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Basic Information
CAS No.: 5762-56-1
Name: TRIS(DIMETHYLAMINO)METHANE
Molecular Structure:
Molecular Structure of 5762-56-1 (TRIS(DIMETHYLAMINO)METHANE)
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
Synthetic route
3728-50-5

butylidenetriphenylphosphorane

1071-38-1

N,N,N',N'-Tetramethylformamidinium chloride

A

5762-56-1

tris(dimethylamino)methane

B

13371-17-0

butyltriphenylphosphonium chloride

C

90601-14-2

<2-(Dimethylamino)-1-propylvinyl>triphenylphosphonium-chlorid

Conditions
ConditionsYield
In tetrahydrofuran; benzene for 20h;A 75%
B 90%
C 67%
16666-78-7

propylidenetriphenylphosphorane

1071-38-1

N,N,N',N'-Tetramethylformamidinium chloride

A

5762-56-1

tris(dimethylamino)methane

B

16721-43-0

n-propyltriphenylphosphonium chloride

C

90601-13-1

<2-(Dimethylamino)-1-ethylvinyl>triphenylphosphonium-chlorid

Conditions
ConditionsYield
In tetrahydrofuran; benzene for 20h;A 75%
B 90%
C 72%
1071-38-1

N,N,N',N'-Tetramethylformamidinium chloride

90601-05-1

Triphenyl<(propylthio)methylen>phosphoran

A

5762-56-1

tris(dimethylamino)methane

B

55064-94-3

triphenyl-propylsulfanylmethyl-phosphonium; chloride

C

90601-15-3

<2-(Dimethylamino)-1-(propylthio)vinyl>triphenylphosphonium-chlorid

Conditions
ConditionsYield
In tetrahydrofuran; benzene for 720h;A 75%
B 90%
C 28%
1071-38-1

N,N,N',N'-Tetramethylformamidinium chloride

1754-88-7

ethylenetriphenylphosphorane

A

5762-56-1

tris(dimethylamino)methane

B

896-33-3

ethyltriphenylphosphonium chloride

C

90601-12-0

<2-(Dimethylamino)-1-methylvinyl>triphenylphosphonium-chlorid

Conditions
ConditionsYield
In tetrahydrofuran; benzene for 20h;A 75%
B 90%
C 76%
1071-38-1

N,N,N',N'-Tetramethylformamidinium chloride

124-40-3

dimethyl amine

5762-56-1

tris(dimethylamino)methane

Conditions
ConditionsYield
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;
2013-91-4

N,N,N',N'-tetramethylformamidinium methyl sulfate

124-40-3

dimethyl amine

5762-56-1

tris(dimethylamino)methane

Conditions
ConditionsYield
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
2214-82-6

Bis(dimethylamino)acetonitrile

124-40-3

dimethyl amine

5762-56-1

tris(dimethylamino)methane

Conditions
ConditionsYield
Stage #1: dimethyl amine With Trimethyl borate; sodium hydride In tetrahydrofuran deprotonation; complexation; cooling;
Stage #2: Bis(dimethylamino)acetonitrile In tetrahydrofuran Substitution; cooling;
77%
1071-38-1

N,N,N',N'-Tetramethylformamidinium chloride

19493-09-5

Methylenetriphenylphosphorane

A

5762-56-1

tris(dimethylamino)methane

B

1031-15-8

methyltriphenylphosphonium chloride

C

90601-11-9

<2-(dimethylamino)vinyl>triphenylphosphonium chloride

Conditions
ConditionsYield
In tetrahydrofuran; benzene for 20h;A n/a
B n/a
C 75%
30388-20-6

N,N,N',N',N'',N''-hexamethylguanidinium chloride

5762-56-1

tris(dimethylamino)methane

Conditions
ConditionsYield
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;
30388-20-6

N,N,N',N',N'',N''-hexamethylguanidinium chloride

124-40-3

dimethyl amine

A

5762-56-1

tris(dimethylamino)methane

B

10524-51-3

Tetrakis(dimethylamino)methan

Conditions
ConditionsYield
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%
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