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CAS No. : | 96-75-3 | MDL No. : | MFCD00035755 |
Formula : | C6H6N2O5S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LTASFWDWBYFZQQ-UHFFFAOYSA-N |
M.W : | 218.19 | Pubchem ID : | 66786 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 49.53 |
TPSA : | 134.59 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -10.21 cm/s |
Log Po/w (iLOGP) : | -0.41 |
Log Po/w (XLOGP3) : | -3.63 |
Log Po/w (WLOGP) : | 1.51 |
Log Po/w (MLOGP) : | -0.46 |
Log Po/w (SILICOS-IT) : | -2.53 |
Consensus Log Po/w : | -1.1 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | 0.91 |
Solubility : | 1770.0 mg/ml ; 8.11 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 1.39 |
Solubility : | 5350.0 mg/ml ; 24.5 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.78 |
Solubility : | 36.5 mg/ml ; 0.167 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 4.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.68 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate; In sulfolane; acetonitrile; at 75 - 80℃; | 1. Phosphorus oxychloride (316 g, 192 mL, 2.06 mol, 1.8 equivalents) was slowly added to a suspension of 2-amino-5-nitrobenzenesulfonic acid (250 g, 1.15 mol, 1.00 equivalent) in a mixture of acetonitrile (2.54 kg, 2.0 L, 8 vol) and sulfolane (254 g, 200 mL, 0.8 vol) at ambient temperature. [0053] 2. This mixture was stirred at 75-80 C. for 3-5 h, and then the supernatant was slowly transferred to NH4OH solution (28-30%, 1.5 L, 6 vol) such that the temperature was maintained below 30 C. [0054] 3. The reaction mixture was stirred at ambient temperature ca. 2 h, and was then concentrated under reduced pressure at ca. 50 C. to a minimum volume to obtain a slurry. [0055] 4. This slurry was aged at ca. 50 C. for ca. 2 h and then slowly cooled to ca. 10 C. and aged at ca. 10 C. for ca. 2 h. The solid was filtered and washed with water (3×250 mL, 3×1 vol) to give a yellow product which was dried at ca. 50 C. under vacuum for 2 days to yield 203.8 g of II (2-amino-5-nitro-benzenesulfonamide, See also compound described in Dragovich, P. S.; Thompson, P. A; Reubsam, F. WO 2010/042834, herein incorporated by reference in its entirety) in 81.9% yield with 99.0% purity by AN HPLC (area normalized high performance liquid chromatography). | |
With trichlorophosphate; at 25 - 120℃; for 3.5h;Product distribution / selectivity; | Alternatively, 2-amino-5-nitrobenzenesulfonamide can be prepared as follows: To a suspension of <strong>[96-75-3]2-amino-5-nitro-benzenesulfonic acid</strong> (3.00 g, 13.75 mmol) in sulfolane (10 mL) was slowly added phosphorous oxychloride (3.43 mL, 37.47 mmol) at 25 0C. The mixture was heated at 120 0C for 3.5 h, allowed to cool to 25 0C and diluted with dichloromethane (50 mL). The mixture was filtered and the precipitate was washed with dichloromethane (50 mL). The filtrate was treated with ammonia gas for 10 minutes while cooling in an ice bath and then stirred at 25 0C for 5 minutes. The yellow solid was collected by vacuum filtration and the precipitate was further washed with dichloromethane (2 x 50 mL), cold water (2 x 50 mL) and dried in vacuo for 16 h at 60 0C to afford the desired product, 2-amino-5-nitrobenzenesulfonamide (1.46 g, 6.73 mmol, 49% yield) as a brown solid. 1H NMR (400 MHz, DMSO-^) delta: 6.89 (d, J= 9.1 Hz, IH), 7.19 (bs, 2H), 7.37 (bs, 2H), 8.07 (dd, J1 = 8.9 Hz, J2 = 2.3 Hz, IH), 8.43 (d, J= 3.0 Hz, IH); Alternatively, 2-amino-5-nitrobenzenesulfonamide can be prepared as follows: To a suspension of <strong>[96-75-3]2-amino-5-nitro-benzenesulfonic acid</strong> (3.00 g, 13.75 mmol) in sulfolane (10 mL) was slowly added phosphorous oxychloride (3.43 mL, 37.47 mmol) at 25 0C. The mixture was heated at 120 0C for 3.5 h, allowed to cool to 25 0C and slowly poured into aqueous ammonium hydroxide solution (30 mL) at 25 0C. The pH of the solution was adjusted to ca. 6-7 upon which a solid precipitated. The solid was collected by vacuum filtration and the precipitate was washed water (100 mL) and dried in vacuo for 16 h at 60 0C to afford the desired product, 2-amino-5- nitrobenzenesulfonamide (1.87 g, 8.62 mmol, 63% yield) as a yellow-brown solid. 1H NMR (400 MHz, DMSO-^) delta: 6.89 (d, J= 9.1 Hz, IH), 7.19 (bs, 2H), 7.37 (bs, 2H), 8.07 (dd, J1 = 8.9 Hz, J2 = 2.3 Hz, IH), 8.43 (d, J= 3.0 Hz, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium nitrite; In water; at 5 - 50℃; | (The third process) In 340 parts of 50 C. warm water, 27.3 parts of 2-amino-5-nitrobenzenesulfonic acid was dissolved, 35.6 parts of 35% hydrochloric acid was added thereto, and the resultant solution was then cooled to 5 to 10 C., followed by adding 20.6 parts of 40% aqueous solution of sodium nitrite at the same temperature for diazotization. Then the thus obtained diazo suspension was added to a solution dissolving 37.0 parts of the compound of Formula (39) in 1000 parts of water, at 15 to 20 C., and thereafter the pH value was gradually neutralized at 6.0 to 7.0 with sodium carbonate. After the neutralization, further, stirring was conducted at 15 to 20 C. at pH of 7.0 to 8.0 for 3 hours and the coupling reaction was completed to obtain a reaction solution containing a compound of the following Formula (40). After that, salting out was conducted by the addition of sodium chloride and 300 parts of wet cake of a tetrakisazo compound of Formula (40) was obtained by filtration. | |
With hydrogenchloride; sodium nitrite; In water; at 5℃; for 1h; | 1. Preparation of Dye A; (1) Diazotization Reaction; 4.80 g (0.02 mole) of p-Nitroaniline-o-sulfonic acid was weighed, added in 80 ml of distilled water and dispersed under stirring. 0.14 g of NaNO2 was weighed, added in 10 ml of distilled water and stirred to dissolve it. The reaction mixture was poured into a mixture of 6.0 ml HCl (32%) and 40.00 g crushed ice. After mixing homogeneously, the mixture was added dropwisely into the above dispersion. The reaction mixture was stirred continuously for about 1 hour while keeping the reaction temperature below 5 C. A pale yellow bright crystal was then appeared. After confirming the completeness of the reaction by testing with H acid and I.P. solution (4-N,N-diethylaminobenzaldehyde/Acetic acid), an excess amount of sulfamic acid was added to remove residual NaNO2 (colorless under testing with KI-starch paper). The reaction solution was filtered and the product on the filter was added in 100 ml of distilled water, dispersed by stirring and then placed in a ice bath to keep the temperature below 5 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
As the compound of the formula (IV), the following are given: Aniline, o-, m- or p-toluidine, 2,4- or 2,5-dimethylaniline, 5-methyl-2-methoxyaniline, o-, m- or p-chloroaniline, aniline-2-, -3- or -4-sulfonic acid, aniline-2,5-disulfonic acid, aniline-3,5-disulfonic acid, aniline-2,4-disulfonic acid, 4- or 5-sulfoanthranilic acid, 2-nitroaniline-4-sulfonic acid, 4-nitroaniline-2-sulfonic acid, 3-nitroaniline-6-sulfonic acid, 5-nitro-2-aminoanisole-4-sulfonic acid, 2-methylaniline-4,5-disulfonic acid, 2,5-dichloroaniline-4-sulfonic acid, 4-methylaniline-2-sulfonic acid, ... | ||
aniline-2,4-, -2,5-dicarboxylic acid or -disulfonic acid; ... 4-amino-4'-sulfo-benzanilide; 2-aminoanisol-4-sulfonic acid; 3-aminoanisol-4-sulfonic acid; 6-chloro-2-aminobenzenesulfonic acid; 5-nitro-2-aminobenzenesulfonic acid; 4-chloro-3-aminobenzenesulfonic acid; 6-chloro-3-aminobenzenesulfonic acid; 3-chloro-4-aminobenzenesulfonic acid; ... | ||
aniline-2,4- or -2,5-dicarboxylic acid or -disulfonic acid; ... 4-amino-4'-sulfobenzanilide; 2-aminoanisole-4-sulfonic acid; 3-aminoanisole-4-sulfonic acid; 6-chloro-2-aminobenzenesulfonic acid; 5-nitro-2-aminobenzenesulfonic acid; 4-chloro-3-aminobenzenesulfonic acid; 6-chloro-3-aminobenzenesulfonic acid; 3-chloro-4-aminobenzenesulfonic acid; ... |
which an aromatic diazonium salt, e.g. any of those mentioned in the above, or the following lists: (b) Aromatic amines containing a sulphonic or carboxylic acid group aniline-2,3 and 4-sulphonic acid ... aniline-2,4-disulphonic acid 4- and 5-sulphoanthranilic acid 2-nitroaniline-4-sulphonic acid 4-nitroaniline-2-sulphonic acid 3-nitroaniline-6-sulphonic acid 5-nitro-2-aminoanisole-4-sulphonic acid 2-methylaniline-4,5-disulphonic acid ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium nitrite; In hydrogenchloride; water; | EXAMPLE 106 An aqueous solution of 7 parts of sodium nitrite is added to 18.6 parts of 4-methylsulfonylaminoaniline in 50 parts by volume of 5N hydrochloric acid at 0-5 C. The diazo solution is then poured into a stirred suspension, in 1,000 parts of water, of the coupling product obtained by diazotizing 23.4 parts of 2-hydroxy-3-amino-5-nitrobenzenesulfonic acid in a conventional manner and coupling the product to 11 parts of resorcinol in a medium rendered alkaline with sodium carbonate. After the addition, the pH is increased to 9, and the mixture is stirred until coupling is complete. A diazo solution obtained from 21.8 parts of 2-amino-5-nitrobenzenesulfonic acid in a conventional manner is then allowed to run into the mixture at pH 9-9.5, and stirring is continued until the coupling is complete. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; In sodium hydroxide; | EXAMPLE 2 1 mol of 2-methyl-6-nitro-benzothiazole in 1.2 liters of 3% strength NaOH is boiled until a solution is formed. This is allowed to cool to approx. 30 C., and 1 mol of hydrogen peroxide, in the form of a 35% strength aqueous solution, is added dropwise in the course of approx. 1 hour. The temperature should not exceed 50 C. Thereafter, a further 2 mols of 35% strength hydrogen peroxide are added dropwise in the course of 1 hour, the temperature increasing to the boiling point. The mixture is allowed to cool to 80 C., 10 g of active charcoal and 10 g of a customary filtration aid are added, the mixture is filtered, the filtrate is cooled to 5-10 C., and the 2-amino-5-nitro-benzenesulphonic acid formed is precipitated by the addition of concentrated hydrochloric acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | 2-Amino-5-nitrobenzenesulfonic acid (200.00 g, 0.917 mol) was suspended in warm sulfolane (250 mL) and the suspension was heated to 80 0C. Phosphorous oxychloride (126 mL, 1.375 mol) was added and resulting mixture was heated to 110-120 0C and stirred for 4 h. The resulting solution was cooled to 60 0C and added dropwise into concentrated aqueous ammonium hydroxide solution (800 mL, 11.9 mol) at <10 0C. The flask was rinsed with warm sulfolane (50 mL) and the wash was added into the above reaction mixture. The resulting suspension was stirred at 25 0C for 1 h, heated to 95 0C and stirred for 1 hour. The mixture was cooled to 80 0C and the pH was adjusted to 6-8 with 3.0 M aqueous hydrochloric acid solution (-600 mL) and allowed to cool to 25 0C. The dark green suspension was filtered, and the wet filter cake was washed with water (300 mL) and dried at 60 0C overnight to give the crude product (140 g ) as a green- yellow solid. The crude product was dissolved in 0.5 M aqueous sodium hydroxide solution (1.4 L, 0.7 mol). Charcoal (14 g) was added and the mixture was heated to reflux and stirred for 15 min. The mixture was filtered through Celite and washed with 0.5 M aqueous sodium hydroxide solution (100 mL). The pH of the filtrate was adjusted to 6-8 with concentrated aqueous hydrochloric acid solution (~ 60 mL) and the yellow suspension was allowed to cool to 25 0C. The mixture was filtered and the wet filter cake was washed with water (200 mL) and dried at 60 0C overnight to afford the desired product, 2-amino-5- nitrobenzenesulfonamide (130 g, 0.599 mol, 65%) as a bright yellow powder | |
65% | b) 2-Amino-5-nitrobenzenesulfonamide[00220] 2-Chloro-5-nitro-benzenesulfonamide (1.95 kg, 8.30 mol), ammonium carbonate (1.983 kg, 20.64 mol), and copper (II) sulfate (394 g, 2.47 mol) were charged to an autoclave and diluted with a 30% aqueous ammonium hydroxide solution (11.7 L, 330 mol). The mixture was heated at 118 0C for 3 days and was then cooled to 23 0C. The mixture was filtered and the solids were then washed with water (20 L). This solid was dissolved in hot methanol (20 mL/g), and the mixture was filtered to remove undissolved solids. The filtrate was stored at 4 0C overnight, and the resulting solid product was then filtered. The filtrate was partially concentrated by vacuum distillation and, when the concentrate was cooled to 23 0C, the solid product was then filtered off. The two crops of solid were combined and further dried in vacuo at 45 0C to afford the desired product, 2-amino-5-nitro- benzenesulfonamide (1.10 kg, 5.06 mol, 61%), as a solid. 1H NMR (400 MHz, DMSO-^) delta: 6.89 (d, J= 9.3 Hz, IH), 7.12 (bs, 2H), 7.57 (bs, 2H), 8.07 (dd, J1 = 9.0 Hz, J2 = 2.6 Hz, IH), 8.43 (d, J= 3.0 Hz, IH).[00221] Alternatively, 2-amino-5-nitrobenzenesulfonamide can be prepared as follows:[00222] 2-Amino-5-nitrobenzenesulfonic acid (200.00 g, 0.917 mol) was suspended in warm sulfolane (250 mL) and the suspension was heated to 80 0C. Phosphorous oxychloride (126 mL, 1.375 mol) was added and resulting mixture was heated to 110-120 0C and stirred for 4 h. The resulting solution was cooled to 60 0C and added dropwise into concentrated aqueous ammonium hydroxide solution (800 mL, 11.9 mol) at <10 0C. The flask was rinsed with warm sulfolane (50 mL) and the <n="71"/>wash was added into the above reaction mixture. The resulting suspension was stirred at 25 0C for 1 h, heated to 95 0C and stirred for 1 hour. The mixture was cooled to 80 0C and the pH was adjusted to 6-8 with 3.0 M aqueous hydrochloric acid solution (-600 mL) and allowed to cool to 25 0C. The dark green suspension was filtered, and the wet filter cake was washed with water (300 mL) and dried at 60 0C overnight to give the crude product (140 g ) as a green- yellow solid. The crude product was dissolved in 0.5 M aqueous sodium hydroxide solution (1.4 L, 0.7 mol). Charcoal (14 g) was added and the mixture was heated to reflux and stirred for 15 min. The mixture was filtered through Celite and washed with 0.5 M aqueous sodium hydroxide solution (100 mL). The pH of the filtrate was adjusted to 6-8 with concentrated aqueous hydrochloric acid solution (~ 60 mL) and the yellow suspension was allowed to cool to 25 0C. The mixture was filtered and the wet filter cake was washed with water (200 mL) and dried at 60 0C overnight to afford the desired product, 2-amino-5- nitrobenzenesulfonamide (130 g, 0.599 mol, 65%) as a bright yellow powder, | |
63% | To a suspension of <strong>[96-75-3]2-amino-5-nitro-benzenesulfonic acid</strong> (3.00 g, 13.75 mmol) in sulfolane (10 mL) was slowly added phosphorous oxychloride (3.43 mL, 37.47 mmol) at 25 0C. The mixture was heated at 120 0C for 3.5 h, allowed to cool to 25 0C and slowly poured into aqueous ammonium hydroxide solution (30 mL) at 25 <n="72"/>C. The pH of the solution was adjusted to ca. 6-7 upon which a solid precipitated. The solid was collected by vacuum filtration and the precipitate was washed water (100 mL) and dried in vacuo for 16 h at 60 0C to afford the desired product, 2-amino- 5-nitrobenzenesulfonamide (1.87 g, 8.62 mmol, 63%) as a yellow-brown solid. 1H NMR (400 MHz, OMSO-d6) delta: 6.89 (d, / = 9.1 Hz, IH), 7.19 (bs, 2H), 7.37 (bs, 2H), 8.07 (dd, J1 = 8.9 Hz, J2 = 2.3 Hz, IH), 8.43 (d, / = 3.0 Hz, IH). |
49% | To a suspension of <strong>[96-75-3]2-amino-5-nitro-benzenesulfonic acid</strong> (3.00 g, 13.75 mmol) in sulfolane (10 mL) was slowly added phosphorous oxychloride (3.43 mL, 37.47 mmol) at 25 0C. The mixture was heated at 120 0C for 3.5 h, allowed to cool to 25 0C and diluted with dichloromethane (50 mL). The mixture was filtered and the precipitate was washed with dichloromethane (50 mL). The filtrate was treated with ammonia gas for 10 minutes while cooling in an ice bath and then stirred at 25 0C for 5 minutes. The yellow solid was collected by vacuum filtration and the precipitate was further washed with dichloromethane (2 x 50 mL), cold water (2 x 50 mL) and dried in vacuo for 16 h at 60 0C to afford the desired product, 2-amino-5- nitrobenzenesulfonamide (1.46 g, 6.73 mmol, 49%) as a brown solid. 1H NMR (400 MHz, OMSO-d6) delta: 6.89 (d, / = 9.1 Hz, IH), 7.19 (bs, 2H), 7.37 (bs, 2H), 8.07 (dd, J1 = 8.9 Hz, J2 = 2.3 Hz, IH), 8.43 (d, / = 3.0 Hz, IH). | |
31% | With trichlorophosphate; In sulfolane; at 20 - 120℃; for 3.5h; | POC (6.86 mL, 82.2 mmol) was slowly added to a mixture of 2-amino-5- nitrobenzenesulfonic acid (3.00 g, 27.4 mmol) in sulfolane (20 mL) at r.t. and the mixture was heated at 120 C for 3.5 h. The mixture was allowed to cool to r.t. then slowly poured into cone. NH4OH (60 mL). The resulting precipitate was collected by filtration, washed with water (100 mL) and dried to give the product (1.90 g, 31 % yield) as a yellow solid. LCMS (ES-API): Rt O.43 min; m/z 218.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 2; In a glass beaker, 52.5 g (81.5%) of 2-sulfo-4-nitroaniline are stirred into 800 ml of demineralised water and then 7 ml of 37% hydrochloric acid are added. Cooling to from 0 to 5 C. is then carried out using an ice bath, and 46.4 ml of 4M sodium nitrite are fed in over the course of 45 minutes with the simultaneous addition of a small amount (about 2 ml) of hydrochloric acid. The mixture is further stirred for 40 minutes. The excess of sodium nitrite is destroyed using 1 M aminosulfonic acid.Coupling10.0 g of resorcinol (Fluka purum) are dissolved in 100 ml of demineralised water in a glass beaker. The resulting coupling solution is subsequently added to the ice-cooled diazonium solution over the course of 30 minutes, during which the pH value is maintained at from 2.3 to 3.7 by adding sodium hydrogen carbonate. A thick orange-red suspension is obtained. The pH value is then adjusted to 6.4 using sodium hydrogen carbonate, and diluted with 100 ml of demineralised water. The suspension is further stirred for 150 minutes, and then filtered and subsequently washed with 200 ml of 12% sodium chloride solution. The filter cake is dried in a vacuum cabinet for 12 hours at 70 C. 74 g of a compound of formula (1a) are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 2; Diazotisation; In a reaction flask, 46.8 g of 2-sulfo-4-nitroaniline (85.5%) are stirred into 800 ml of demineralised water and then 5 ml of 37% hydrochloric acid are added. Cooling to from 0 to 5 C. is then carried out using an ice bath, and 45 ml of 4M sodium nitrite are fed in over the course of 40 minutes with the simultaneous addition of a small amount (about 2 ml) of hydrochloric acid. The mixture is stirred for a further 45 minutes. The excess of sodium nitrite is destroyed using 1 M aminosulfonic acid.; Coupling; 100 ml of demineralised water and 150 ml of 2-ethoxyethanol (ethyl cellosolve/ethylene glycol monoethyl ether) are introduced as the initial charge into a glass beaker. 30.3 g of amino-3-methyl-phenylpyrazole (97%) are dissolved therein. 2 drops of 30% sodium hydroxide solution are then added and the mixture is stirred for 45 minutes. The coupler solution is subsequently added over the course of 30 minutes to the ice-cooled diazonium solution, during which the pH value is maintained at from 2.8 to 3.8 by adding sodium hydrogen carbonate. A viscous orange-red suspension is obtained which is diluted with a total of 500 ml of demineralised water. The pH value of the diluted suspension is then adjusted to 6.0 using sodium hydrogen carbonate, and the suspension is further stirred for 90 minutes, filtered and then washed with 400 ml of 12% sodium chloride solution. The filter cake is dried in vacuo for 12 hours at 70 C. A crude product is obtained which contains 94.7 g of the compound of formula (50). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution containing 4-nitroaniline-2-sulfonic acid (21.8 parts) and a 35% aqueous solution of sodium nitrite (21.7 parts) in water (150 parts) was introduced into a solution containing ice water (300 parts) and concentrated hydrochloric acid (35.5 parts), while controlling the temperature at 0 to 5C, and the mixture was stirred for 1 hour at this temperature to effect diazotization. Successively, after excess nitrous acid had been decomposed, 2-amino-8-hydroxynaphthalene-3,6-disulfonic acid (31.9 parts) was added to the reaction mixture, and the mixture was stirred for 12 hours at room temperature, thereby performing a coupling reaction. Thereafter, the reaction mixture was adjusted to pH 8 to 10, and mixed with sodium sulfide (10.7 parts), and the mixture was heated to 60C. and stirred for 3 hours at this temperature to effect reduction of the nitro group. Then, the reaction mixture was mixed with sodium chloride (40 parts) to deposit crystals, which were collected on a filter and washed. The resulting wet cake was dissolved in water (400 parts). The solution was mixed with cyanuric chloride (16.7 parts), and the mixture was stirred for 5 hours at 0 to 10C., while controlling the pH within a range of 4 to 5 using a 20% aqueous solution of sodium carbonate, thereby performing a first condensation compound of formula (1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
a) Synthesis of the dichloro-triazinyl-dyebase common intermediate (IVa) 2-Amino-5-nitrobenzenesulfonic acid (26.6g, 82%-str, 0.100Mol) was suspended in water (500ml) at pH <1.0. Ice (350g) was added, followed by sodium nitrite (6.9g, 0.100Mol) in water (40ml) over 2 minutes, keeping pH <1.2. Reaction was stirred for 15 mins, excess nitrite quenched by adding sulfamic acid (0.1g), then 2-amino-8-naphthol-3,6-disulfonic acid (44.6 g, 0.090mol) was added and the pH adjusted and held at pH 3.0 for 2 hrs. The reaction mixture was adjusted to pH 9.0 and heated to 40C. Na2S (26.0 g, 60% str, 0.200 mol) was added, the reaction stirred for 15 minutes before pH was adjusted to 1.0 and NaCl (10%w/v, 110g) added. The resultant suspension was stirred for 30 mins and the solid collected by filtration. The solid was washed with NaCl solution (20%-w/v, 500ml) then dissolved in water (600ml) by stirring for 1 hr at pH 7.0. The reaction mixture was stirred vigorously, solid cyanuric chloride (11.99 g, 0.065 Mol) added and pH was regulated at 3.7-4.0 for 60 minutes then adjusted to and held at pH 7.5 for 60 minutes. HPLC analysis revealed the solubilized material (IVa) to be a single component. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 27; 21.8 parts of 4-nitroaniline-2-sulfonic acid are suspended in 400 parts of water and neutralized with aqueous sodium hydroxide solution. 6.9 parts of sodium nitrite are added, and the suspension is stirred until everything has dissolved. The solution is added dropwise at 0-5 C. to initially charged 0 parts of ice and 30 parts of hydrochloric acid (31%) followed by stirring for 60 minutes. Excess nitrite is removed by addition of sulfamic acid. A solution of 33.3 parts of 6-amino-4-hydroxy-3-hydroxysulfonylmethyinaph-thalene-2-sulfonic acid in 300 parts of water is cooled to 10 C. This solution is added to the diazonium salt solution and the pH is adjusted to 6.0 by adding sodium carbonate solution. This affords a dye solution which in the form of the free acid contains a compound of the formula (10); The solution of the compound (10) is adjusted to pH 8.5 with aqueous sodium hydroxide solution and heated to 35-40 C. A solution of 5.6 parts of NaHS in 50 parts of water is added dropwise and the pH is kept constant at 8.5 by the addition of hydrochloric acid. The compound obtained is precipitated by addition of 150 parts of sodium chloride, filtered off and washed with aqueous sodium chloride solution. The compound obtained conforms in the form of its free acid to the formula (9a); 53.2 parts of compound (9a) are dissolved in 500 parts of water. The solution is cooled to 15 C. and at this temperature 13.4 parts of 2,4,6-trifluoropyrimidine are added dropwise over an hour. During this addition the pH is held at 6.5 by adding aqueous sodium carbonate solution. Addition is followed by a further hour's stirring at 30 to 35 C. The end point of the reaction is determined by thin layer chromatography. The dye of Example 14 is precipitated as an isomer mixture by addition of sodium chloride, filtered off and dried.; The dye dyes cotton in a bluish red shade |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Diazotizing aniline-2,5-disulphonic 0.07 mol (20.3 g) of aniline-2,5-disulphonic acid were dissolved in 80 g of water and 17.5 g of hydrochloric acid (concentration: 37 wt.-%). Then, 0.075 mol (5.17 g) of sodium nitrite in 15 g of water were added at a temperature of 5 C to yield a diazotised solution. Excess of sodium nitrite was removed with 5.8 g of a 10 wt.-% solution of sulfamic acid.A solution of diazotised 4-Nitroaniline-2-sulphonic acid prepared in the same way as in Example 1 was added in order to couple the diazotised 4-Nitroaniline-2-sulphonic acid to the intermediate I25. During addition, the pH was maintained at a value of 5.0 to 6.0 by adding of a 30 wt.-% solution of NaOH. The pH of the resulting reaction mixture was then adjusted to a value of 12 with a 30 wt.-% solution of NaOH, warmed to 40 C and stirred 1 hour at that temperature. The mixture was then cooled down to room temperature, the product was precipitated with EtOH and filtered off. The precipitated dye 25 was dried. Dye 25 was obtained in a 70 % overall yield |
Tags: 96-75-3 synthesis path| 96-75-3 SDS| 96-75-3 COA| 96-75-3 purity| 96-75-3 application| 96-75-3 NMR| 96-75-3 COA| 96-75-3 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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