Naphthalene-2-sulfonyl chloride

Arylalkylsulfones ate important intermediates obtained by alkylation of arylsulfinic acids. The latter ate obtained by reduction of the corresponding sulfonyl chloride. This reduction process is simple and of general appHcation involving the addition of the isolated sulfonyl chloride paste to excess aqueous sodium sulfite followed by salting-out the product and isolation. With mote rigorous reduction conditions, such as zinc/acid, sulfonyl chlorides ate reduced through to aryknercaptans, eg, 2-mercaptonaphthalene is manufactured from naphthalene-2-sulfonyl chloride. 

Naphthalene-2-sulfonyl chloride [93-11-8] M 226.7, m 74-76°, 78°, 79°, b 148°/0.6mm, 201°/13mm. Crystd (twice) from benzene/pet ether (1 1 v/v). Purified as the 2-sulfonyl chloride. [Fierz-Davaid and Weissenbach Helv Chim Acta 3 2312 1920.] The sulfonamide has m 217° (from EtOH). 

Various substituted aromatic compounds can be converted into sulfonyl chlorides by dissolution in five parts of chloroform, dropwise addition of five parts of chlorosulfuric acid at 0°, and keeping for 20 minutes at room temperature. The products are isolated by decomposition with ice, washing of the chloroform layer with water, removal of the solvent, recrystallization of the residue from dry low-boiling light petroleum or from chloroform, and drying in a vacuum over concentrated sulfuric acid. The following benzene-and naphthalene-sulfonyl chlorides were obtained in this way 217... 

GABA ( C-U), specific activity > 170 mCi/mmol L-Glycine ( C-U), specific activity > 90 mCi/mmol Taurine ( 0), specific activity > 90 mCi/mmol Dimethylamino-1-naphthalene sulfonyl chloride 5-(methyl H), specific activity > 10 Ci/mmol... 

Aryl Sulfonylation. Several compounds in this class have been studied. The conditions for reaction with proteins are similar to those used in benzoylation. The reagents used include benzene sulfonyl chloride (219, 209) )8-naphthalene sulfonyl chloride (220) and p-toluene sulfonyl chloride (221) and they may be indicated by the general formula R-SOj-Cl. 

In the presence of an excess of concentrated hydrochloric acid and the calculated amount of NaN02, the chloro derivatives of the aliphatic acids are obtained, often in good yield.- The most valuable reaction of amino acids for use in the qualitative laboratory is the preparation of acyl derivatives. Valuable reagents for this purpose are benzoyl chloride, benzene sulfonyl chloride, 3-naphthalene sulfonyl chloride, and 8-anthraquinonc sulfonyl chloride, all of which may be used with aqueous solutions of amino acids, since these acyl chlorides are only slowly decomposed by water. When benzoyl chloride is used, the product obtained may be contaminated with a small amount of benzoic acid, which may usually be removed because of its greater solubility in ether. The benzoyl derivatives of the amino acids are often rather sparingly soluble in ether as is true of many amides. 

These are compounds that are used to react with non-fluorescent organic compounds to produce fluorescent derivatives, which can then be determined directly by spectrofluorimetry, or by liquid chromatography with fluorescence detection. For example, amines may be determined by coupling with dansyl chloride (5-Dimethylamino-l-naphthalene-sulfonyl chloride)... 

Naphthalene-l-sulfonyl chloride [85-46-1] M 226.7, m 64-67°, 68°, b 147.S°/0.9mm, 147.S°/13mm. If the IR indicates the presence of OH then treat with an equal weight of PCI5 and heat at ca 100° for 3h, cool and pour into ice + H2O, stir well and filter off the solid. Wash the solid with cold H2O and dry the solid in a vacuum desiccator over P2O5 + solid KOH. Extract the solid with pet ether (b 40-60°) filter off any insoluble solid and cool. Collect the crystalline sulfonyl chloride and recryst from pet ether or C6H6 pet ether. If large quantities are available then it can be distd under high vacuum. [Fierz-Davaid and Weissenbach Helv Chim Acta 3 2312 1920.] The sulfonamide has m 150° (from EtOH or H2O). 

Substances 5-(Dimethylamino)-naphthalene-l-sulfonyl chloride Sodium carbonate, anhydrous Methanol Ethanol (96< 7o)... 

Lanthanide(III) triflates catalyze the nitration of a range of simple aromatic compounds (benzene, toluene, biphenyl, m- and p-xylene, naphthalene) in good to excellent yield using stoichiometric quantities of 69% nitric acid.276 Bismuth(III) triflate was found to catalyze sulfonylation of aromatics with aromatic sulfonyl chlorides with similar high efficiency.277... 

Since BAs occurring in food do not exhibit satisfactory absorbance or fluorescence in the visible or ultraviolet range, chemical derivatization, either pre- (35-37) or postcolumn (38), is usually used for their detection in HPLC. The most frequently employed reagents for precolumn derivatization are fluorescamine, aminoquinolyl-lV-hydroxysuccinimidyl carbamate (AQC) (39, 40), 9-fluorenylmethyl chloroformate (FMOC) (41-43), 4-dimethylaminoazobenzene-4 -sul-fonyl chloride (dabsylchloride, DBS) (44), N-acetylcysteine (NAC) (45,46), and 5-dimethyl-amino-1-naphthalene-1-sulfonyl chloride (dansylchloride, DNS) (47,48), phthalaldehyde (PA), and orf/to-phthaldialdehyde (OPA) (49-51), together with thiols such as 3-mercaptopropionic acid (MPA) (37) and 2-mercaptoethanol (ME) (35,49). 

There is surprisingly little reliable information on the sulfonation of benzo[6]thiophene or its derivatives. Benzo[6]thiophene is more readily sulfonated than naphthalene.699 Reaction with concentrated sulfuric acid at 80° gives a mixture of mono-, di-, and trisulfonic acids, reaction with 70% sulfuric acid at 80° gives a monosulfonic acid,699 and reaction with 18% oleum gives a disulfonic acid 86 in each case the orientation of the products is unknown. Treatment of benzo[6]thiophene with concentrated sulfuric acid in acetic anhydride at 20° gives 3-acetylbenzo[6]thiophene (ca. 10%) and a sulfonation product (isolated as the potassium salt), which was believed to be the 3-sulfonic acid.660 Recently, the sulfonation product has been shown to contain the 2- (8%) and 3-isomer (92%), by conversion into the sulfonyl chlorides and reduction to a separable mixture of 2- and 3-mercaptobenzo[6]thiophene.84... 

Mw = 9300, Mw/Mn = 5.07). The poly (p-hydroxy styrene) was PHP-6817-24, obtained from Marusen Oil Co. (Mn = 3900, Mw = 10200, Mw/Mn = 2.62). Kodak micro positive developer 934 (934 developer) (predominantly tetramethyl ammonium hydroxide in water) was used at various dilutions with deionized water. M-cresyl naphthalene diazo-quinone sulfonate was prepsured by a pyridine catalyzed condensation of m-cresol with naphthalene diazoguinone sulfonyl chloride. 

SYNS 1 -CHLOROSULFONYL-5-DIMETHYL-AMINONAPHTHALENE DANSYL DANSYL CHLORIDE DIMETHYLAMINONAPHTHALENE-SULFONYL CHLORIDE 1-DIMETHYLAAIINO-NAPHTHALENE-5-SULFONYL CHLORIDE 1-piMETHYXAMINO)-5-NAPHTHALENESULFONYL-CHLORIDE 5-DIMETHYLAMINONAPHTHYL-5-SL LFONYL CHLORIDE... 

Excess Acid. The helpful function of excess sulfuric acid as an inexpensive, low-viscosity solvent for most sulfonic acids is often overlooked because of the difficulty of recovering a product dissolved in it, or because of the disposal problem often encountered. Sulfonation of most of the hydroxyl, amino, nitro, and carboxylic derivatives of benzene, naphthalene, and anthraquinone is facilitated in this manner by the presence of excess acid. The same effect applies to anthraquinone itself, to petroleum lubricant fractions during sulfonation to mahogany and green acids, and to the sulfation of fatty oils. Chlorosulfonic acid, used in large excess for the conversion of aromatic compounds to sulfonyl chlorides by chlorosulfona-tion, functions in a similar manner. 

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