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N,N,N',N'-Tetramethylethylenediamine

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Name

N,N,N',N'-Tetramethylethylenediamine

EINECS 203-744-6
CAS No. 110-18-9 Density 0.817 g/cm3
PSA 6.48000 LogP 0.10960
Solubility miscible with water Melting Point -55 °C(lit.)
Formula C6H16N2 Boiling Point 121 °C at 760 mmHg
Molecular Weight 116.206 Flash Point 10 °C
Transport Information UN 2372 3/PG 2 Appearance Colorless to slightly yellow liquid
Safety 16-26-36/37/39-45 Risk Codes 11-20/22-34-20/21/22
Molecular Structure Molecular Structure of 110-18-9 (N,N,N',N'-Tetramethylethylenediamine) Hazard Symbols FlammableF,CorrosiveC
Synonyms

1,2-Ethanediamine,N,N,N',N'-tetramethyl- (9CI);Ethylenediamine, N,N,N',N'-tetramethyl-(6CI,8CI);(2-(Dimethylamino)ethyl)dimethylamine;1,2-Bis(dimethylamino)ethane;2,5-Dimethyl-2,5-diazahexane;Dabco TMEDA;Dimethyl[2-(dimethylamino)ethyl]amine;Kaolizer 11;MR;MR (amine);N,N,N',N'-Tetramethyl-1,2-diaminoethane;N,N,N',N'-Tetramethyl-1,2-ethanediamine;N,N,N',N'-Tetramethyl-1,2-ethylenediamine;Propamine D;TEMED;TMED;TMEDA;Tetrameen;Toyocat TE;

Article Data 83

N,N,N',N'-Tetramethylethylenediamine Synthetic route

124-40-3

dimethyl amine

106-93-4

ethylene dibromide

110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 24h;100%
In chloroform at 20℃; for 24h;100%
124-40-3

dimethyl amine

74-86-2

acetylene

110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
With 1-ethyl-2-pyrrolidinone; sodium stannate(IV) trihydrate; alumina; calcium hydroxide at 45 - 80℃; for 6h; Reagent/catalyst; Temperature; Autoclave; Inert atmosphere;98.6%
50-00-0

formaldehyd

107-15-3

ethylenediamine

110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
With oxalic acid at 100 - 120℃; Eschweiler-Clarke methylation;96%
With hydrogen In methanol at 130℃; under 15001.5 Torr; for 4.5h; Autoclave;89%
With formic acid for 11h; Eschweiler-Clarke reaction; Reflux;80%
at 130 - 160℃;
With water at 130 - 160℃; im Autoklaven;
67-56-1

methanol

107-15-3

ethylenediamine

110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
With hydrogen at 180℃; under 7500.75 Torr;91.6%
With hydrogen at 180℃; under 7500.75 Torr;91.6%
89184-58-7

Li(1+)*((H3C)2NCH2)2*(C5H5)V(C3H5)2(1-)=(Li((H3C)2NCH2)2)((C5H5)V(C3H5)2)

201230-82-2

carbon monoxide

A

tetracarbonyl(η(5)-cyclopentadienyl)vanadium(I)

B

592-42-7

1,5-Hexadien

C

110-18-9

N,N,N,N,-tetramethylethylenediamine

D

dilithium (η-cyclopentadienyl)tri(carbonyl)vanadate

Conditions
ConditionsYield
In tetrahydrofuran reaction of CO with (LiTMEDA)(CpV(C3H5)2) in THF (Ar); formation of 1,5-hexadiene in the reaction soln., extn. of the residue with toluene, filtering off the solid and drying to give Li2(CpV(CO)3), evapn. of the filtrate to dryness and subliming the residue in a high vacuum at 80°C to give CpV(CO)4;A 91%
B 46%
C n/a
D n/a
366-18-7

[2,2]bipyridinyl

[(N,N,N′,N′-tetramethylethylenediamine)Ni{CH2C(CH3)C(CH3)CH2COO}]

A

(CH2C(CH3)C(CH3)CH2COO)Ni((C5H4N)2)

B

110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
In diethyl ether vigorously stirring a suspension of (3,4,5-η3)-3,4-dimethyl-3-pentenylato-N,N,N',N'-tetramethylethylenediaminenickel(II) in ether with 2,2'-bipyridine (CO2 or Ar); filtn. of the formed brown yellow ppt. after 24 h, shaking with THF fora few hours, filtn. and washing the residue with ether, drying in vacuo, elem. anal.;A 90%
B n/a

Roussin's red salt dianion

C6H16N2*2HNO(1-)*Fe(2+)

A

110-18-9

N,N,N,N,-tetramethylethylenediamine

B

Fe4H2N8O8S2(2-)

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.333333h; Inert atmosphere; Schlenk technique;A n/a
B 86%
141-46-8

Glycolaldehyde

124-40-3

dimethyl amine

A

108-01-0

2-(N,N-dimethylamino)ethanol

B

110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
With platinum on carbon; hydrogen In ethanol at 25℃; under 30003 Torr; for 12h; Solvent; Pressure; Reagent/catalyst; Autoclave;A 84%
B 8%
With 5%-palladium/activated carbon; hydrogen In ethanol at 25 - 80℃; under 30003 Torr; for 3h; Autoclave;A 35%
B 40%
1020084-83-6

[4-Et(C6H4)C(NSiMe3)2]Li(TMEDA)

10026-11-6

zirconium(IV) chloride

A

110-18-9

N,N,N,N,-tetramethylethylenediamine

cis-[4-Et(C6H4)C(NSiMe3)2]2ZrCl2

C

lithium chloride

Conditions
ConditionsYield
In toluene at 0℃; for 3h; Cooling; Schlenk technique;A n/a
B 83%
C n/a
1020084-88-1

[2-OMe(C6H4)C(NSiMe3)2]Li(TMEDA)

10026-11-6

zirconium(IV) chloride

A

110-18-9

N,N,N,N,-tetramethylethylenediamine

cis-[2-OMe(C6H4)C(NSiMe3)2]2ZrCl2

C

lithium chloride

Conditions
ConditionsYield
In toluene at 0℃; for 3h; Cooling; Schlenk technique;A n/a
B 82%
C n/a

N,N,N',N'-Tetramethylethylenediamine Chemical Properties

Molecular formula: C6H16N2
Molar mass: 116.24 g/mol 
EINECS: 203-744-6 
Index of Refraction: 1.437
Density: 0.817 g/cm3
Flash Point: 10 °C
Sensitive: Hygroscopic
Melting point: -55 °C(lit.)
Storage tempreture: Store at RT.
Water solubility: Miscible
Enthalpy of Vaporization: 35.91 kJ/mol
Boiling Point: 121 °C at 760 mmHg
Vapour Pressure: 14.9 mmHg at 25 °C
Solubility: H2O: 10 mg/mL at 20 °C, clear, colorless
Appearance: Colorless to slightly yellow liquid
Structure of N,N,N',N'-Tetramethylethylenediamine (CAS NO.110-18-9):
                      
Product Category of N,N,N',N'-Tetramethylethylenediamine (CAS NO.110-18-9): Biochemistry;Reagents for Electrophoresis

N,N,N',N'-Tetramethylethylenediamine Uses

 N,N,N',N'-Tetramethylethylenediamine (CAS NO.110-18-9) is widely used as a ligand for metal ions. It is used with ammonium persulfate to catalyze the polymerization of acrylamide when making polyacrylamide gels, and can be used in gel electrophoresis for the separation of proteins or nucleic acids.

N,N,N',N'-Tetramethylethylenediamine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 630mg/kg (630mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(6), Pg. 55, 1984.
quail LD50 oral > 316mg/kg (316mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rabbit LD50 skin 5390mg/kg (5390mg/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
rabbit LD50 subcutaneous 1230mg/kg (1230mg/kg)   Toxicologist. Vol. 15, Pg. 19, 1995.
rat LC50 inhalation 1318ppm/4H (1318ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
BEHAVIORAL: ATAXIA
BEHAVIORAL: IRRITABILITY
Toxicologist. Vol. 8, Pg. 249, 1988.
rat LD50 oral 268mg/kg (268mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES
SPINAL CORD: OTHER DEGENERATIVE CHANGES
Toxicologist. Vol. 15, Pg. 19, 1995.

N,N,N',N'-Tetramethylethylenediamine Consensus Reports

Reported in EPA TSCA Inventory.

N,N,N',N'-Tetramethylethylenediamine Safety Profile

Moderately toxic by ingestion. Mildly toxic by skin contact. A skin and severe eye irritant. Flammable when exposed to heat or flame; can react with oxidizing materials. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.
Hazard Codes: FlammableF,CorrosiveC,IrritantXi
Risk Statements: 11-20/22-34-20/21/22 
R11:Highly flammable. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R20/22:Harmful by inhalation and if swallowed. 
R34:Causes burns.
Safety Statements: 16-26-36/37/39-45 
S16:Keep away from sources of ignition. 
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.)

N,N,N',N'-Tetramethylethylenediamine Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

N,N,N',N'-Tetramethylethylenediamine Specification

 N,N,N',N'-Tetramethylethylenediamine , its cas register number is 110-18-9. It also can be called 1,2-Di(dimethylamino)ethane ; TMEDA ; and TEMED . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately.

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