Tetramethylguanidine Property

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

PH

12.7 (10g/l, H2O, 25℃)

Relative polarity

5.5

Odor

mild ammoniacal odor

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.

InChIKey

KYVBNYUBXIEUFW-UHFFFAOYSA-N

LogP

-0.49 at 20℃

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

Hazard Codes 

C

Risk Statements 

22-34-20/22-10

Safety Statements 

26-27-36/37/39-45-16

RIDADR 

UN 2920 8/PG 2

WGK Germany 

1

F 

9-23

Autoignition Temperature

222 °C

Hazard Note 

Harmful/Corrosive

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29252000

Toxicity

LD50 orally in Rabbit: 835 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H290May be corrosive to metals

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Tetramethylguanidine Chemical Properties,Usage,Production

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℃).

Uses

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

Uses

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

Uses

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.

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.]