110-18-9

Basic information

• Product Name: N,N,N',N'-Tetramethylethylenediamine
• 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
• CAS NO: 110-18-9
• Molecular Formula: C₆H₁₆N₂
• Molecular Weight: 116.2
• EINECS: 203-744-6
• Product Categories: Intermediates;Pyridines;Biochemistry;Reagents for Electrophoresis;Aliphatics;Amines
• Mol File: 110-18-9.mol
• Article Data: 83

Chemical Properties

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

Safety Data

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

Usage

Chemical Properties

Colorless to slightly yellow liquid

Uses

N,N,N',N'-Tetramethylethylenediamine is used as polymerization accelerator in gel electrophoresis, solvent and oxidizing reagent.

Uses

anti-hyperlipidemic, plant growth stimulator, pathogen growth inhibitor, confers plant disease resistance

Uses

Polymerization accelerator in gel electrophoresis, solvent and oxidizing reagent.

Definition

ChEBI: An ethylenediamine derivative in which each nitrogen carries two methyl substituents. It is widely employed both as a ligand for metal ions and as a catalyst in organic polymerisation.

General Description

A water-white colored liquid with a fishlike odor. Flash point 68°F. Less dense than water. Vapors heavier than air. Used to make other chemicals.

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.]

Synthetic route

dimethyl amine (124-40-3) + ethylene dibromide (106-93-4) → N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 24h;	100%
In chloroform at 20℃; for 24h;	100%

dimethyl amine (124-40-3) + acetylene (74-86-2) → N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
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) + ethylenediamine (107-15-3) → N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
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) + ethylenediamine (107-15-3) → N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
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) + carbon monoxide (201230-82-2) → tetracarbonyl(η(5)-cyclopentadienyl)vanadium(I) + 1,5-Hexadien (592-42-7) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + dilithium (η-cyclopentadienyl)tri(carbonyl)vanadate

Conditions	Yield
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) + [(N,N,N′,N′-tetramethylethylenediamine)Ni{CH2C(CH3)C(CH3)CH2COO}] → (CH2C(CH3)C(CH3)CH2COO)Ni((C5H4N)2) + N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
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+) → N,N,N,N,-tetramethylethylenediamine (110-18-9) + Fe4H2N8O8S2(2-)

Conditions	Yield
In acetonitrile at 20℃; for 0.333333h; Inert atmosphere; Schlenk technique;	A n/a B 86%

Glycolaldehyde (141-46-8) + dimethyl amine (124-40-3) → 2-(N,N-dimethylamino)ethanol (108-01-0) + N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
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) + zirconium(IV) chloride (10026-11-6) → N,N,N,N,-tetramethylethylenediamine (110-18-9) + cis-[4-Et(C6H4)C(NSiMe3)2]2ZrCl2 + lithium chloride

Conditions	Yield
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) + zirconium(IV) chloride (10026-11-6) → N,N,N,N,-tetramethylethylenediamine (110-18-9) + cis-[2-OMe(C6H4)C(NSiMe3)2]2ZrCl2 + lithium chloride

Conditions	Yield
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) + zirconium(IV) chloride (10026-11-6) → N,N,N,N,-tetramethylethylenediamine (110-18-9) + cis-[3-OMe(C6H4)C(NSiMe3)2]2ZrCl2 + lithium chloride

Conditions	Yield
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) + zirconium(IV) chloride (10026-11-6) → N,N,N,N,-tetramethylethylenediamine (110-18-9) + cis-[4-OMe(C6H4)C(NSiMe3)2]2ZrCl2 + lithium chloride

Conditions	Yield
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) + zirconium(IV) chloride (10026-11-6) → N,N,N,N,-tetramethylethylenediamine (110-18-9) + cis-[4-n-Bu(C6H4)C(NSiMe3)2]2ZrCl2 + lithium chloride

Conditions	Yield
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) + zirconium(IV) chloride (10026-11-6) → N,N,N,N,-tetramethylethylenediamine (110-18-9) + cis-[(3-C4H3O)C(NSiMe3)2]2ZrCl2 + lithium chloride

Conditions	Yield
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) → 5,7-di-tert-butylhydroxy-3,3-dimethyl-1-boraindane (112506-16-8) + N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
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) → hydroxy(2,4,6-tri-tert-butylphenyl)borane (112506-15-7) + N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
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) → N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
With methanol; nickel at 175 - 200℃; under 40452.9 Torr; Hydrogenation;

formaldehyd (50-00-0) + ethylenediammonium sulfate (22029-36-3) → N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
at 130 - 140℃; Destillation des Reaktionsprodukts mit Kalilauge;

sodium methylate (124-41-4) + 4,5-epoxy-3,6-dimethoxy-17,17-dimethyl-morphina-6,8-dienium; iodide (19826-49-4) → N,N,N,N,-tetramethylethylenediamine (110-18-9)

4,5-epoxy-6-hydroxy-3-methoxy-17,17-dimethyl-1-sulfo-morphinanium betaine + furan-2,3,5(4H)-trione pyridine (1:1) → N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
at 140℃; unter Druck;

dimethyl amine (124-40-3) + 2-(dimethylamino)ethyl chloride (107-99-3) → N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
With xylene

formaldehyd (50-00-0) + formic acid (64-18-6) + ethylenediamine (107-15-3) → N,N,N,N,-tetramethylethylenediamine (110-18-9)

2-(dimethylamino)ethyl chloride (107-99-3) → 2-(N,N-dimethylamino)ethanol (108-01-0) + N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
With alkalies

ethene (74-85-1) + dimethyl amine (124-40-3) → N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
Multistep reaction;

aminoethylpiperazine (140-31-8) + formaldehyd (50-00-0) + formic acid (64-18-6) + 1,2-dichloro-ethane (107-06-2) → N,N'-dimethylpiperazine (106-58-1) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + 1-<2-(diethylamino)ethyl>-4-methylpiperazine + N,N'-dimethyl-N,N'-bis<2-(4-methyl-1-piperazinyl)ethyl>ethylenediamine

Conditions	Yield
Mechanism;

...Expand

aminoethylpiperazine (140-31-8) + formaldehyd (50-00-0) + formic acid (64-18-6) + 1,2-dichloro-ethane (107-06-2) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + 1-<2-(diethylamino)ethyl>-4-methylpiperazine + N,N'-dimethyl-N,N'-bis<2-(4-methyl-1-piperazinyl)ethyl>ethylenediamine

Conditions	Yield
Multistep reaction. Further byproducts given;

1,4,8,11-tetramethyl-1,4,8,11-tetra-azacyclotetradecane (41203-22-9) + 9-(n-propyl)fluorenyllithium tetramethylenediamine complex → N,N,N,N,-tetramethylethylenediamine (110-18-9) + 9-(n-propyl)fluorenyllithium hexamethyltetraazacyclotetradecane complex

Conditions	Yield
In toluene at 25℃; Rate constant;

(1-ethyl-propenyl)-dimethyl-amine (32317-47-8) + N,N,N',N'-tetramethyl-1,2-diaminoethane-H+ (71889-99-1) → N,N,N,N,-tetramethylethylenediamine (110-18-9) + C7H15N*H(1+)

Conditions	Yield
ICR double resonance, proton affinity;

N,N-Dimethylisobutenylamin (20916-47-6) + N,N,N',N'-tetramethyl-1,2-diaminoethane-H+ (71889-99-1) → N,N,N,N,-tetramethylethylenediamine (110-18-9) + C6H13N*H(1+)

Conditions	Yield
ICR double resonance, proton affinity;

ethylene glycol (107-21-1) + dimethyl amine (124-40-3) → 2-(N,N-dimethylamino)ethanol (108-01-0) + N,N,N,N,-tetramethylethylenediamine (110-18-9)

Conditions	Yield
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) + allylmagnesium bromide (2622-05-1) → Bis(allylmagnesiumchlorid-TMEDA)

Conditions	Yield
In tetrahydrofuran at 20℃; for 12h;	100%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + C5H7BrMg*2C4H8O → C6H16N2*C5H7BrMg

Conditions	Yield
In tetrahydrofuran; pentane for 2h; Ambient temperature;	100%

tetrahydrofuran (109-99-9) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + diphenylphosphane (829-85-6) → 4C12H10PTe2(1-)*C6H16N2*14C4H8O*4Li(1+)

Conditions	Yield
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) + triphenyltin chloride (639-58-7) + zinc (7440-66-6) → Ph3SnZnCl * N,N,N',N'-tetramethylethylenediamine

Conditions	Yield
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)) + N,N,N,N,-tetramethylethylenediamine (110-18-9) → [η**3-2-propenyl](N,N,N',N'-tetramethylethylenediamine)palladium(II) dichloro(η**3-2-propenyl)palladate(II) (80533-23-9)

Conditions	Yield
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) + N,N,N,N,-tetramethylethylenediamine (110-18-9) → (N,N,N',N'-tetramethylethylenediamine)tetracarbonylmolybdenum(0) (23301-98-6) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0)

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

{Li(μ-OB(CH(SiMe3)2)2}2 + N,N,N,N,-tetramethylethylenediamine (110-18-9) → LiOB(CH(SiMe3)2)2((Me2NCH2)2) (127161-53-9)

Conditions	Yield
In hexane react. at 25°C; filtering, filtrate at -20°C;	100%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + titanium tetrachloride (7550-45-0) → tetrachloro(N,N,N',N'-tetramethylethane-1,2-diamine)titanium(IV) (19033-22-8)

Conditions	Yield
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 + N,N,N,N,-tetramethylethylenediamine (110-18-9) → N,N,N',N',-tetramethylethylenediamine*2AlH3 (72049-53-7)

Conditions	Yield
In diethyl ether at 25°C; ppt. collected by centrifugation, washed with Et2O, dried, elem. anal.;	100%

(cyclooctadienyl)(cyclopentadienyl)ruthenium chloride + N,N,N,N,-tetramethylethylenediamine (110-18-9) → [(η5-C5H5)RuCl(N,N,N',N'-tetramethylethylenediamine)] (260066-12-4)

Conditions	Yield
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) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + bis(dibenzylideneacetone)-palladium(0) (32005-36-0) → PdI(4-NO2C6H4)(N,N,N',N'-tetramethylethylenediamine) (191667-18-2)

Conditions	Yield
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) + 4-Iodoacetophenone (13329-40-3) + bis(dibenzylideneacetone)-palladium(0) (32005-36-0) → PdI(4-MeCOC6H4)(N,N,N',N'-tetramethylethylenediamine) (191667-17-1)

Conditions	Yield
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) + 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

Conditions	Yield
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) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + di-μ-chloro-bis[η**3-2-butenyl]dipalladium → [η**3-2-butenyl](N,N,N',N'-tetramethylethylenediamine)palladium(II) tetrafluoroborate

Conditions	Yield
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) + 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)

Conditions	Yield
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) + 3,5-bis(3,5-dimethoxybenzocarboxymethyl)benzyl bromide (176650-93-4) → N,N'-ethane-1,2-diyl N,N'-[3,5-bis(3,5-dimethoxybenzyloxy)benzyloxy] N,N,N',N'-tetramethylammonium dibromide

Conditions	Yield
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) + ThCl4(dimethoxyethane)2 → ThCl4(N,N-tetramethylethylenediamine)2

Conditions	Yield
In tetrahydrofuran excess N,N-tetramethylethylenediamine;	100%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + [ThCl4(1,2-dimethoxyethane)2] (639084-65-4) → ThCl4(Me2NCH2CH2NMe2)2 (159472-32-9)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h;	100%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + [Zr(C5H4NC(CH3)(CH2NSitBuMe2)2)(NNPh2)(Li(py))(phenylacetylene(-1H))] → [Zr(C5H4NC(CH3)(CH2NSitBuMe2)2)(NNPh2)(Li(tetramethylethylenediamine))(phenylacetylene(-1H))]

Conditions	Yield
In toluene at 20℃;	100%

iodotrifluoromethane (2314-97-8) + N,N,N,N,-tetramethylethylenediamine (110-18-9) → 2CF3I*C6H16N2

Conditions	Yield
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) + 2-bromo-N-hexylethanamide (5439-32-7) → C22H48N4O2(2+)*2Br(1-)

Conditions	Yield
In chloroform at 85℃; for 24h;	100%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + 2-Bromo-N-(n-octyl)acetamide (5326-97-6) → C26H56N4O2(2+)*2Br(1-)

Conditions	Yield
In chloroform at 85℃; for 24h;	100%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + 2-bromo-N-decyl-acetamide (5345-68-6) → C30H64N4O2(2+)*2Br(1-)

Conditions	Yield
In chloroform at 85℃; for 24h;	100%
In acetonitrile for 1h; Reflux;	44%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + [(tris(tert-butoxy)siloxy)2chromium(II)]2 → [chromium(II)(tris(tert-butoxy)siloxy)2(N,N,N′,N′-tetramethylethylenediamine)]

Conditions	Yield
In hexane at 25℃; Inert atmosphere; Glovebox;	100%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + C38H68Li2N6O2 → C21H40LiN5

Conditions	Yield
In diethyl ether for 1h;	100%

2-ethylhexyl bromide (18908-66-2) + N,N,N,N,-tetramethylethylenediamine (110-18-9) → N-(2-(dimethylamino)ethyl)-2-ethyl-N,N-dimethylhexan-1-aminium bromide

Conditions	Yield
for 12h; Reflux;	100%

1,3,5-tris(1-imidazolyl)benzene + N,N,N,N,-tetramethylethylenediamine (110-18-9) + 2H2NO3(1-)*(x)H2O*Pd(2+) → C96H144N36Pd6

Conditions	Yield
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) + 4-(bromomethyl)benzophenone (32752-54-8) → ethylenebis(4-benzoylbenzyldimethylammonium) dibromide

Conditions	Yield
In chloroform at 20℃; for 72h;	99.7%
In chloroform at 20℃; for 72h;	99.7%
In chloroform

nido-NB10H13 + N,N,N,N,-tetramethylethylenediamine (110-18-9) + lithium triethylborohydride (22560-16-3) → Li(1+)*2(CH3)2N(CH2)2N(CH3)2*{NB10H12}(1-)={Li((CH3)2N(CH2)2N(CH3)2)2}{NB10H12}

Conditions	Yield
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%

Upstream product

• 50-00-0 Formaldehyde 
• 107-15-3 Ethylenediamine 
• 6153-56-6 Oxalic acid dihydrate 
• 30525-89-4 Paraformaldehyde 

Downstream Products

• 480444-12-0 1 1'-BIS(DIPHENYLPHOSPHINO)FERROCENE 
• 40972-86-9 2,3-Dimethoxyphenylboronic acid 
• 127446-35-9 N-(4-FORMYL-PYRIDIN-3-YL)-2,2-DIMETHYL-PROPIONAMIDE 
• 84680-95-5 1,1'-BIS(DI-TERT-BUTYLPHOSPHINO)FERROCENE 
• 97239-80-0 1,1'-BIS(DIISOPROPYLPHOSPHINO)FERROCENE 
• 166330-10-5 (OXYDI-2,1-PHENYLENE)BIS(DIPHENYLPHOSPHINE) 
• 886851-50-9 2-MORPHOLINO-5-(TRIFLUOROMETHYL)BENZALDEHYDE 
• 171178-43-1 5-AMINO-2-FLUORO-ISONICOTINIC ACID 
• 1271-48-3 1,1'-FERROCENEDICARBOXALDEHYDE 
• 20873-58-9 5-(METHYLTHIO)THIOPHENE-2-CARBOXYLIC ACID 
• 58483-95-7 5-AMINO-2-CHLOROPYRIDINE-4-CARBOXYLIC ACID 
• 12150-46-8 1,1'-Bis(diphenylphosphino)ferrocene 
• 127979-74-2 2-(TRIFLUOROMETHOXY)BENZAMIDE 
• 95408-38-1 1-DIPHENYLPHOSPHINO-1'-(DI-TERT-BUTYLPH& 
• 35700-40-4 2,3-DIHYDROBENZOFURAN-7-CARBOXYLIC ACID 
• 4565-29-1 5-ACETYL-2-THIOPHENECARBALDEHYDE 
• 1455-18-1 3-METHYLBENZO[B]THIOPHENE 
• 1291-47-0 1,1'-DIMETHYLFERROCENE 
• 161265-03-8 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene 
• 18781-31-2 2-ACETYL-3-METHYLBENZO[B]THIOPHENE 
• 23074-10-4 5-ETHYL-2-FURALDEHYDE 
• 183741-91-5 5-AMINO-2-METHOXY-ISONICOTINIC ACID 
• 1207-12-1 4,6-DIMETHYLDIBENZOTHIOPHENE 
• 95408-45-0 1,1'-Bis (di-t-butylphosphino)ferrocene palladium dichloride, 
• 171178-46-4 5-[(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROISONICOTINIC ACID 
• 22053-74-3 3-METHYLBENZO[B]THIOPHENE-2-CARBOXALDEHYDE 

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