste gas, waste water and industrial residue) is small, the synthesizing method is suitable for industrialized production, and the larger implementing value and social and economical benefits are realized.

A sulfuric acid west pula Tanzania method for the preparation of

The invention relates to a preparation method of Pramiracetam sulfate. The preparation method comprises the steps of using N, N-diisopropylethanolamine as a starting raw material, and conducting chlorination and ammonolysis to obtain an intermediate N, N- diisopropylethylene diamine; then conducting acylation, substitution, salt forming and refining to obtain the Pramiracetam sulfate. The preparation method of the Pramiracetam sulfate has the characteristics that the reaction process is safe and controllable, the cost of used raw materials and solvent is low and the raw materials and the solvent are easy to obtain; organic solvent is very easy to recycle, the emission of organic matters is greatly reduced, and the environmental friendliness is improved; since the intermediate N-[(2-diisopropyl amino) ethyl]-chloroacetamide is not separated and purified, the reaction equipment is simplified, and the operation process is enabled to be more high-efficient.

Synthesis and characterization of N-substitutional ethylenediamine derivatives

N-Substituted and N,N-disubstituted ethylenediamine derivatives were prepared rapidly in aqueous conditions from 30 to 76 % yields, respectively, on a multi-gram scale starting from inexpensive and commercially available starting materials. The steps involved Michael addition, hydrazinolysis and Curtius rearrangements. The highlight of this method lies on its convenience and economy in accessing these intermediates.

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.

Phthalocyanines

Storage-stable aqueous compositions containing dissolved water-soluble novel acid addition salts of poly(N-substituted sulfonamido) phthalocyanines which are prepared by the interaction of a single acid or a mixture of acids and poly(N-substituted sulfonamido) phthalocyanines, are useful for direct dyeing, particularly the dyeing of cellulose.

Novel monoazo and disazo colorants

This invention relates to novel (N-substituted sulfonamido) monoazo and disazo compounds, to acid-addition salts of said azo compounds which are useful as direct dyes particularly in the dyeing of cellulose, to novel (N-substituted sulfonamido) substituted nitrobenzene, aniline and acetanilide intermediates to said azo compounds and to methods of preparation of said azo compounds and said intermediates to said azo compounds.

N-Aminoalkylenesulfonamido substituted monoazo colorants

This invention relates to novel mixtures consisting essentially of monoazo compounds and disazo compounds which are substituted with x (N-substituted sulfonamido) groups, to acid-addition salts of said azo compounds, useful as direct dyes particularly in the dyeing of cellulose, and to methods of preparation of said mixtures of (N-substituted sulfonamido) substituted monoazo and disazo compounds.

Novel compositions and processes

Storage-stable aqueous compositions containing dissolved water-soluble novel acid addition salts of poly(N-substituted sulfonamido) phthalocyanines which are prepared by the interaction of a single acid or a mixture of acids and poly(N-substituted sulfonamido) phthalocyanines, are useful for direct dyeing, particularly the dyeing of cellulose.

Long-range anisotropic effects of long chain amides

In 1H-NMR spectra of amids with long-chain aliphatic N-substituents one observes - despite of the free mobility of the aliphatic chain - splitting of the signals of the terminal methyl groups which is caused by the hindered rotation of the amide bond. - Keywords: Amides; Hindered rotation; 1H-NMR