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CAS No.: | 5762-56-1 |
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Name: | TRIS(DIMETHYLAMINO)METHANE |
Article Data: | 22 |
Molecular Structure: | |
Formula: | C7H19 N3 |
Molecular Weight: | 145.248 |
Synonyms: | N,N,N',N',N'',N''-Hexamethylmethanetriamine;Tris(N,N-dimethylamino)methane; Tris(dimethylamino)methane |
Density: | 0.873g/cm3 |
Boiling Point: | 143.8°Cat760mmHg |
Flash Point: | 28.2°C |
Hazard Symbols: | F,C |
Risk Codes: | R11; R34 |
Safety: | 1901162 |
PSA: | 9.72000 |
LogP: | -0.04520 |
butylidenetriphenylphosphorane
N,N,N',N'-Tetramethylformamidinium chloride
A
tris(dimethylamino)methane
B
butyltriphenylphosphonium chloride
C
<2-(Dimethylamino)-1-propylvinyl>triphenylphosphonium-chlorid
Conditions | Yield |
---|---|
In tetrahydrofuran; benzene for 20h; | A 75% B 90% C 67% |
propylidenetriphenylphosphorane
N,N,N',N'-Tetramethylformamidinium chloride
A
tris(dimethylamino)methane
B
n-propyltriphenylphosphonium chloride
C
<2-(Dimethylamino)-1-ethylvinyl>triphenylphosphonium-chlorid
Conditions | Yield |
---|---|
In tetrahydrofuran; benzene for 20h; | A 75% B 90% C 72% |
N,N,N',N'-Tetramethylformamidinium chloride
Triphenyl<(propylthio)methylen>phosphoran
A
tris(dimethylamino)methane
B
triphenyl-propylsulfanylmethyl-phosphonium; chloride
C
<2-(Dimethylamino)-1-(propylthio)vinyl>triphenylphosphonium-chlorid
Conditions | Yield |
---|---|
In tetrahydrofuran; benzene for 720h; | A 75% B 90% C 28% |
N,N,N',N'-Tetramethylformamidinium chloride
ethylenetriphenylphosphorane
A
tris(dimethylamino)methane
B
ethyltriphenylphosphonium chloride
C
<2-(Dimethylamino)-1-methylvinyl>triphenylphosphonium-chlorid
Conditions | Yield |
---|---|
In tetrahydrofuran; benzene for 20h; | A 75% B 90% C 76% |
N,N,N',N'-Tetramethylformamidinium chloride
dimethyl amine
tris(dimethylamino)methane
Conditions | Yield |
---|---|
Stage #1: dimethyl amine With Trimethyl borate; sodium hydride In tetrahydrofuran deprotonation; complexation; cooling; Stage #2: N,N,N',N'-Tetramethylformamidinium chloride In tetrahydrofuran Addition; cooling; | 84% |
Stage #1: dimethyl amine With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -78 - 20℃; for 0.5h; Inert atmosphere; Stage #2: N,N,N',N'-Tetramethylformamidinium chloride In tetrahydrofuran; diethyl ether; hexane at 0 - 20℃; for 8h; | 71% |
With lithium | |
With n-butyllithium 1.) THF, hexane, 0 deg C, 30 min, 2.) RT, 18 h; Yield given. Multistep reaction; |
N,N,N',N'-tetramethylformamidinium methyl sulfate
dimethyl amine
tris(dimethylamino)methane
Conditions | Yield |
---|---|
Stage #1: dimethyl amine With Trimethyl borate; sodium hydride In tetrahydrofuran deprotonation; complexation; cooling; Stage #2: N,N,N',N'-tetramethylformamidinium methyl sulfate In tetrahydrofuran Addition; cooling; | 77% |
With potassium tert-butylate |
Conditions | Yield |
---|---|
Stage #1: dimethyl amine With Trimethyl borate; sodium hydride In tetrahydrofuran deprotonation; complexation; cooling; Stage #2: Bis(dimethylamino)acetonitrile In tetrahydrofuran Substitution; cooling; | 77% |
N,N,N',N'-Tetramethylformamidinium chloride
Methylenetriphenylphosphorane
A
tris(dimethylamino)methane
B
methyltriphenylphosphonium chloride
C
<2-(dimethylamino)vinyl>triphenylphosphonium chloride
Conditions | Yield |
---|---|
In tetrahydrofuran; benzene for 20h; | A n/a B n/a C 75% |
N,N,N',N',N'',N''-hexamethylguanidinium chloride
tris(dimethylamino)methane
Conditions | Yield |
---|---|
With sodium bis(2-methoxyethoxy)aluminium dihydride In benzene at 60℃; for 1h; | 55% |
With Trimethyl borate; sodium hydride In tetrahydrofuran at 20℃; for 30h; Product distribution; Further Variations:; Reagents; conc./ratio; time; Reduction; |
N,N,N',N',N'',N''-hexamethylguanidinium chloride
dimethyl amine
A
tris(dimethylamino)methane
B
Tetrakis(dimethylamino)methan
Conditions | Yield |
---|---|
Stage #1: dimethyl amine With Trimethyl borate; sodium hydride In tetrahydrofuran for 0.25h; deprotonation; complexation; cooling; Stage #2: N,N,N',N',N'',N''-hexamethylguanidinium chloride In tetrahydrofuran at 20℃; for 48h; Addition; reduction; | A 50% B 11% |