N,N,N',N'-Tetramethylmethanediamine supplier

Name
N,N,N',N'-TETRAMETHYLDIAMINOMETHANE
EINECS 200-124-7
CAS No. 51-80-9
Article Data43
CAS DataBase
Density 0.813g/cm³
Solubility Fully miscible in water.
Melting Point -55°C
Formula C5H14 N2
Boiling Point 85 °C(lit.)
Molecular Weight 102.18
Flash Point °C
Transport Information
Appearance slightly yellow liquid
Safety Poison by intraperitoneal route. Flammable liquid and very dangerous fire hazard when exposed to powerful oxidizers, heat or open flame. When heated to decomposition it emits toxic fumes of NO_x. See also AMINES.
Risk Codes 11-34
Molecular Structure
Hazard Symbols F,C
Synonyms 2,4-Dimethyl-2,4-diazapentane;Bis(dimethylamino)methane;Dimethyl[(dimethylamino)methyl]amine;Methylenebis(dimethylamine);N,N,N',N'-Tetramethyldiaminomethane;N,N,N',N'-Tetramethylmethanediamine;N,N,N',N'-Tetramethylmethylenediamine;NSC166169;NSC 54796;Tetramethylmethanediamine;
PSA 6.48000
LogP 0.06710

Synthetic route

: 50-00-0
formaldehyd

: 124-40-3
dimethyl amine

: 51-80-9
bis-(dimethylamino)methane

Conditions

Conditions	Yield
In water at 0 - 20℃;	92%
With potassium hydroxide at 20 - 25℃;	89%
Cooling with ice;	81%

: (Me2N)2Zr[iPrNC(NMe2)NiPr]2

: 80937-33-3
oxygen

A: 51-80-9
bis-(dimethylamino)methane

B: Zr(=O)[iPrNC(NMe2)NiPr]2

C: {Zr(μ-O)[iPrNC(NMe2)NiPr]2}2

D: {Zr(μ-O)[iPrNC(NMe2)NiPr]2}n

E: 124-40-3
dimethyl amine

Conditions

Conditions	Yield
In toluene at 90℃; under 760.051 Torr; for 40h; Kinetics; Temperature; Reagent/catalyst; Solvent; Schlenk technique;	A n/a B n/a C n/a D 62% E n/a

...Expand

: Zr(NMe2)2[MeC(NiPr)2]2

: 80937-33-3
oxygen

A: 51-80-9
bis-(dimethylamino)methane

B: {(μ-O)Zr[MeC(NiPr)2]2}n

C: {(μ-O)Zr[MeC(NiPr)2]2}2

D: 124-40-3
dimethyl amine

Conditions

Conditions	Yield
In benzene-d6 at 70℃; Concentration; Temperature;	A 1.09 mg B 58.4% C n/a D 0.125 mg

...Expand

: Zr(NMe2)2[MeC(NiPr)2]2

: 80937-33-3
oxygen

A: 51-80-9
bis-(dimethylamino)methane

B: {(μ-O)Zr[MeC(NiPr)2]2}2

C: {(μ-O)Zr[MeC(NiPr)2]2}n

D: 124-40-3
dimethyl amine

Conditions

Conditions	Yield
In benzene-d6 at 70℃; under 760.051 Torr; for 288h; Inert atmosphere;	A 1.1 mg B n/a C 58% D 0.13 mg

...Expand

: (Me2N)2Hf[iPrNC(NMe2)NiPr]2

: 80937-33-3
oxygen

A: 51-80-9
bis-(dimethylamino)methane

B: {Hf(μ-O)[iPrNC(NMe2)NiPr]2}2

C: {Hf(μ-O)[iPrNC(NMe2)NiPr]2}n

D: 124-40-3
dimethyl amine

Conditions

Conditions	Yield
In benzene-d6 at 70℃; under 760.051 Torr; for 45h; Reagent/catalyst; Schlenk technique;	A n/a B n/a C 40% D n/a

...Expand

: 88470-22-8
N-Methoxy-N-chloro-N',N'-dimethylurea

: 124-40-3
dimethyl amine

A: 51-80-9
bis-(dimethylamino)methane

B: 632-22-4
tetramethylurea

Conditions

Conditions	Yield
at 0℃; for 1h;	A 26.4% B 9.1%

...Expand

: 123-91-1
1,4-dioxane

: 1585-74-6
dimethylchloroamine

: 557-18-6
diethylmagnesium

: 124-40-3
dimethyl amine

: 51-80-9
bis-(dimethylamino)methane

...Expand

: 1585-74-6
dimethylchloroamine

: 51-80-9
bis-(dimethylamino)methane

Conditions

Conditions	Yield
With silver

: 14002-21-2
dimethylaminomethanol

: 51-80-9
bis-(dimethylamino)methane

Conditions

Conditions	Yield
bei der Destillation;
With potassium hydroxide
With dimethyl amine

: 75-09-2
dichloromethane

: 124-40-3
dimethyl amine

: 51-80-9
bis-(dimethylamino)methane

Conditions

Conditions	Yield
at 70℃;
at 70℃;

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

A: 51-80-9
bis-(dimethylamino)methane

B: 75-50-3
trimethylamine

Conditions

Conditions	Yield
With sodium tetrahydroborate; bis(cyclopentadienyl)titanium dichloride at 95℃; for 1h; Mechanism; effect of titanium complex concentration on the induction period;
With sodium tetrahydroborate; bis(cyclopentadienyl)titanium dichloride at 87℃; for 1h;

: 88-27-7
N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine

A: 51-80-9
bis-(dimethylamino)methane

B: 4359-97-1
2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone

C: 2950-01-8
1,2-di(3',5'-di-tert-butyl-4'-hydroxyphenyl)ethene

D: 17329-93-0
4-(dimethylamino)methylene-2,6-di-tert-butylcyclohexa-2,5-dien-1-one

E: 124-40-3
dimethyl amine

F: 1620-98-0
3,5-di-t-butyl-4-hydroxybenzaldehyde

Conditions

Conditions	Yield
With water In xylene at 125℃; for 7h; Product distribution; Rate constant; Thermodynamic data; effect of addition of stearic acid or TFA; Ea; other solvent, temperature;

...Expand

: 704915-64-0
tetra-N-ethyl-2-methyl-2-nitro-propanediyldiamine

Raney nickel: Raney nickel

: 51-80-9
bis-(dimethylamino)methane

Conditions

Conditions	Yield
Hydrogenation;

: 60-29-7
diethyl ether

: 1585-74-6
dimethylchloroamine

copper bronze: copper bronze

A: 51-80-9
bis-(dimethylamino)methane

B 1.3.5-trimethyl-hexahydro-1.3.5-triazine: 1.3.5-trimethyl-hexahydro-1.3.5-triazine

...Expand

: 1585-74-6
dimethylchloroamine

silver: silver

A: 51-80-9
bis-(dimethylamino)methane

B: 506-59-2
N,N-dimethylammonium chloride

...Expand

: 64-17-5
ethanol

: 3735-92-0
N,N,S-trimethyldithiocarbamate

sodium: sodium

A: 51-80-9
bis-(dimethylamino)methane

B: 75-50-3
trimethylamine

C: 5188-07-8
sodium thiomethoxide

D Na2S: Na2S

...Expand

: 2,2-bis-dimethylaminomethyl-3-hydroxy-propionaldehyde ; dihydrochloride

sodium amalgam: sodium amalgam

A: 50-00-0
formaldehyd

B: 51-80-9
bis-(dimethylamino)methane

C: 261528-91-0
1,1-Bis(dimethylaminomethyl)-2-ethanol

Conditions

Conditions	Yield
in schwach saurer Loesung;

...Expand

: Zr(NMe2)2[MeC(NiPr)2]2

: {(μ-η2:η2-O2)Zr[MeC(NiPr)2]2}3

A: 51-80-9
bis-(dimethylamino)methane

B: {(μ-O)Zr[MeC(NiPr)2]2}2

C: {(μ-O)Zr[MeC(NiPr)2]2}n

D: 124-40-3
dimethyl amine

Conditions

Conditions	Yield
In benzene-d6 Inert atmosphere;

...Expand

: Zr(NMe2)2[MeC(NiPr)2]2

: 7722-84-1
dihydrogen peroxide

A: 51-80-9
bis-(dimethylamino)methane

B: {(μ-O)Zr[MeC(NiPr)2]2}2

C: {(μ-O)Zr[MeC(NiPr)2]2}n

D: 124-40-3
dimethyl amine

Conditions

Conditions	Yield
In benzene-d6 Inert atmosphere;

...Expand

: 1353053-97-0
triethylsiloxymethyl-N,N-dimethylamine

: 109-89-7
diethylamine

A: 51-80-9
bis-(dimethylamino)methane

B: 102-53-4
bis-(diethylamino)methane

C: 85413-87-2
N'-N-Diethyl-N'-,N'-dimethyl-methanediamine

Conditions

Conditions	Yield
In benzene-d6 Sealed tube; Inert atmosphere;

...Expand

: 50-00-0
formaldehyd

: 506-59-2
N,N-dimethylammonium chloride

: 51-80-9
bis-(dimethylamino)methane

Conditions

Conditions	Yield
In water at 20℃; for 0.5h; Cooling with ice;

: 51-80-9
bis-(dimethylamino)methane

: 30354-18-8
N,N-dimethyl(methylene)ammonium chloride

Conditions

Conditions	Yield
With acetyl chloride In diethyl ether for 2h;	100%
With acetyl chloride In diethyl ether at 20℃; Cooling with ice;	90%
With acetyl chloride In tert-butyl methyl ether at 0 - 30℃; for 0.5h; Inert atmosphere;	83.7%

: 51-80-9
bis-(dimethylamino)methane

: 132629-08-4
6-Bromo-2-[(4-chloro-phenylamino)-methyl]-5-hydroxy-1-methyl-1H-indole-3-carboxylic acid ethyl ester

: 6-Bromo-2-[(4-chloro-phenylamino)-methyl]-4-dimethylaminomethyl-5-hydroxy-1-methyl-1H-indole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
In 1,4-dioxane Heating;	100%

: 51-80-9
bis-(dimethylamino)methane

: tetraethylcyclohexane-trans-1,2-bis(aminomethylphosphonate)

: [(3aS,7aS)-3-(Diethoxy-phosphorylmethyl)-octahydro-benzoimidazol-1-ylmethyl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
at 80℃;	100%

: 251106-06-6
4-(1H-benzoimidazole-5-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester

: 51-80-9
bis-(dimethylamino)methane

: 1254162-61-2
4-(3-dimethylaminomethyl-3H-benzoimidazole-6-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With succinic acid anhydride; potassium carbonate In dichloromethane at 20 - 23℃; for 6h;	100%

: 51-80-9
bis-(dimethylamino)methane

: 1592-20-7
4-Vinylbenzyl chloride

: N,N'-(methylene)bis(N,N-dimethyl-1-(4-vinylphenyl)methanaminium) chloride

Conditions

Conditions	Yield
In acetonitrile at 50℃; for 48h; Inert atmosphere;	100%

: 51-80-9
bis-(dimethylamino)methane

: 536-74-3
phenylacetylene

: 2568-65-2
N,N-dimethyl-3-phenyl-2-propyn-1-amine

Conditions

Conditions	Yield
With C14H20Cu2I2N2O2S2 In toluene Reagent/catalyst;	99.8%
With samarium nitrate at 80℃; for 6h; Reactivity; Reagent/catalyst; Solvent; Inert atmosphere; neat (no solvent);	98%

: 51-80-9
bis-(dimethylamino)methane

: 108-95-2
phenol

: 120-65-0
ortho-dimethylaminomethylphenol

Conditions

Conditions	Yield
	99.5%

: 51-80-9
bis-(dimethylamino)methane

: 108-95-2
phenol

: 15827-34-6
2,6-bis-<(dimethyamino)methyl>phenol

Conditions

Conditions	Yield
	99.5%

: 51-80-9
bis-(dimethylamino)methane

: 91837-36-4
3H-2,1-benzoxathiolan-3-one 1-oxide

: N,N-dimethylmethyleneimmonium salt of dimethylamide of 0-(oxysulfinyl)isobutyric acid

Conditions

Conditions	Yield
In diethyl ether at 4℃; Acylation;	99%

: 51-80-9
bis-(dimethylamino)methane

: 57-13-6
urea

: 52663-01-1
N,N′-bis[(dimethylamino)methyl]urea

Conditions

Conditions	Yield
With SmCl3*6H2O In ethanol; chloroform at 20℃; for 1h; Reagent/catalyst; Solvent; Time;	99%
With samarium(III) chloride hexahydrate In ethanol for 8h;	99%

: 51-80-9
bis-(dimethylamino)methane

: 17356-08-0
thiourea

: 98425-53-7
N,N′-bis[(dimethylamino)methyl]thiourea

Conditions

Conditions	Yield
With SmCl3*6H2O In ethanol; chloroform at 20℃; for 1h;	99%
With samarium(III) chloride hexahydrate In ethanol; chloroform for 8h; Heating;	99%

: 145834-67-9
1-(4-fluorophenyl)-2-[5-(trifluoromethyl)-2-pyridyl]ethanone

: 51-80-9
bis-(dimethylamino)methane

: 1-(4-fluorophenyl)-2-[5-(trifluoromethyl)-2-pyridyl]prop-2-en-1-one

Conditions

Conditions	Yield
With acetic anhydride In dichloromethane at -15℃; for 0.0833333h; Inert atmosphere;	99%
With acetic anhydride at 0℃; for 0.0833333h;	1.4 g

: 51-80-9
bis-(dimethylamino)methane

: 116718-51-5
7-hydroxy-3-(4-methoxyphenyl)-8-methyl-4H-chromen-4-one

: 6-[(N,N-dimethylamino)methyl]-7-hydroxy-3-(4-methoxyphenyl)-8-methyl-4H-chromen-4-one

Conditions

Conditions	Yield
In 2-methoxy-ethanol at 70 - 124℃; for 16h;	99%

: 51-80-9
bis-(dimethylamino)methane

: ethyl 6-bromo-5-hydroxy-2-(((3-hydroxyphenyl)thio)methyl)-1-methyl-1H-indole-3-carboxylate

: ethyl 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-2-(((3-hydroxyphenyl)thio)methyl)-1-methyl-1H-indole-3-carboxylate

Conditions

Conditions	Yield
In dichloromethane for 3.5h; Inert atmosphere; Reflux;	99%
In dichloromethane for 3.5h; Inert atmosphere; Reflux;	34 mg

: 51-80-9
bis-(dimethylamino)methane

: C14H22O5

: C15H22O5

Conditions

Conditions	Yield
With acetic anhydride; acetic acid In dichloromethane at 20℃; for 10h; Cooling with ice; Inert atmosphere;	99%
With acetic anhydride; acetic acid In dichloromethane at 20℃; for 10h; Cooling with ice;	99%

: 51-80-9
bis-(dimethylamino)methane

: 14335-48-9
trichlorophosphazotrichlorooxoethane

: dimethylamidodichlorophosphazotrichlorooxoethane

Conditions

Conditions	Yield
In benzene for 1h;	98%

: 51-80-9
bis-(dimethylamino)methane

: 5382-00-3
Diphenyl phosphorochloridite

: 19620-78-1
O,O-diphenyl N-dimethylamidophosphite

Conditions

Conditions	Yield
In benzene	98%

: 61160-18-7
3-benzyloxy-2-methyl-1H-pyridin-4-one

: 51-80-9
bis-(dimethylamino)methane

: 174095-91-1
2-methyl-3-benzyloxy-5-(N,N-dimethyl)aminomethyl-pyridin-4-one

Conditions

Conditions	Yield
In ethanol for 20h; Heating;	98%

: 51-80-9
bis-(dimethylamino)methane

: 96754-91-5
3-(2,3-dihydro-1,4-benzodioxin-6-yl)-7-hydroxyisoflavone

: 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-8-[(N,N-dimethylamino)methyl]-7-hydroxy-4H-chromen-4-one

Conditions

Conditions	Yield
In 1,4-dioxane Heating;	98%
In isopropyl alcohol Reflux;

: 51-80-9
bis-(dimethylamino)methane

: 194925-84-3
(S)-2-Benzyl-4-methyl-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione

: (1S,4S)-2-Benzyl-1-dimethylaminomethyl-4-methyl-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione

Conditions

Conditions	Yield
With trifluoroacetic acid at 65℃; for 3.5h;	98%

: 51-80-9
bis-(dimethylamino)methane

: 54799-50-7
(4S)-2,4-dimethyl-2,4-dihydro-(1H)-pyrazino<2,1-b>quinazoline-3,6-dione

: (1S,4S)-1-Dimethylaminomethyl-2,4-dimethyl-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione

Conditions

Conditions	Yield
With trifluoroacetic acid at 65℃; for 3.5h;	98%

: 6,12,18,24-tetramethoxy-2,8,14,20-tetrapentylresorcin[4]arene

: 51-80-9
bis-(dimethylamino)methane

: C64H100N4O8

Conditions

Conditions	Yield
Stage #1: bis-(dimethylamino)methane With potassium carbonate; acetyl chloride In dichloromethane for 0.5h; Stage #2: 6,12,18,24-tetramethoxy-2,8,14,20-tetrapentylresorcin[4]arene In dichloromethane at 20℃; for 120h;	98%

: 51-80-9
bis-(dimethylamino)methane

: 629-05-0
n-octyne

: 1150626-72-4
N,N-dimethyl-N-(non-2-yn-1-yl)amine

Conditions

Conditions	Yield
With copper dichloride at 80℃; for 6h; Reactivity; Solvent; Reagent/catalyst; Inert atmosphere; neat (no solvent);	98%

: 51-80-9
bis-(dimethylamino)methane

: 1289157-09-0
prop-2-yn-1-yl 3-methylbutanoate

: 1289157-13-6
4-(dimethylamino)but-2-yn-1-yl 3-methylbutanoate

Conditions

Conditions	Yield
With copper(l) chloride at 80℃; for 6h; Inert atmosphere; Neat (no solvent);	98%

: 109-79-5
1-butanethiol

: 51-80-9
bis-(dimethylamino)methane

: 62142-30-7
1-(butylsulfanyl)-N,N-dimethylmethanamine

Conditions

Conditions	Yield
With samarium(III) chloride hexahydrate at 60℃; for 1.5h; Inert atmosphere; chemoselective reaction;	98%

: 110-66-7
n-pentanethiol

: 51-80-9
bis-(dimethylamino)methane

: 1369272-96-7
N,N-dimethyl-1-(pentylsulfanyl)methaneamine

Conditions

Conditions	Yield
With samarium(III) chloride hexahydrate at 60℃; for 1.5h; Inert atmosphere; chemoselective reaction;	98%

: 1639-09-4
heptanethiol

: 51-80-9
bis-(dimethylamino)methane

: 1369272-97-8
1-(heptylsulfanyl)-N,N-dimethylmethanamine

Conditions

Conditions	Yield
With samarium(III) chloride hexahydrate at 60℃; for 1.5h; Inert atmosphere; chemoselective reaction;	98%

: 51-80-9
bis-(dimethylamino)methane

: C22H21N3O7S

: C23H21N3O7S

Conditions

Conditions	Yield
With acetic anhydride In acetonitrile at 23℃;	98%

: 51-80-9
bis-(dimethylamino)methane

: 478-48-8
1-4,6-dihydroxy-2-methoxy-3-methylphenylbutan-1-one

: 1-[3-((dimethylamino)methyl)-2,4-dihydroxy-6-methoxy-5-methylphenyl]butan-1-one

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h;	98%
In dichloromethane at 20℃;

: 617-86-7
triethylsilane

: 51-80-9
bis-(dimethylamino)methane

A: 3550-35-4
1,1,1-triethyl-N,N-dimethylsilylamine

B: 75-50-3
trimethylamine

Conditions

Conditions	Yield
With nickel at 140 - 150℃;	A 97% B n/a

...Expand

N,N,N',N'-Tetramethylmethanediamine Chemical Properties

Product Name: N,N,N',N'-Tetramethylmethanediamine (CAS NO.51-80-9)

Molecular Formula: C₅H₁₄N₂
Molecular Weight: 102.18g/mol
Mol File: 51-80-9.mol
Einecs: 200-124-7
Appearance: Slightly yellow liquid
Melting Point: -55°C
Boiling point: 82.5 °C at 760 mmHg
Storage Temperature: Flammables area
Density: 0.749 g/mL at 25 °C(lit.)
Refractive index: n20/D 1.401(lit.)
Stability: Stable, but highly flammable. Incompatible with acids, acid chlorides, acid anhydrides, strong oxidizing agents, carbon dioxide.
Surface Tension: 25.5 dyne/cm
Enthalpy of Vaporization: 32.31 kJ/mol
Vapour Pressure: 78.4 mmHg at 25°C
XLogP3-AA: 0.4
H-Bond Donor: 0
H-Bond Acceptor: 2
Structure Descriptors of N,N,N',N'-Tetramethylmethanediamine (CAS NO.51-80-9):
IUPAC Name: N,N,N',N'-Tetramethylmethanediamine
Canonical SMILES: CN(C)CN(C)C
InChI: InChI=1S/C5H14N2/c1-6(2)5-7(3)4/h5H2,1-4H3
InChIKey: VGIVLIHKENZQHQ-UHFFFAOYSA-N

N,N,N',N'-Tetramethylmethanediamine Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	220mg/kg (220mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 734, 1966.
quail	LD50	oral	> 316mg/kg (316mg/kg)		Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.

N,N,N',N'-Tetramethylmethanediamine Consensus Reports

Reported in EPA TSCA Inventory.

N,N,N',N'-Tetramethylmethanediamine Safety Profile

Poison by intraperitoneal route. Flammable liquid and very dangerous fire hazard when exposed to powerful oxidizers, heat or open flame. When heated to decomposition it emits toxic fumes of NO_x. See also AMINES.
Safety Information of N,N,N',N'-Tetramethylmethanediamine (CAS NO.51-80-9):
Hazard Codes: F,C Corrosive
Risk Statements: 11-34
11: Highly Flammable
34: Causes burns
Safety Statements: 16-26-36/37/39-45
16: Keep away from sources of ignition - No smoking
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves
39: Wear eye/face protection
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)

N,N,N',N'-Tetramethylmethanediamine Specification

N,N,N',N'-Tetramethylmethanediamine ,its CAS NO. is 51-80-9,the synonyms is AI3-26640 ; Bis(dimethylamino)methane ; Dimethyl((dimethylamino)methyl)amine ; EINECS 200-124-7 ; Methylenebis(dimethylamine) ; Methylenediamine, N,N,N',N'-tetramethyl- ; N,N,N',N'-Tetramethyldiaminomethan ; NSC 166169 ; Tetramethylmethylenediamine .

Product Name

N,N,N',N'-TETRAMETHYLDIAMINOMETHANE

Synthetic route

N,N,N',N'-Tetramethylmethanediamine Chemical Properties

N,N,N',N'-Tetramethylmethanediamine Toxicity Data With Reference

N,N,N',N'-Tetramethylmethanediamine Consensus Reports

N,N,N',N'-Tetramethylmethanediamine Safety Profile

N,N,N',N'-Tetramethylmethanediamine Specification

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