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| CAS No.: | 5762-56-1 |
|---|---|
| Name: | TRIS(DIMETHYLAMINO)METHANE |
| 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% |
