CAS No.5762-56-1,TRIS(DIMETHYLAMINO)METHANE Suppliers

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NMR spectra and their temperature-dependence has been reported for tris(dimethylamino)methane. Tris(dimethylamino)methane reacts with crowded ?-(o-nitrophenyl) ketone to yield tetrahydroquinoline derivative. Package:5, 25 g in glass bottle Applicatio

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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

Conditions	Yield
In tetrahydrofuran; benzene for 20h;	A 75% B 90% C 67%

...Expand

: 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

Conditions	Yield
In tetrahydrofuran; benzene for 20h;	A 75% B 90% C 72%

...Expand

: 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

Conditions	Yield
In tetrahydrofuran; benzene for 720h;	A 75% B 90% C 28%

...Expand

: 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

Conditions	Yield
In tetrahydrofuran; benzene for 20h;	A 75% B 90% C 76%

...Expand

: 1071-38-1
N,N,N',N'-Tetramethylformamidinium chloride

: 124-40-3
dimethyl amine

: 5762-56-1
tris(dimethylamino)methane

Conditions

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;

: 2013-91-4
N,N,N',N'-tetramethylformamidinium methyl sulfate

: 124-40-3
dimethyl amine

: 5762-56-1
tris(dimethylamino)methane

Conditions

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

: 2214-82-6
Bis(dimethylamino)acetonitrile

: 124-40-3
dimethyl amine

: 5762-56-1
tris(dimethylamino)methane

Conditions

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%

: 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

Conditions	Yield
In tetrahydrofuran; benzene for 20h;	A n/a B n/a C 75%

...Expand

: 30388-20-6
N,N,N',N',N'',N''-hexamethylguanidinium chloride

: 5762-56-1
tris(dimethylamino)methane

Conditions

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;

: 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

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%

...Expand

: 2214-82-6
Bis(dimethylamino)acetonitrile

: 3585-33-9
lithium dimethylamide

: 5762-56-1
tris(dimethylamino)methane

Conditions

Conditions	Yield
In tetrahydrofuran; hexane

: 2013-91-4
N,N,N',N'-tetramethylformamidinium methyl sulfate

: 5762-56-1
tris(dimethylamino)methane

Conditions

Conditions	Yield
With sodium thioethylate In diethyl ether Heating;

: 3275-24-9
tetrakis(dimethylamino)titanium

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 5762-56-1
tris(dimethylamino)methane

Conditions

Conditions	Yield
In diethyl ether

: 121-43-7
Trimethyl borate

: 124-40-3
dimethyl amine

: 632-22-4
tetramethylurea

: 503-38-8
trichloromethyl chloroformate

A: 996-70-3
Tetrakis(dimethylamino)ethylen

B: 36555-00-7
Tris(dimethylamino)methoxy-ethylen

C: 5762-56-1
tris(dimethylamino)methane

Conditions

Conditions	Yield
Stage #1: dimethyl amine; tetramethylurea; trichloromethyl chloroformate In tetrahydrofuran at 20℃; Substitution; condensation; Stage #2: Trimethyl borate With sodium hydride In tetrahydrofuran at 20℃; for 24h; Substitution; Title compound not separated from byproducts;

...Expand

: 124-41-4
sodium methylate

: 1071-38-1
N,N,N',N'-Tetramethylformamidinium chloride

A: 1186-70-5
bis(dimethylamino)methoxymethane

B: 5762-56-1
tris(dimethylamino)methane

C: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

Conditions

Conditions	Yield
In tetrahydrofuran at 21℃; Title compound not separated from byproducts.;

...Expand

: 1071-38-1
N,N,N',N'-Tetramethylformamidinium chloride

: 14593-46-5
sodium tert-pentoxide

A: 5762-56-1
tris(dimethylamino)methane

B: 147196-94-9
tert-pentoxy-bis(dimethylamino)methane

C: 1174130-81-4
N,N-dimethylformamide di-tert-pentoxyacetal

Conditions

Conditions	Yield
In tetrahydrofuran; toluene at 20℃; for 48h; Product distribution / selectivity;

...Expand

: 865-47-4
potassium tert-butylate

: N,N,N',N'-tetramethylformamidinium hexafluorophosphate

A: 5762-56-1
tris(dimethylamino)methane

B: 5815-08-7
tert-Butoxybis(dimethylamino)methane

C: 36805-97-7
N,N-dimethylformamide di-tert-butyl acetal

Conditions

Conditions	Yield
In tetrahydrofuran at 50℃; for 1h;

...Expand

: 865-47-4
potassium tert-butylate

: 2013-91-4
N,N,N',N'-tetramethylformamidinium methyl sulfate

A: 5762-56-1
tris(dimethylamino)methane

B: 5815-08-7
tert-Butoxybis(dimethylamino)methane

C: 36805-97-7
N,N-dimethylformamide di-tert-butyl acetal

Conditions

Conditions	Yield
In tetrahydrofuran at 60℃; for 1h;

...Expand

: 865-47-4
potassium tert-butylate

: 3218-35-7
N,N,N',N'-Tetramethylformamidinium-(p-toluolsulfonat)

A: 5762-56-1
tris(dimethylamino)methane

B: 5815-08-7
tert-Butoxybis(dimethylamino)methane

C: 36805-97-7
N,N-dimethylformamide di-tert-butyl acetal

Conditions

Conditions	Yield
In tetrahydrofuran at 50℃; for 1h;

...Expand

: 5762-56-1
tris(dimethylamino)methane

: 189333-18-4
3-oxo-9-azaspiro[5.5]undec-4-ene-9-carboxylic acid benzyl ester

: 1301214-81-2
8-(dimethylaminomethylene)-9-oxo-3-azaspiro[5.5]undec-10-ene-3-carboxylic acid benzyl ester

Conditions

Conditions	Yield
In toluene for 5h; Reflux;	100%
In toluene at 110℃; for 5h; Inert atmosphere;	100%
In toluene for 5h; Reflux;	100%
In toluene for 5h; Reflux;	100%
In toluene at 100℃; for 15h;	99%

: 5762-56-1
tris(dimethylamino)methane

: C23H34O6Si

: 85925-72-0
C26H39NO6Si

Conditions

Conditions	Yield
at 120℃; for 16h;	99%

: 7746-94-3
5,5-diphenyldihydrofuran-2(3H)-one

: 5762-56-1
tris(dimethylamino)methane

: 127074-68-4
3-Dimethylaminomethylen-5,5-diphenyl-dihydro-2(3H)-furanon

Conditions

Conditions	Yield
at 100℃;	94%

: 5762-56-1
tris(dimethylamino)methane

: 81336-67-6
5,6:7,8-di-O-isopropylidene-D-manno-oct-1,4-lactone

: (R)-3-[1-Dimethylamino-meth-(E)-ylidene]-5-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-dihydro-furan-2-one

Conditions

Conditions	Yield
at 70℃; for 120h;	94%

: 5762-56-1
tris(dimethylamino)methane

: 115407-73-3
δ,δ-Diphenyl-δ-valerolacton

: 127074-67-3
3-Dimethylaminomethylen-6,6-diphenyl-tetrahydro-2(2H)pyranon

Conditions

Conditions	Yield
at 100℃; for 6h;	93%

: 5762-56-1
tris(dimethylamino)methane

: (1R*,6S*,7S*,8S*)-7,8-isopropylidenedioxy-1-pentyl-3,9-dioxabicyclo<4.2.1>nonan-4-one

: (1R*,6R*,7S*,8S*)-5-(dimethylaminomethylene)-7,8-isopropylidenedioxy-1-pentyl-3,9-dioxabicyclo<4.2.1>nonan-4-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; for 1h;	91%

: 880815-43-0
5-diethylcarbamoyl-5-ethyl-4-methyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester

: 5762-56-1
tris(dimethylamino)methane

: 880815-51-0
5-diethylcarbamoyl-4-((E)-2-dimethylamino-vinyl)-5-ethyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 17h;	90%
In N,N-dimethyl-formamide at 20℃; for 17h; Product distribution / selectivity;	90%

: 880815-64-5
(S)-5-diethylcarbamoyl-5-ethyl-4-methyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester

: 5762-56-1
tris(dimethylamino)methane

: 880815-66-7
(S)-5-diethylcarbamoyl-4-((E)-2-dimethylamino-vinyl)-5-ethyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 17h;	90%

: 5762-56-1
tris(dimethylamino)methane

: 124-46-9, 20734-13-8, 100224-74-6, 593-85-1
guanidine hydrogen carbonate

: 477789-22-3
N6-(2-(4-phenylpiperazin-1-yl)-ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine

: 2-Amino-6-[N-propyl-(N-(4-phenylpiperazin-1-yl)-ethyl)amino]-5,6,7,8-tetrahydrobenzopyrimidine

Conditions

Conditions	Yield
Stage #1: tris(dimethylamino)methane; N6-(2-(4-phenylpiperazin-1-yl)-ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine In toluene at 90℃; for 4h; Stage #2: guanidine hydrogen carbonate In ethanol for 17h; heating;	88%

...Expand

: 61798-21-8
4,7-diaza-1,9-decadiene

: 5762-56-1
tris(dimethylamino)methane

: 125815-73-8
1,3-diallyl-2-dimethylaminoimidazolidine

Conditions

Conditions	Yield
In hexane for 2h; Heating;	87%

: 5762-56-1
tris(dimethylamino)methane

: 128856-61-1
(5S,1'S)-5-{1',2'-dihydroxy-1',2'-O-isopropylidene-ethyl}-tetrahydrofuran-2-one

: 128856-62-2
(4S,5R)-2(E)-N,N-dimethylaminomethylidene-4-<5,6-O-(1-methylethylidene)>-γ-hexanolactone

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 67℃;	85%

: 5762-56-1
tris(dimethylamino)methane

: (+/-)-trans-4-propyl-3,4,4a,5,6,7,8,8a-octahydro-2H-1,4-benzoxazin-6-one

: (+/-)-trans-(E)-7-dimethylaminomethylidene-4-propyl-2,3,4,4a,5,6,8,8a-octahydro-1,4-benzoxazin-6-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 65℃; for 16h; Condensation;	85%

: 50598-37-3
4-methyl-4-phenyldihydrofuran-2(3H)-one

: 5762-56-1
tris(dimethylamino)methane

: 313219-82-8
3-[1-Dimethylamino-meth-(Z)-ylidene]-4-methyl-4-phenyl-dihydro-furan-2-one

Conditions

Conditions	Yield
at 70℃; for 12h; Substitution;	85%

: 5762-56-1
tris(dimethylamino)methane

: C11H11(2)HO2

: C11H9(2)HO2C3H7N

Conditions

Conditions	Yield
at 70℃; for 12h; Substitution;	85%

: 5762-56-1
tris(dimethylamino)methane

: 5943-53-3
N,N,N',N'-tetramethyl-selenurea

Conditions

Conditions	Yield
With selenium In xylene for 44h; Heating;	82%

: 2-anilino-4-(pyrrolid-2-on-1-ylmethyl)pyrimidine

: 5762-56-1
tris(dimethylamino)methane

: 797793-43-2
2-anilino-4-[1-(pyrrolid-2-on-1-yl)-2-(dimethylamino)vinyl]pyrimidine

Conditions

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 130℃; for 6h;	81%

: 5762-56-1
tris(dimethylamino)methane

: 1309233-72-4
(2S,3S,2'S,5'R)-3-dimethoxymethyl-2',5'-dimethoxy-3,4,2',5'-tetrahydro-2H-2,2'-bifuranyl-5-one

: 1309233-60-0
(2S,3S,2'S,5'R)-3-dimethoxymethyl-4-dimethylaminomethylene-2',5'-dimethoxy-3,4,2',5'-tetrahydro-2H-2,2'-bifuranyl-5-one

Conditions

Conditions	Yield
In toluene at 70℃; for 48h; Inert atmosphere;	81%

: 5762-56-1
tris(dimethylamino)methane

: 138040-08-1, 138040-09-2
(3aS,7aR)-1-Methyl-3a-(2-nitro-phenyl)-octahydro-indol-4-one

: (3aRS, 6RS, 11bSR)-3-methyl-2,3,3a,4,5,6,7,11b-octahydro-1H-6,11b-methanopyrrolo<2,3-e><1>benzazocin-12-one

: 3-methyl-5-(dimethylaminomethylene)-3a-(o-nitrophenyl) octahydroindol-4-one

Conditions

Conditions	Yield
In tetrahydrofuran for 5h; Heating; Yields of byproduct given;	A 80% B n/a
In tetrahydrofuran for 5h; Heating; Yield given;	A 80% B n/a

...Expand

: 5762-56-1
tris(dimethylamino)methane

: 130739-00-3
diethyl methylenebis<(ethoxymethyl)phosphinate>

A: C7H18NO3P

B: O-ethyl(ethoxymethyl)(2-dimethylamino)vinylphosphonate

Conditions

Conditions	Yield
With zinc(II) chloride at 160 - 170℃; Title compound not separated from byproducts;	A n/a B 76%
With zinc(II) chloride at 160 - 170℃;	A n/a B 76%

...Expand

: 7257-25-2
7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one

: 5762-56-1
tris(dimethylamino)methane

: 871112-20-8
7-[(dimethylamino)methylidene]-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; for 3h;	76%
In DMF (N,N-dimethyl-formamide) at 70℃; for 3h;

: 623-73-4
diazoacetic acid ethyl ester

: 5762-56-1
tris(dimethylamino)methane

: 2-Diazo-3,3-bis-dimethylamino-propionic acid ethyl ester

Conditions

Conditions	Yield
at 20℃; for 0.5h;	75%

: 5762-56-1
tris(dimethylamino)methane

: 35059-50-8
t-butyl diazoacetate

: 2-Diazo-3,3-bis-dimethylamino-propionic acid tert-butyl ester

Conditions

Conditions	Yield
at 20℃; for 20h;	74%

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