1,4-di-tert-butyl-1,4-diazabutadiene
N,N'-di-tert-butylethylenediamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride at 0 - 20℃; | 89% |
With sodium tetrahydroborate In methanol at 0 - 25℃; Inert atmosphere; |
N-((E,2E)-2-{[(E)-1,1-dimethylethyl]imino}ethylidene)-2-methyl-2-propanamine
N,N'-di-tert-butylethylenediamine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol for 3h; | 81% |
Conditions | Yield |
---|---|
In hexane; water for 72h; Heating; | 72% |
In water 1.) 0 deg C to ambient temperature (slowly), 2.) reflux, overnight; | 70% |
Stage #1: ethylene dibromide; tert-butylamine With sodium hydroxide In water at 0℃; for 1h; Stage #2: In water at 25℃; for 72h; | 56% |
With water |
ethylene dibromide
tert-butylamine
A
N,N'-di-tert-butylethylenediamine
B
1,4,7-tri-tert-butyl-1,4,7-triazaheptane
C
1,4-di-tert-butylpiperazine
Conditions | Yield |
---|---|
In water at 20℃; for 72h; | A 70% B 2% C 9% |
N-((E,2E)-2-{[(E)-1,1-dimethylethyl]imino}ethylidene)-2-methyl-2-propanamine
A
N,N'-di-tert-butylethylenediamine
B
1-tert-Butyl-3-(tert-butylamino)pyrrol
C
1-tert-Butyl-3,4-bis(tert-butylamino)pyrrol
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol for 1.5h; | A 8% B 30% C 24% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; |
N,N'-di-tert-butylethylenediamine
1,3-di-tert-butyl-2-chloro-1,3,2-diazaphospholidine
Conditions | Yield |
---|---|
With triethylamine; phosphorus trichloride In toluene at 20℃; for 2h; | 100% |
With phosphorus trichloride In benzene 1) 18h, r.t., 2) reflux, 24h; | 87% |
With triethylamine; phosphorus trichloride In toluene at 0 - 20℃; Inert atmosphere; Glovebox; Schlenk technique; | 81% |
N,N'-di-tert-butylethylenediamine
1,2-bis(t-butylamino)ethane dihydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water | 100% |
With hydrogenchloride In ethanol |
N,N'-di-tert-butylethylenediamine
Conditions | Yield |
---|---|
With water-d2 In dimethylsulfoxide-d6 at 25℃; for 1h; Inert atmosphere; | 100% |
With deuteromethanol at 20℃; for 1h; | 98% |
N,N'-di-tert-butylethylenediamine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 98% |
formaldehyd
N,N'-di-tert-butylethylenediamine
N,N'-di-tert-butyl-N,N'-dimethyl-ethylenediamine
Conditions | Yield |
---|---|
With formic acid In water for 16h; Eschweiler-Clarke reaction; Heating; | 97% |
With formic acid In water Heating; | 65% |
Conditions | Yield |
---|---|
Stage #1: chloroacetyl chloride In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: N,N'-di-tert-butylethylenediamine In dichloromethane at 20℃; Inert atmosphere; | 94% |
With potassium carbonate In dichloromethane at 50℃; for 12h; Inert atmosphere; | 68.9% |
Conditions | Yield |
---|---|
In methanol at -40 - 20℃; | 92% |
4,4'-bis(dibromoboryl)biphenyl
N,N'-di-tert-butylethylenediamine
Conditions | Yield |
---|---|
Stage #1: 4,4'-bis(dibromoboryl)biphenyl With triethylamine In toluene at 0 - 20℃; Stage #2: N,N'-di-tert-butylethylenediamine In hexane for 3h; Heating; | 92% |
With Et3N In toluene under Ar; soln. of B compd. in toluene added dropwise to chilled soln. (0°C) of Et3N in toluene; warmed to 20°C; neat (t-BuNHCH2)2added; heated under reflux for 3 h; cooled to room temp.; filtered; filtrate concd.; crystd. at -30°C for 12 h; recrystd. from toluene; elem. anal.; | 92% |
tetrakis(actonitrile)copper(I) hexafluorophosphate
N,N'-di-tert-butylethylenediamine
3,5-di-tert-butyl-o-benzoquinone
Conditions | Yield |
---|---|
In tetrahydrofuran under N2; soln. of diamine added to soln. of Cu complex in dry THF; stirred at room temp. for 5 min; treated with t-Bu2C6H2O2; stirred for 2 h; concd.; Et2O added; filtered; solid rinsed with pentane; dried under N2 for 4 h; | 90% |
trimethylamine alane
N,N'-di-tert-butylethylenediamine
Al((CH3)3CNCH2CH2NHC(CH3)3)((CH3)3CNCH2CH2NC(CH3)3)
Conditions | Yield |
---|---|
In diethyl ether byproducts: H2; molar ratio ligand:Al-compd.=2:1, -80°C (30 min), then 20°C (2.5 h); solvent removal (vac.), recrystn. (hexane, -30°C, 9 days); | 89.2% |
formaldehyd
N,N'-di-tert-butylethylenediamine
1,3-bis(1,1-dimethylethyl)imidazolidin-2-ylidene
Conditions | Yield |
---|---|
89% | |
In diethyl ether |
2,5-bis(dibromoboryl)thiophene
N,N'-di-tert-butylethylenediamine
Conditions | Yield |
---|---|
With triethylamine In hexane for 3h; Heating; | 89% |
With triethylamine In hexane (Ar); using Schlenk techniques; addn. dropwise soln. of C4H2S(BBr2)2 in hexane to soln. of NEt3 in hexane at 0°C; pptn., sepn. of ppt., warming to ambient temp.; addn. of N,N'-di-tert-butyl-ethylenediamine; reflux for 3 h; filtration, evapn. to dryness; crystn. from pentane at -30°C, elem. anal.; | 89% |
N,N'-di-tert-butylethylenediamine
trimethylaminealane
Al((CH3)3CNCH2CH2NHC(CH3)3)((CH3)3CNCH2CH2NC(CH3)3)
Conditions | Yield |
---|---|
In diethyl ether byproducts: H2, NMe3; (argon); addn. of diamine to AlH3*NMe3 in Et2O at -80°C, stirring(30 min), warming to 20°C, stirring (2.5 h); filtration, removal of volatiles (vac.), recrystn. (hexane, -30°C, 9 d); elem. anal.; | 89% |
N,N'-di-tert-butylethylenediamine
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 20℃; for 2h; | 86% |
N,N'-di-tert-butylethylenediamine
[(η5-C5H4BNa(tBu)CH2CH2Nb(tBu))(η5-C5H5)Fe](B-Nb)
Conditions | Yield |
---|---|
With NEt3 In hexane byproducts: (Et3NH)Br; under dry O2-free N2; soln. (10 ml) of (C5H5)Fe(C5H4)BBr2 (7.8 mmol) added to chilled (0°C) soln. (50 ml) of NEt3 (15.6 mmol); warmed toroom temp.; neat N,N'-di-tert-butylethane-1,2-diamine (8.00 mmol) added dropwise; refluxed (3 h); filtered; filtrate concd. to dryness; residue distd. (250°C, 1E-6bar); elem. anal.; | 86% |
Glyoxal
N,N'-di-tert-butylethylenediamine
trans-1,4-di-tert-butyl-2,3-dihydroxypiperazine
Conditions | Yield |
---|---|
In water for 0.166667h; Mechanism; var. temp. and solvent; other N,N'-disubstituted ethylenediamines; | 85% |
In water for 0.166667h; | 85% |
Glyoxal
N,N'-di-tert-butylethylenediamine
1,3-di-tert-butyl-2-imidazolidinecarboxaldehyde
Conditions | Yield |
---|---|
In water at 60℃; for 0.0833333h; | 85% |
(S)-3,3'-diphenyl-2,2'-dihydroxy-1,1'-dinaphthyl
dichloromethane
N,N'-di-tert-butylethylenediamine
diethylzinc
Conditions | Yield |
---|---|
In dichloromethane under N2; soln. of Et2Zn in CH2Cl2 added to soln. of the (S)-dinaphthyl and diamine in CH2Cl2, stirred at room temp. for 30 min; diffusion of hexane vapor into soln., crystals washed with Et2O and dried in vacuo; elem. anal.; | 85% |
methylcymantrenyl(3-dibromo)borane
N,N'-di-tert-butylethylenediamine
[((3-Me)[1-BNa(tBu)CH2CH2Nb(tBu)]C5H3)Mn(CO)3](B-Nb)
Conditions | Yield |
---|---|
With NEt3 In hexane byproducts: (Et3NH)Br; under dry O2-free N2; neat CH3(C5H3)BBr2Mn(CO)3 (13.6 mmol) added to chilled (0°C) soln. (100 ml) of NEt3 (27.1 mmol); warmed to room temp.; neat N,N'-di-tert-butylethane-1,2-diamine (27.1 mmol) added dropwise; refluxed (3 h); filtered; evapd.; residue distd. (150°C, 1E-6 bar); dissolved in n-pentane (40 ml); kept (-30°C, 7 d); elem. anal.; | 85% |
trimethylamine alane
N,N'-di-tert-butylethylenediamine
(AlH2)(NH(C(CH3)3)CH2CH2N(C(CH3)3))
Conditions | Yield |
---|---|
In diethyl ether byproducts: H2; molar ratio ligand:Al-compd.=1:1, -80°C, then 20°C (1 h); filtration, concn. (vac.), crystn. (-26°C, 7 days); elem. anal.; | 85% |
N,N'-di-tert-butylethylenediamine
1,1'-bis(1,3-di-tert-butyl-1,3,2-diazaborolidinyl)ferrocene
Conditions | Yield |
---|---|
With NEt3 In hexane byproducts: (Et3NH)Br; under dry O2-free N2; soln. (40 ml) of Fe((C5H4)BBr2)2 (7.6 mmol) addedto chilled (0°C) soln. (100 ml) of NEt3 (30.4 mmol); warmed to r oom temp.; neat N,N'-di-tert-butylethane-1,2-diamine (8.00 mmol) added dropwise; refluxed (4 h); filtered; filtrate concd. to dryness; residue dissolved in n-hexane (20 ml); kept (-80°C, 7 d); elem. anal.; | 85% |
With NEt3 In hexane byproducts: Et3NHBr; under Ar or N2 using Schlenk technique; to ferrocene deriv. soln. in hexane at 5°C, added mixt. of amines with stirring at 0°C; stirred for 1 h; ppt. removed by filtration; 50% solvent removed from filtrate in vacuo; recrystd. from hexane at -30°C; | 78% |
N,N'-di-tert-butylethylenediamine
trimethylaminealane
Conditions | Yield |
---|---|
In diethyl ether byproducts: H2, NMe3; (argon); addn. at -80°C, warming to ca. 20°C, stirring (1 h); filtration, concn. (vac.), crystn. after 7 d at -26°C; elem. anal.; | 85% |
N,N'-di-tert-butylethylenediamine
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 20℃; for 2h; | 84% |
N,N'-di-tert-butylethylenediamine
boron tribromide
2-bromo-1,3-di-tert-butyl-1,3,2-diazaborolidine
Conditions | Yield |
---|---|
With triethylamine In hexane under inert atm. soln. BBr3 in hexane was added slowly at 0°C to soln. Et3N on hexane, warmed to room temp., soln. N,N'-di-tert-butylethylenediamine in hexane was added and heated under reflux for 3 h; soln. was filtered and evapd. to dryness; elem. anal.; | 84% |
1,3,5-tris(dibromoboryl)benzene
N,N'-di-tert-butylethylenediamine
Conditions | Yield |
---|---|
Stage #1: 1,3,5-tris(dibromoboryl)benzene With triethylamine In toluene at 0 - 20℃; Stage #2: N,N'-di-tert-butylethylenediamine In hexane for 3h; Heating; | 82% |
With Et3N In toluene under Ar; soln. of B compd. in toluene added dropwise to chilled soln. (0°C) of Et3N in toluene; warmed to 20°C; neat (t-BuNHCH2)2added; heated under reflux for 3 h; cooled to room temp.; filtered; filtrate concd.; crystd. at -30°C for 12 h; recrystd. from toluene; elem. anal.; | 82% |
Conditions | Yield |
---|---|
In ethyl acetate Glovebox; Inert atmosphere; | 82% |
cis-bis(dimethylsulfoxide)dichloroplatinum(II)
N,N'-di-tert-butylethylenediamine
cis(PtCl2(t-Bu2en))
Conditions | Yield |
---|---|
In methanol slow addn. of educts dissolved in methanol, 65 h stirring at room temp., yellow soln., concn. under reduced pressure, filtration; crystn. by cooling to 0 ° C, filtration, washing (MeOH), drying, elem. anal; | 80% |
Chemistry informtion about N,N-Di-Tert-Butylethylenediamine (CAS NO.4062-60-6) is:
IUPAC Name: N,N'-Ditert-Butylethane-1,2-Diamine
Synonyms: 1,2-Ethanediamine, N,N'-Bis(1,1-Dimethylethyl)- ; Ar81242 ; N,N’-Bis(1,1-Dimethylethyl)-1,2-Ethanediamine ; N,N’-Bis(1,1-Dimethylethyl)-2-Ethanediamine ; N,N'-Di-Tert-Butylethylenediamine ; N,N-Di-Tert-Butylethylenediamine ; N,N'-Di-T-Butyl Ethylene Diamine ; 1,2-Bis(Tert-Butylamino)Ethane
MF: C10H24N2
MW: 172.31
EINECS: 223-769-6
Density: 0.815 g/cm3
Flash Point: 76.7 °C
Boiling Point: 208.7 °C at 760 mmHg
Vapour Pressure: 0.21 mmHg at 25°C
Enthalpy of Vaporization: 44.5 kJ/mol
Refractive Index: n20/D 1.43(lit.)
BRN: 1738432
Following is the molecular structure of N,N-Di-Tert-Butylethylenediamine (CAS NO.4062-60-6) is:
1. | skn-rbt 500 µL/24H MLD | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0535667 . | ||
2. | orl-rat LDLo:5 g/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0535667 . | ||
3. | skn-rbt LDLo:200 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0535667 . |
A poison by ingestion. Low toxicity by ingestion. A mild skin irritant. When heated to decomposition it emits toxic vapors of NOx.
Hazard Codes:
C
Risk Statements:
R34:Causes burns.
Safety Statements:
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 2735 8/PG 2
WGK Germany: 3
RTECS: KH8587137
F:
F 10 Keep under argon.
F 34 Sensitive to CO2.
HazardClass: 8
PackingGroup: II
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