Tetramethylguanidine

Synonym(s):N,N,N′,N′-Tetramethylguanidine;1,1,3,3-Tetramethylguanidine;N,N,N′,N′-Tetramethylguanidine

CAS NO.：80-70-6
Empirical Formula: C5H13N3
Molecular Weight: 115.18
MDL number: MFCD00008323
EINECS: 201-302-7
SAFETY DATA SHEET (SDS)
Update Date: 2025-04-29 15:35:11

What is Tetramethylguanidine?

Chemical properties

N,N,N',N' -Tetramethylguanidine (TMG) [80-70-6], C5H13N3, Mr 115.18, is a stable, unusually strong base, pKa 13.6 (25 ℃), with a free imino group. It is a colorless to light-yellow liquid, miscible with water and common organic solvents: 0.92 g/cm3 (25 ℃), bp 160 ℃, vapor pressure 0.03 kPa (25℃).

The Uses of Tetramethylguanidine

Base employed in the preparation of alkyl nitriles from alkyl halides and 3′-alkylthymidines from 3′-nitrothymidines.

The Uses of Tetramethylguanidine

1,1,3,3-Tetaramethylguanidine is used as a strong, non-nucleophilic base for alkylations in organic synthesis. 1,1,3,3-Tetramethylguanidine is an efficient and selective catalyst for the benzoylation of alcohols.

The Uses of Tetramethylguanidine

Tetramethylguanidine (TMG) is used as polyurethane foam catalyst, as accelerator for the syntheses of polysulfured rubber, as a strong base in the photochemical (e.g. couplers) and in the pharmaceutical (e.g. steroids) industries. Product Data Sheet

Flammability and Explosibility

Flammable

Synthesis

Prepared from cyanogen chloride and dimethylamine in a 1 : 2 molar ratio, TMG is used as a polyurethane foam catalyst, in the preparation of pigments for color photography, and in steroid synthesis.

Purification Methods

Reflux it over granulated BaO, then fractionally distil it. Protect it from CO2. [Beilstein 4 IV 227.]

Properties of Tetramethylguanidine

Melting point:	-30 °C
Boiling point:	162-163 °C (lit.)
Density	0.916 g/mL at 20 °C (lit.)
vapor pressure	0.2 mm Hg ( 20 °C)
refractive index	n20/D 1.469
Flash point:	140 °F
storage temp.	Store below +30°C.
solubility	Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
pka	15.20±0.70(Predicted)
form	Liquid
color	APHA: ≤150
Odor	mild ammoniacal odor
PH	12.7 (10g/l, H2O, 25℃)
Relative polarity	5.5
explosive limit	1.0-7.5%(V)
Water Solubility	miscible
Sensitive	Air Sensitive
BRN	969608
Dielectric constant	23.100000000000001
Stability:	Stable. Combustible. Incompatible with strong oxidizing agents, mineral and organic acids, carbon dioxide. Air-sensitive.
CAS DataBase Reference	80-70-6(CAS DataBase Reference)
NIST Chemistry Reference	N,N,N',N'-Tetramethylguanidine(80-70-6)
EPA Substance Registry System	Guanidine, N,N,N',N'-tetramethyl- (80-70-6)

Safety information for Tetramethylguanidine

Signal word	Danger
Pictogram(s)	Flame Flammables GHS02 Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07
GHS Hazard Statements	H226:Flammable liquids H290:Corrosive to Metals H302:Acute toxicity,oral H314:Skin corrosion/irritation
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.