Diisopropylethylamine

Diisopropylethylamine is abbreviated as DIPEA (also known as DIEA or i-Pr₂NEt) and is commonly referred to as Hünig's base. It has the CAS number 7087-68-5, a molecular formula of C₈H₁₉N, and a molecular weight of 129.24. It appears as a colorless to pale yellow transparent liquid with the pungent odor characteristic of amines and is indispensable in organic synthesis.

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Product Introduction

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Key physicochemical properties

Appearance: Diisopropylethylamine is a colorless to pale yellow transparent liquid with a pungent, amine-like odor
Boiling point: Approx. 126.5–129°C; Melting point: Approx. −46°C
Density: 0.742 g/cm³ (25°C); Flash point: Approx. 10–11°C (highly flammable; GHS Category 2 flammable liquid)
Basicity: Conjugate acid pKa ≈ 10.5–10.9 (comparable to or slightly weaker than triethylamine); characterized by significant steric hindrance and extremely low nucleophilicity
Solubility: Highly soluble in DCM, THF, alcohols, and ethers; sparingly soluble in water (approx. 3.9 g/L at 20°C)

Typical Applications

Solid-Phase Peptide Synthesis (SPPS): Used in conjunction with coupling agents such as HATU, HBTU, or DIC to activate carboxyl groups and act as an acid scavenger, thereby suppressing amino acid racemization.
Amide/Sulfonamide Condensation: Absorbs HX during the reaction of acid chlorides or sulfonyl chlorides with amines, preventing amine deactivation via protonation.
Mitsunobu, Suzuki, Buchwald–Hartwig, etc.: Acts as a non-nucleophilic base or co-base to stabilize the active centers of metal catalysts.
Pharmaceutical/Agrochemical Intermediates: Facilitates the highly selective synthesis of nucleosides, anti-tumor agents, sulfonylurea herbicides, and more.

Safety, Storage, and Transportation

GHS Hazard Statements: H225 Highly flammable; H302 Harmful if swallowed; H318 Causes serious eye damage; H331 Toxic if inhaled; H335 May cause respiratory irritation.
Vapors are heavier than air and prone to accumulating in low-lying areas, posing a risk of flashback; reacts exothermically with strong acids, strong oxidizing agents, and acyl chlorides.
Handling: Work in a fume hood; use anti-static measures and explosion-proof electrical equipment; wear nitrile gloves and safety goggles. For spills, absorb with sand or earth; do not flush directly with water (amines dissolve in water exothermically and spread contamination).
Storage: Store diisopropylethylamine in a sealed container in a cool place (<25°C); store away from ignition sources and oxidizing agents; typically stored in steel drums. Literature suggests avoiding long-term contact with copper or copper-alloy containers.