4097-88-5

Basic information

• Product Name: N-METHYL-2,2'-DIAMINODIETHYLAMINE
• Synonyms: 2,2'-METHYLIMINOBIS(ETHYLAMINE);N,N-BIS(2-AMINOETHYL)METHYLAMINE;N-METHYL-2,2'-DIAMINODIETHYLAMINE;N-(2-AMINOETHYL)-N-METHYLETHANEDIAMINE;Methyldiaminodiethylamine;N(sup 2)-methyldiethylenetriamine;N-(2-Aminoethyl)-N'-methylethane-1,2-diamine;2,2'-DiaMino-N-MethyldiethylaMine
• CAS NO: 4097-88-5
• Molecular Formula: C₅H₁₅N₃
• Molecular Weight: 117.19
• Mol File: 4097-88-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 84 °C / 14mmHg
• Flash Point: 84°C
• Appearance: /
• Density: 0,91 g/cm3
• Refractive Index: 1.4690-1.4720
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 9.91±0.10(Predicted)
• CAS DataBase Reference: N-METHYL-2,2'-DIAMINODIETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYL-2,2'-DIAMINODIETHYLAMINE(4097-88-5)
• EPA Substance Registry System: N-METHYL-2,2'-DIAMINODIETHYLAMINE(4097-88-5)

Safety Data

• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 2735
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4097-88-5(Hazardous Substances Data)

Usage

General Description

N-Methyl-2,2'-Diaminodiethylamine is a chemical compound also known as N-Methyldiethanolamine. It is an organic compound used for a variety of industrial and scientific applications. It is a colorless liquid and is soluble in water. It is used most commonly used in the gas industry where it absorbs acid gases in a gas stream. The chemical also has uses in petroleum refining and in the creation of dyes and pharmaceuticals. Handling the compound requires careful adherence to safety protocols, as it can cause burns and serious eye damage, as well as being harmful if inhaled.

Synthetic route

N-methyliminodiacetonitrile (5423-24-5) → 1-methyl-piperazine (109-01-3) + 1,5-diamino-3-azamethylpentane (4097-88-5)

Conditions	Yield
With hydrogen In methanol at 120 - 600℃; under 15001.5 Torr; Temperature; Solvent; Reagent/catalyst;	A 92.4% B 6.8%

N1-(2-aminoethyl)-N1-methylethane-1,2-diamine trihydrochloride (70578-32-4) → 1,5-diamino-3-azamethylpentane (4097-88-5)

Conditions	Yield
With sodium methylate In methanol at 0 - 5℃; for 3h; Large scale;	88%

N,N di(dimethyl-2,5 pyrolido-2 ethyl), N methylamine (121259-51-6) → 1,5-diamino-3-azamethylpentane (4097-88-5)

Conditions	Yield
With potassium carbonate In ethanol at 80℃; for 96h; Heating;	26%

N,N'-(3-methyl-3-aza-pentanediyl)-bis-benzenesulfonamide (132066-02-5) → 1,5-diamino-3-azamethylpentane (4097-88-5)

Conditions	Yield
With sulfuric acid

nitrogen mustard (51-75-2) → 1,5-diamino-3-azamethylpentane (4097-88-5)

Conditions	Yield
(i) phthalimide , (ii) aq. HCl; Multistep reaction;

phthalimide (136918-14-4) + N-Methyldiethanolamine (105-59-9) → 1,5-diamino-3-azamethylpentane (4097-88-5) + N-(2-hydroxyethyl)-N-methylethylenediamine (5753-50-4)

Conditions	Yield
With hydrogenchloride; water 1.) 100 deg C, 4 h; 2.) 90 deg C, 50 h; Yield given. Multistep reaction;
With hydrogenchloride; water 1.) 100 deg C, 4 h; 2.) 90 deg C, 50 h; Multistep reaction;

mechlorethamine hydrochloride (55-86-7) → 1-methyl-piperazine (109-01-3) + 1,5-diamino-3-azamethylpentane (4097-88-5)

Conditions	Yield
With ammonia; sodium carbonate In water-d2 Title compound not separated from byproducts;

1,5-diamino-3-azamethylpentane (4097-88-5) + Tert-butyl isocyanate (1609-86-5) → bis[(N'-tert-butylureido)-N-ethyl]-N-methylamine (613221-93-5)

Conditions	Yield
In tetrahydrofuran at 20℃;	96.2%

4,7-dichloroquinoline (86-98-6) + 1,5-diamino-3-azamethylpentane (4097-88-5) → N1-(2-aminoethyl)-N2-(7-chloroquinolin-4-yl)-N1-methylethane-1,2-diamine (947699-91-4)

Conditions	Yield
In neat (no solvent) at 125℃; for 2h;	95%
at 90 - 135℃; for 4h;	92%
at 70℃;	57%
In neat (no solvent) at 90℃; Inert atmosphere;	57%
With potassium phosphate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 90℃; for 17h; Inert atmosphere;	1.39 g

1,5-diamino-3-azamethylpentane (4097-88-5) + 2-nitrophenyl isocyanate (3320-86-3) → C19H23N7O6

Conditions	Yield
at 20℃; Cooling with ice;	94%

3-((2-acrylamidoethyl)dimethylammonio)propane-1-sulfonate + 1,5-diamino-3-azamethylpentane (4097-88-5) → C15H35N5O4S

Conditions	Yield
In water at 20℃; Solvent; Temperature;	92.9%

2,6-Pyridinedicarboxaldehyde (5431-44-7) + 1,5-diamino-3-azamethylpentane (4097-88-5) → C24H40N8*6ClH*5H2O

Conditions	Yield
Stage #1: 2,6-Pyridinedicarboxaldehyde; 1,5-diamino-3-azamethylpentane With sodium tetrahydroborate In ethanol at 20℃; for 2h; Stage #2: With hydrogenchloride; water In 1,4-dioxane	92%

1,5-diamino-3-azamethylpentane (4097-88-5) + 2,7-naphthalenedicarboxaldehyde (19800-49-8) → 6,16-dimethyl-3,6,9,13,16,19-hexaaza-1,11(2,7)-dinaphthalenacycloicosaphane-2,9,12,19-tetraene

Conditions	Yield
In acetonitrile at 20℃; for 96h;	92%

1,5-diamino-3-azamethylpentane (4097-88-5) + 3-ethoxysalicylaldehyde (492-88-6) → C23H31N3O4

Conditions	Yield
In chloroform for 2h; Heating;	90%

gadolinium(III) chloride hexahydrate + ethanol (64-17-5) + 1,5-diamino-3-azamethylpentane (4097-88-5) + 3,3'-bis(2-hydroxybenzaldehyde) (121073-78-7) → Gd(CH3N(C2H4NCHOC6H4OC2H4)2O)(H2O)3(C2H5OH)(3+)*3Cl(1-)*2C2H5OH=(Gd(CH3N(C2H4NCHOC6H4OC2H4)2O)(H2O)3(C2H5OH))Cl3*2C2H5OH

Conditions	Yield
In ethanol to EtOH soln. 3,3'-(3-oxapentane-1,5-diyldioxy)bis(2-hydroxybenzaldehyde) 1,5-diamino-3-azamethylpentane in EtOH was added dropwise and refluxedfor 15 min, GdCl3*6H2O in EtOH was added and refluxed for 2 h; soln. was evapd. to dryness, residue was treated with EtOH, filtered, and dried in vacuo; elem. anal.;	90%

1,5-diamino-3-azamethylpentane (4097-88-5) + 3-nitro-benzaldehyde (99-61-6) → C19H21N5O4 (1221070-26-3)

Conditions	Yield
In ethanol for 12h; Inert atmosphere;	90%

1,5-diamino-3-azamethylpentane (4097-88-5) + Chlorodiisopropylphosphane (40244-90-4) → C17H41N3P2

Conditions	Yield
With triethylamine In tetrahydrofuran Inert atmosphere; Schlenk technique;	90%

1-chloro-7-methoxy-4-nitro-10H-acridin-9-one (21814-48-2) + 1,5-diamino-3-azamethylpentane (4097-88-5) → 1,1'-<(methylimino)bis(2,1-ethanediylimino)>bis<7-methoxy-4-nitro-9(10H)-acridinone>

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 80℃; for 3h;	88%

1,5-diamino-3-azamethylpentane (4097-88-5) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (2-((2-aminoethyl)(methyl)amino)ethyl)carbamate (263162-13-6)

Conditions	Yield
With dmap In chloroform at 20℃; for 16h;	88%
In tetrahydrofuran at 0 - 20℃; for 20.5h;	46%
In dichloromethane at 0 - 20℃; for 3h;	30%

7-chloro-4-bromo-quinoline (98519-65-4) + 1,5-diamino-3-azamethylpentane (4097-88-5) → N2-(7-Chloro-4-quinolinyl)-N1-[2-[(7-chloro-4-quinolinyl)amino]ethyl]-N1-methyl-1,2-ethanediamine (1391426-22-4)

Conditions	Yield
With potassium phosphate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 90℃; for 18h; Inert atmosphere;	88%
With potassium phosphate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane; water at 120℃; for 16h; Inert atmosphere; Sealed tube;	43%

1,5-diamino-3-azamethylpentane (4097-88-5) + p-toluenesulfonyl chloride (98-59-9) → N,N'-((methylazanediyl)bis(ethane-2,1-diyl))bis(4-methylbenzenesulfonamide) (92462-68-5)

Conditions	Yield
With sodium hydroxide In diethyl ether at 40℃; for 3h;	87%

fac-[CoCl3(1,4,7-triazacyclononane)] (58723-65-2) + 1,5-diamino-3-azamethylpentane (4097-88-5) → Co((C2H4NH)3)(NH2C2H4N(CH3)C2H4NH2)(3+)*3ClO4(1-) = [Co((C2H4NH)3)(NH2C2H4N(CH3)C2H4NH2)](ClO4)3

Conditions	Yield
With HClO4 In isopropyl alcohol 50°C, 8h; chromy. (Sephadex-C-25, HClO4); evapn.; addn. of ethanol or propanol; pptn.; elem. anal.;	87%

1,5-diamino-3-azamethylpentane (4097-88-5) + 1-chloro-4-nitro-9,10-dihydro-9-acridinone (20621-51-6) → 1,1'-<(methylimino)bis(2,1-ethanediylimino)>bis<4-nitro-9(10H)-acridinone>

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 80℃; for 3h;	86%

1,5-diamino-3-azamethylpentane (4097-88-5) + 5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) → 5-dimethylamino-naphthalene-1-sulfonic acid {2-[(2-amino-ethyl)-methyl-amino]-ethyl}-amide

Conditions	Yield
In ethyl acetate at 0℃; for 2h; Inert atmosphere;	86%
With triethylamine In chloroform at 0℃; for 1h;	70%

1,5-diamino-3-azamethylpentane (4097-88-5) + 1-nitro-9-oxo-9,10-dihydroacridine-4-carbonyl fluoride (482371-94-8) → C33H27N7O8

Conditions	Yield
With pyridine In N,N-dimethyl-formamide for 4h;	86%

1,5-diamino-3-azamethylpentane (4097-88-5) + {2-[2-(2-acetylamino-thiazol-4-yl)-acetylamino]-thiazol-4-yl}-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester (328563-74-2) → 2-(2-acetylamino-thiazol-4-yl)-N-{4-[(2-{[2-(2-{2-[2-(2-acetylamino-thiazol-4-yl)-acetylamino]-thiazol-4-yl}-acetylamino)-ethyl]-methyl-amino}-ethylcarbamoyl)-methyl]-thiazol-2-yl}-acetamide

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 4h;	85%

1,5-diamino-3-azamethylpentane (4097-88-5) + acryloyl chloride (814-68-6) → N,N'-bis(acrylamidoethyl)methylamine

Conditions	Yield
With sodium hydroxide In dichloromethane at 0℃; for 3h;	85%
With sodium hydroxide In dichloromethane; water at 0℃; for 5h; Solvent; Temperature;

6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid (694479-56-6) + 1,5-diamino-3-azamethylpentane (4097-88-5) → C33H31F6N5O4 (950856-73-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 3h;	84%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 3h;	84%

1,5-diamino-3-azamethylpentane (4097-88-5) + 4-chloro-7-trifluoromethyl quinoline (346-55-4) → N1-methyl-N1-(2-((7-trifluoromethyl)quinolin-4-yl)aminoethyl)propane-1,3-diamine (1220244-29-0)

Conditions	Yield
In neat (no solvent) at 140℃; for 2h;	83%

1,5-diamino-3-azamethylpentane (4097-88-5) + 2-(2,6-dioxotetrahydro-2H-pyran-3-yl)-1H-benzo[f]isoindole-1,3(2H)-dione (458151-04-7) → 2-(3-(1,3-dioxo-1H-benzo[f]isoindol-2(3H)-yl)-2,6-dioxopiperidin-1-yl)-N-(2-(3-(1,3-dioxo-1H-benzo[f]isoindol-2(3H)-yl)-2,6-dioxopiperidin-1-yl)ethyl)-N-methylethanamine hydrochloride (1187431-11-3)

Conditions	Yield
Stage #1: 1,5-diamino-3-azamethylpentane; 2-(2,6-dioxotetrahydro-2H-pyran-3-yl)-1H-benzo[f]isoindole-1,3(2H)-dione In N,N-dimethyl-formamide at 20℃; for 48h; Stage #2: With hydrogenchloride In water pH=1; Stage #3: With acetic anhydride; acetyl chloride for 48h; Reflux;	81%

1,5-diamino-3-azamethylpentane (4097-88-5) + 2H-isoindole-1-carbaldehyde → C23H25N5

Conditions	Yield
In ethanol for 13h; Reflux; Inert atmosphere;	81%

nickel(II) perchlorate hexahydrate + 1,5-diamino-3-azamethylpentane (4097-88-5) + water (7732-18-5) + potassium selenocyanate (3425-46-5) → (bis(2-aminoethyl)methylamine)nickel(II)di(selenocyanate)(H2O)

Conditions	Yield
In water a soln. of Ni salt added dropwise to a soln. of amine, a soln. of KSeCNadded slowly, kepted in desicator over CaCl2; crysts. separated, washed (chilled water), dried (CaCl2); elem. anal., TGA;	80%

cadmium(II) perchlorate hexahydrate + 1,5-diamino-3-azamethylpentane (4097-88-5) + potassium selenocyanate (3425-46-5) → [Cd(N''-methyldiethylenetriamine)(SeCN)2]

Conditions	Yield
In water aq. soln. of KSeCN was added to aq. soln. of Cd(ClO4)*6H2O with stirringfor 10 min, ligand was added slowly, stirred for 30 min; filtered, kept in CaCl2 desiccator for a few ds; elem. anal.;	80%

1,5-diamino-3-azamethylpentane (4097-88-5) + mesitylene-2-carboxylic acid chloride (938-18-1) → N,N'-((methylazanediyl)bis(ethane-2,1-diyl))bis(2,4,6-trimethylbenzamide)

Conditions	Yield
With sodium hydroxide In dichloromethane at 0 - 25℃; for 12h;	80%

4,7-dichloroquinoline (86-98-6) + 1,5-diamino-3-azamethylpentane (4097-88-5) → N2-(7-Chloro-4-quinolinyl)-N1-[2-[(7-chloro-4-quinolinyl)amino]ethyl]-N1-methyl-1,2-ethanediamine (1391426-22-4)

Conditions	Yield
In neat (no solvent) at 90℃; Inert atmosphere;	79.3%

Upstream product

• 136918-14-4 phthalimide 
• 105-59-9 N-Methyldiethanolamine 
• 70578-32-4 N¹-(2-aminoethyl)-N¹-methylethane-1,2-diamine trihydrochloride 
• 5423-24-5 N-methyliminodiacetonitrile 
• 51-75-2 nitrogen mustard 
• 132066-02-5 N,N'-(3-methyl-3-aza-pentanediyl)-bis-benzenesulfonamide 
• 121259-51-6 N,N di(dimethyl-2,5 pyrolido-2 ethyl), N methylamine 
• 55-86-7 mechlorethamine hydrochloride 

Downstream Products

• 132066-02-5 N,N'-(3-methyl-3-aza-pentanediyl)-bis-benzenesulfonamide 
• 92462-68-5 N,N'-((methylazanediyl)bis(ethane-2,1-diyl))bis(4-methylbenzenesulfonamide) 
• 263162-13-6 tert-butyl N-[2-[(2-aminoethyl)(methyl)amino]ethyl]carbamate 
• 1391426-22-4 N²-(7-Chloro-4-quinolinyl)-N¹-[2-[(7-chloro-4-quinolinyl)amino]ethyl]-N¹-methyl-1,2-ethanediamine 
• 1526928-79-9 C₁₉H₂₃N₇O₄S₂ 

Relevant articles and documents

Synthesis method of 2,2'-diamido-N-methyldiethylamine

The invention discloses a synthesis method of 2,2'-diamido-N-methyldiethylamine. The synthesis method is characterized in that acetic anhydride is added dropwise into N-methyldiethanolamine, ripeningis conducted after dropping dropwise adding is completed, and a compound II is obtained; phthalimide is added into the compound II, heating and ripening are conducted after adding is completed, and acompound III is obtained; 6N hydrochloric acid is added into the compound III, then heating and ripening are conducted after adding is completed, and a compound IV is obtained; and sodium methoxide isadded into the compound IV, and ripening at the low temperature is conducted after adding is completed. The technological method for synthesizing high-purity 2,2'-diamido-N-methyldiethylamine has theadvantages of being low in cost, high in yield, simple in purification technology, convenient to operate and suitable for industrialized production, the GC purity of the prepared 2,2'-diamido-N-methyldiethylamine can be as high as 99% or above, and the total yield is 60% or above.

SYNTHESE DE SPERMINE ET DE SPERMIDINE SELECTIVEMENT SUBSTITUEES SUR LES FONCTIONS AMINES SECONDAIRES

Protection of the primary amino group of various polyamines followed by alkylation or benzoylation at the secondary amino group and finally removal of the protecting group leads to the N-methyl (23, Scheme 3), N-benzoyl (11, Scheme 1) (ethylenetriamine, N-benzoyl spermidine (22, Scheme 3), N,N'-methyl (27, Scheme 4)-ethyl (28, Scheme 4), -propyl (16, Scheme 2) -benzoyl (15, Scheme 2) spermine.

Specific ligands for the affinity chromatography of cholinergic proteins

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