Product Name

  • Name

    Tetramethylguanidine

  • EINECS 201-302-7
  • CAS No. 80-70-6
  • Article Data15
  • CAS DataBase
  • Density 0.9 g/cm3
  • Solubility miscible with water
  • Melting Point -30 °C
  • Formula C5H13N3
  • Boiling Point 163.2 °C at 760 mmHg
  • Molecular Weight 115.178
  • Flash Point 60 °C
  • Transport Information UN 2920 8/PG 2
  • Appearance liquid
  • Safety 26-27-36/37/39-45-16
  • Risk Codes 22-34-20/22-10
  • Molecular Structure Molecular Structure of 80-70-6 (Tetramethylguanidine)
  • Hazard Symbols
  • Synonyms Guanidine,1,1,3,3-tetramethyl- (6CI,8CI);1,1,3,3-Tetramethylguanidine;
  • PSA 30.33000
  • LogP 0.14410

Synthetic route

cyanogen iodide
506-78-5

cyanogen iodide

dimethyl amine
124-40-3

dimethyl amine

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
With diethyl ether
1-Nitro-4-nitromethyl-benzene; compound with N,N,N',N'-tetramethyl-guanidine
126661-09-4

1-Nitro-4-nitromethyl-benzene; compound with N,N,N',N'-tetramethyl-guanidine

A

1-nitro-4-(nitromethyl)benzene
1610-26-0

1-nitro-4-(nitromethyl)benzene

B

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
In 1,3,5-trimethyl-benzene at 30℃; Equilibrium constant; Irradiation; other solvents;
1-Ethoxy-2,2-bis-(4-nitro-phenyl)-ethenol; compound with N,N,N',N'-tetramethyl-guanidine

1-Ethoxy-2,2-bis-(4-nitro-phenyl)-ethenol; compound with N,N,N',N'-tetramethyl-guanidine

A

ethyl bis-(4-nitrophenyl)acetate
40748-64-9

ethyl bis-(4-nitrophenyl)acetate

B

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
In tetrahydrofuran at 10.3 - 34.8℃; Kinetics; Equilibrium constant;
methyl iodide compound of tetramethylthiourea

methyl iodide compound of tetramethylthiourea

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
With ethanol; ammonia at 100℃;
pentamethylisothiuronium-iodide

pentamethylisothiuronium-iodide

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
With ammonia; water
dimethyl amine
124-40-3

dimethyl amine

S.N.N-trimethyl-isothiourea

S.N.N-trimethyl-isothiourea

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
With ethanol; mercury dichloride
NCNMe2
1467-79-4

NCNMe2

dimethyl amine
124-40-3

dimethyl amine

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
With N,N-dimethylammonium chloride at 100℃; for 12h;
1,1,3,3-tetramethylgyanidine-gallane (1/1)
325774-15-0

1,1,3,3-tetramethylgyanidine-gallane (1/1)

A

gallium
7440-55-3

gallium

B

hydrogen
1333-74-0

hydrogen

C

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
at 85 - 90℃; Thermodynamic data;
C2H5FO*C5H13N3

C2H5FO*C5H13N3

A

2-fluoroethanol
371-62-0

2-fluoroethanol

B

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C4H4F6O*C5H13N3

C4H4F6O*C5H13N3

A

1,1,1,3,3,3-hexafluoro-2-methylpropan-2-ol
1515-14-6

1,1,1,3,3,3-hexafluoro-2-methylpropan-2-ol

B

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C3H2F6O*C5H13N3

C3H2F6O*C5H13N3

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

phenol
108-95-2

phenol

tetramethylguanidinum phenolate

tetramethylguanidinum phenolate

Conditions
ConditionsYield
at 4℃; for 20h;100%
In tetrachloromethane at 25℃; Equilibrium constant; ΔH; other temp.: 40, 57, 75 deg C; other solvent: CHCl3 (25, 36, 50, 65 deg C);
In tetrachloromethane at 25℃; other temp.; solvent CHCl3;
at 20℃;
benzyl 2-methylene-4-phenylbutanoate
118786-28-0

benzyl 2-methylene-4-phenylbutanoate

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

benzyl 2-((methoxyphosphinyl)methyl)-4-phenylbutanoate
153642-81-0

benzyl 2-((methoxyphosphinyl)methyl)-4-phenylbutanoate

Conditions
ConditionsYield
With trimethyl orthoformate In ethyl acetate100%
C25H23NO6

C25H23NO6

2-chloro-4,6-dimethoxy-1 ,3,5-triazine
3140-73-6

2-chloro-4,6-dimethoxy-1 ,3,5-triazine

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

1,1,3,3-tetramethylguanidine hydrochloride
1729-17-5

1,1,3,3-tetramethylguanidine hydrochloride

Conditions
ConditionsYield
Stage #1: 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; N,N,N',N'-tetramethylguanidine In acetonitrile at 0 - 5℃; for 0.5h;
Stage #2: C25H23NO6 In acetonitrile for 12h;
100%
N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

bis(dimethylamino)methaniminium DL-2-amino-3-(1H-indol-3-yl)propanoate

bis(dimethylamino)methaniminium DL-2-amino-3-(1H-indol-3-yl)propanoate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 23h;100%
L-phenylalanine
63-91-2

L-phenylalanine

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

bis(dimethylamino)methaniminium (L)-2-amino-3-phenylpropanoate
55378-77-3

bis(dimethylamino)methaniminium (L)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 75h;100%
iodotrifluoromethane
2314-97-8

iodotrifluoromethane

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

TMG•CF3I

TMG•CF3I

Conditions
ConditionsYield
at -78 - 23℃; Schlenk technique; Inert atmosphere;100%
at -78 - 23℃; Inert atmosphere;100%
Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

TMG•CF3CF2I

TMG•CF3CF2I

Conditions
ConditionsYield
at -78 - 23℃; Schlenk technique; Inert atmosphere;100%
at -78 - 23℃; Inert atmosphere;100%
1-cyclohexyl-3-(4-nitrophenyl)carbodiimide

1-cyclohexyl-3-(4-nitrophenyl)carbodiimide

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

1-cyclohexyl-2-(4-nitrophenyl)-4,4,5,5-tetramethylbiguanide

1-cyclohexyl-2-(4-nitrophenyl)-4,4,5,5-tetramethylbiguanide

Conditions
ConditionsYield
In toluene at 25℃; for 1h;100%
ciprofloxacin
85721-33-1

ciprofloxacin

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

C17H18FN3O3*C5H13N3

C17H18FN3O3*C5H13N3

Conditions
ConditionsYield
In methanol; water at 20℃; for 3h;100%
D-6-methoxy-α-methyl-2-naphthaleneacetic acid sodium salt
55577-80-5

D-6-methoxy-α-methyl-2-naphthaleneacetic acid sodium salt

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

C14H14O3*C5H13N3

C14H14O3*C5H13N3

Conditions
ConditionsYield
Stage #1: D-6-methoxy-α-methyl-2-naphthaleneacetic acid sodium salt With Amberlyst 15 hydrogen In methanol
Stage #2: N,N,N',N'-tetramethylguanidine In methanol at 20℃; for 1h;
100%
3-imidazolyl-3-(4-methoxyphenyl)propionic acid

3-imidazolyl-3-(4-methoxyphenyl)propionic acid

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

C13H14N2O3*C5H13N3

C13H14N2O3*C5H13N3

Conditions
ConditionsYield
In methanol at 60℃; for 0.5h; Inert atmosphere;100%
In methanol at 60℃; for 0.5h; Inert atmosphere;100%
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
118072-93-8

1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

bis(dimethylamino)methaniminium hydrogen (1-hydroxy-2-(1H-imidazol-1-yl)-1-phosphonoethyl)phosphonate

bis(dimethylamino)methaniminium hydrogen (1-hydroxy-2-(1H-imidazol-1-yl)-1-phosphonoethyl)phosphonate

Conditions
ConditionsYield
In methanol; water for 1h;100%
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
118072-93-8

1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

bis(bis(dimethylamino)methaniminium) (1-hydroxy-2-(1H-imidazol-1-yl)ethane-1,1-diyl)bis(hydrogen phosphonate)

bis(bis(dimethylamino)methaniminium) (1-hydroxy-2-(1H-imidazol-1-yl)ethane-1,1-diyl)bis(hydrogen phosphonate)

Conditions
ConditionsYield
In methanol; water for 1h;100%
3,3,4,4,5,5,6,6,7,7,8,8,8,9,10,10,10,10-heptadecafluoro-1-decathioacetic acid
54207-61-3

3,3,4,4,5,5,6,6,7,7,8,8,8,9,10,10,10,10-heptadecafluoro-1-decathioacetic acid

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

C12H7F17O2S*C5H13N3

C12H7F17O2S*C5H13N3

Conditions
ConditionsYield
In methanol for 2h; Reflux;100%
3,3,4,4,5,5,6,6,7,7,8,8,9,9,9,10,10,10-heptadecafluoro-1-decane-6-thiohexanoic acid

3,3,4,4,5,5,6,6,7,7,8,8,9,9,9,10,10,10-heptadecafluoro-1-decane-6-thiohexanoic acid

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

C16H15F17O2S*C5H13N3

C16H15F17O2S*C5H13N3

Conditions
ConditionsYield
In methanol for 2h; Reflux;100%
2,4,6-tris(trifluoromethyl)benzoyl chloride
135130-97-1

2,4,6-tris(trifluoromethyl)benzoyl chloride

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

N,N,N',N'-tetramethyl-N''-(2,4,6-tris-trifluoromethyl-benzoyl)-guanidine

N,N,N',N'-tetramethyl-N''-(2,4,6-tris-trifluoromethyl-benzoyl)-guanidine

Conditions
ConditionsYield
In diethyl ether at 20℃; for 0.5h;99%
N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

4-methylbenzenesulfonic acid 1,1,3,3-tetramethylguanidine salt
321709-95-9

4-methylbenzenesulfonic acid 1,1,3,3-tetramethylguanidine salt

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 20℃;99%
6-Aminopenicillanic Acid
551-16-6

6-Aminopenicillanic Acid

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

C8H12N2O3S*C5H13N3

C8H12N2O3S*C5H13N3

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1.5h;99%
1H,1H,2H,2H-perfluoro-1-decyl succinic acid monoester

1H,1H,2H,2H-perfluoro-1-decyl succinic acid monoester

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

C14H9F17O4*C5H13N3

C14H9F17O4*C5H13N3

Conditions
ConditionsYield
In methanol Heating;99%
ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

N,N,N',N'-tetramethylguanidinium thiocyanate

N,N,N',N'-tetramethylguanidinium thiocyanate

Conditions
ConditionsYield
In methanol at 20℃; for 1h;99%
(triphenylphosphine)gold(I) chloride
14243-64-2

(triphenylphosphine)gold(I) chloride

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

(tetramethylguanidine)(triphenylphosphane)gold(I) triflate
197569-91-8

(tetramethylguanidine)(triphenylphosphane)gold(I) triflate

Conditions
ConditionsYield
In tetrahydrofuran (N2); stirring the Au complex and AgO3SCF3 in THF at 0°C for 30 min, filtration, addn. of tetramethylguanidine, reacting 1 h; solvent removal, addn. of CH2Cl2, crystn. upon layering with pentane; elem. anal.;98%
(1,1';3',1''-terphenyl)-2'-ol
2432-11-3

(1,1';3',1''-terphenyl)-2'-ol

diethylzinc
557-20-0

diethylzinc

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

[zinc(2,6-(C6H5)2-C6H3O)2(1,1,3,3-tetramethylquanidine)2]
1228276-48-9

[zinc(2,6-(C6H5)2-C6H3O)2(1,1,3,3-tetramethylquanidine)2]

Conditions
ConditionsYield
In hexane byproducts: C2H6; (Et)2Zn (1.0 mmol) added to soln. of HNC(N(CH3)2)2 (2.0 mmol) and HOC6H3(C6H5)2 (2.0 mmol); ppt. dissolved in THF, volatiles evapd. over 24 h; elem. anal.;98%
1,4-butane sultone
1633-83-6

1,4-butane sultone

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

4-(1,1,3,3-tetramethylguanidine-2-yl)butylsulfonic acid
1294516-89-4

4-(1,1,3,3-tetramethylguanidine-2-yl)butylsulfonic acid

Conditions
ConditionsYield
In toluene at 80 - 85℃; for 4h;98%
3-methyl-1-sulphonic acid imidazolium chloride
905707-78-0

3-methyl-1-sulphonic acid imidazolium chloride

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

[1,1,3,3-tetramethylguanidinium chloride][1-methylimidazolium-3-sulfonate]

[1,1,3,3-tetramethylguanidinium chloride][1-methylimidazolium-3-sulfonate]

Conditions
ConditionsYield
In dichloromethane at 20℃;98%
ibuprofen
15687-27-1

ibuprofen

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

C13H18O2*C5H13N3

C13H18O2*C5H13N3

Conditions
ConditionsYield
In methanol at 20℃; for 3h;98%
[Et3N-SO3H]ClSO3

[Et3N-SO3H]ClSO3

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

[TMG-H][TEA-H][(HCl)(HSO4)2]

[TMG-H][TEA-H][(HCl)(HSO4)2]

Conditions
ConditionsYield
In dichloromethane at 20℃;98%
dibutyl phosphate
107-66-4

dibutyl phosphate

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

C8H19O4P*C5H13N3

C8H19O4P*C5H13N3

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h; Inert atmosphere;98%
N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

tris(tetramethylguanido)sulfonium chloride

tris(tetramethylguanido)sulfonium chloride

Conditions
ConditionsYield
With sulfur tetrachloride In dichloromethane97%
diethylzinc
557-20-0

diethylzinc

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

[Zn3(μ-1,1,3,3-tetramethylguanidinate))4(Et)2]
1000401-32-0

[Zn3(μ-1,1,3,3-tetramethylguanidinate))4(Et)2]

Conditions
ConditionsYield
In hexane byproducts: ethane; (Ar); addn. dropwise of Zn(Et)2 (3 equiv.) to soln. of 1,1,3,3-tetramethylguanidine (4 equiv.) in hexane; stirring for 30 min; evapn. of solvent, crystn., recrystn. from concd. hexanes soln. at -37°C; elem. anal.;97%
Ethyl isothiocyanate
542-85-8

Ethyl isothiocyanate

4-chlorobenzoylmethyl bromide
536-38-9

4-chlorobenzoylmethyl bromide

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

(4-chlorophenyl)(4-(dimethylamino)-2-(ethylamino)thiazol-5-yl)methanone
1264379-59-0

(4-chlorophenyl)(4-(dimethylamino)-2-(ethylamino)thiazol-5-yl)methanone

Conditions
ConditionsYield
Stage #1: Ethyl isothiocyanate; N,N,N',N'-tetramethylguanidine In acetone at 20℃; for 0.5h;
Stage #2: 4-chlorobenzoylmethyl bromide In acetone at 20℃;
97%

Tetramethylguanidine Chemical Properties

Molecular formula: C5H13N3
Molecular Weight: 115.18 g/mol
Molecular Structure of Tetramethylguanidine (CAS NO.80-70-6):
 
EINECS: 201-302-7
Appearance: liquid
Melting Point: -30 °C 
Boiling Point: 163.2 °C at 760 mmHg
Flash Point: 60 °C 
Density: 0.918 g/mL at 25 °C(lit.)
Storage Temp.: 2-8 °C
Water Solubility: miscible
Index of Refraction: 1.455
Molar Refractivity: 34.66 cm3
Molar Volume: 127.5 cm3
Surface Tension: 27.7 dyne/cm
XLogP3: 0.4
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 2
Exact Mass: 115.110947
MonoIsotopic Mass: 115.110947
Topological Polar Surface Area: 30.3
Heavy Atom Count: 8 
Canonical SMILES: CN(C)C(=N)N(C)C
InChI: InChI=1S/C5H13N3/c1-7(2)5(6)8(3)4/h6H,1-4H3
InChIKey: KYVBNYUBXIEUFW-UHFFFAOYSA-N
EINECS: 201-302-7
Product Categories: Various hydrocyanic acid derivatives; Hydrocyanic acid derivatives

Tetramethylguanidine Uses

 Tetramethylguanidine (80-70-6) is used as as accelerator for the syntheses of polysulfured rubber, polyurethane foam catalyst, as a strong base in the photochemical (e.g. couplers) and in the pharmaceutical (e.g. steroids) industries.

Tetramethylguanidine Safety Profile

Hazard Codes: CorrosiveC
Risk Statements: 22-34-20/22-10 
R22:Harmful if swallowed. 
R34:Causes burns. 
R20/22:Harmful by inhalation and if swallowed. 
R10:Flammable.
Safety Statements: 26-27-36/37/39-45-16 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S27:Take off immediately all contaminated clothing. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S16:Keep away from sources of ignition.
RIDADR: UN 2920 8/PG 2
WGK Germany: 1
F: 9-23
Hazard Note: Harmful/Corrosive
HazardClass: 8
PackingGroup: II
HS Code: 29252000

Tetramethylguanidine Specification

 Tetramethylguanidine (CAS NO.80-70-6) is also named as AI3-51030 ; CCRIS 6689 ; N,N,N',N'-Tetramethylguanidine ; NSC 148309 ; Guanidine, 1,1,3,3-tetramethyl- (8CI) ; Guanidine, N,N,N',N'-tetramethyl- . Tetramethylguanidine (CAS NO.80-70-6) is a strong amine base with a higher pKa than typical amines. It is highly water soluble so easily removed from other chemicals in a chemical process.

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