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
• Article Data: 6

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

Chemical Properties

Colorless to pale yellow transparent liquid

Uses

2-{[2-(Dimethylamino)ethyl]methylamino}ethanol (dmemH) has been used in the preparation of new iron clusters:[Fe7O4(O2CPh)11(dmem)2][Fe7O4 (O2CMe)11(dmem)2][Fe6O2(OH)4(O2CBut)8(dmem)2]

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

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

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.

2,3,4,5-TETRAHYDRO-1H-1,5-BENZODIAZEPINE DERIVATIVE AND MEDICINAL COMPOSITION

The present invention has its object to provide a 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine derivative represented with the Formula (1) , or the pharmaceutically acceptable salt, which is effective as a therapeutic and prophylactic agent for diabetes, diabetic nephropathy, or glomerulosclerosis.

Process for converting heat stable amine salts to heat regenerable amine salts

Processes are disclosed for converting heat stable amine salts to heat regenerable amine salts using a modified electrodialysis zone (140). The processes of the present invention can be used to reduce the level of heat stable salts in a lean solvent stream in an acid gas removal process and can be integrated with the acid gas removal process to utilize process streams as a source of ions.