2212-32-0

Basic information

• Product Name: N-Methyl-N-(N,N-dimethylaminoethyl)-aminoethanol
• Synonyms: N,N,N’-Trimethyl-N’-(2-hydroxyethyl)-1,2-ethanediamine;N-[2-(Dimethylamino)ethyl]-N-methylethanolamine;CATALYST JD-36;N,N,N''-Trimethyl-N''-(2-hydroxyethyl)-ethylenediamine;2-[Methyl[2-(dimethylamino)ethyl]amino]ethanol;DABCO T;N,N,N′-trieMthylaMinoethyl-N′-MethylaMinoehylanol;LUPRAGEN(R) N 400
• CAS NO: 2212-32-0
• Molecular Formula: C₇H₁₈N₂O
• Molecular Weight: 146.23
• EINECS: 218-658-4
• Product Categories: Amino Alcohols;Organic Building Blocks;Oxygen Compounds;Excellent fogging performance and PVC staining performance
• Mol File: 2212-32-0.mol

Chemical Properties

• Boiling Point: 207 °C(lit.)
• Flash Point: 188 °F
• Appearance: /
• Density: 0.904 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0541mmHg at 25°C
• Refractive Index: n20/D 1.4539(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 14.72±0.10(Predicted)
• Water Solubility: 1000g/L at 20℃
• CAS DataBase Reference: N-Methyl-N-(N,N-dimethylaminoethyl)-aminoethanol(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-N-(N,N-dimethylaminoethyl)-aminoethanol(2212-32-0)
• EPA Substance Registry System: N-Methyl-N-(N,N-dimethylaminoethyl)-aminoethanol(2212-32-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 2212-32-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Methyl-N-(N,N-dimethylaminoethyl)-aminoethanol is used as a building block for the synthesis of pharmaceutical compounds due to its versatile amine groups, which can be easily modified to create a wide range of drug molecules.
Used in Chemical Industry:
N-Methyl-N-(N,N-dimethylaminoethyl)-aminoethanol is used as a reagent in the preparation of new iron clusters, such as [Fe7O4(O2CPh)11(dmem)2] and [Fe7O4(O2CMe)11(dmem)2][Fe6O2(OH)4(O2CBut)8(dmem)2]. These iron clusters have potential applications in various fields, including catalysis and materials science.
Used in Research and Development:
N-Methyl-N-(N,N-dimethylaminoethyl)-aminoethanol is used as a research compound for exploring its chemical properties and potential applications in various fields, such as organic synthesis, coordination chemistry, and drug discovery.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C7H18N2O/c1-8(2)4-5-9(3)6-7-10/h10H,4-7H2,1-3H3

Synthetic route

formaldehyd (50-00-0) + 2-(2-Aminoethylamino)ethanol (111-41-1) → 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0)

Conditions	Yield
Stage #1: formaldehyd; 2-(2-Aminoethylamino)ethanol at 80 - 90℃; for 0.5h; Stage #2: With formic acid at 80 - 90℃; for 2h; Stage #3: In butan-1-ol at 120℃; for 4h; Temperature; Solvent;	95.2%
With 5%-palladium/activated carbon; hydrogen at 100 - 110℃; under 11251.1 Torr; for 4.5h; Reagent/catalyst; Temperature; Pressure; Inert atmosphere; Autoclave;	90.4%
With formic acid In water for 4h; Heating;	70%
With formic acid

(2-hydroxyethyl)(methyl)amine (109-83-1) + 2-(dimethylamino)ethyl chloride (107-99-3) → 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0)

Conditions	Yield
With potassium carbonate In ethanol Heating;

cerium(IV) isopropoxide + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) → {cerium(IV)(OiPr)3(μ-OC2H4NMeC2H4NMe2)}2

Conditions	Yield
In toluene the aminoalcohol is added to a soln. of Ce(OiPr)4 in toluene at room temp, stirring for 12 h (under argon using Schlenk tubes); evapn. to dryness, the crude product is recrystd. in a mixt. of toluene and CH2Cl2, crystals are obtained at -30°C, elem. anal.;	96%

bis(bis(trimethylsilyl)amido)zinc(II) + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) → Zn(2+)*2(CH3)2NCH2CH2N(CH3)CH2CH2O(1-)=Zn(OCH2CH2N(CH3)CH2CH2N(CH3)2)2

Conditions	Yield
In hexane byproducts: HN(Si(CH3)3)2; under dry N2; alcohol added to soln. of Zn-compd., exothermic reaction, stirred for 16h,; volatiles removed in vac., solidified on standing for 1-2d; elem. anal.;	95%

cerium(IV) isopropoxide + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) → Ce3O4(OiPr)2(OC2H4NMeC2H4NMe2)2

Conditions	Yield
In toluene the aminoalcohol is added to a soln. of Ce(OiPr)4 (ratio 2:1) in toluene at room temp, stirring for 12 h (under argon using Schlenk tubes); isolated by concentration from the reaction medium, elem. anal.;	95%

carbon disulfide (75-15-0) + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) → C8H17N2OS2(1-)*Na(1+)

Conditions	Yield
Stage #1: 2-{[2-(dimethylamino)ethyl]methylamino}ethanol With sodium hydride In tetrahydrofuran at -20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: carbon disulfide In tetrahydrofuran for 1h; Inert atmosphere; Schlenk technique;	91%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + C51H108Cl6O3Si9 → C93H210N12O9Si9

Conditions	Yield
With triethylamine In diethyl ether at 20℃; for 16h; Inert atmosphere;	88%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + C105H234Cl12O3Si21 → C189H438N24O15Si21

Conditions	Yield
With triethylamine In diethyl ether at 20℃; for 16h; Inert atmosphere;	85%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) → lithium-2-(2-(dimethylamino)ethyl(methyl)amino)ethan-1-oxide

Conditions	Yield
With n-butyllithium In hexane at -40 - 20℃; for 4h; Schlenk technique; Inert atmosphere;	85%
With n-butyllithium In hexane at -40 - 20℃; for 4h; Schlenk technique; Glovebox; Inert atmosphere;	85%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + copper(II) methoxide (1184-54-9, 18213-24-6) → Cu(OCH2CH2N(CH3)CH2CH2N(CH3)2)2

Conditions	Yield
In not given prepd. by the alcohol-exchange procedure described by Singh, J. V.; Baranwal, B. P.; Mehrotra, R. C.; T. Anorg. Allg. Chem. 1981, 477, 235; crystn. from hexane and distn. of mother liquor;	83%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + phthalocyanine silicon(IV) dichloride (19333-10-9) → C46H50N12O2Si (1233238-04-4)

Conditions	Yield
With pyridine In toluene for 4h; Reflux;	81%
With pyridine In toluene for 36h; Reflux; Inert atmosphere;	81%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + diethylzinc (557-20-0) → C9H22N2OZn

Conditions	Yield
In hexane at -78 - 20℃; Inert atmosphere;	79%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + diethylzinc (557-20-0) → [(ethyl)Zn(2-{[2-(dimethylamino)ethyl]-methylamino}ethanol)]2

Conditions	Yield
In hexane at -78 - 50℃; Inert atmosphere; Schlenk technique;	77%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + C80H50N8O2S8Si → C94H82N12O2S8Si

Conditions	Yield
In toluene for 12h; Reflux; Inert atmosphere;	76%

4-Nitrophthalonitrile (31643-49-9) + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) → 4-(2-{[2-(dimethylamino)ethyl](methyl)amino}ethoxy)phthalonitrile

Conditions	Yield
Stage #1: 4-Nitrophthalonitrile; 2-{[2-(dimethylamino)ethyl]methylamino}ethanol In N,N-dimethyl-formamide at 35℃; for 0.25h; Inert atmosphere; Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 35℃; for 144h; Inert atmosphere;	74%

1-{bis-[3-(chloro-dimethyl-silanyl)-propyl]-methyl-silanyl}-3-[tris-(3-{bis-[3-(chloro-dimethyl-silanyl)-propyl]-methyl-silanyl}-propyl)-silanyl]-propane + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) → C112H268N16O8Si13

Conditions	Yield
With triethylamine In diethyl ether at 20℃;	72%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + dimethylcadmium (506-82-1) → [(methyl)Cd(2-{[2-(dimethylamino)ethyl]-methylamino}ethanol)]2

Conditions	Yield
In hexane at -78 - 20℃; for 1h; Inert atmosphere; Schlenk technique;	72%

dysprosium(III) nitrate pentahydrate + [Fe3O(O2CPh)6(H2O)3](NO3) + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + acetonitrile (75-05-8) → C42H54DyFe2N5O14*0.6C2H3N

Conditions	Yield
With triethylamine In methanol at 20℃; for 2h;	69%

holmium(III) nitrate pentahydrate + [Fe3O(O2CPh)6(H2O)3](NO3) + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + acetonitrile (75-05-8) → C42H54Fe2HoN5O14*0.6C2H3N

Conditions	Yield
With triethylamine In methanol at 20℃; for 2h;	60%

yttrium(lll) nitrate hexahydrate + [Fe3O(O2CPh)6(H2O)3](NO3) + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + acetonitrile (75-05-8) → C42H54Fe2N5O14Y*0.6C2H3N

Conditions	Yield
With triethylamine In methanol at 20℃; for 2h;	60%

gadolinium(III) nitrate hexahydrate + [Fe3O(O2CPh)6(H2O)3](NO3) + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + acetonitrile (75-05-8) → C42H54Fe2GdN5O14*0.6C2H3N

Conditions	Yield
With triethylamine In methanol at 20℃; for 2h;	59%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + tetra[3-(dimethylchlorosilyl)propyl]silane (161638-89-7) → N-{2-[dimethyl-(3-{tris-[3-({2-[(2-dimethylamino-ethyl)-methyl-amino]-ethoxy}-dimethyl-silanyl)-propyl]-silanyl}-propyl)-silanyloxy]-ethyl}-N,N',N'-trimethyl-ethane-1,2-diamine

Conditions	Yield
With triethylamine In diethyl ether at 20℃;	57%

terbium(III) nitrate hexahydrate + [Fe3O(O2CPh)6(H2O)3](NO3) + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + acetonitrile (75-05-8) → C42H54Fe2N5O14Tb*0.6C2H3N

Conditions	Yield
With triethylamine In methanol at 20℃; for 2h;	57%

lanthanum nitrate pentahydrate + [Fe3O(O2CPh)6(H2O)3](NO3) + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + acetonitrile (75-05-8) → C42H54Fe2LaN5O14*0.8C2H3N

Conditions	Yield
With triethylamine In methanol at 20℃; for 2h;	56%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + propargyl bromide (106-96-7) → N,N,N'-trimethyl-N'-(2-(prop-2-inyloxy)ethyl)ethano-1,2-diamine (1356038-24-8)

Conditions	Yield
Stage #1: 2-{[2-(dimethylamino)ethyl]methylamino}ethanol With sodium hydride In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Stage #2: propargyl bromide In tetrahydrofuran; hexane; toluene at -30 - 20℃; Inert atmosphere;	51%

[(μ3-oxo)hexakis(benzoate)triaquatriiron(III)] nitrate + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) → [Fe7O4(O2CPh)11(dmem)2]

Conditions	Yield
In acetonitrile Fe-compound reacted with organic ligand in 1:2 molar ratio in MeCN;	45%

2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + 1-(4-fluorophenyl)ethanone (403-42-9) → 4'-{2-[N,N-(2-dimethylaminoethyl)methylamino]ethoxy}acetophenone

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 3h;	43%

sodium benzoate (532-32-1) + tetraethylammonium μ-oxohexachlorodiferrate(III) + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + acetonitrile (75-05-8) → Fe7O4(O2CPh)11(2-[[2-(dimethylamino)ethyl]methylamino]ethanol(1-))2*0.5MeCN

Conditions	Yield
In acetonitrile (under aerobic conditions); soln. of Fe-complex and sodium benzoate in MeCN treated with ligand, stirred for few h; filtered, allowed to stand at room temp. for 3 d;	40%

sodium benzoate (532-32-1) + iron(III) chloride hexahydrate + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + acetonitrile (75-05-8) → Fe7O4(O2CPh)11(2-[[2-(dimethylamino)ethyl]methylamino]ethanol(1-))2*0.5MeCN

Conditions	Yield
In acetonitrile byproducts: NaCl; (under aerobic conditions); soln. of FeCl3*6H2O and sodium benzoate in MeCN treated with ligand, stirred for 3 h; filtered, left at room temp. for 5 d;	30%

manganese(II) nitrate hydrate + gadolinium(III) nitrate hexahydrate + 2-{[2-(dimethylamino)ethyl]methylamino}ethanol (2212-32-0) + sodium pivalate (1184-88-9) → [Mn2GdO(O2CBu-t)2(2-([2-(dimethylamino)ethyl]methylamino)ethanolate)2(NO3)3]

Conditions	Yield
With NEt3 In methanol; acetonitrile 2-(2-((dimethylamino)ethyl)methylamino)ethanol, sodium pivalate, NEt3, added to MeCN/MeOH soln. of Mn(NO3)2, Gd(NO3)3; stirred for 3 h; filtered; crystd. by Et2O diffusion after 2 d; filtered; washed with Et2O; vac. dried; elem. anal.;	20%

Upstream product

• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 50-00-0 formaldehyd 
• 111-41-1 2-(2-Aminoethylamino)ethanol 

Downstream Products

• 1086391-53-8 5-[3-(4-{2-[(2-dimethylaminoethyl)methylamino]ethoxy}-3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]-1,3-dihydrobenzo-imidazol-2-one 
• 1028806-70-3 C₁₆H₂₇N₃O₂ 

Relevant articles and documents

Preparation method of N, N, N'-trimethyl-N'-ethoxyl-ethanediamine

The invention discloses a preparation method of N, N, N'-trimethyl-N'-ethoxyl-ethanediamine. The preparation method comprises the following steps: adding hydroxyethyl ethylenediamine and paraformaldehyde to a vessel, and dropwise adding formic acid in stirring, wherein the molar ratio of hydroxyethyl ethylenediamine to paraformaldehyde to formic acid is 1: (3-3.3): (3-3.3), and the reaction is carried out for 1 to 2 hours at the temperature of 50 to 110 DEG C; performing pressure-reduction steaming to obtain water generated in the reaction after the reaction is finished, so as to obtain reacting liquid; adding alcohols substances to the obtained reacting liquid to perform an ester exchange reaction so as to obtain purified reacting liquid; and performing pressure-reduction distilling on the obtained reacting liquid so as to separate out the alcohols substance and N, N, N'-trimethyl-N'-ethoxyl-ethanediamine, wherein the alcohols substances are recycled.

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The invention discloses a synthesizing method for N,N,N'-trimethyl-N'-ethoxyl-ethidene diamin.The synthesizing method comprises the following steps that firstly, synthesizing is carried out, wherein ethoxyl ethylenediamine, methanal substances, a catalyst and hydrogen are added into an autoclave to carry out a reaction in a sealed state with the reaction temperature ranging from 80 DEG C to 120 DEG C, the reaction pressure regulated with hydrogen to be 0-3 MPa and the reaction time ranging from 3 h to 7 h, the autoclave is opened after the reaction is finished, reaction liquor is filtered, and filter liquor is collected; secondly, separating is carried out, wherein the filter liquor obtained in the first step is subjected to atmospheric distillation to remove water, vacuum distillation is carried out, and N,N,N'-trimethyl-N'-ethoxyl-ethidene diamin is obtained.

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