Йодид бензилтриметиламмония

Description

Benzyltrimethylammonium iodide is a quaternary ammonium salt, a cationic compound from the benzyltrialkylammonium family of reagents used as phase transfer catalysts and methylating agents. Formula C10H16N,I, CAS number 4525-46-6, synonyms benzyldimethylaminomethiodide, trimethylbenzylammonium iodide.

Basic Attributes

• Chemical formula: C10H16N,I
• Molecular weight: 277.15
• Exact weight: 277.03300
• BRN: 3917007
• EU number: 224-861-9
• NSC Number: 31974
• HS code: 29239000
• PSA Features: 0
• XLogP3: -1.10320

Physico-chemical characteristics

• Melting point: 179 °C
• Flammability characteristics: highly flammable; combustion produces toxic nitrogen oxides, ammonia and iodide vapors

Toxicity

• Intraperitoneal, mice, LD50: 41 mg/kg
• Intravenous, mice, LD50: 5.6 mg/kg
• GHS classification: H302 (100%) - harmful if swallowed

Scope of application

As a quaternary ammonium salt with a benzyl and three methyl groups on nitrogen, the compound belongs to the benzyltrialkylammonium family of reagents used in organic synthesis as phase transfer catalysts (by analogy with the chloride and hydroxide forms of the same cation, known as the Triton B reagent) - they accelerate alkylation, esterification and condensation reactions in two-phase aqueous-organic systems, and are also used as sources of the methylating or benzylating moiety in individual synthetic circuits.

Safety Information

• Hazard class code: 20/21/22-36/37/38
• Safety instructions: 26-36/37/39-36
• RTECS number: BO8585000
• Tags: Xn
• Precautions: P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Storage conditions

Store in a dry, well-ventilated, cool place, away from food materials. The substance is flammable and, when burned, releases toxic nitrogen oxides and ammonia and iodide vapors, so work should be carried out away from sources of open flame and using respiratory protection.

Comparison with chloride and hydroxide forms

The iodide salt of benzyltrimethylammonium is less common in phase transfer catalysis than the chloride or hydroxide forms of the same cation (the latter is known as the Triton B reagent and is used as a strong organic base), but the iodide anion makes the compound a useful reagent where it is necessary to introduce iodide as a nucleophile or where the less nucleophilic chloride does not provide the required rate of anion exchange reaction.

The choice between the chloride, bromide and iodide forms of the cation in practice is determined by the required nucleophilicity of the anion and its solubility in a particular reaction solvent.