Dimethyl-amine sulphate

Surfactants Ionic, anionic (e.g., sodium dodecyl sulphate, Cj2H250S03 Na ), cationic (e.g., cetyl trimethyl ammonium chloride, Ci,H33-N+(CH3)3C1-), zwitterionic [e.g., 3-dimethyldodecylamine propane sulphonate (betaine CJ2H25-N" (CH3)2-CH2-CH2-CH2-S03)], nonionic, alcohol ethoxylates C H2 +i-0-(CH2-CH2-0) -H, alkyl phenol ethoxylates C H2 +i-CgH4-0-(CH2-CH2-0) -H, amine oxides (e.g., decyl dimethyl amine oxide, C10H21-N ( 113)2 0), and amine ethoxylates. 

Dimethyl Sulphate Method for hydroxy compounds and for primary and secondary amines, acid amides, etc. The substance is dissolved or suspended in water, a small excess (above the theoretical) of sodium hydroxide added and then the theoretical quantity of dimethyl sulphate, the mixture being finally shaken without external warming. Methylation is usually rapid, the dimethyl sulphate being converted to methyl hydrogen sulphate... 

The Formaldehyde-Formic Acid Method, This method applies to primary and secondary amines, which when boiled with a formalin-formic acid mixture undergo complete methylation to the corresponding tertiary amine. This method has the advantage over the dimethyl sulphate method in that quaternary salts clearly cannot be formed. 

Incorporating a tertiary amine into dimethyl sulphate without using any solvent caused a violent detonation. 

Of some importance as textile dyes are aza analogues of polymethine (cyanine) dyes. Azacarbocyanines result when Fischer s aldehyde is heated with primary aromatic amines. Thus Cl Basic Yellow 11 (6.220) is obtained when Fischer s aldehyde is condensed with 2,4-dimethoxyaniline. The equivalent reaction with 2-methylindoline gives Cl Basic Yellow 21 (6.221), which has superior light fastness but has been classified by ETAD as toxic [73]. The tinctorially strong golden yellow diazacarbocyanine dye Cl Basic Yellow 28 (6.222) is prepared by coupling diazotised p-anisidine with Fischer s base (6.223), followed by quaternisation with dimethyl sulphate. Some triazacarbocyanine dyes are also used commercially. 

Hindered di-t-alkylamines RNHBu1 (R = t-Bu, t-octyl or 1-adamantyl) have been synthesized from t-alkylamines as follows. Reaction with peracetic acid gave the nitrosoalkanes RNO, which were treated with t-butyl radicals, generated from t-butylhydrazine and lead(IV) oxide, to yield t-butyloxyhydroxylamines. Reduction with sodium naphthalide in THF gave the products (equation 12). The di-t-alkyl-amines are inert to methyl iodide and dimethyl sulphate but can be alkylated by methyl fluorosulphonate42. 

Abbreviations BSA, bovine serum albumin Chi, chlorophyll DCPIP, 2, 6-dichlorophenol indophenol DMBQ, 2, 6-dimethyl-l, 4-benzoquinone DTT, dithiothreitol Fd, ferredoxin Hepes, N-2-hydroxyethyl-piperazine N -2-ethane sulphonate LDAO, lauryldimethyl amine oxide Mes, 4-morpholine ethane sulphonic acid MV, methyl viologen PAGE, polyacrylamide gel electrophoresis PRuK, phosphoribulokinase PS, photosystem Ru5P, ribulose 5-phosphate SDS, sodium dodecyl sulphate TMPD, N, N, N, N -tetramethyl paraphenylene diamine TRX. thioredoxin... 

Dimethyl sulphate, before being employed as a war gas, was used in industry as a methylating agent for amines and phenols. In recent years it has also been employed as a catalyst in the preparation of cellulose esters. ... 

Dimethyl sulphate also reacts with amines. For instance, with the aromatic primary amines it forms the methyl sulphate of the primary amine, together with the corresponding secondary base (Ullmann) ... 

The tertiary amines in ethereal or benzene solution react with dimethyl sulphate, forming quaternary ammonium compounds. 

Metabolism of foreign compounds is not necessarily detoxication. This has already been indicated in examples and will become more apparent later in this book. This may involve activation by a phase 1 or phase 2 pathway or transport to a particular site followed by metabolism. Thus, sulphate conjugation and acetylation may be involved in the metabolic activation of /V-hydroxy aromatic amines, glutathione conjugation may be important in the nephrotoxicity of compounds, methylation in metal toxicity, glucuronidation in the carcinogenicity of /1-naphthylamine and 3, 2 -dimethyl-4-aminobiphenyl. 

Reaction of isoandrololactam acetate with dimethyl sulphate gave o-methyliso-andrololactim acetate (178). Treatment of (178) with allylmagnesium bromide afforded the amine (179), which when oxidized with w-chloroperbenzoic acid yielded the steroidal nitroxide (180), with the NO group incorporated into the steroid skeleton. ... 

Attempts have also been made to solvent-extract thorium directly from the sulphate liquor obtained by the acid breakdown of monazite. Tributyl phosphate can be used as the solvent provided a large concentration of nitric acid is added to the liquor before extraction. In order to make the process economic, a high proportion of the nitric acid must then be recovered by distillation of the raffinate liquor. Processes are also being developed which are based upon the use of higher alkyl phosphate or amine solvents to extract from sulphate solutions without the addition of nitric acid, as in the case of uranium. For example bis(l-isobutyl 1-3-5 dimethyl-hexyl) amine, di-2-ethylhexyl hydrogen phosphate and Primene JM-T have been used. 

N-(prop-2-ynyl)amines to l-aminopropa-l,2-dienes followed by acid hydrolysis (e.g. Scheme 50). Treatment of the lithiated intermediate with dimethyl sulphate instead of methanol gives the 3-methylaldehyde, and deuterium atoms can also be introduced specifically. 

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