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Z101591 Aldrich

Aldrich® diazomethane-generator apparatus

24/25 Clear-Seal joint



General description

MNNG is mutagenic and exposure may cause skin sensitivity. While MNNG is more convenient for the generation of small quantities of diazomethane, Diazald is the preferred reagent for large-scale production of diazomethane. However, the following procedure is verified and recommended for use on a small ~0.3 mmol substrate scale. For larger substrate amounts, one of the Diazald distillation apparatuses should be used to generate diazomethane.

Typical Generator Procedure:
To the outside tube of the Aldrich MNNG diazomethane generation apparatus, add 4-methoxybenzoic acid (0.465 g, 0.300 mmol) and ether (3.0 mL). To the inside tube, add Diazald (0.367 g, 1.71 mmol) and carbitol (1.0 mL). Assemble the two parts and immerse the lower part of the outer tube in an ice bath. After equilibrating to the cooling bath temperature, Slowly inject, dropwise through the septum via a syringe, aqueous KOH (37%, ~1.5 mL).

Shake the apparatus gently by hand to ensure mixing of reactants within the inner tube, while being careful not to allow these reactants to spill into the outer tube. The solution in the outer tube may became yellow in color and will persisted, indicating an excess of diazomethane. After 50 min, open the apparatus. Carefully add solid silicic acid (0.151 g) to the inner tube to destroy unreacted diazomethane. Evaporate the yellow ether solution in the outside tube under a gentle stream of nitrogen affording methyl 4-methoxybenoate as a white solid product (0.490 g, 98.4%). Analysis by GC/MS indicates the material to be analytically pure.

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Aldrich is a registered trademark of Sigma-Aldrich Co. LLC

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Z411736 Aldrich® diazomethane-generator with System 45 compatible connection, for the preparation of diazomethane without ether

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