Chloromethyl compounds toxicity

Several chlorophyll derivatives have been prepared by electrophilic substitution, inter alia by formylation reactions. Adopting methods from corrin chemistry.50 alkylation with chloro-methyl methyl ether (caution toxic),32k chloromethyl methyl sulfide,51 and dichloromethyl methyl ether (caution toxic)52 in the presence of Lewis acids are the methods of choice to introduce carbon residues into the chlorin frame work. The compounds listed below have been prepared by these methods. 

The toxicity of chromium and inorganic chromium compounds Bis (chloromethyl) ether... 

It was important to determine whether the fluorine atom must be attached directly to the phosphorus atom in order to produce phosphorofluoridate-like activity. For this purpose we treated the toxic di-sec.-butyl phosphorofluoridate1 with diazomethane and obtained a compound which was undoubtedly di- ec.-butyl fluoromethylphosphonate (XIX). Unlike the parent phosphorofluoridate, the fluoromethylphosphonate was only slightly toxic and produced negligible myosis. (It may be mentioned here that thionyl chloride and carbonyl chloride were converted by means of diazomethane into bis-(chloromethyl)-sulphoxide and S-dichloroacetone respectively.)... 

Chloromethyl-5,6,7,8-tetrahydrobcnzo[b]thieno[2,3-chronic toxicity studies showed the compound to be safe. It was concluded that compound 179 can be developed as a potential antihyperlipaemic drug (90AF567). 

For a new compound when there is no information upon which to predict risks or toxicity, a level of the acute LD50/1, 000 might serve as a preliminary control standard for most toxicological effects. For carcinogenicity, a worse case could be assumed, and the limit would be that of a potent known carcinogen, e.g., bis-chloromethyl ether. The lower value (toxicity or carcinogenicity) would be the limit. 

The other members of this family of compounds are phosphorodithioic acid derivatives. Of these, menazon, 0,0-dimethyl-S-(4,6-diamino-l,3,5-triazin-2-yl)-methyl phosphorodithioate (78), distinguishes itself by its low toxicity to warmblooded animals. It is prepared by cyclisation of biguanide and ethyl chloroacetate, upon which the 2-chloromethyl-4,6 iaminotriazine formed is reacted with sodium 0,0-dimethyl phosphorodithioate (Anonym, 1958). 

Bis(2-chloroisopropyl)ether exhibited moderately toxic and carcinogenic actions in test animals. The acute inhalation toxicity of this compound is considerably lower than those of bis(chloromethyl)ether and bis (chloroethyl)ether. Exposure to its vapors can cause irritation of the eyes and upper respiratory tract. Inhalation of 700 ppm of this compound in air for 5 hours proved fatal to rats. 

Monochlorodimethyl ether, CH3OCH2CI (MCDE) [1, 13, 14], though a rather toxic compound, is also considered to be a suitable bifunctional crosslinking reagent. Its reaction with polystyrene proceeds quantitatively through the intermediate stage of chloromethylation the introduced... 

Prior to the introduction of synthetic pyrethroids, insect-resist agents were based mainly on speciality materials, such as polychloro chloromethyl sulfonamido diphenyl ether (PSCDs) (Eulan U33, Eulan WA New). The production of these compounds has been discontinued, however, because of a combination of environmental toxicity (149) and cost. One speciality insect-resist agent based on sulcofuron (Mitin FF), released in 1939 (153), retains a small market share for specific applications where cost is less important and where high resistance to wet conditions is required. It has also been used on wool insulation where it also has low volatility and provides resistance to rotting (154). 

CAUTION As described later in Chapter 2, the reaction of formaldehyde with hydrogen chloride has been shown to lead to the spontaneous production of the now known carcinogen te(chloromethyl) ether. In addition, other aldehydes (crotonaldehyde, acetaldehyde, acrolein, etc.) are also toxic [7], Toxicity limits for some representative compounds in air... 

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