Replacement of carcinogenic solvent HMPA by DMI in insect sex pheromone synthesis

Hexamethylphosphoric triamide (HMPA) is a good solvent for the alkylation of terminal acetylenes; however, it has been proven to be a carcinogen towards rats and should be considered as a serious risk to man when a large-scale synthesis is involved. Thus the search for a safe alternative is importan...

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Bibliographic Details
Published in:Journal of chemical ecology 1990-12, Vol.16 (12), p.3245-3253
Main Authors: Lo, C.C. (TACTRI, Taiwan, R.O.C.), Chao, P.M
Format: Article
Language:English
Subjects:
ADOXOPHYES
AMIDAS
AMIDE
Animal, plant and microbial ecology
Biological and medical sciences
COMPOSE HETEROCYCLIQUE
COMPOSE ORGANOAZOTE
COMPUESTO ORGANICO DEL NITROGENO
COMPUESTOS HETEROCICLICOS
CONTROL DE INSECTOS
FEROMONAS
Fundamental and applied biological sciences. Psychology
General aspects. Techniques
Invertebrates
Lepidoptera
LUTTE ANTIINSECTE
Methods and techniques (sampling, tagging, trapping, modelling...)
NEOPLASMAS
NEOPLASME
PHEROMONE
SEXE
SEXO
SOLVANT
SOLVENTES
Tortricidae
TOXICIDAD
TOXICITE
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Summary:Hexamethylphosphoric triamide (HMPA) is a good solvent for the alkylation of terminal acetylenes; however, it has been proven to be a carcinogen towards rats and should be considered as a serious risk to man when a large-scale synthesis is involved. Thus the search for a safe alternative is important. The physical properties of 1,3-dimethyl-2-imidazolidinone (DMI) are similar to DMPU (1,3-dimethyl-2-oxo-hexahydropyrimidine) and HMPA, but the potential toxicological risk of DMI is less than DMPU and HMPA. When used in the alkylation of terminal acetylenes, DMI is comparable with HMPA, thus it is a good alternative solvent to the carcinogen HMPA in the alkylation because it provides a safer working environment than DMPU and HMPA
ISSN:0098-0331
1573-1561
DOI:10.1007/bf00982095