Arsonates

HVORGN 0 00 NITRGN 0 00 OXYGEN 0.00 CRBMOX 0.00 ARSON 0 00 METHAN 0.00 CRBTCL 0 15... 

Arylarsonic acids have usually a very low solubility in cold water. They are however amphoteric, since with, for example, sodium hydroxide they form sodium salts as above and with acids such as hydrochloric acid they form salts of the type [CaHjAsCOHljlCl. Both types of salt are usually soluble in water, and to isolate the free acid the aqueous solution has to be brought to the correct pH for most arsonic acids this can be achieved by niaking the solution only just acid to Congo Red, when the free acid will usually rapidly separate. 

Arsonic acids, like carboxylic and sulphonic acids (pp. 349, 353), usually give crystalline benzylthiouronium salts. Add just sufficient dilute aqueous sodium hydroxide dropwise with shaking to a suspension of 0 5 g. of phenylarsonic acid in 10 ml. of water to give a clear solution. Then add 0 5 g. of benzylthiouronium chloride dissolved in 10 ml. of water. Filter off the precipitated benzylthiouronium salt, wash with water and dry m.p. 114-117° it tends to dissociate on attempted recrystallisation. 

The conversion of an aromatic diazonium compound into the corresponding arsonic acid by treatment with sodium arsenite in the presence of a catalyst, such as copper or a copper salt, is called the Bart reaction. A modification of the reaction employs the more stable diazonium fluoborate in place of the diazonium chlorid.i. This is illustrated by the preparation of />-nitrophenylarsonic acid ... 

Elderd, D. M. Kildahl, N. K. Berka, L. H. Experiments for Modern introductory Ghemistry identification of Arson Accelerants by Gas Ghromatography, /. Chem. Educ. 1996, 73, 675-677. 

Cm OROC ARSONS AND Cm OROHYDROC ARSONS - Cm OROPRENE] (Vol6)... 

U.S. demand for [CPD OROC ARSONS AND CPD OROHYDROC ARSONS - SURVEY] (Vol5) Vinylidene chloride-acrylomtrile copolymers [9010-76-8]... 

Searching a crime scene is a complex process (25), involving poHce, crime scene technicians, and forensic scientists. The procedure requires careful documentation, collection, and preservation of the evidence. Trace evidence (26) in criminal investigations typically consists of hairs (27,28) both natural and synthetic fibers (qv) (29,30), fabrics glass (qv) (31,32) plastics (33) sod plant material budding material such as cement (qv), paint (qv), stucco, wood (qv), etc (34), flammable fluid residues (35,36), eg, in arson investigations explosive residues, eg, from bombings (37,38) (see Explosives and propellents), and so on. 

J. F. Boudreau and co-workers, Mn o and Arson Investigation Survey and Assessment, National Institute of Law Enforcement and Criminal Justice, Law... 

Acetarsone. Acetarsone (3-acetamido-4-hydroxyphenyl arsonic acid) (13), also known as acetarsol, stovarsol, and Ehrlich 594, forms white prisms from water. 

Good yields of phenylarsine [822-65-17, C H As, have been obtained by the reaction of phenylarsenic tetrachloride [29181-03-17, C H AsCl, or phenyldichloroarsine [696-28-6], C3H3ASCI25 with lithium aluminum hydride or lithium borohydride (41). Electrolytic reduction has also been used to convert arsonic acids to primary arsines (42). Another method for preparing primary arsines involves the reaction of arsine with calcium and subsequent addition of an alkyl haUde. Thus methylarsine [593-52-2], CH As, is obtained in 80% yield (43) ... 

A large number of polymeric substances, (RAs) or (ArAs), are also known (113). They are usually prepared by the reduction of arsonic acids with hypophosphorous acid (100,114) or sodium dithionite (115). Most of these polymers have not been well characterized. An insoluble, purple material, poly(methylarsinidene) [26403-94-1], (CH As), prepared by the interaction of methylarsine and a dihalomethylarsine, however, has been shown by an x-ray investigation to have a ladderlike polymeric stmcture in which the inter-mng distances correspond to one-electron bonds (116) ... 

Arsonic and Arsinic Acids. The arsonic acids, compounds of the type RAsO(OH)2, are among the most important organic arsenicals. The ahphatic arsonic acids are generally prepared by the Meyer reaction ie, heating an alkyl haUde with As O in alkaline solution ... 

Where X is Br or Q, the free acids may be obtained by acidification of the alkaline solution, but where X is I, the acids must be isolated as salts to avoid reduction of the arsonic acids by HI. Rather than using alkyl haUdes, alkyl or dialkyl sulfates or alkyl arenesulfonates can be used. Primary alkyl haUdes react rapidly and smoothly, secondary haUdes react only slowly, whereas tertiary haUdes do not give arsonic acids. AHyl haUdes undergo the Meyer reaction, but vinyl hahdes do not. Substituted alkyl haUdes can be used eg, ethylene chlorohydrin gives 2-hydroxyethylarsonic acid [65423-87-2], C2H2ASO4. Arsinic acids, R2AsO(OH), are also readily prepared by substituting an alkaU metal arsonite, RAs(OM)2, for sodium arsenite ... 

The Bart reaction is successful with a wide variety of aromatic and heterocycHc amines. A variation in which an aromatic amine, in the presence of arsenic trichloride, is dia2oti2ed in an organic solvent (the ScheUer reaction) has also found wide appHcation. Both arsonic and arsinic acids can be prepared by the ScheUer reaction which often gives better yields than the Bart reaction with electron-attracting substituents on the aromatic ring. For the commercial preparation of 4-aminophenylarsonic acid [98-50-0] (arsaniUc acid), C HgAsNO, and 4-hydroxyphenylarsonic acid [98-14-6] C H AsO, the Bnchamp reaction is used ... 

Arsonic and arsinic acids have found a number of industrial uses. They have been used as corrosion inhibitors for iron and steel, additives to motor fuel, agricultural bactericides, herbicides, and fungicides. 3-Nitro-4-hydroxyphenylarsonic acid (roxarsone) [121 -19-7] C H AsNOg, has found widespread use as an additive to poultry feed for the control of coccidiosis and other poultry diseases (122,123). Arsanilic acid [98-50-0] C HgAsNO, has also been used for this purpose (124) and for growth promotion in swine. It is manufactured and suppHed by Duphar Nutrition Co., Inc., Fleming Laboratories, Inc., Dr. Mayfield Laboratories, Inc., and Whitmoyer Laboratories, Inc. 4-Nitrophenylarsonic acid [98-72-6] C H AsNO and... 

Both arsonic and arsinic acids give precipitates with many metal ions, a property which has found considerable use in analytical chemistry. Of particular importance are certain a2o dyes (qv) containing both arsonic and sulfonic acid groups which give specific color reactions with a wide variety of transition, lanthanide, and actinide metal ions. One of the best known of these dyes is... 

A number of esters of arsonic and arsinic acids have been prepared. One method involves the oxidation of dialkyl alkylarsonites with selenium dioxide ... 

A better method involves the use of silver salts of arsonic acids ... 

Carbarsone (Amebarsone) was once widely used for the treatment of intestinal amebiasis. Like other arsonic acids, however, carbarsone may cause skin rashes and even damage to the vision. Although it is stiU available for medicinal use, it is really obsolete as an amebicide because less toxic and more effective nonarsenicals are now available (174). 

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