Dimethyl sulfoxide , solubility

Solubility. Very slightly soluble in water (< 1 mg/mL at 17 °C) very soluble in acetone and dimethyl sulfoxide soluble in chloroform, diethyl ether and ethanol (National Toxicology Program, 1991)... 

Salts of the brown-black [Co(en)2(SCH2CH2NH2)]2 are stable indefinitely in air and are stable for days in solutions of dilute aqueous acid at moderate (60°) temperatures. The solid perchlorate salt will ignite in a Bunsen burner flame or on contact with a hot surface, but presents no hazard in solution. The perchlorate salt is the most soluble of those listed above, being very soluble in H20 (0.4 M at 25°),s TVJV-dimethylformamide (DMF), and dimethyl sulfoxide, soluble in triethyl phosphate, methanol, and tetrahydrothiophene 1,1-dioxide... 

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. 

Sodium Borohydride. Sodium borohydride [16940-66-2] is a thermally stable, white crystalline soHd that decomposes in vacuo above 400°C. The heat of formation is —192 kJ/mol (—45.9 kcal/mol). NaBH is hygroscopic and absorbs water rapidly from moist air to form a dihydrate that decomposes slowly to sodium metaborate and hydrogen. It is soluble in many solvents including water, alcohols, Hquid ammonia and amines, glycol ethers, and dimethyl sulfoxide. 

Lithium Acetylide. Lithium acetyhde—ethylenediamine complex [50475-76-8], LiCM7H -112X01120112X112, is obtained as colodess-to-light-tan, free-flowing crystals from the reaction of /V-lithoethylenediamine and acetylene in an appropriate solvent (131). The complex decomposes slowly above 40°O to lithium carbide and ethylenediamine. Lithium acetyhde—ethylenediamine is very soluble in primary amines, ethylenediamine, and dimethyl sulfoxide. It is slightly soluble in ether, THF, and secondary and tertiary amines, and is insoluble in hydrocarbons. 

Strong acids and strong alkaUes can severely bum the skin, chromium compounds can produce skin rashes, and repeated exposure to solvents causes removal of natural oils from the skin. Infection is always a concern for damaged skin. Absorption through the skin is possible for materials that are appreciably soluble iu both water and oil, eg, nitrobenzene, aniline, and tetraethyllead. Other materials can be absorbed if first dissolved iu extremely good solvents, eg, dimethyl sulfoxide. Subcutaneous iujection can occur accidentally by direct exposure of the circulatory system to a chemical by means of a cut or scratch or iuadvertent penetration of the skin with a hypodermic needle. 

Pesticide Solvent. The majority of organic fungicides, insecticides, and herbicides (qv) are soluble in DMSO, including such difficult-to-solvate materials as the substituted ureas and carbamates (see Fungicides, agricultural Insect control technology Pesticides). Dimethyl sulfoxide forms cosolvent systems of enhanced solubiUty properties with many solvents (109). 

Solubility. Poly(vinyl alcohol) is only soluble in highly polar solvents, such as water, dimethyl sulfoxide, acetamide, glycols, and dimethylformamide. The solubiUty in water is a function of degree of polymerization (DP) and hydrolysis (Fig. 4). Fully hydrolyzed poly(vinyl alcohol) is only completely soluble in hot to boiling water. However, once in solution, it remains soluble even at room temperature. Partially hydrolyzed grades are soluble at room temperature, although grades with a hydrolysis of 70—80% are only soluble at water temperatures of 10—40°C. Above 40°C, the solution first becomes cloudy (cloud point), followed by precipitation of poly(vinyl alcohol). 

Cellulose dissolved in suitable solvents, however, can be acetylated in a totally homogeneous manner, and several such methods have been suggested. Treatment in dimethyl sulfoxide (DMSO) with paraformaldehyde gives a soluble methylol derivative that reacts with glacial acetic acid, acetic anhydride, or acetyl chloride to form the acetate (63). The maximum degree of substitution obtained by this method is 2.0 some oxidation also occurs. Similarly, cellulose can be acetylated in solution with dimethylacetamide—paraformaldehyde and dimethylformamide-paraformaldehyde with a potassium acetate catalyst (64) to provide an almost quantitative yield of hydroxymethylceUulose acetate. 

Several cleaning formulations for specific uses contain unreacted polyamines. Examples include mixtures of ammonium alkylbenzenesulfonate, solvents, and PIP which give good cleaning and shine performance on mirrors and other hard surfaces without rinsing (305), and a hard-surface cleaner composed of a water-soluble vinyl acetate—vinyl alcohol copolymer, EDA, cyclohexanone [108-94-1] dimethyl sulfoxide [67-68-5] a surfactant, and water (306). TEPA, to which an average of 17 moles of ethylene oxide are added, improves the clay sod removal and sod antiredeposition properties of certain hquid laundry detergents (307). 

NaBH4 is soluble in water, alcohols, pyridine, dioxane, dimethoxyethane, diglyme and triglyme. All these solvents, as well as aqueous tetrahydrofuran and aqueous dimethylformamide, have been used for reductions. The reductions go very slowly in di- and triglyme so these solvents are not suitable for preparative work. In some reductions in dry pyridine and dry dimethyl sulfoxide, reaction only takes place on aqueous work-up. This... 

The addition proceeds most smoothly with highly functionalized (more polar) steroids as seen in examples by Bernstein and others. The polar reaction conditions pose solubility problems for lipophilic androstane, cholestane and pregnane derivatives. Improved yields can be obtained in some cases by using dimethyl sulfoxide or t-butanol " as solvents and by using sodium A-bromobenzenesulfonamide or l,3-dibromo-5,5-dimethyl hydantoin (available from Arapahoe Chemicals) as a source of positive bromine. The addition of bromo acetate and bromo formate to steroid olefins has been studied to a limited extent. ... 

In practice, few alkenes are soluble in water, and bromohydrin formation is often carried out in a solvent such as aqueous dimethyl sulfoxide, CH3SOCFI3 (DMSO), using a reagent called W-brornosuccinimide ( rBS) as a source of Br2. NBS is a stable, easily handled compound that slowly decomposes in water to yield Br2 at a controlled rate. Bromine itself can also be used... 

Soluble organic solvents have often been used as cosolvents to solubilize miscible organic substrates. Since organic compounds including solvents are possibly incorporated inside of the enzyme, they may affect the stereoselectivity of enzymatic reactions. For example, dimethyl sulfoxide (DMSO) (10%) enhance not only chemical yield but also enantioselectivity of yeast reduction. Thus, the poor yield of 23% with 80% ee was increased to 65% yield with >99% ee (Figure 8.20) [17]. 

The sodium and potassium salts of glutaconaldehyde are soluble only in polar solvents such as water, dimethyl sulfoxide, N,N-dimethylformamide, pyridine, and methanol. However, the stable tetrabutylammonium salt is soluble in relatively nonpolar solvents such as chloroform and ethyl acetate. It may be prepared from the potassium salt in the following manner. In a 1-1. Erlenmeyer flask equipped with a magnetic stirring bar are placed a solution of 13.6g. (0.1 mole) of crude glutaconaldehyde potassium salt in 200 ml. of water and a solution of 33.9 g. (0.1 mole) of tetrabutyl-ammonium hydrogen sulfate in 200 ml. of ice-cold water, the pH of wliich was adjusted to 10 by adding aqueous 2M sodium hydroxide. 

Researchers studying polypeptide and polypeptide hybrid systems have also processed vesicles using two solvents. This method usually involves a common organic solvent that solubilizes both blocks and an aqueous solvent that solublizes only the hydrophilic block. The two solvents can be mixed with the polypeptide or polypeptide hybrid system at the same time or added sequentially. The choice of organic solvent depends heavily upon the properties of the polypeptide material, and commonly used solvents include dimethylformamide (DMF) [46, 59], methanol (MeOH) [49], dimethyl sulfoxide (DMSO) [50, 72], and tetrahydrofuran (THF) [44, 55]. Vesicles are usually formed when the organic solvent is slowly replaced with an aqueous solution via dialysis or removed through evaporation however, some vesicles have been reported to be present in the organic/aqueous mixture [49]. 

Absorption rates of carbon dioxide were measured in organic solutions of glycidyl methacrylate at 101.3 kPa to obtain the reaction kinetics between carbon dioxide and glycidyl methacrylate using tricaprylylmethylammonium chloride(Aliquat 336) as catalysts. The reaction rate constants were estimated by the mass transfer mechanism accompanied by the pseudo-first-order fast reaction. An empirical correlation between the reaction rate constants and the solubility parameters of solvents, such as toluene, A-methyl-2-pirrolidinone, and dimethyl sulfoxide was presented. 

Phenol, the simplest and industrially more important phenolic compound, is a multifunctional monomer when considered as a substrate for oxidative polymerizations, and hence conventional polymerization catalysts afford insoluble macromolecular products with non-controlled structure. Phenol was subjected to oxidative polymerization using HRP or soybean peroxidase (SBP) as catalyst in an aqueous-dioxane mixture, yielding a polymer consisting of phenylene and oxyphenylene units (Scheme 19). The polymer showed low solubility it was partly soluble in DMF and dimethyl sulfoxide (DMSO) and insoluble in other common organic solvents. 

The sulfonylated and acylated PPO presents solubility characteristics which are completely different from those of the parent PPO. Table V presents the solubility of some modified structures compared to those of unmodified PPO. It is very important to note that, after sulfonylation, most of the polymers become soluble in dipolar aprotic solvents like dimethyl sulfoxide (DMSO), N,N— dimethylformamide (DMF) and N,N-dimethylacetamide (DMAC). At the same time it is interesting to mention that, while PPO crystallizes from methylene chloride solution, all the sulfonylated polymers do not crystallize and form indefinitely stable solutions in methylene chloride. Only some of the acetylated polymers become soluble in DMF and DMAC, and none are soluble in DMSO. The polymers acetylated with aliphatic acid chlorides such as propionyl chloride are also soluble in acetone. 

---