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[ CAS No. 27503-81-7 ] {[proInfo.proName]}

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Chemical Structure| 27503-81-7
Chemical Structure| 27503-81-7
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Product Details of [ 27503-81-7 ]

CAS No. :27503-81-7 MDL No. :MFCD00053007
Formula : C13H10N2O3S Boiling Point : -
Linear Structure Formula :- InChI Key :UVCJGUGAGLDPAA-UHFFFAOYSA-N
M.W : 274.30 Pubchem ID :33919
Synonyms :
PBSA

Safety of [ 27503-81-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 27503-81-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 27503-81-7 ]

[ 27503-81-7 ] Synthesis Path-Downstream   1~7

YieldReaction ConditionsOperation in experiment
Aus Benzimidazol IIc u. Chlorsulfonsaeure;
Aus Sulfonylchlorid IV u. H2O;
Aus IVc*HCl u. H2O;
The organic UV-photoprotective agents which are more particularly preferred are selected from among the following compounds: Ethylhexyl Salicylate, Butyl Methoxydibenzoylmethane, Ethylhexyl Methoxycinnamate, Phenylbenzimidazole Sulfonic Acid, 4-Methylbenzylidene Camphor, Disodium Phenyl Dibenzimidazole Tetrasulfonate, Anisotriazine, Ethylhexyl triazone, Diethylhexyl Butamido Triazone, ...
In a preferred embodiment, the care lotion according to the invention contains a combination of water-soluble and lipid-soluble UV protection factors. Suitable water-soluble UV protection factors are, for example, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid p-methoxycinnamic acid diethanolamine salt p-aminobenzoic acid 2-phenylbenzimidazole-5-sulfonic acid triethanolamine salicylate and lauryl-[3-(p-dimethylamainobenzamido)-propyl]-dimethyl ammonium-p-toluenesulfonate.
The organic UV-photoprotective agents which are more particularly preferred are selected from among the following compounds: Ethylhexyl Salicylate, Butyl Methoxydibenzoylmethane, Ethylhexyl Methoxycinnamate, Phenylbenzimidazole Sulfonic Acid, Terephthalylidene Dicamphor Sulfonic Acid, 4-Methylbenzylidene Camphor, Anisotriazine, Ethylhexyl triazone, Diethylhexyl Butamido Triazone, ...
The following compounds are particularly preferably employed as UV B filters: ... 2-Ethylhexyl p-methoxycinnamate; 3-(4'-methylbenzylidene)-d,l-camphor; 2-Hydroxy-5-methoxybenzophenone; 2-Hadroxy-4-methoxybenzophenone-5-sulphonic acid; 2-Phenylbenzimidazole-5-sulphonic acid.
1 Example 1 Example 1 A 1 1 three-necked flask is initially charged with 275 g (2.70 mol) of 96% sulfuric acid and subsequently 54.1 g (0.50 mol) of 1,2-phenylenediamine are carefully introduced. 85.5 g (0.70 mol) of benzoic acid are added to the suspension, which at this point has a temperature of about 120° C., and the mixture is heated while stirring (clear solution from about 130° C.) to about 200° C. for 5 hours, during which a small proportion of the benzoic acid sublimes. The mixture is then allowed to cool to about 150° C. and is stirred into 1 l of cold water, which warms to about 65° C. The mixture is stirred for a further hour at 65° C. and the precipitate is then filtered off with suction and washed with water at a temperature of 80° C. until free of sulfate. The dried crude product (83 g) is suspended in 830 ml of water and the pH is adjusted to 8 with 32% sodium hydroxide solution. After addition of 6.5 g of activated carbon the mixture is stirred for a further 30 minutes at room temperature and subsequently clarified by filtration. The filtrate is heated to 80° C. and the pH is adjusted to 3 with concentrated hydrochloric acid. The precipitated Eusolex 232 is filtered off with suction while warm, washed with 2 l of water at a temperature of 90° C. and dried to constant weight in a vacuum drying cabinet at 75° C. and 20 mbar. 67.0 g (245 mmol, 49% of theory) of 2-phenylbenzimidazole-5-sulfonic acid are obtained, 410° C. (decomposition).
4 Example 4 Example 4 A 1 l three-necked flask is initially charged with 275 g (2.70 mol) of 96% sulfuric acid and subsequently 85.5 g (0.70 mol) of benzoic acid are introduced. 54.1 g (0.50 mol) of 1,2-phenyleneamine [sic] are carefully added, during which the mixture warms to about 100° C.; the mixture is then heated while stirring (clear solution from about 130° C.) to about 180° C. for 2 hours, during which a small proportion of the benzoic acid sublimes. The mixture is then stirred into 1 l of cold water, which warms to about 65° C. The mixture is stirred for a further hour at 65° C. and the precipitate is then filtered off with suction and washed with water at a temperature of 80° C. until free of sulfate. The dried crude product (83 g) is suspended in 830 ml of water and the pH is adjusted to 8 with 32 % sodium hydroxide solution. After addition of 6.5 g of activated carbon the mixture is stirred for a further 30 minutes at room temperature and subsequently clarified by filtration. The filtrate is heated to 80° C. and the pH is adjusted to 3 with concentrated hydrochloric acid. The precipitated Eusolex 232 is filtered off with suction while warm, washed with 2 l of water at a temperature of 90° C. and dried to constant weight in a vacuum drying cabinet at 75° C. and 20 mbar. 67.0 g (245 mmol, 49% of theory) of 2-phenylbenzimidazole-5-sulfonic acid are thus obtained.
f) sulphonic acid and its derivatives, for example: sodium hydroxymethoxybenzophenone sulphonate; 2-phenylbenzimdazole-5-sulphonic acid; and terephthalylidene dicamphor sulphonic acid (available commercially from L'Oreal under the trade name Meroxyl); 3-(4-methylbenzylidene)camphor; 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate; and
The following compounds are particularly preferably used as UV filters: ... 2-ethylhexyl p-methoxycinnamate; 3-(4'-methylbenzylidene)-d,1-camphor; 2-hydroxy-5-methoxybenzophenone; 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid; 2-phenylbenzimidazole-5-sulphonic acid.
Additional organic UV filters which are more particularly preferred are selected from the following compounds: Ethylhexyl Salicylate, Phenylbenzimidazole Sulfonic Acid, Terephthalylidene Dicamphor Sulfonic Acid, 4-Methylbenzylidene Camphor, Anisotriazine, Ethylhexyl Triazone, Diethylhexyl Butamido Triazone, 2,4,6-tris-(diisobutyl 4'-amino-benzalmalonate)-s-triazine, n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)-benzoate, ...
The organic screening agents which are more particularly preferred are selected from among the following compounds: ... Ethylhexyl Methoxycinnamate, Butyl Methoxydibenzoylmethane, Phenylbenzimidazole Sulfonic Acid, n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate, ...
The organic screening agents which are more particularly preferred are selected from among the following compounds: Ethylhexyl Salicylate, Ethylhexyl Methoxycinnamate, Butyl Methoxydibenzoylmethane, Phenylbenzimidazole Sulfonic Acid, n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate, 4-Methylbenzylidene camphor, Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetra-sulfonate, 2,4,6-Tris(diisobutyl 4'-aminobenzalmalonate)-s-triazine, ...
The preferred additional organic photoprotective agents are selected from among: Ethylhexyl Methoxycinnamate; Homosalate; Ethylhexyl Salicylate; Phenylbenzimidazole Sulfonic Acid; n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate; 4-Methylbenzylidene camphor; Terephthalylidene Dicamphor Sulfonic Acid; Disodium Phenyl Dibenzimidazole Tetrasulfonate; Methylene bis-Benzotriazolyl Tetramethylbutylphenol; ...
The preferred organic screening agents are selected from: Ethylhexyl Methoxycinnamate, Ethylhexyl Salicylate, Homosalate, Butyl Methoxydibenzoylmethane, Phenylbenzimidazole Sulfonic Acid, n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate, 4-Methylbenzylidene camphor, Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetrasulfonate, ...
claim 1 , wherein the sun filter is selected from: 4-aminobenzoic acid; 2-phenylbenzimidazole-5-sulfonic acid; 3,3'-(1,4-phenylidenedimethylidene-bis-(7,7-dimethyl-2-oxobicyclo[2,2,1]-hept-1-ylmethanesulphonic) acid or benzylidene-camphor sulphonic acid; α-(oxo-2-bornylidene-3)-toluene-4-sulphonic acid or terephthalylidene-camphor sulphonic acid; 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid; 2,2'-(1,4-phenylene)-bis-1H-benzimidazole-4,6-disulphonic acid; salicylic acid; 3,3'-carbonyl-bis-(4-hydroxy-6-methoxy)benzene sulphonic acid; 2-cyano-3,3-diphenylacrylic acid; and ...
The organic UV screens which are more particularly preferred are chosen from the following compounds: Ethylhexyl salicylate, Ethylhexyl triazone, Butyl Methoxydibenzoylmethane, Ethylhexyl Methoxycinnamate, Phenylbenzimidazole Sulfonic Acid, Terephthalylidene Dicamphor Sulfonic Acid, 4-Methylbenzylidene camphor, Anisotriazine, Ethylhexyl triazone, ...
The preferred organic screening agents are selected from: Ethylhexyl Methoxycinnamate, Ethylhexyl Salicylate, Homosalate, Phenylbenzimidazole Sulfonic Acid, n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate, 4-Methylbenzylidene Camphor, Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetrasulfonate, Methylene Bis-Benzotriazolyl Tetramethylbutylphenol, ...
The preferred organic screening agents are chosen from: Butylmethoxydibenzoylmethane, Ethylhexyl Methoxycinnamate, Ethylhexyl Salicylate, Homosalate, Phenylbenzimidazole Sulfonic Acid, n-Hexyl 2-(4-diethylamino-2-hydroxy-benzoyl)benzoate, Terephthalylidene Dicamphor Sulfonic Acid, Methylene Bis-Benzotriazolyl Tetramethylbutyl-phenol, Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, ...
Benzoxazole Derivatives: 2,4-Bis[4-[5-(1,1-dimethylpropyl)benzoxazol-2-yl]phenylimino]-6-[(2-ethylhexyl)imino]-1,3,5-triazine, sold under the name of Uvasorb K2A by Sigma 3V, and mixtures thereof. The preferential organic screening agents are chosen from: Ethylhexyl Methoxycinnamate, Ethylhexyl Salicylate, Homosalate, Butyl Methoxydibenzoylmethane, Phenylbenzimidazole Sulfonic Acid, n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate, 4-Methylbenzylidene Camphor, Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetrasulfonate, ...
With sodium hydrogensulfite In ethanol; water at 80℃; for 24h; EXAMPLE 1 Preparation of 2- (3, 4-dihydroxy-phenyl) -1H- benzoimidazole-5-sulfonic acid General procedure: EXAMPLE 1 Preparation of 2- (3, 4-dihydroxy-phenyl) -1H- benzoimidazole-5-sulfonic acid In 5 ml of ethanol 100 mg of 3, 4-diamine-benzenesulfonic acid sulfate salt (0.35 mmol) , 48 mg of 3,4 dihydroxybenzaldehyde (0.35 mmol) and 0.7 ml of sodium bisulfite solution IN (0.7 mmol) were mixed. The reaction mixture was placed at 80°C for 24 hours. After having evaporated the solvents, the raw product was treated with 5 ml of solution 5M of HC1. The precipitate was then filtered and the product recrystallized from methanol. The compound showed a maximum absorption in the UV region at 313 nm. All of the compounds object of the invention were prepared with analogous procedure from suitably substituted reactants.

  • 2
  • [ 27503-81-7 ]
  • [ 27503-82-8 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride In 1,4-dioxane for 0.5h; Heating / reflux; 5; 17 To prepare phenylbenzimidazole sulfonyl chloride, 0.5 g of phenylbenzimidazole sulfonic acid (274 g/mole) (1.8 mmoles) was added to 50 ml of dry dioxane and stirred under reflux until dissolved. 0.21 g of thionyl chloride (3.6 mmoles) was added to the reaction and the mixture refluxed for 30 minutes. After 30 minutes the reflux condenser was replaced by a still head and the solvent was removed by distillation to a final volume of 5 ml of dioxane still in the flask.
With thionyl chloride at 20℃; Reflux; 1.3 Step 3. Preparation of 2-phenyl-1H-benzoimidazole-5-sulfonyl chloride; Thionyl chloride (100 mL) and 2-phenyl-1H-benzoimidazole-5-sulfonic acid (24.5 g, 89.4 mmol) were combined at room temperature. To the resulting slurry was added 2 drops of DMF. The mixture was stirred at room temperature overnight. The reaction mixture was then poured into toluene, and the resulting solid was collected by filtration, washed with toluene and dried under vacuum to provide 48.6 g of product which still contained some starting material. This crude product (43.7 g) was then treated with 250 mL of thionyl chloride and 1 mL of DMF. The resulting mixture was heated to reflux for 3.5 h, stirred at room temperature for 3 h. Considerable swelling occurs, the reaction appeared to solidify, and an additional 150 mL of thionyl chloride was added with additional stirring. The reaction mixture was then cooled, toluene was added, and the product was collected by filtration, washed with toluene, and dried undervacuum to give 51 g of a white solid (MS: (M+H)+=293.1).
  • 3
  • [ 93-58-3 ]
  • [ 27503-81-7 ]
YieldReaction ConditionsOperation in experiment
3 Example 3 Example 3 The procedure is as in Example 1 but using 95.3 g (0.70 mol) of methyl benzoate instead of benzoic acid. 64.0 g (233 mmol, 47% of theory) of 2-phenylbenzimidazole-5-sulfonic acid are obtained.
  • 4
  • [ 7474-78-4 ]
  • [ 65-85-0 ]
  • [ 27503-81-7 ]
YieldReaction ConditionsOperation in experiment
With chloro-trimethyl-silane; In water; N,N-dimethyl-formamide; at 110℃; for 0.5h;Microwave irradiation; 3,4-Diaminobenzenesulfonic acid (18.82 g, 0.01 mol) and benzoic acid (12.21 g and 0.01 mol) were dissolved in DMF and water (1:1 vpercent) solution. Using trimethylsilyl chloride as the catalyst, the mixture was heated in the microwave reactor at 110°C for 0.5 h. After heating, it was adjusted to 10 of pH value. In the end, the precipitation was filtered and separated. The blocked crystal of the product was obtained on recrystallization. After removal of water molecules from the products, the characterizations were measured. 1H-NMR (dimethyl sulfoxide [DMSO]): 8.28 (d), 7.90 (s), 7.59 (d), 7.51 (d), 7.41 (s), 5 (s) ppm; 13C-NMR (DMSO): 152.9, 145.5, 140.2, 137.9, 134.7, 131.1, 129.2, 127.5, 120.7, 116.5, 113.2 ppm. Anal. calcd. for C13H10N2O3S (310.32): C, 50.31; H, 3.22; N, 9.02; S, 10.33; found C, 50.66; H, 3.81; N, 9.25; S, 10.79. IR spectrum (cm?1), 3375, 2857, 1632, 1601, 1568, 1514, 1496, 1375, 1212, 1089, 1030, 870, 777, 683, 614.
  • 5
  • [ 27503-81-7 ]
  • [ 1357271-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / N,N-dimethyl-formamide / 20 °C / Reflux 2: triethylamine / dichloromethane / 0.17 h / 20 °C
  • 6
  • [ 716-79-0 ]
  • [ 27503-81-7 ]
YieldReaction ConditionsOperation in experiment
98.7% With sulfuric acid at 40 - 85℃; 2-1; 2-2; 2-3; 2-4; 2-1; 2-2 Example 2-4 Add 40 g (0.206 mol) of 2-phenylbenzimidazole to 150 g (1.53 mol) of concentrated sulfuric acid in five batches at a controlled temperature of 40 to 50 °C. After the materials are added to the mixture, the next batch of 2-Phenyl benzimidazole. After the addition was completed, the reaction mixture was heated to 85 °C and the reaction was continued until the content of 2-phenylbenzimidazole was less than 1% to complete the reaction. Then, the sulfonated solution was added to 300 g of water, and then heated to 80 °C and stirred for 1 h, and filtered to obtain 180.5 g of a filter cake. The filter cake was washed with 200 g of water, stirred at 80 ° C for 1 h, and filtered to obtain 140 g of filter cake. After vacuum drying, 55.1 g of 2-phenylbenzimidazole-5-sulfonic acid (HS) was obtained, with a content of 93.4%, and the content of 2-phenylbenzimidazole-4-sulfonic acid (isomer) was 6.25%, and the yield was 91.1 % (HS-p-phenylbenzimidazole). The reaction conditions were the same as in Example 2-2, except that the reaction system was added with 5 g of Cu-ZSM-5 catalyst, and the reaction temperature was raised to 60 °C. The ZSM-5 catalyst has a silicon-to-aluminum ratio of 100, and its preparation method is: The ZSM-5 catalyst was immersed in a 5 (weight)% potassium dihydrogen phosphate solution at 20 °C for 4h, and filtered, and the obtained solid was calcined at 500 °C for 1h at a high temperature in a muffle furnace;The ZSM-5 catalyst was further immersed in a 20 (weight)% copper sulfate solution at 20 °C for 3 hours, and filtered, and the obtained solid was dried at 110 °C for 3 hours and calcined at 550 °C for 2 hours.
88% With chlorosulfonic acid; sulfuric acid In 1,2-dichloro-ethane at 76℃; for 6h; 1; 2; 3; 4; 5 Example 2 140g (1.2mol) of chlorosulfonic acid was slowly dropped into 200g of 100% sulfuric acid under stirring, mixed evenly and set aside.Put 194g (1.0mol) of 2-phenylbenzimidazole and 1000g of dichloroethane into a 2L reaction bottle, stir and heat up to 76 ° C, drop the mixed acid prepared above into the reaction bottle for reaction, and the dropping time is 3 hours. After the dropwise addition, the reaction was continued for 3 hours, and the hydrogen chloride gas generated during the reaction was absorbed with the lye.After the reaction, the stirring was stopped and allowed to stand for separation. The light yellow solution in the upper layer was ethylene dichloride, which could be directly applied to the next batch of reaction without adding any losses after distillation.The lower layer of dark liquid was dropped into 2000L of vigorously stirred water, and the hydrolysis temperature was controlled at 10 ° C.After filtration and separation, the obtained white solid was crude 2-phenylbenzimidazole-5-sulfonic acid.Put all the obtained crude product in 2000L of water, add sodium hydroxide solution dropwise with stirring at 25 ° C to adjust the pH to 9, to fully dissolve the solid, then add activated carbon to stir decolorization for 30 minutes, filter out the activated carbon; add 80g dropwise to the filtered clear solution Acetic acid was acidified to PH2.5 and white solid precipitated.After filtration and separation, the solid was dried to obtain 241 g of 2-phenylbenzimidazole-5-sulfonic acid with a molar yield of 88.0% and HPLC purity of 99.4%.
88% With chlorosulfonic acid; sulfuric acid In 1,2-dichloro-ethane at 76℃; for 6h; 1-5 Example 2 Slowly drip 140 g (1.2 mol) of chlorosulfonic acid into the stirring 200 g of 100% sulfuric acid, and mix well for use. Put 194g (1.0mol) 2-phenylbenzimidazole and 1000g dichloroethane into a 2L reaction flask, stir and raise the temperature to 76 °C, drop the mixed acid configured above into the reaction flask for reaction, the dropping time is 3 hours, After the dripping is completed, the reaction is maintained for 3 hours, and the hydrogen chloride gas generated during the reaction is absorbed by the lye.After the reaction, the stirring is stopped and the mixture is allowed to stand for stratification. The upper light yellow solution is dichloroethane, which can be directly applied to the next batch reaction without distilling and adding the loss. The lower dark liquid was dropped into 2000L of vigorously agitated water, and the hydrolysis temperature was controlled at 10°C. It is separated by filtration, and the obtained white solid is the crude 2-phenylbenzimidazole-5-sulfonic acid.Put all the obtained crude product into 2000L water, add dropwise sodium hydroxide solution under stirring at 25 to adjust the pH to 9 to fully dissolve the solid, then add activated carbon and stir for 30 minutes to decolorize, filter out the activated carbon; add 80g dropwise to the filtered clear solution Acetic acid acidified to pH 2.5, and a white solid precipitated. After filtration and separation, the solid was dried to obtain 241 g of 2-phenylbenzimidazole-5-sulfonic acid with a molar yield of 88.0% and an HPLC purity of 99.4%
  • 7
  • [ 366-18-7 ]
  • [ 7732-18-5 ]
  • copper dichloride [ No CAS ]
  • [ 27503-81-7 ]
  • C30H26ClCuN4O4S*H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: water; copper dichloride; 2-phenyl-1H-benzimidazole-5-sulfonic acid With sodium hydroxide at 20℃; for 2h; Stage #2: [2,2]bipyridinyl In ethanol at 80℃; for 12h; 1-6 0.2mmol catalyst CuCl2, 0.2mmol raw material 2-phenylbenzimidazole-5-sulfonic acid dissolved in 10mL deionized water, add 0.2mmol NaOH and stir at room temperature for 2h, then,Add 0.2mmol 2,2'-bipyridine in 10mL ethanol solution to the above solution and heat to reflux at 80°C for 12h, then cool to room temperature. Filter and place at room temperature.After 7d, blue massive crystals were obtained.
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