Tetramethylguanidine

Tetramethylguanidine is a colorless to pale yellow, transparent, oily liquid with a faint ammoniacal odor. It is one of the most commonly used guanidine bases in organic synthesis, characterized by high basicity and excellent non-nucleophilic properties. It is completely miscible with water and miscible with methanol, ethanol, acetone, toluene, DMF, and DMSO. It reacts with CO₂ to form guanidine carbonate salts and forms stable salts with acids. It is sensitive to air (absorbing CO₂ and moisture) and requires storage under nitrogen in a sealed container.

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Product Introduction

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Basic physical properties

Appearance: Colorless to slightly yellow oily liquid (APHA ≤150)
Melting point: ≤ -30 ℃
Boiling point: 160–162 ℃ (atmospheric pressure), 52–54 ℃ / 1.47 kPa (11 mmHg)
Density: 0.916–0.918 g/cm³ (20 ℃)
Refractive index: n²⁰ᴅ ≈ 1.469
Flash point: 60–65 ℃ (closed cup, approx. 140 ℉); flammable liquid (GHS Category 3)
Vapor pressure: Approx. 0.2 mmHg (0.27 hPa) at 20 ℃; low volatility
Solubility: Completely miscible with water; miscible with methanol, ethanol, acetone, toluene, DMF, and DMSO; LogP ≈ -0.49
pKa: Predicted pKa in water 15.2±0.7, commonly cited value 13.6 (higher in DMSO); pH of 0.5% aqueous solution ≈ 12.7
Dielectric constant: Approx. 23.1

Primary Uses

Pharmaceutical synthesis: Solubilizer/carboxyl protecting agent for cephalosporins (e.g., cefradine, cephalexin, cefoperazone); dissolves 7-ADCA, 7-ACA, and 6-APA; enables metal-free catalytic condensation (replacing metal bases)
PU catalyst: Catalyzes isocyanate–hydroxyl/water reactions in flexible and rigid polyurethane foams; offers a good balance between gelation and blowing, with lower odor than tertiary amines
General-purpose base for organic synthesis: Michael addition, esterification/transesterification, amidation, dehydrohalogenation, glycosylation (in carbohydrate chemistry), and benzoylation of alcohols (high selectivity)
Epoxy curing accelerator, textile leveling agent (nylon/wool), ionic liquid precursor

Safety and Physiology

Toxicity: Low to moderate toxicity; oral LD₅₀ (rat) ≈ 1.6 g/kg (H302: Harmful if swallowed).
Corrosivity: Skin/Eye Category 1A corrosive (H314); skin contact causes burns, eye contact may cause permanent damage; may be corrosive to metals (H290).
GHS: Danger; H226 (Flammable), H290 (Corrosive to metals), H302 (Harmful if swallowed), H314 (Causes severe skin burns and eye damage).
Storage and Transport: UN 2920, Class 8 (PG II); store under nitrogen blanket in a cool, well-ventilated area (≤30°C), isolated from strong acids, strong oxidizers, and CO₂; wear alkali-resistant gloves and safety goggles.

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