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Tetramethylguanidine

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Tetramethylguanidine Basic information

Product Name:
Tetramethylguanidine
Synonyms:
  • N,N’-Tetramethylguanidine
  • 1,1,3,3-Tetramethyl Guanidine (TMG)
  • 1,1,3,3-Tetramethylgyanidine, 97+%
  • 1,1,3,3-Tetramethylguanidine,99%
  • N,N,N,N-Tetramethy1 Guanidine
  • 1,1,3,3-Tetramethylguanidin
  • TMG
  • 1,1,3 tetramethyl guanidine
CAS:
80-70-6
MF:
C5H13N3
MW:
115.18
EINECS:
201-302-7
Product Categories:
  • Various hydrocyanic acid derivatives
  • Glycosylating Reagents
  • Bioactive Small Molecules
  • Building Blocks
  • Carbohydrate Chemistry
  • Cell Biology
  • Hydrocyanic acid derivatives
  • Chemical Biology
  • Chemical Synthesis
  • Guanidines
  • Nitrogen Compounds
  • Organic Building Blocks
  • T
  • Antidote / Antibiotic / Antimicrobial
  • 80-70-6
Mol File:
80-70-6.mol
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Tetramethylguanidine Chemical Properties

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)
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Safety Information

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
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

MSDS

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Tetramethylguanidine Usage And Synthesis

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.]

Tetramethylguanidine Preparation Products And Raw materials

Preparation Products

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