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  • 110-18-9 Structure
  • Basic information

    1. Product Name: N,N,N',N'-Tetramethylethylenediamine
    2. Synonyms: N1,N1,N2,N2-tetraMethylethane-1,2-diaMine;N,N,N',N'-Tetramethylethane-1,2-diamine, electrophoresis grade;1,2-EthanediaMine,N1,N1,N2,N2-tetraMethyl-;Four MethylEthylenediaMine;N,N,N',N'-TetraMethylethylenediaMine >=99.5%, purified by redistillation;N,N,N',N'-TetraMethylethylenediaMine ReagentPlus(R), 99%;N,N,N',N'-Tetramethylethylenediamine Vetec(TM) reagent grade, >=99%;AZINPHOS METHYL NEAT
    3. CAS NO:110-18-9
    4. Molecular Formula: C6H16N2
    5. Molecular Weight: 116.2
    6. EINECS: 203-744-6
    7. Product Categories: Intermediates;Pyridines;Biochemistry;Reagents for Electrophoresis;Aliphatics;Amines
    8. Mol File: 110-18-9.mol
    9. Article Data: 47
  • Chemical Properties

    1. Melting Point: −55 °C(lit.)
    2. Boiling Point: 120-122 °C(lit.)
    3. Flash Point: 50 °F
    4. Appearance: Clear colorless to slightly yellow/Liquid
    5. Density: 0.775 g/mL at 20 °C(lit.)
    6. Vapor Density: 4 (vs air)
    7. Vapor Pressure: 21 hPa (20 °C)
    8. Refractive Index: n20/D 1.4179(lit.)
    9. Storage Temp.: Store at RT.
    10. Solubility: H2O: 10 mg/mL at 20 °C, clear, colorless
    11. PKA: 10.40, 8.26(at 25℃)
    12. Explosive Limit: 1-9%(V)
    13. Water Solubility: miscible
    14. Sensitive: Hygroscopic
    15. Stability: Stable. Highly flammable. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, copper, mercury.
    16. Merck: 14,9134
    17. BRN: 1732991
    18. CAS DataBase Reference: N,N,N',N'-Tetramethylethylenediamine(CAS DataBase Reference)
    19. NIST Chemistry Reference: N,N,N',N'-Tetramethylethylenediamine(110-18-9)
    20. EPA Substance Registry System: N,N,N',N'-Tetramethylethylenediamine(110-18-9)
  • Safety Data

    1. Hazard Codes: F,C,Xi
    2. Statements: 11-20/22-34-20/21/22
    3. Safety Statements: 16-26-36/37/39-45
    4. RIDADR: UN 2372 3/PG 2
    5. WGK Germany: 1
    6. RTECS: KV7175000
    7. F: 3-8-10-34
    8. TSCA: Yes
    9. HazardClass: 3
    10. PackingGroup: II
    11. Hazardous Substances Data: 110-18-9(Hazardous Substances Data)

110-18-9 Usage

Description

N,N,N',N'-Tetramethylethylenediamine, also known as Tetramethylethylenediamine (TMEDA), is an ethylenediamine derivative in which each nitrogen carries two methyl substituents. It is a water-white colored liquid with a fish-like odor and has a flash point of 68°F. TMEDA is less dense than water, and its vapors are heavier than air. It is widely employed both as a ligand for metal ions and as a catalyst in organic polymerization.

Uses

Used in Gel Electrophoresis:
N,N,N',N'-Tetramethylethylenediamine is used as a polymerization accelerator in gel electrophoresis, enhancing the process and improving the separation of DNA fragments.
Used in Chemical Synthesis:
TMEDA serves as a solvent and oxidizing reagent in various chemical reactions, facilitating the synthesis of different compounds.
Used in Pharmaceutical Industry:
N,N,N',N'-Tetramethylethylenediamine is used as an anti-hyperlipidemic agent, helping to lower high levels of lipids in the blood and reducing the risk of cardiovascular diseases.
Used in Agriculture:
TMEDA acts as a plant growth stimulator, promoting the growth and development of plants. It also functions as a pathogen growth inhibitor, protecting plants from harmful pathogens, and conferring plant disease resistance.
Used in Chemical Production:
N,N,N',N'-Tetramethylethylenediamine is used to make other chemicals, contributing to the synthesis of various compounds in the chemical industry.
Chemical Properties:
TMEDA is a colorless to slightly yellow liquid, which is less dense than water and has vapors heavier than air.

Air & Water Reactions

Highly flammable. Slightly soluble in water. Sensitive to heat and may be sensitive to air .

Reactivity Profile

N,N,N',N'-Tetramethylethylenediamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion. Mddly toxic by slun 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 MINES.

Purification Methods

Dry TMEDA partially with molecular sieves (Linde type 4A), then distil it in a vacuum from butyl lithium. This treatment removes all traces of primary and secondary amines and water. [Hay et al. J Chem Soc, Faraday Trans 1 68 1 1972.] Or dry it with KOH pellets, reflux for 2hours with one-sixth its weight of n-butyric anhydride (to remove primary and secondary amines) and fractionally distil it. Reflux it with fresh KOH, and distil it under nitrogen. [Cram & Wilson J Am Chem Soc 85 1245 1963.] It was also distilled from Na. Store it sealed under N2. The dipicrate has m 263o(dec). [Beilstein 4 H 250, 4 I 415, 4 II 690, 4 III 512, 4 IV 1172.]

Check Digit Verification of cas no

The CAS Registry Mumber 110-18-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 110-18:
(5*1)+(4*1)+(3*0)+(2*1)+(1*8)=19
19 % 10 = 9
So 110-18-9 is a valid CAS Registry Number.

110-18-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • TCI America

  • (T0147)  N,N,N',N'-Tetramethylethylenediamine  >98.0%(GC)(T)

  • 110-18-9

  • 25mL

  • 80.00CNY

  • Detail
  • TCI America

  • (T0147)  N,N,N',N'-Tetramethylethylenediamine  >98.0%(GC)(T)

  • 110-18-9

  • 100mL

  • 165.00CNY

  • Detail
  • TCI America

  • (T0147)  N,N,N',N'-Tetramethylethylenediamine  >98.0%(GC)(T)

  • 110-18-9

  • 500mL

  • 380.00CNY

  • Detail
  • Alfa Aesar

  • (A12536)  N,N,N',N'-Tetramethylethylenediamine, 99%   

  • 110-18-9

  • 100ml

  • 227.0CNY

  • Detail
  • Alfa Aesar

  • (A12536)  N,N,N',N'-Tetramethylethylenediamine, 99%   

  • 110-18-9

  • 500ml

  • 722.0CNY

  • Detail
  • Alfa Aesar

  • (A12536)  N,N,N',N'-Tetramethylethylenediamine, 99%   

  • 110-18-9

  • 2500ml

  • 3072.0CNY

  • Detail
  • Aldrich

  • (411019)  N,N,N′,N′-Tetramethylethylenediamine  ≥99.5%, purified by redistillation

  • 110-18-9

  • 411019-100ML

  • 872.82CNY

  • Detail
  • Aldrich

  • (411019)  N,N,N′,N′-Tetramethylethylenediamine  ≥99.5%, purified by redistillation

  • 110-18-9

  • 411019-1L

  • 5,136.30CNY

  • Detail
  • Aldrich

  • (411019)  N,N,N′,N′-Tetramethylethylenediamine  ≥99.5%, purified by redistillation

  • 110-18-9

  • 411019-2L

  • 8,693.10CNY

  • Detail

110-18-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N,N',N'-tetramethylethylenediamine

1.2 Other means of identification

Product number -
Other names Tetrameen

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Functional fluids (open systems),Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:110-18-9 SDS

110-18-9Synthetic route

dimethyl amine
124-40-3

dimethyl amine

ethylene dibromide
106-93-4

ethylene dibromide

N,N,N,N,-tetramethylethylenediamine
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%
dimethyl amine
124-40-3

dimethyl amine

acetylene
74-86-2

acetylene

N,N,N,N,-tetramethylethylenediamine
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%
formaldehyd
50-00-0

formaldehyd

ethylenediamine
107-15-3

ethylenediamine

N,N,N,N,-tetramethylethylenediamine
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;
methanol
67-56-1

methanol

ethylenediamine
107-15-3

ethylenediamine

N,N,N,N,-tetramethylethylenediamine
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%
Li(1+)*((H3C)2NCH2)2*(C5H5)V(C3H5)2(1-)=(Li((H3C)2NCH2)2)((C5H5)V(C3H5)2)
89184-58-7

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

carbon monoxide
201230-82-2

carbon monoxide

A

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

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

B

1,5-Hexadien
592-42-7

1,5-Hexadien

C

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

D

dilithium (η-cyclopentadienyl)tri(carbonyl)vanadate

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
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

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

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

A

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

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

B

N,N,N,N,-tetramethylethylenediamine
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

Roussin's red salt dianion

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

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

A

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

B

Fe4H2N8O8S2(2-)

Fe4H2N8O8S2(2-)

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

Glycolaldehyde

dimethyl amine
124-40-3

dimethyl amine

A

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

2-(N,N-dimethylamino)ethanol

B

N,N,N,N,-tetramethylethylenediamine
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%
[4-Et(C6H4)C(NSiMe3)2]Li(TMEDA)
1020084-83-6

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

zirconium(IV) chloride
10026-11-6

zirconium(IV) chloride

A

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

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

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

C

lithium chloride

lithium chloride

Conditions
ConditionsYield
In toluene at 0℃; for 3h; Cooling; Schlenk technique;A n/a
B 83%
C n/a
[2-OMe(C6H4)C(NSiMe3)2]Li(TMEDA)
1020084-88-1

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

zirconium(IV) chloride
10026-11-6

zirconium(IV) chloride

A

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

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

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

C

lithium chloride

lithium chloride

Conditions
ConditionsYield
In toluene at 0℃; for 3h; Cooling; Schlenk technique;A n/a
B 82%
C n/a
[3-OMe(C6H4)C(NSiMe3)2]Li(TMEDA)

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

zirconium(IV) chloride
10026-11-6

zirconium(IV) chloride

A

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

cis-[3-OMe(C6H4)C(NSiMe3)2]2ZrCl2

cis-[3-OMe(C6H4)C(NSiMe3)2]2ZrCl2

C

lithium chloride

lithium chloride

Conditions
ConditionsYield
In toluene at 0℃; for 3h; Cooling; Schlenk technique;A n/a
B 79%
C n/a
[4-OMe(C6H4)C(NSiMe3)2]Li(TMEDA)
1020084-86-9

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

zirconium(IV) chloride
10026-11-6

zirconium(IV) chloride

A

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

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

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

C

lithium chloride

lithium chloride

Conditions
ConditionsYield
In toluene at 0℃; for 3h; Cooling; Schlenk technique;A n/a
B 78%
C n/a
[4-n-Bu(C6H4)C(NSiMe3)2]Li(TMEDA)
1020084-84-7

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

zirconium(IV) chloride
10026-11-6

zirconium(IV) chloride

A

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

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

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

C

lithium chloride

lithium chloride

Conditions
ConditionsYield
In toluene at 0℃; for 3h; Cooling; Schlenk technique;A n/a
B 70%
C n/a
[(3-C4H3O)C(NSiMe3)2]Li(TMEDA)
1206534-47-5

[(3-C4H3O)C(NSiMe3)2]Li(TMEDA)

zirconium(IV) chloride
10026-11-6

zirconium(IV) chloride

A

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

B

cis-[(3-C4H3O)C(NSiMe3)2]2ZrCl2

cis-[(3-C4H3O)C(NSiMe3)2]2ZrCl2

C

lithium chloride

lithium chloride

Conditions
ConditionsYield
In toluene at 0℃; for 3h; Cooling; Schlenk technique;A n/a
B 68%
C n/a
(tetramethylethylenediamine)lithium trihydro(2,4,6-tri-tert-butylphenyl)borate
112506-19-1

(tetramethylethylenediamine)lithium trihydro(2,4,6-tri-tert-butylphenyl)borate

A

5,7-di-tert-butylhydroxy-3,3-dimethyl-1-boraindane
112506-16-8

5,7-di-tert-butylhydroxy-3,3-dimethyl-1-boraindane

B

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
With hydrogenchloride; water In diethyl ether; water byproducts: H2, LiCl; addn. of HCl to ether soln. of borate (0°C), stirring (room temp., 1 h), aq. HCl addn.; drying of etheral phase (Na2SO4), solvent removal (vacuum), repptn. (pentane); elem. anal.;A 53%
B n/a
(tetramethylethylenediamine)lithium trihydro(2,4,6-tri-tert-butylphenyl)borate
112506-19-1

(tetramethylethylenediamine)lithium trihydro(2,4,6-tri-tert-butylphenyl)borate

A

hydroxy(2,4,6-tri-tert-butylphenyl)borane
112506-15-7

hydroxy(2,4,6-tri-tert-butylphenyl)borane

B

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
With water In tert-butyl alcohol byproducts: H2, LiOH; stirring (0°C, 6h, room temp., 12 h); solvent removal (vacuum), addn. of ether/water, drying of ether phase (Na2SO4), solvent removal (vacuum), recrystn. (pentane); elem. anal.;A 36%
B n/a
(2-hydroxyethyl)(methyl)amine
109-83-1

(2-hydroxyethyl)(methyl)amine

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
With methanol; nickel at 175 - 200℃; under 40452.9 Torr; Hydrogenation;
formaldehyd
50-00-0

formaldehyd

ethylenediammonium sulfate
22029-36-3

ethylenediammonium sulfate

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
at 130 - 140℃; Destillation des Reaktionsprodukts mit Kalilauge;
sodium methylate
124-41-4

sodium methylate

4,5-epoxy-3,6-dimethoxy-17,17-dimethyl-morphina-6,8-dienium; iodide
19826-49-4

4,5-epoxy-3,6-dimethoxy-17,17-dimethyl-morphina-6,8-dienium; iodide

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

4,5-epoxy-6-hydroxy-3-methoxy-17,17-dimethyl-1-sulfo-morphinanium betaine

4,5-epoxy-6-hydroxy-3-methoxy-17,17-dimethyl-1-sulfo-morphinanium betaine

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
at 140℃; unter Druck;
dimethyl amine
124-40-3

dimethyl amine

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

2-(dimethylamino)ethyl chloride

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
With xylene
formaldehyd
50-00-0

formaldehyd

formic acid
64-18-6

formic acid

ethylenediamine
107-15-3

ethylenediamine

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

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

2-(dimethylamino)ethyl chloride

A

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

2-(N,N-dimethylamino)ethanol

B

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
With alkalies
ethene
74-85-1

ethene

dimethyl amine
124-40-3

dimethyl amine

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
Multistep reaction;
aminoethylpiperazine
140-31-8

aminoethylpiperazine

formaldehyd
50-00-0

formaldehyd

formic acid
64-18-6

formic acid

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

A

N,N'-dimethylpiperazine
106-58-1

N,N'-dimethylpiperazine

B

1,4-diaza-bicyclo[2.2.2]octane
280-57-9

1,4-diaza-bicyclo[2.2.2]octane

C

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

D

1-<2-(diethylamino)ethyl>-4-methylpiperazine

1-<2-(diethylamino)ethyl>-4-methylpiperazine

E

N,N'-dimethyl-N,N'-bis<2-(4-methyl-1-piperazinyl)ethyl>ethylenediamine

N,N'-dimethyl-N,N'-bis<2-(4-methyl-1-piperazinyl)ethyl>ethylenediamine

Conditions
ConditionsYield
Mechanism;
aminoethylpiperazine
140-31-8

aminoethylpiperazine

formaldehyd
50-00-0

formaldehyd

formic acid
64-18-6

formic acid

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

A

1,4-diaza-bicyclo[2.2.2]octane
280-57-9

1,4-diaza-bicyclo[2.2.2]octane

B

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

C

1-<2-(diethylamino)ethyl>-4-methylpiperazine

1-<2-(diethylamino)ethyl>-4-methylpiperazine

D

N,N'-dimethyl-N,N'-bis<2-(4-methyl-1-piperazinyl)ethyl>ethylenediamine

N,N'-dimethyl-N,N'-bis<2-(4-methyl-1-piperazinyl)ethyl>ethylenediamine

Conditions
ConditionsYield
Multistep reaction. Further byproducts given;
1,4,8,11-tetramethyl-1,4,8,11-tetra-azacyclotetradecane
41203-22-9

1,4,8,11-tetramethyl-1,4,8,11-tetra-azacyclotetradecane

9-(n-propyl)fluorenyllithium tetramethylenediamine complex

9-(n-propyl)fluorenyllithium tetramethylenediamine complex

A

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

B

9-(n-propyl)fluorenyllithium hexamethyltetraazacyclotetradecane complex

9-(n-propyl)fluorenyllithium hexamethyltetraazacyclotetradecane complex

Conditions
ConditionsYield
In toluene at 25℃; Rate constant;
(1-ethyl-propenyl)-dimethyl-amine
32317-47-8

(1-ethyl-propenyl)-dimethyl-amine

N,N,N',N'-tetramethyl-1,2-diaminoethane-H+
71889-99-1

N,N,N',N'-tetramethyl-1,2-diaminoethane-H+

A

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

B

C7H15N*H(1+)

C7H15N*H(1+)

Conditions
ConditionsYield
ICR double resonance, proton affinity;
N,N-Dimethylisobutenylamin
20916-47-6

N,N-Dimethylisobutenylamin

N,N,N',N'-tetramethyl-1,2-diaminoethane-H+
71889-99-1

N,N,N',N'-tetramethyl-1,2-diaminoethane-H+

A

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

B

C6H13N*H(1+)

C6H13N*H(1+)

Conditions
ConditionsYield
ICR double resonance, proton affinity;
ethylene glycol
107-21-1

ethylene glycol

dimethyl amine
124-40-3

dimethyl amine

A

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

2-(N,N-dimethylamino)ethanol

B

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

Conditions
ConditionsYield
With tris(triphenylphosphine)ruthenium(II) chloride at 120℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With ruthenium trichloride at 120℃; for 2.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

allylmagnesium bromide
2622-05-1

allylmagnesium bromide

Bis(allylmagnesiumchlorid-TMEDA)

Bis(allylmagnesiumchlorid-TMEDA)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 12h;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

C5H7BrMg*2C4H8O

C5H7BrMg*2C4H8O

C6H16N2*C5H7BrMg

C6H16N2*C5H7BrMg

Conditions
ConditionsYield
In tetrahydrofuran; pentane for 2h; Ambient temperature;100%
tetrahydrofuran
109-99-9

tetrahydrofuran

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

diphenylphosphane
829-85-6

diphenylphosphane

4C12H10PTe2(1-)*C6H16N2*14C4H8O*4Li(1+)

4C12H10PTe2(1-)*C6H16N2*14C4H8O*4Li(1+)

Conditions
ConditionsYield
Stage #1: tetrahydrofuran; N,N,N,N,-tetramethylethylenediamine; diphenylphosphane With n-butyllithium In tetrahydrofuran; hexane
Stage #2: With tellurium In tetrahydrofuran; hexane at -78 - 20℃;
100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

triphenyltin chloride
639-58-7

triphenyltin chloride

Ph3SnZnCl * N,N,N',N'-tetramethylethylenediamine

Ph3SnZnCl * N,N,N',N'-tetramethylethylenediamine

Conditions
ConditionsYield
In acetonitrile; benzene Electrolysis; absence of oxygen and moisture; W-cathode, Zn suspended on Pt-anode, 30 V, 25 mA, 3.0 h, Et4NClO4 electrolyte; sepn. of pptd. product (further crop on addn. of petroleum ether), washing (petroleum ether), drying (vac.); elem. anal.;100%
bis(η3-allyl-μ-chloropalladium(II))

bis(η3-allyl-μ-chloropalladium(II))

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

[η**3-2-propenyl](N,N,N',N'-tetramethylethylenediamine)palladium(II) dichloro(η**3-2-propenyl)palladate(II)
80533-23-9

[η**3-2-propenyl](N,N,N',N'-tetramethylethylenediamine)palladium(II) dichloro(η**3-2-propenyl)palladate(II)

Conditions
ConditionsYield
In acetone TMEDA added to -50°C soln.; stirred 1 h at -50°C; solvent vac. removed; recrystd. from acetone/toluene at -20°C; elem. anal.;100%
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

A

(N,N,N',N'-tetramethylethylenediamine)tetracarbonylmolybdenum(0)
23301-98-6

(N,N,N',N'-tetramethylethylenediamine)tetracarbonylmolybdenum(0)

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
{Li(μ-OB(CH(SiMe3)2)2}2

{Li(μ-OB(CH(SiMe3)2)2}2

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

LiOB(CH(SiMe3)2)2((Me2NCH2)2)
127161-53-9

LiOB(CH(SiMe3)2)2((Me2NCH2)2)

Conditions
ConditionsYield
In hexane react. at 25°C; filtering, filtrate at -20°C;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

titanium tetrachloride
7550-45-0

titanium tetrachloride

tetrachloro(N,N,N',N'-tetramethylethane-1,2-diamine)titanium(IV)
19033-22-8

tetrachloro(N,N,N',N'-tetramethylethane-1,2-diamine)titanium(IV)

Conditions
ConditionsYield
In hexane at 0℃; for 1h; Inert atmosphere;100%
In benzene solns. mixed at 10-20°C; filtered, washed (benzene), dried (vac.); elem. anal.;>99
In pentane solns. mixed at 10-20°C; filtered, washed (pentane), dried (vac.); elem. anal.;>99
aluminium hydride

aluminium hydride

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

N,N,N',N',-tetramethylethylenediamine*2AlH3
72049-53-7

N,N,N',N',-tetramethylethylenediamine*2AlH3

Conditions
ConditionsYield
In diethyl ether at 25°C; ppt. collected by centrifugation, washed with Et2O, dried, elem. anal.;100%
(cyclooctadienyl)(cyclopentadienyl)ruthenium chloride

(cyclooctadienyl)(cyclopentadienyl)ruthenium chloride

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

[(η5-C5H5)RuCl(N,N,N',N'-tetramethylethylenediamine)]
260066-12-4

[(η5-C5H5)RuCl(N,N,N',N'-tetramethylethylenediamine)]

Conditions
ConditionsYield
In acetone soln. of Ru-complex and ligand in acetone was stirred at room temp. for 2 h under Ar; solvent was removed under vac., washed with pentane;100%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

bis(dibenzylideneacetone)-palladium(0)
32005-36-0

bis(dibenzylideneacetone)-palladium(0)

PdI(4-NO2C6H4)(N,N,N',N'-tetramethylethylenediamine)
191667-18-2

PdI(4-NO2C6H4)(N,N,N',N'-tetramethylethylenediamine)

Conditions
ConditionsYield
In not given byproducts: dibenzylideneacetone; N2-atmosphere; according to Markies, A. J. et al.: J. Organomet. Chem. 482 (1994) 191; elem. anal.;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

4-Iodoacetophenone
13329-40-3

4-Iodoacetophenone

bis(dibenzylideneacetone)-palladium(0)
32005-36-0

bis(dibenzylideneacetone)-palladium(0)

PdI(4-MeCOC6H4)(N,N,N',N'-tetramethylethylenediamine)
191667-17-1

PdI(4-MeCOC6H4)(N,N,N',N'-tetramethylethylenediamine)

Conditions
ConditionsYield
In not given byproducts: dibenzylideneacetone; N2-atmosphere; according to Markies, A. J. et al.: J. Organomet. Chem. 482 (1994) 191; elem. anal.;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

di-μ-chloro-bis[η**3-2-butenyl]dipalladium

di-μ-chloro-bis[η**3-2-butenyl]dipalladium

[(η**3-2-butenyl)(N,N,N',N'-tetramethylethylenediamine)palladium(II)] dichloro(η**3-2-butenyl)palladate

[(η**3-2-butenyl)(N,N,N',N'-tetramethylethylenediamine)palladium(II)] dichloro(η**3-2-butenyl)palladate

Conditions
ConditionsYield
In acetone TMEDA added dropwise at -50°C, stirred 1 h at -50°C; solvent vac. evapd.; trituration with ether, dried in vac.; elem. anal.;100%
silver tetrafluoroborate
14104-20-2

silver tetrafluoroborate

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

di-μ-chloro-bis[η**3-2-butenyl]dipalladium

di-μ-chloro-bis[η**3-2-butenyl]dipalladium

[η**3-2-butenyl](N,N,N',N'-tetramethylethylenediamine)palladium(II) tetrafluoroborate

[η**3-2-butenyl](N,N,N',N'-tetramethylethylenediamine)palladium(II) tetrafluoroborate

Conditions
ConditionsYield
In tetrahydrofuran byproducts: AgCl; π-2-butenylpalladium chloride dimer dissolved in THF; AgBF4 added; stirred 10 min; AgCl removed and washed with THF; TMEDA added dropwise toTHF extracts, stirred 10 min; solvent vac. removed; elem. anal.;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

di-μ-chloro-bis[η**3-3-phenyl-2-propenyl]dipalladium

di-μ-chloro-bis[η**3-3-phenyl-2-propenyl]dipalladium

[η**3-3-phenyl-2-propenyl](N,N,N',N'-tetramethylethylenediamine)palladium(II) dichloro(η**3-3-phenyl-2-propenyl)palladate(II)

[η**3-3-phenyl-2-propenyl](N,N,N',N'-tetramethylethylenediamine)palladium(II) dichloro(η**3-3-phenyl-2-propenyl)palladate(II)

Conditions
ConditionsYield
In acetone TMEDA added dropwise to -50°C soln.; stirred 1 h at -50°C; solvent vac. removed; elem. anal.;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

3,5-bis(3,5-dimethoxybenzocarboxymethyl)benzyl bromide
176650-93-4

3,5-bis(3,5-dimethoxybenzocarboxymethyl)benzyl bromide

N,N'-ethane-1,2-diyl N,N'-[3,5-bis(3,5-dimethoxybenzyloxy)benzyloxy] N,N,N',N'-tetramethylammonium dibromide

N,N'-ethane-1,2-diyl N,N'-[3,5-bis(3,5-dimethoxybenzyloxy)benzyloxy] N,N,N',N'-tetramethylammonium dibromide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 70℃; Inert atmosphere;100%
In N,N-dimethyl-formamide at 70℃; for 15h; Inert atmosphere;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

ThCl4(dimethoxyethane)2

ThCl4(dimethoxyethane)2

ThCl4(N,N-tetramethylethylenediamine)2

ThCl4(N,N-tetramethylethylenediamine)2

Conditions
ConditionsYield
In tetrahydrofuran excess N,N-tetramethylethylenediamine;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

[ThCl4(1,2-dimethoxyethane)2]
639084-65-4

[ThCl4(1,2-dimethoxyethane)2]

ThCl4(Me2NCH2CH2NMe2)2
159472-32-9

ThCl4(Me2NCH2CH2NMe2)2

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.5h;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

[Zr(C5H4NC(CH3)(CH2NSitBuMe2)2)(NNPh2)(Li(py))(phenylacetylene(-1H))]

[Zr(C5H4NC(CH3)(CH2NSitBuMe2)2)(NNPh2)(Li(py))(phenylacetylene(-1H))]

[Zr(C5H4NC(CH3)(CH2NSitBuMe2)2)(NNPh2)(Li(tetramethylethylenediamine))(phenylacetylene(-1H))]

[Zr(C5H4NC(CH3)(CH2NSitBuMe2)2)(NNPh2)(Li(tetramethylethylenediamine))(phenylacetylene(-1H))]

Conditions
ConditionsYield
In toluene at 20℃;100%
iodotrifluoromethane
2314-97-8

iodotrifluoromethane

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

2CF3I*C6H16N2

2CF3I*C6H16N2

Conditions
ConditionsYield
at -78℃; for 0.333333h; Schlenk technique; Inert atmosphere; Reflux;100%
at -78℃; for 0.333333h; Inert atmosphere; Reflux;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

2-bromo-N-hexylethanamide
5439-32-7

2-bromo-N-hexylethanamide

C22H48N4O2(2+)*2Br(1-)

C22H48N4O2(2+)*2Br(1-)

Conditions
ConditionsYield
In chloroform at 85℃; for 24h;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

2-Bromo-N-(n-octyl)acetamide
5326-97-6

2-Bromo-N-(n-octyl)acetamide

C26H56N4O2(2+)*2Br(1-)

C26H56N4O2(2+)*2Br(1-)

Conditions
ConditionsYield
In chloroform at 85℃; for 24h;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

2-bromo-N-decyl-acetamide
5345-68-6

2-bromo-N-decyl-acetamide

C30H64N4O2(2+)*2Br(1-)

C30H64N4O2(2+)*2Br(1-)

Conditions
ConditionsYield
In chloroform at 85℃; for 24h;100%
In acetonitrile for 1h; Reflux;44%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

[(tris(tert-butoxy)siloxy)2chromium(II)]2

[(tris(tert-butoxy)siloxy)2chromium(II)]2

[chromium(II)(tris(tert-butoxy)siloxy)2(N,N,N′,N′-tetramethylethylenediamine)]

[chromium(II)(tris(tert-butoxy)siloxy)2(N,N,N′,N′-tetramethylethylenediamine)]

Conditions
ConditionsYield
In hexane at 25℃; Inert atmosphere; Glovebox;100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

C38H68Li2N6O2

C38H68Li2N6O2

C21H40LiN5

C21H40LiN5

Conditions
ConditionsYield
In diethyl ether for 1h;100%
2-ethylhexyl bromide
18908-66-2

2-ethylhexyl bromide

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

N-(2-(dimethylamino)ethyl)-2-ethyl-N,N-dimethylhexan-1-aminium bromide

N-(2-(dimethylamino)ethyl)-2-ethyl-N,N-dimethylhexan-1-aminium bromide

Conditions
ConditionsYield
for 12h; Reflux;100%
1,3,5-tris(1-imidazolyl)benzene

1,3,5-tris(1-imidazolyl)benzene

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

2H2NO3(1-)*(x)H2O*Pd(2+)

2H2NO3(1-)*(x)H2O*Pd(2+)

C96H144N36Pd6

C96H144N36Pd6

Conditions
ConditionsYield
Stage #1: N,N,N,N,-tetramethylethylenediamine; 2H2NO3(1-)*(x)H2O*Pd(2+) In dimethyl sulfoxide at 80℃; for 0.166667h;
Stage #2: 1,3,5-tris(1-imidazolyl)benzene In dimethyl sulfoxide at 80℃; for 2h;
100%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

4-(bromomethyl)benzophenone
32752-54-8

4-(bromomethyl)benzophenone

ethylenebis(4-benzoylbenzyldimethylammonium) dibromide

ethylenebis(4-benzoylbenzyldimethylammonium) dibromide

Conditions
ConditionsYield
In chloroform at 20℃; for 72h;99.7%
In chloroform at 20℃; for 72h;99.7%
In chloroform
nido-NB10H13

nido-NB10H13

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Li(1+)*2(CH3)2N(CH2)2N(CH3)2*{NB10H12}(1-)={Li((CH3)2N(CH2)2N(CH3)2)2}{NB10H12}

Li(1+)*2(CH3)2N(CH2)2N(CH3)2*{NB10H12}(1-)={Li((CH3)2N(CH2)2N(CH3)2)2}{NB10H12}

Conditions
ConditionsYield
In tetrahydrofuran byproducts: B(C2H5)3, H2; addn. of Li(BHEt3) in THF to soln. of the borane at -78°C, stirred for 5 min at room temp., volatiles removed in vac., addn. of THF, addn. of tmeda;; concentrated, washed three times with pentane, dried;;99%

110-18-9Relevant articles and documents

Copper(I) halide complexes with N,N′-diallyl-N,N,N′,N′- tetramethylethylenediaminium (L2+). Synthesis and crystal structures of the complexes [L0.5CuCl2], [L0.5CuCl 0.72Br1.28], and [L0.5CuBr2]

Monchak,Goreshnik,Mys'Kiv

, p. 143 - 148 (2011)

The Eschweiler-Clarke reaction of ethylenediamine with formaldehyde and formic acid yielded N,N,N′,N′-tetramethylethylenediamine, which was alkylated with allyl chloride or allyl bromide to give the corresponding N,N′-diallyl-N,N,N′,N′-tetramethylethylenediaminium (L 2+) dihalides. In methanolic solutions of copper(II) halide and an appropriate ligand, ac electrochemical synthesis with copper wire electrodes afforded single crystals of Cu(I) complexes with L2+: [L 0.5CuCl2] (I), [L0.5CuCl0.72Br 1.28] (II), and [L0.5CuBr2] (III). The crystal structures of complexes I-III were determined by X-ray diffraction study. The isostructural crystals of I and II are monoclinic, space group P21/n, Z = 4. For I: a = 7.632(4) A, b = 11.318(5) A, c = 10.635(5) A, β = 98.551(7)°, V = 908.4(7) A3. For II: a = 7.7415(7) A, b = 11.4652(9) A, c = 10.7267(10) A, β = 98.351(4)°, V = 942.0(2) A3. The organic cation L 2+ acts as a bridge linking a pair of separate cuprous halide fragments Cu2X4. Although being isostoichiometric with I and II, complex III has a different structure. The crystals of III are monoclinic, space group P21/c, a = 6.519(2) A, b = 9.060(3) A, c = 16.284(6) A, β = 97.219(4)°, V = 954.2(6) A3, Z = 4. In structure III, the inorganic fragment forms infinite polymer chains (CuBr 2 - ) n . The organic and inorganic parts are held together only by electrostatic interactions. Structures I-III are stabilized by hydrogen bonds (C)H...X (2.6-2.9 A).

Brown,Newton

, p. 1117,1118-1120 (1966)

Cleavable cationic antibacterial amphiphiles: Synthesis, mechanism of action, and cytotoxicities

Hoque, Jiaul,Akkapeddi, Padma,Yarlagadda, Venkateswarlu,Uppu, Divakara S. S. M.,Kumar, Pratik,Haldar, Jayanta

, p. 12225 - 12234 (2012)

The development of novel antimicrobial agents having high selectivity toward bacterial cells over mammalian cells is urgently required to curb the widespread emergence of infectious diseases caused by pathogenic bacteria. Toward this end, we have developed a set of cationic dimeric amphiphiles (bearing cleavable amide linkages between the headgroup and the hydrocarbon tail with different methylene spacers) that showed high antibacterial activity against human pathogenic bacteria (Escherichia coli and Staphylococcus aureus) and low cytotoxicity. The Minimum Inhibitory Concentrations (MIC) were found to be very low for the dimeric amphiphiles and were lower or comparable to the monomeric counterpart. In the case of dimeric amphiphiles, MIC was found to decrease with the increase in the spacer chain length (n = 2 to 6) and again to increase at higher spacer length (n > 6). It was found that the compound with six methylene spacers was the most active among all of the amphiphiles (MICs = 10-13 μM). By fluorescence spectroscopy, fluorescence microscopy, and field-emission scanning electron microscopy (FESEM), it was revealed that these cationic amphiphiles interact with the negatively charged bacterial cell membrane and disrupt the membrane integrity, thus killing the bacteria. All of the cationic amphiphiles showed low hemolytic activity (HC50) and high selectivity against both gram-positive and gram-negative bacteria. The most active amphiphile (n = 6) had a 10-13-fold higher HC50 than did the MIC. Also, this amphiphile did not show any cytotoxicity against mammalian cells (HeLa cells) even at a concentration above the MIC (20 μM). The critical micellar concentration (CMC) values of gemini surfactants were found to be very low (CMC = 0.30-0.11 mM) and were 10-27 times smaller than the corresponding monomeric analogue (CMC = 2.9 mM). Chemical hydrolysis and thermogravimetric analysis (TGA) proved that these amphiphiles are quite stable under both acidic and thermal conditions. Collectively, these properties make the newly synthesized amphiphiles potentially superior disinfectants and antiseptics for various biomedical and biotechnological applications.

Modulation spectroscopy. Kinetics for the self-reactions of some α-aminoalkyl radicals in solution

Marriott, Paul R.,Castelhano, Arlindo L.,Griller, David

, p. 274 - 278 (1982)

The optical spectra and reaction kinetics of some α-aminoalkyl radicals, RCHN(CH2R)2; R = H, Me, Ph, were measured in solution using the technique of modulation spectroscopy.These radicals undergo diffusion controlled self-reaction with rate constants ca. 109 M-1 s-1.When R=Ph, the absorption spectrum has a well defined maximum at 346 nm; ε = 3390 M-1 cm-1, while the spectra when R = H or Me were less intense (ε346nm ca. 500 M-1 cm-1) and tailed into the visible.These spectra are substantially red-shifted when compared with those of simple alkyl radicals, an effect which is thought to be due to the interaction between the unpaired electron and the lone pair of electrons on nitrogen.

Unusual reactivity patterns of 1,3,6,8-tetraazatricyclo-[4.4.1.1 3,8]-dodecane (TATD) towards some reducing agents: Synthesis of TMEDA

Rivera, Augusto,Rios-Motta, Jaime

, p. 1471 - 1481 (2007)

N,N,N′,N′-Tetramethylethylenediamine (TMEDA) can be synthesized by simple reduction of 1,3,6,8-tetraazatricyclo-[4.4.1.1.3,8] dodecane (TATD), an aminal cage type amine, with formic acid. The aminal can be converted to TMEDA in high yield very easily and in a very short time. We comment on the scope and limitations of the reduction of this aminal and propose a possible reaction mechanism.

COMPLEXES OF 9-PROPYLFLUORENYL ION PAIRS WITH TERTIARY POLYAMINES IN APOLAR SOLVENTS

Helary, G.,Lefevre-Jenot, L.,Fontanille, M.,Smid, J.

, p. 139 - 146 (1981)

The complexation of tetramethylethylenediamine (TMEDA), hexamethyltriethylenetetramine (HMTT) and tetramethyltetraazacyclotetradecane (TMTCT) with ion pairs of 9-(n-propyl)fluorenyllithium (PFl-, Li+) and n-butyl-9-(n-propyl)fluorenylmagnesium (BuPFlMg) in cyclohexane was studied by optical spectroscopy.The results can be explained in terms of externally complexed tight ion pairs and ligand-separated ion pairs, the latter complexes being much less soluble.With HMTT and PFl-, Li+, the only complexes formed are (PFl-, Li+)2 HMTT (λm 357 nm) and PFl-, HMTT, Li+ (λm 383 nm).The reaction of PFl-, Li+, TMEDA with TMTCT to form the loose ion pair complex PFl-, TMTCT, Li+ has a rate constant in toluene of 250 M-1 sec-1.With the magnesium compound, the amines form only a loose ion pair complex, e.g., BuMg+, TMEDA, PFl- (λm 382 nm).

Ginmanini et al.

, p. 484,485, 487 (1976)

A METHOD FOR PREPARING ALKYLATED AMINES

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Page/Page column 31; 32, (2021/09/11)

The present invention pertains to a method for preparing an alkylated amine by reacting a primary or secondary amine with an alcohol in the presence of hydrogen, a metal catalyst supported by photosensitive titanium oxide, and UV irradiation. Advantageously, the reaction can be carried out under mild reaction conditions.

Preparation method of tetramethylethylenediamine

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Paragraph 0051-0067, (2020/08/02)

The invention discloses a preparation method of tetramethylethylenediamine, and the method comprises the following steps: adding a pyrrolidone series solvent and composite catalyst TZOH into an autoclave, covering the autoclave with an autoclave cover, carrying out nitrogen displacement, introducing acetylene, introducing dimethylamine after the temperature is stable, heating the autoclave to 70-120 DEG C, and keeping the temperature for 3-8 hours; after the heat preservation is finished, cooling, discharging the residual pressure into the pyrrolidone series solvent, applying to the next batch, filtering materials in the autoclave, and recovering a catalyst; and rectifying mother liquor to obtain the product tetramethylethylenediamine; according to the method, the tetramethylethylenediamine can be prepared, basically no waste water or waste residue is generated, excessive raw materials, solvents and catalysts can be recycled, the element utilization rate is high, and compared with theprior art that a large amount of formaldehyde-containing waste water or industrial waste salt is generated, the environment-friendly advantage is obvious.

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