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Diethyl bis(hydroxymethyl)malonate is used as a reagent for preparing 1,3-dioxanes from acetals, aldehydes and ketones. It is also used as an intermediate for the preparation of substituted malonic, acrylic and isobutyric esters, for conversion to the useful dienophiles, ?-bromomethylacrylic acid and its ethyl ester and to bis(bromomethyl)acetic acid and its methyl ester.
Ross A. Miller.; Fengrui Lang.; Benjamin Marcune.; Daniel Zewge.; Zhiguo J. Song.; Sandor Karady. A Practical Process for the Preparation of Azetidine-3-carboxylic Acid. Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry. 2003, 33 (19), 3347-3353.
Shiyue Fang.; Donald E. Bergstrom. Reversible Biotinylation Phosphoramidite for 5-End-Labeling, Phosphorylation, and Affinity Purification of Synthetic Oligonucleotides. Bioconjugate Chem. 2003, 14 (1), 80-85.
Intermediate for the preparation of substituted malonic, acrylic and isobutyric esters: J. Chem. Soc., 257 (1930); J. Org. Chem., 20, 780 (1955). For conversion to the useful dienophiles, ɑ-bromomethylacrylic acid and its ethyl ester, see: Org. Synth. Coll., 7, 210 (1990), and to bis(bromomethyl)acetic acid and its methyl ester, Org. Synth. Coll., 7, 319 (1990).
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant