Solubility in Alcohols

Naphthalene, CioHs, colourless solid, m.p. 80°, insoluble in water, soluble in alcohol, characteristic odour. Anthracene, CjH4 C2H2 CjH4, m.p. 216°, white crystals when pure, with a faint blue fluorescence, but often very pale yellow crystals insoluble in water, slightly soluble in alcohol. Phenanthrene, m.p. 98°, and biphenyl, m.p. 69°, are white solids. 

When semicarbazide Ls heated in the absence of a carbonyl compound for long periods, condensation to blurea, NHjCONHNHCONHj, m.p. 247-250 (decomp.), may result occasionally this substance may be produced in the normal preparation of a semicarbazone that forms slowly. Biurea is sparingly soluble in alcohol and soluble in hot water, whereas semicarbazones with melting points in the same range are insoluble in water this enables it to be readily distinguished from a semicarbazone. 

Eosin (Tetrabromofluorescein). Place 16 5 g. of powdered fluorescein and 80 ml. of rectified (or methylated) spirit in a 250 ml. flask. Support a small dropping funnel, containing 36 g. (12 ml.) of bromine, above the flask make sure that the stopcock of the funnel is well lubricated before charging the latter with bromine. Add the bromine diopwise during about 20 minutes. When half the bromine has been introduced, and the fluorescein has been converted into dibromofluor-escein, all the solid material disappears temporarily since the dibromo derivative is soluble in alcohol with further addition of bromine the tetrabromofluorescein (sparingly soluble in alcohol) separates out. Allow the reaction mixture to stand for 2 hours, filter ofiF the eosin at the pump, wash it with alcohol, and dry at 100°. The yield of eosin (orange-coloured powder) is 25 g. 

Most xanthene dyes are classified as basic dyes by their method of appHcation acid dyes can be produced by introduction of sulfonic acid groups. The fluoresceins, which contain carboxy and hydroxy substituents, are also acid dyes for coloration of silk. Some of the fluoresceins in which the carboxy group has been esterified, are soluble in alcohol or other organic solvents and can be classified as solvent dyes. Mordant dyes can be produced by introducing o-dihydroxy or sahcyhc acid groups (2), which when metallised can have very good lightfastness. 

Trifluoromethanesulfonic acid is miscible in all proportions with water and is soluble in many polar organic solvents such as dimethylformamide, dimethyl sulfoxide, and acetonitrile. In addition, it is soluble in alcohols, ketones, ethers, and esters, but these generally are not suitably inert solvents. The acid reacts with ethyl ether to give a colorless, Hquid oxonium complex, which on further heating gives the ethyl ester and ethylene. Reaction with ethanol gives the ester, but in addition dehydration and ether formation occurs. 

Cimetidine. This agent, also known as Tagamet [51481-61-9] C qH N S (1) is soluble in alcohol, slightly soluble in water, very slightly soluble in chloroform, and insoluble in ether. The hydrochloride is freely soluble in water, soluble in alcohol, very slightly soluble in chloroform, and practically insoluble in ether. The method of preparation of cimetidine is available (2). 

Castor Oil. Castor oil [8001-79-4] (qv) is the fixed oil from the seeds of Picinus communis Linne. Pale yellowish or almost colorless, it is a transparent viscid Hquid with a faint, mild odor and a bland taste followed by a slightly acrid and usually nauseating taste. Its specific gravity is between 0.945 and 0.965. Castor oil is soluble in alcohol, and miscible with anhydrous alcohol, glacial acetic acid, chloroform, and diethyl ether. It consists chiefly of the glycerides of ricinoleic acid [141 -22-0], and isoricinoleic acid [73891-08-4], found in the small intestine. The seed contains a highly... 

Docusate Calcium. Dioctyl calcium sulfosuccinate [128-49-4] (calcium salt of l,4-bis(2-ethylhexyl)ester butanedioic acid) (11) is a white amorphous soHd having the characteristic odor of octyl alcohol. It is very slightly soluble in water, and very soluble in alcohol, polyethylene glycol 400, and com oil. It may be prepared directly from dioctyl sodium sulfo succinate dissolved in 2-propanol, by reaction with a methan olic solution of calcium chloride. 

Docusate Sodium. Aerosol OT, Colace, and Doxinate are trade names of docusate sodium [577-11-7] (dioctyl sodium sulfo succinate, sodium salt of l,4-bis(2-etliylhexyl)estet butanedioic). This white, wax-like, plastic sohd, with a characteristic odor suggestive of octyl alcohol, is usually available in the form of pellets. One gram of the sodium salt slowly dissolves in about 70 mL water. Docusate sodium is freely soluble in alcohol and glycerol, very... 

A.cetohexamide. Acetohexamide or l-[(p-acetylphenyl)sulfon5l]-3-cyclohex-ylurea, mol wt 324.42, is a white, practically odorless crystalline powder that has the trade name Dymelor. It is practically insoluble in water and in ether, soluble in pyridine and in dilute solutions of alkaU hydroxides, and slightly soluble in alcohol and in chloroform. 

Chlorpropamide. Chlorpropamide (l-[(p-chlorophenyl)sulfonyl]-3-propylurea), mol wt 276.75, is a white, crystalline powder, having a slight odor, mp 127—129°C. It is sold as Diabinese, is soluble in water at pH 6 (2.2 mg/mL), and practically insoluble at pH 7.3, soluble in alcohol, and sparingly soluble in chloroform, ether, and benzene. 

Tola mide. Tola2imide (l-(hexahydro-lJT-a2epin-l-yl)-3-(p-tolysulfonyl)urea), mol wt 311.40, is a white to off-white crystalline powder, ododess or having a slight odor, mp 170—173°C, with a piC of —3.6 at 25°C and 5.68 at 37.5°C. It is very slightly soluble in water, freely soluble in chloroform, soluble in acetone, and slightly soluble in alcohol. The trade name is Tolinase. 

Tolbutamide. Tolbutamide (l-but5l-3-(p-tolylsulfonyl)urea), with mol wt 270.35, is known as Orinase. It is a white to off-white practically ododess crystalline powder having a slightly bitter taste, mp 126—132°C. It is practically insoluble in water, and soluble in alcohol and chloroform. The toxicity of tolbutamide appears to be low, and reactions are similar to those observed with other sulfonylureas. 

Methylene iodide [75-11-6], CH2I2, also known as diio dome thane, mol wt 267.87, 94.76% I, mp 6.0°C, and bp 181°C, is a very heavy colorless Hquid. It has a density of 3.325 g/mL at 20°C and a refractive index of 1.7538 at 4°C. It darkens in contact with air, moisture, and light. Its solubiHty in water is 1.42 g/100 g H2O at 20°C it is soluble in alcohol, chloroform, ben2ene, and ether. Methylene iodide is prepared by reaction of sodium arsenite and iodoform with sodium hydroxide reaction of iodine, sodium ethoxide, and hydroiodic acid on iodoform the oxidation of iodoacetic acid with potassium persulfate and by reaction of potassium iodide and methylene chloride (124,125). Diiodoform is used for determining the density and refractive index of minerals. It is also used as a starting material in the manufacture of x-ray contrast media and other synthetic pharmaceuticals (qv). 

Tris(2,4-pentanedionato)iron(III) [14024-18-1], Fe(C H202)3 or Fe(acac)3, forms mby red rhombic crystals that melt at 184°C. This high spin complex is obtained by reaction of iron(III) hydroxide and excess ligand. It is only slightly soluble in water, but is soluble in alcohol, acetone, chloroform, or benzene. The stmcture has a near-octahedral arrangement of the six oxygen atoms. Related complexes can be formed with other P-diketones by either direct synthesis or exchange of the diketone into Fe(acac)3. The complex is used as a catalyst in oxidation and polymerization reactions. 

Acetophenone. Acetophenone [98-86-2] (methyl phenyl ketone) is a colorless Hquid that forms laminar crystals at low temperature (mp 20°C). It has a characteristic sweet orange blossom odor, and is soluble in alcohols and ethers. It is found in nature in oil of casatoreum, obtained from beavers oil of labdanum, recovered from plants and in buds of balsam poplar. It can be prepared by the Friedel-Crafts reaction (qv) of acetyl chloride with benzene in the presence of aluminum chloride however, this route is of Htde commercial significance. 

Lead nitrate [10099-74-8] Pb(N02)2, mol wt 331.23, sp gr 4.53, forms cubic or monoclinic colorless crystals. Above 205°C, oxygen and nitrogen dioxide are driven off, and basic lead nitrates are formed. Above 470°C, lead nitrate is decomposed to lead monoxide and Pb O. Lead nitrate is highly soluble in water (56.5 g/100 mL at 20°C 127 g/100 mL at 100°C), soluble in alkalies and ammonia, and fairly soluble in alcohol (8.77 g/100 mL of 43% aqueous ethanol at 22°C). Lead nitrate is readily obtained by dissolving metallic lead, lead monoxide, or lead carbonate in dilute nitric acid. Excess acid prevents the formation of basic nitrates, and the desired lead nitrate can be crystallized by evaporation. 

Magnesium iodide is soluble in alcohols and many other organic solvents, and forms numerous addition compounds with alcohols, ethers, aldehydes, esters, and amines. One example is magnesium iodide dietherate [29964-67-8], Mgl2 prepared by gradual addition of iodine to a... 

The covalent character of mercury compounds and the corresponding abiUty to complex with various organic compounds explains the unusually wide solubihty characteristics. Mercury compounds are soluble in alcohols, ethyl ether, benzene, and other organic solvents. Moreover, small amounts of chemicals such as amines, ammonia (qv), and ammonium acetate can have a profound solubilizing effect (see COORDINATION COMPOUNDS). The solubihty of mercury and a wide variety of mercury salts and complexes in water and aqueous electrolyte solutions has been well outlined (5). 

Naphthalenol. 1-Naphthol, a-naphthol, or l-hydroxynaphthalene/P(9-/j5 -iJ forms colorless needles, mp 96°C, bp 288°C, which tend to become colored on exposure to air or light. It is almost insoluble in water, but readily soluble in alcohol, ether, and benzene. 1-Naphthol and 2-naphthol are found in coal tar (56). 

Absolute. This is concentrated extract obtained by treatment of a concrete or other hydrocarbon-type extract of a plant or plant part with ethanol. It is usually Hquid and should be totally soluble in alcohol. By this method, waxes, hydrocarbons (including terpenoid), as well as most of the odorless material of the concrete are removed from the extract. 

Anhydrous ammonium oxalate is obtained when the monohydrate is dehydrated at 65°C. The monohydrate is a colorless crystal or white powder, and dissolves in water at 0°C up to 2.17 wt %, and 50°C up to 9.63 wt %. It is slightly soluble in alcohol and insoluble in ether. It is used for textiles, leather tanning, and precipitation of rare-earth elements. 

At room temperature phenol is a white, crystalline mass. Phenol gradually turns pink if it contains impurities or is exposed to heat or light. It has a distinctive sweet, tarry odor, and burning taste. Phenol has limited solubiUty in water between 0 and 65°C. Above 65.3°C phenol and water are miscible in all proportions. It is very soluble in alcohol, ben2ene, chloroform, ether, and partially disassociated organics in general. It is less soluble in paraffinic hydrocarbons. The important physical properties of phenol are Hsted in Table 1. 

Sulfonamide groups can be introduced into phthalocyanines to make them soluble in alcohols and glycol ethers. Their main appHcations are transparent paints, flexo and gravure printing inks, wood stains, plastics, and ballpoint inks. This includes products Hke Solvent Blue 24 (Cl 74380),... 

These compounds are highly soluble in water. AMP, AMPD, AEPD, and DMAMP are completely miscible in water at 20 °C the solubihty of AB is 250 g/100 mL H2O at 20°C. They are generally very soluble in alcohols, slightly soluble in aromatic hydrocarbons, and nearly insoluble in aliphatic hydrocarbons tris(hydroxymethy1)aminomethane [77-86-1] is appreciably soluble only in water (80 g/100 mL at 20°C) and methanol. 

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