Bis(2-dimethylaminoethyl) ether supplier

Name
Bis(2-dimethylaminoethyl) ether
EINECS 221-220-5
CAS No. 3033-62-3
Article Data28
CAS DataBase
Density 0.883 g/cm³
Solubility Soluble
Melting Point
Formula C₈H₂₀N₂O
Boiling Point 194.8 °C at 760 mmHg
Molecular Weight 160.26
Flash Point 46.2 °C
Transport Information UN 2927 6.1/PG 2
Appearance A clear or yellow liquid
Safety 26-36/37/39-45
Risk Codes 20-22-24-34
Molecular Structure
Hazard Symbols T
Synonyms Ethylamine,2,2'-oxybis[N,N-dimethyl- (6CI,7CI,8CI);1,5-Bis(dimethylamino)-3-oxapentane;2,2'-Oxybis[N,N-dimethylethanamine];2,2'-Oxybis[N,N-dimethylethylamine];A133;A 99 (amine);BL 19;Bis(dimethylaminoethyl) ether;Bis[2-(dimethylamino)ethyl] ether;Dabco BL 11;Dabco BL 19;Dabco BL 19I;ET33B;Jeffcat ZF 20;Jeffcat ZM 20;Kaolizer 12P;MinicoTMDA;N,N,N',N'-Tetramethyl-2,2'-oxybis[ethylamine];N,N,N',N'-Tetramethyl-3-oxapentane-1,5-diamine;N,N,N',N'-Tetramethylbisaminoethyl ether;NP 99;NSC 109887;Niax A 1;Niax A99;PC CAT NP 90;Texacat ZF 20;Toyocat ETS;ZF 20;Ethanamine,2,2'-oxybis[N,N-dimethyl-;
PSA 15.71000
LogP 0.12620

Synthetic route

: 108-01-0
2-(N,N-dimethylamino)ethanol

: 124-40-3
dimethyl amine

: 74-86-2
acetylene

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
With potassium hydroxide In dibutyl ether at 100℃; for 5h;	90.4%

...Expand

: 108-01-0
2-(N,N-dimethylamino)ethanol

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
In water at 175 - 180℃; for 3h; Temperature; Time;	78.5%
With 4-methyl-morpholine; ammonium tungstate at 145 - 155℃; for 15h; Reagent/catalyst; Autoclave; Inert atmosphere; Sealed tube;	73.6%
With sulfuric acid at 190℃; for 12h; Temperature; Reagent/catalyst;	65%

: 108-01-0
2-(N,N-dimethylamino)ethanol

: 105-59-9
N-Methyldiethanolamine

A: 2-((2-(2-(dimethylamino)ethoxy)ethyl)methyl-amino)-ethanol

B: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
With 4-methyl-morpholine; silica-alumina at 145 - 155℃; for 15h; Catalytic behavior; Reagent/catalyst; Time; Concentration; Temperature; Autoclave; Inert atmosphere; Sealed tube; Overall yield = 95.6 %;	A 76.4% B 75 g

...Expand

: 1704-62-7
1-O-Dimethylaminoethyl-ethylenglykol

: 124-40-3
dimethyl amine

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
With hydrogen at 220℃; under 15001.5 - 142514 Torr; for 8h; Temperature; Pressure;	74.63%
With hydrogen at 200℃; under 5931.67 Torr; Product distribution / selectivity;	47 %Chromat.

: 108-01-0
2-(N,N-dimethylamino)ethanol

: 107-99-3
2-(dimethylamino)ethyl chloride

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
With sodium hydroxide; adogen 464 In tetrahydrofuran for 6h; Heating;	35%

: 124-40-3
dimethyl amine

: 111-44-4
3-oxa-1,5-dichloropentane

: 71-43-2
benzene

A: 109-02-4
4-methyl-morpholine

B: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
at 140℃;

...Expand

: 124-40-3
dimethyl amine

: 111-44-4
3-oxa-1,5-dichloropentane

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
With ethanol at 120℃;
With benzene at 140℃;

: 37616-36-7
sodium N,N-dimethylethanolamine

: 107-99-3
2-(dimethylamino)ethyl chloride

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
With toluene

: 107-99-3
2-(dimethylamino)ethyl chloride

: 71-43-2
benzene

sodium-compound of acetamide: sodium-compound of acetamide

A: 108-01-0
2-(N,N-dimethylamino)ethanol

B: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

C: 1421-89-2
2-(dimethylamino)ethyl acetate

D: 3197-11-3
N-<2-(dimethylamino)ethyl>acetamide

Conditions

Conditions	Yield
Produkt5: 1,2-Bis-dimethylamino-aethan;

...Expand

: 1704-62-7
1-O-Dimethylaminoethyl-ethylenglykol

: 74-89-5
methylamine

A: 109-02-4
4-methyl-morpholine

B: 93240-93-8
N,N,N'-trimethylbis(aminoethyl)ether

C: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
With hydrogen at 195℃; under 11879 Torr; for 23.3h; Product distribution / selectivity; Compressed gas(es);	A 3.1 %Chromat. B 44.3 %Chromat. C 1.6 %Chromat.
With hydrogen; potassium nitrate at 200℃; under 4395.7 Torr; Product distribution / selectivity;
With hydrogen at 200℃; under 4369.84 Torr; Product distribution / selectivity;

...Expand

: 124-40-3
dimethyl amine

: 111-46-6
diethylene glycol

A: 1704-62-7
1-O-Dimethylaminoethyl-ethylenglykol

B: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
With hydrogen; γ-Al2O3 (45 weight %), CuO (55 weight %), hydrogenated at 190℃; under 15001.5 Torr; Product distribution / selectivity;
Stage #1: diethylene glycol With C39H57ClNP2Rh In 5,5-dimethyl-1,3-cyclohexadiene; ethanol at -78℃; for 0.5h; Autoclave; Inert atmosphere; Stage #2: dimethyl amine In 5,5-dimethyl-1,3-cyclohexadiene; ethanol at 150℃; under 112511 Torr; for 120h; Solvent; Reagent/catalyst; Pressure; Autoclave; Inert atmosphere;

...Expand

: 1704-62-7
1-O-Dimethylaminoethyl-ethylenglykol

A: 110-91-8
morpholine

B: 109-02-4
4-methyl-morpholine

C: 93240-93-8
N,N,N'-trimethylbis(aminoethyl)ether

D: 85322-63-0
2-(2-aminoethoxy)-N,N-dimethylethanamine

E: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

F: 65286-55-7
bis-(2-(N,N-dimethylamino)ethoxyethyl)methylamine

G: 1257084-24-4
[2-(2-amino-ethoxy)-ethyl]-[2-(2-dimethylamino-ethoxy)-ethyl]-methyl-amine

H: 1257084-22-2
bis-(2-(N,N-dimethylamino)ethoxyethyl)amine

I: 1257084-23-3
[2-(2-dimethylamino-ethoxy)-ethyl]-[2-(2-methylamino-ethoxy)-ethyl]-amine

Conditions

Conditions	Yield
With ammonia; copper chromite at 200℃; under 52505.3 Torr; Product distribution / selectivity; Industry scale;

...Expand

: 124-40-3
dimethyl amine

: 111-46-6
diethylene glycol

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
With hydrogen; shaped bodies of reduced CuO/γ-Al2O3 (55 wt%/45 wt%) at 210℃; under 15001.5 Torr; Product distribution / selectivity;

: 1704-62-7
1-O-Dimethylaminoethyl-ethylenglykol

: 74-89-5
methylamine

A: 93240-93-8
N,N,N'-trimethylbis(aminoethyl)ether

B: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
With copper chromite at 166℃; under 7500.75 Torr; for 513h;	A 26.81 %Chromat. B 19.37 %Chromat.

...Expand

: 1704-62-7
1-O-Dimethylaminoethyl-ethylenglykol

: 75-50-3
trimethylamine

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
Stage #1: 1-O-Dimethylaminoethyl-ethylenglykol With thionyl chloride In toluene for 1.5h; Reflux; Stage #2: trimethylamine at 50 - 80℃; for 3h; Stage #3: With ethylenediamine at 100 - 170℃; for 3h; Temperature; Autoclave;	132 g

: 1704-62-7
1-O-Dimethylaminoethyl-ethylenglykol

: 124-40-3
dimethyl amine

A: 109-02-4
4-methyl-morpholine

B: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

Conditions

Conditions	Yield
With hydrogen at 230℃; under 11400.8 Torr; Temperature; Pressure; Reagent/catalyst;

...Expand

: 34270-90-1
2,2'-diiodoethyl ether

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: N,N,N',N'-tetramethyl-1,7-diaza-4,10-dioxacyclododecane di-iodide

Conditions

Conditions	Yield
In acetonitrile under 7500600 Torr; for 48h; Mechanism; Quantum yield; Ambient temperature; further substrates and reactants;	99%
In acetonitrile under 7500600 Torr; for 48h; Ambient temperature;	99%
In acetonitrile at 25℃; under 8250660 Torr; for 20h;	99%

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 110431-62-4
1,2-bis-(2-iodoethoxy)benzene

: N,N,N',N'-tetramethyl-5,6-benzo-1,10-diaza-4,7,13-trioxacyclopentadecane di-iodide

Conditions

Conditions	Yield
In acetonitrile under 7500600 Torr; for 48h; Ambient temperature;	96%
In acetonitrile at 25℃; under 8250660 Torr; for 20h;	96%

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 36839-55-1
1,2-bis-(2-iodoethoxy)ethane

: N,N,N',N'-tetramethyl-1,10-diaza-4,7,13-trioxacyclopentadecane di-iodide

Conditions

Conditions	Yield
In acetonitrile under 7500600 Torr; for 48h; Ambient temperature;	95%
In acetonitrile at 25℃; under 8250660 Torr; for 20h;	95%

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 143-15-7
1-dodecylbromide

: 2,2'-bis(dodecyldimethylammonium)diethyl ether dibromide

Conditions

Conditions	Yield
In water; acetonitrile at 80℃; for 55h; Solvent;	95%

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 123436-89-5
1-(bromomethyl)-4-(dodecyloxy)benzene

: bis{2-N,N-dimethyl-N-[p-(n-dodecyloxybenzyl)]ammonium} bromide ethyl ether

Conditions

Conditions	Yield
In acetonitrile for 1h; Reflux;	94%

: 592-55-2
2-Bromoethyl ethyl ether

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 2,2'-oxybis(N-(2-ethoxyethyl)-N,N-dimethylethanammonium) bromide

Conditions

Conditions	Yield
In acetone for 24h; Cooling with ice; Reflux;	88%

: 112-29-8
1-bromo dodecane

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: bis(N-decyl-N,N-dimethylethylammonium)ether dibromide

Conditions

Conditions	Yield
In acetonitrile at 80℃; for 55h;	83%

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 40949-94-8
potassium hexamethylsilazane

: C40H112K4N8O2Si8

Conditions

Conditions	Yield
In hexane Inert atmosphere; Schlenk technique;	66%

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 40949-94-8
potassium hexamethylsilazane

: C22H58KN5O2Si2

Conditions

Conditions	Yield
In hexane Inert atmosphere; Schlenk technique;	62%

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 1279010-11-5
2-tert-butyl-4,5-di-(1,1-dimethylpropyl) imidazole

: 133766-06-0
bis(tetrahydrofuran)strontium di(bis(trimethylsilyl)amide)

: 1279016-87-3
bis(2-tert-butyl-4,5-di-tert-amylimidazolyl)(2,2'-oxybis(N,N-dimethylethylamine))strontium

Conditions

Conditions	Yield
In hexane at 20℃; Inert atmosphere;	43%

...Expand

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 109-72-8, 29786-93-4
n-butyllithium

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 1779-25-5
diisobutylaluminum chloride

: [Li(μ-2,2,6,6-tetramethylpiperidide)(μ-bis[2-(N,N-dimethylamino)ethyl]ether)Al(isobutyl)2]

Conditions

Conditions	Yield
Stage #1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium In hexane at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: diisobutylaluminum chloride In hexane for 1h; Inert atmosphere; Schlenk technique; Stage #3: Bis<2-(N,N-dimethylamino)aethyl>aether In hexane Inert atmosphere; Schlenk technique;	42%

...Expand

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 106-89-8
epichlorohydrin

: N,N′-(oxybis(ethane-2,1-diyl))bis(3-chloro-2-hydroxy-N,N-dimethylpropan-1-aminium) chloride

Conditions

Conditions	Yield
With hydrogenchloride In water at 25 - 70℃; for 6h; pH=< 2 - 8.5;	39.4%

: 1202-34-2
di(pyridin-2-yl)amine

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: [(N,N,N′,N′-tetramethyldiaminoethylether)Na(2,2′-dipyridylamide)]2

Conditions

Conditions	Yield
Stage #1: di(pyridin-2-yl)amine With butylsodium In hexane for 1h; Inert atmosphere; Schlenk technique; Stage #2: Bis<2-(N,N-dimethylamino)aethyl>aether In hexane at -30℃; for 48h; Inert atmosphere; Schlenk technique;	37%

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 3525-44-8
butylsodium

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 7681-82-5
sodium iodide

: C30H90IN5Na5Si10(1-)*C16H40N4NaO2(1+)

Conditions

Conditions	Yield
Stage #1: butylsodium; 1,1,1,3,3,3-hexamethyl-disilazane In hexane for 2h; Inert atmosphere; Schlenk technique; Stage #2: sodium iodide In hexane for 24h; Inert atmosphere; Schlenk technique; Stage #3: Bis<2-(N,N-dimethylamino)aethyl>aether In hexane for 15h; Inert atmosphere; Schlenk technique;	36%

...Expand

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 1-lithio-2-tert-butyl-1,2-dihydropyridine

: C17H34LiN3O

Conditions

Conditions	Yield
In tetrahydrofuran; hexane at -30℃; for 168h; Inert atmosphere;	32%

: 74-96-4
ethyl bromide

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 64049-67-8
N,N'-diethyl-N,N,N',N'-tetramethyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; dibromide

Conditions

Conditions	Yield
With acetone

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 100-44-7
benzyl chloride

: 63722-05-4
N,N'-dibenzyl-N,N,N',N'-tetramethyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; dichloride

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 75-03-6
ethyl iodide

: N,N'-diethyl-N,N,N',N'-tetramethyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; diiodide

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 105-39-5
chloroacetic acid ethyl ester

: N,N'-bis-ethoxycarbonylmethyl-N,N,N',N'-tetramethyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; dichloride

Conditions

Conditions	Yield
With acetone
In isopropyl alcohol for 8h; Reflux;

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: 74-88-4
methyl iodide

: 2576-43-4
hexa-N-methyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; diiodide

Conditions

Conditions	Yield
With ethanol

: 3033-62-3
Bis<2-(N,N-dimethylamino)aethyl>aether

: F-bis[2-(N,N-dimethylamino)ethyl] ether

Conditions

Conditions	Yield
With hydrogen fluoride In water electrochemical fluorination; Yield given;

Bis(2-dimethylaminoethyl) ether Chemical Properties

The Molecular Structure of Bis(2-dimethylaminoethyl) ether (CAS NO.3033-62-3):

Empirical Formula: C₈H₂₀N₂O
Molecular Weight: 160.2572
Appearance: A clear or yellow liquid
Nominal Mass: 160 Da
Average Mass: 160.2572 Da
Monoisotopic Mass: 160.157563 Da
Index of Refraction: 1.445
Molar Refractivity: 48.29 cm³
Molar Volume: 181.4 cm³
Surface Tension: 29.1 dyne/cm
Density: 0.883 g/cm³
Flash Point: 46.2 °C
Enthalpy of Vaporization: 43.1 kJ/mol
Boiling Point: 194.8 °C at 760 mmHg
Vapour Pressure: 0.433 mmHg at 25°C
Classification Code: Reproductive Effect; Skin / Eye Irritant; TWA (0.05 ppm); STEL (0.15 ppm); Skin / Eye Irritant; TWA (0.05 ppm); STEL (0.15 ppm); Skin
IUPAC: 2-(2-dimethylaminoethyloxy)-N,N-dimethylethanamine
Synonyms: Lupragen(r) n 205 ; Lupragen(r) n 206 ; Di-[2-(n,n-dimethylaminoethyl)]ether ; Dabco(r) 2039 ; Dabco(r) dc4000 ; Dabco(r) dc5582 ; Dabco(r) dc5598 ; Dabco(r) dc5599

Bis(2-dimethylaminoethyl) ether Toxicity Data With Reference

1.	skn-rbt 500 mg open SEV	UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 12/27/71 .
2.	skn-rbt 100 mg/24H SEV	JTOTDO Journal of Toxicology, Cutaneous and Ocular Toxicology. 5 (1986),3.
3.	eye-rbt 1 mg SEV	UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 12/27/71 .
4.	eye-rbt 250 µg/24H SEV	85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986721.
5.	orl-rat LD50:1070 mg/kg	JTOTDO Journal of Toxicology, Cutaneous and Ocular Toxicology. 5 (1986),3.
6.	skn-rbt LD50:280 µL/kg	AIHAAP American Industrial Hygiene Association Journal. 30 (1969),470.

Bis(2-dimethylaminoethyl) ether Consensus Reports

Bis(2-dimethylaminoethyl) ether (CAS NO.3033-62-3) was reported in EPA TSCA Inventory.

Bis(2-dimethylaminoethyl) ether Safety Profile

Poison by skin contact. Moderately toxic by ingestion. Experimental reproductive effects. A severe skin and eye irritant. See also ETHERS. When Bis(2-dimethylaminoethyl) ether was heated to decomposition, it emits toxic fumes of NO_x.
Hazard Codes: Toxic T
Risk Statements: 20-22-24-34
R20: Harmful by inhalation
R22: Harmful if swallowed
R24: Toxic in contact with skin
R34: Causes burns
Safety Statements: 26-36/37/39-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2927 6.1/PG 2
WGK Germany: 2
RTECS: KR9460000
HazardClass: 3
PackingGroup: III

Bis(2-dimethylaminoethyl) ether Standards and Recommendations

ACGIH TLV: TWA 0.05 ppm; STEL 0.15 ppm (skin))

Product Name

Bis(2-dimethylaminoethyl) ether

Synthetic route

Bis(2-dimethylaminoethyl) ether Chemical Properties

Bis(2-dimethylaminoethyl) ether Toxicity Data With Reference

Bis(2-dimethylaminoethyl) ether Consensus Reports

Bis(2-dimethylaminoethyl) ether Safety Profile

Bis(2-dimethylaminoethyl) ether Standards and Recommendations

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