134030-21-0

Basic information

• Product Name: N,N'-Bis(2,4,6-trimethylphenyl)ethylenediamine
• Synonyms: N,N'-Bis(2,4,6-trimethylphenyl)ethylenediamine;N,N'-Bis(2,4,6-trimethylphenyl)ethane-1,2-diamine;2,4,6-triMethyl-N-{2-[(2,4,6-triMethylphenyl)aMino]ethyl}aniline;N1,N2-Dimesitylethane-1,2-diamine;1,2-Ethanediamine, N1,N2-bis(2,4,6-trimethylphenyl)-
• CAS NO: 134030-21-0
• Molecular Formula: C₂₀H₂₈N₂
• Molecular Weight: 296.45
• EINECS: -0
• Mol File: 134030-21-0.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 471.5±33.0 °C(Predicted)
• Appearance: /
• Density: 1.033
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.28±0.50(Predicted)
• CAS DataBase Reference: N,N'-Bis(2,4,6-trimethylphenyl)ethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Bis(2,4,6-trimethylphenyl)ethylenediamine(134030-21-0)
• EPA Substance Registry System: N,N'-Bis(2,4,6-trimethylphenyl)ethylenediamine(134030-21-0)

Safety Data

• Hazardous Substances Data: 134030-21-0(Hazardous Substances Data)

Synthetic route

N,N'-bis(2,4,6-trimethylphenyl)ethanediimine (56222-36-7) → N,N'-dimesityl-1,2-ethanediamine (134030-21-0)

Conditions	Yield
With hydrogen; tris(pentafluorophenyl)borane In (2)H8-toluene at 120℃; under 3040.2 Torr; for 24h;	99%
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 20℃; for 3h;	99%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;	98%

(E,E)-N1,N2-bis(2,4,6-trimethylphenyl)ethane-1,2-diimine (56222-36-7) → N,N'-dimesityl-1,2-ethanediamine (134030-21-0)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃;	95%
With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 24h;

N,N′-bis(2,4,6-trimethylphenyl)oxalamide (91325-46-1) → N,N'-dimesityl-1,2-ethanediamine (134030-21-0)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 120℃; for 1.5h; Microwave irradiation;	75%

N1,N2-dimesitylethane-1,2-diaminium chloride (258278-23-8) → N,N'-dimesityl-1,2-ethanediamine (134030-21-0)

Conditions	Yield
With sodium hydrogencarbonate for 1h;	7%

2,4,6-trimethylaniline (88-05-1) → N,N'-dimesityl-1,2-ethanediamine (134030-21-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O; acetone View Scheme
Multi-step reaction with 2 steps 1: 92 percent / formic acid / methanol; H2O / 3 h / 20 °C 2: 97 percent / NaBH4 / tetrahydrofuran; methanol / 2 h View Scheme
Multi-step reaction with 2 steps 1: 86 percent / H2O; methanol / 12 h / 22 °C 2: 96 percent / NaCNBH3; coc. aq. HCl / methanol View Scheme

2,4,6-trimethylphenyl bromide (576-83-0) → N,N'-dimesityl-1,2-ethanediamine (134030-21-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 99 percent / 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride; Pd(dba)2; t-BuOK / dioxane / 10 h / 80 °C 2: 87 percent / Acid hydrolysis 3: 92 percent / formic acid / methanol; H2O / 3 h / 20 °C 4: 97 percent / NaBH4 / tetrahydrofuran; methanol / 2 h View Scheme

N-(diphenyl methylene)-2,4,6-trimethylaniline (67565-93-9) → N,N'-dimesityl-1,2-ethanediamine (134030-21-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / Acid hydrolysis 2: 92 percent / formic acid / methanol; H2O / 3 h / 20 °C 3: 97 percent / NaBH4 / tetrahydrofuran; methanol / 2 h View Scheme

Glyoxal (131543-46-9) + 2,4,6-trimethylaniline (88-05-1) → N,N'-dimesityl-1,2-ethanediamine (134030-21-0)

Conditions	Yield
Stage #1: Glyoxal; 2,4,6-trimethylaniline Stage #2: With sodium tetrahydroborate In ethanol

2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid ethyl ester (79354-30-6) → N,N'-dimesityl-1,2-ethanediamine (134030-21-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: boric acid / 1 h / 180 °C 2: lithium aluminium tetrahydride / diethyl ether / 1.5 h / 120 °C / Microwave irradiation View Scheme

Glyoxal (131543-46-9) + 4-isopropoxy-2,6-dimethylaniline (100054-69-1) + 2,4,6-trimethylaniline (88-05-1) → N1,N2-bis(4-isopropoxy-2,6-dimethylphenyl)ethylene-1,2-diamine + N1-(2,4,6-trimethylphenyl)-N2-(4-isopropoxy-2,6-dimethylphenyl)ethane-1,2-diamine + N,N'-dimesityl-1,2-ethanediamine (134030-21-0)

Conditions	Yield
Stage #1: Glyoxal; 4-isopropoxy-2,6-dimethylaniline; 2,4,6-trimethylaniline With acetic acid In water; isopropyl alcohol at 20℃; for 4h; Stage #2: With methanol; sodium tetrahydroborate In tetrahydrofuran at 20℃; for 5h;

orthoformic acid triethyl ester (122-51-0) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → N,N'-dimesityl-4,5-dihydro-1H-imidazolium tetrafluoroborate

Conditions	Yield
With ammonium tetrafluoroborate at 120℃;	100%
With ammonium tetrafluroborate for 3h; cyclocondensation; Heating;	54%

orthoformic acid triethyl ester (122-51-0) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride (173035-10-4)

Conditions	Yield
With ammonium chloride at 110℃; for 1.5h;	97%
With hydrogenchloride In diethyl ether; water at 110℃; for 24h;	70%
With ammonium chloride at 110℃; for 1.5h;

perfluorobenzaldehyde (653-37-2) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 1,3-di(2,4,6-trimethylphenyl)-2-(pentafluorophenyl)-2,4,5-trihydroimidazole (782479-45-2)

Conditions	Yield
With acetic acid at 20℃; for 16h;	90%
With acetic acid	71%
With acetic acid at 20℃; for 24h;	65%
With acetic acid at 20℃; for 16h;	35%

palladium dichloride + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → C20H28Cl2N2Pd

Conditions	Yield
In tetrahydrofuran at 55℃; for 18h; Inert atmosphere;	90%

3,5-Bis(trifluoromethyl)benzaldehyde (401-95-6) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 1,3-bis(2,4,6-trimethylphenyl)-2-(3,5-bis(trifluoromethyl)phenyl)imidazolidine

Conditions	Yield
With acetic acid	87%

thiophosgene (463-71-8) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinethione

Conditions	Yield
With sodium carbonate In tetrahydrofuran at 20℃;	85%
With sodium carbonate In tetrahydrofuran at 20℃;	85%

lead(II) bis(trimethylsilyl)amide (55147-59-6, 65455-92-7) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → (2,4,6-trimethylphenyl)N(CH2)2N(2,4,6-trimethylphenyl)Pb (1093656-77-9)

Conditions	Yield
In toluene room temp.;	85%

N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 2,5-di(2,4,6-trimethylphenyl)-1,2,5-thiadiazolidine-1-oxide (1180524-84-8)

Conditions	Yield
With thionyl chloride; triethylamine In diethyl ether at 0℃; for 12h;	83%
With thionyl chloride; triethylamine In diethyl ether at 0 - 20℃;	83%

2,3,5,6-tetrafluorobenzaldehyde (19842-76-3) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 1,3-bis(2,4,6-trimethylphenyl)-2-(2,3,5,6-tetrafluorophenyl)imidazolidine

Conditions	Yield
With acetic acid	82%

(C2H5)3N*BF3 (368-37-6) + boron trifluoride diethyl etherate (109-63-7) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 1,3-bis(2,4,6-trimethylphenyl)-2-fluoro-1,3,2-diazaborolidine

Conditions	Yield
In toluene at 200℃; Microwave irradiation; Schlenk technique; Inert atmosphere;	78%

triethylaluminum (97-93-8) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → [AlEt(μ-2,4,6-Me3C6H2NCH2CH2N-2,4,6-Me3C6H2)](n)

Conditions	Yield
In benzene soln. of AlEt3 added by pipette to soln. of diamine in Schlenk flask in drybox, stirred for 15 h at room temp., heated to reflux for 22 h; vac. distn., washing (pentane), elem. anal.;	76.2%

N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 2-chloro-1,3-bis-(2,4,6-trimethylphenyl)[1,3,2]diazaphospholidine (314730-64-8)

Conditions	Yield
With 4-methyl-morpholine; phosphorus trichloride In tetrahydrofuran at -78 - 20℃; for 19h;	73%
With triethylamine; phosphorus trichloride In dichloromethane at 20℃; for 1h;
With triethylamine; phosphorus trichloride In tetrahydrofuran at -78℃;
With triethylamine; phosphorus trichloride In dichloromethane
With triethylamine; phosphorus trichloride In tetrahydrofuran at -78 - 20℃; for 6.25h; Inert atmosphere; Schlenk technique; Glovebox;

N,N'-dimesityl-1,2-ethanediamine (134030-21-0) + Trifluoroacetaldehyde ethyl hemiacetal (433-27-2) → 1,3-bis(2,4,6-trimethylphenyl)-2-(trifluoromethyl)imidazolidine

Conditions	Yield
With magnesium sulfate; toluene-4-sulfonic acid In toluene at 40℃; for 24h;	68%

orthoformic acid triethyl ester (122-51-0) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 1,3-dimesitylimidazolinium chloride

Conditions	Yield
With ammonium chloride at 110℃; for 2h;	66%

boron tribromide (10294-33-4) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → (C2H4N2(2,4,6-Me3C6H2)2)BBr (1082608-16-9)

Conditions	Yield
With ((CH3)2CH)2NCH2CH3 In not given treatment of diamine deriv. with boron compd. in presence of amine deriv.;	64%

N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → (C2H4N2(2,4,6-Me3C6H2)2)BBr (1082608-16-9)

Conditions	Yield
Stage #1: N,N'-dimesityl-1,2-ethanediamine With boron tribromide In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Inert atmosphere;	64%

tetrahydrofuran (109-99-9) + uranium(IV) chloride (10026-10-5) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → C44H60N4OU

Conditions	Yield
Stage #1: N,N'-dimesityl-1,2-ethanediamine With benzyl potassium In tetrahydrofuran for 0.166667h; Stage #2: tetrahydrofuran; uranium(IV) chloride for 1h;	46%

thiophosgene (463-71-8) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) + Di-n-amylamine (2050-92-2) → C42H70N4S2

Conditions	Yield
Stage #1: thiophosgene; N,N'-dimesityl-1,2-ethanediamine With triethylamine In tetrahydrofuran at 0 - 20℃; Stage #2: Di-n-amylamine at 100℃; for 24h;	40%

trimethylamine alane (16842-00-5, 855944-65-9) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → [{κ2-((mesytil)NCH2)2}AlH(trimethylamine)]

Conditions	Yield
In diethyl ether at 25℃; for 16h; Glovebox; Inert atmosphere;	39%

uranium(IV) chloride (10026-10-5) + sodium cyclopentadienide + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → C30H36N2U

Conditions	Yield
Stage #1: N,N'-dimesityl-1,2-ethanediamine With benzyl potassium In tetrahydrofuran for 0.166667h; Stage #2: uranium(IV) chloride; sodium cyclopentadienide In tetrahydrofuran for 1h;	39%

thiophosgene (463-71-8) + diethylamine (109-89-7) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → C30H46N4S2

Conditions	Yield
Stage #1: thiophosgene; N,N'-dimesityl-1,2-ethanediamine With triethylamine In tetrahydrofuran at 0 - 20℃; Stage #2: diethylamine at 100℃; for 24h;	38%

chloral (75-87-6) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 1,3-bis(2,4,6-trimethylphenyl)-2-(trichloromethyl)imidazolidine (260054-47-5)

Conditions	Yield
at 20℃; for 17h;	36%

tin(ll) chloride + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → ((CH3)3C6H2N(CH2)2N(CH3)3C6H2Sn)2 (1083333-49-6)

Conditions	Yield
With C4H9Li In diethyl ether; hexane (Ar, glovebox); 1.6 M soln. of n-BuLi in hexane was added to soln. of diimine in Et2O at 0°C, stirred for 2 h, suspn. of SnCl2 in Et2O was added at -78°C, warmed to room temp., stirred for 2 h; evapd., extd. with nhexane, extract was filtered, filtrate concd. in vac, left at -18°C fo crystn., elem. anal.;	15%

orthoformic acid triethyl ester (122-51-0) + N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 2-ethoxy-1,3-bis[(2,4,6-trimethyl)phenyl]imidazolidine (465543-02-6)

Conditions	Yield
Stage #1: orthoformic acid triethyl ester; N,N'-dimesityl-1,2-ethanediamine With hydrogenchloride In diethyl ether at 200℃; for 2h; Stage #2: With potassium hydride for 0.5h;

N,N'-dimesityl-1,2-ethanediamine (134030-21-0) → 1,3-dimesityl-1,3,2-diazaphospholidine-2-oxide

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl3; Et3N / CH2Cl2 / 1 h / 20 °C 2: 0.94 g / H2O / CH2Cl2 / 20 °C View Scheme

Upstream product

• 56222-36-7 N,N'-bis(2,4,6-trimethylphenyl)ethanediimine 
• 56222-36-7 (E,E)-N¹,N²-bis(2,4,6-trimethylphenyl)ethane-1,2-diimine 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 131543-46-9 Glyoxal 
• 100054-69-1 4-isopropoxy-2,6-dimethylaniline 
• 88-05-1 2,4,6-trimethylaniline 
• 258278-23-8 N¹,N²-dimesitylethane-1,2-diaminium chloride 
• 67565-93-9 N-(diphenyl methylene)-2,4,6-trimethylaniline 
• 79354-30-6 2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid ethyl ester 
• 91325-46-1 N,N′-bis(2,4,6-trimethylphenyl)oxalamide 

Downstream Products

• 173035-10-4 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride 
• 782479-45-2 1,3-di(2,4,6-trimethylphenyl)-2-(pentafluorophenyl)-2,4,5-trihydroimidazole 
• 173035-11-5 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene 
• 260054-47-5 1,3-bis(2,4,6-trimethylphenyl)-2-(trichloromethyl)imidazolidine 
• 1083333-49-6 ((CH₃)3C₆H₂N(CH₂)2N(CH₃)3C₆H₂Sn)2 
• 1082608-16-9 (C₂H₄N₂(2,4,6-Me₃C₆H₂)2)BBr 
• 1180524-84-8 2,5-di(2,4,6-trimethylphenyl)-1,2,5-thiadiazolidine-1-oxide 
• 1330191-22-4 2-(diphenylphosphanyl)-1,3-dimesityl-1,3,2-diazaphospholidine 

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