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[ CAS No. 89-36-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 89-36-1
Chemical Structure| 89-36-1
Chemical Structure| 89-36-1
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Product Details of [ 89-36-1 ]

CAS No. :89-36-1 MDL No. :MFCD00020756
Formula : C10H10N2O4S Boiling Point : -
Linear Structure Formula :- InChI Key :CWJQQASJVVAXKL-UHFFFAOYSA-N
M.W : 254.26 Pubchem ID :66638
Synonyms :

Calculated chemistry of [ 89-36-1 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 68.15
TPSA : 95.42 Ų

Pharmacokinetics

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) : -7.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.99
Log Po/w (XLOGP3) : 0.02
Log Po/w (WLOGP) : 1.37
Log Po/w (MLOGP) : 0.84
Log Po/w (SILICOS-IT) : 0.5
Consensus Log Po/w : 0.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.56
Solubility : 7.03 mg/ml ; 0.0277 mol/l
Class : Very soluble
Log S (Ali) : -1.58
Solubility : 6.75 mg/ml ; 0.0266 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.23
Solubility : 1.5 mg/ml ; 0.00592 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.52

Safety of [ 89-36-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:1759
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 89-36-1 ]

* 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 [ 89-36-1 ]

[ 89-36-1 ] Synthesis Path-Downstream   1~73

  • 1
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  • 3
  • [ 673-41-6 ]
  • [ 89-36-1 ]
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  • 4
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  • 5
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  • [ 89-36-1 ]
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  • 6
  • [ 459-44-9 ]
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  • 7
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  • [ 89-36-1 ]
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  • 8
  • [ 348-06-1 ]
  • [ 89-36-1 ]
  • [ 84875-71-8 ]
  • 9
  • [ 85074-70-0 ]
  • [ 89-36-1 ]
  • sodium 4-(4-<(4-dihexadecylaminophenyl)imino>-4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-)benzenesulfonate [ No CAS ]
  • 10
  • [ 89-36-1 ]
  • 2-(2-Anilinovinyl)-3-octodecylbenzo<d><1,3>thiazolium-(4-chlorbenzolsulfonat) [ No CAS ]
  • Kalium-4-<4-<2-(2,3-dihydro-3-octadecylbenzo<d><1,3>thiazol-2-yliden)ethyliden>-3-methyl-5-oxo-2-pyrazolin-1-yl>benzolsulfonat [ No CAS ]
  • 13
  • 2-cyano-4-nitrobenzenediazonium hydrogen sulphate [ No CAS ]
  • [ 89-36-1 ]
  • 3-methyl-1-(p-sulfophenyl)pyrazole-4,5-dione 4-(2-cyano-4-nitrophenyl)hydrazone [ No CAS ]
  • 14
  • [ 67916-07-8 ]
  • [ 89-36-1 ]
  • 3-methyl-1-(p-sulfophenyl)pyrazole-4,5-dione 4-(2-cyanophenyl)hydrazone [ No CAS ]
  • 15
  • [ 89-36-1 ]
  • 4-bromo-2-cyano-benzenediazonium; hydrogen sulfate [ No CAS ]
  • 3-methyl-1-(p-sulfophenyl)pyrazole-4,5-dione 4-(4-bromo-2-cyanophenyl)hydrazone [ No CAS ]
  • 16
  • [ 89-36-1 ]
  • [ 4857-47-0 ]
  • 3-hydroxy-4-{<i>N</i>'-[3-methyl-5-oxo-1-(4-sulfo-phenyl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-naphthalene-1-sulfonic acid [ No CAS ]
  • 17
  • [ 94205-62-6 ]
  • [ 89-36-1 ]
  • 2-(4-{<i>N</i>'-[3-methyl-5-oxo-1-(4-sulfo-phenyl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-quinoline-4-carboxylic acid [ No CAS ]
  • 18
  • [ 89-36-1 ]
  • [ 475474-43-2 ]
  • 6-bromo-2-(4-{<i>N</i>'-[3-methyl-5-oxo-1-(4-sulfo-phenyl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-quinoline-4-carboxylic acid [ No CAS ]
  • 19
  • [ 89-36-1 ]
  • [ 475474-44-3 ]
  • 2-(4-{<i>N</i>'-[3-methyl-5-oxo-1-(4-sulfo-phenyl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-6-nitro-quinoline-4-carboxylic acid [ No CAS ]
  • 20
  • [ 2365-44-8 ]
  • [ 89-36-1 ]
  • 3-methyl-1-(p-sulfophenyl)pyrazole-4,5-dione 4-(2-cyanophenyl)hydrazone [ No CAS ]
  • 21
  • [ 2438-71-3 ]
  • [ 89-36-1 ]
  • 3-methyl-1-(p-sulfophenyl)pyrazole-4,5-dione 4-(4-bromo-2-cyanophenyl)hydrazone [ No CAS ]
  • 22
  • [ 89-36-1 ]
  • 3-diazo-5-nitro-1,3-dihydro-2H-indol-2-one [ No CAS ]
  • 3-methyl-1-(p-sulfophenyl)pyrazole-4,5-dione 4-(2-cyano-4-nitrophenyl)hydrazone [ No CAS ]
  • 23
  • [ 947-95-5 ]
  • [ 50-01-1 ]
  • [ 89-36-1 ]
  • [ 1057507-69-3 ]
  • 24
  • [ 1242840-80-7 ]
  • [ 89-36-1 ]
  • [ 442651-05-0 ]
  • 25
  • [ 141-97-9 ]
  • [ 98-71-5 ]
  • [ 89-36-1 ]
  • 26
  • [ 88-51-7 ]
  • [ 89-36-1 ]
  • C17H13ClN4O7S2(2-)*Ca(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
SYNTHESIS EXAMPLE 122.1 g (0.1 mol) of 2-amino-4-chloro-5-methylbenzene-1-sulfonic acid are introduced into 200 ml of water and dissolved with 9.1 ml of aqueous sodium hydroxide solution (33%) by heating, clarified and admixed with 25.0 ml of hydrochloric acid (31%). The suspension obtained is cooled to 15 C. and diazotized by addition of 13.3 ml of a 40% sodium nitrite solution.To 400 ml of water and 11.1 ml of aqueous sodium hydroxide solution (33%) are added 25.4 g (0.1 mol) of 1-(4'-sulfophenyl)-3-methyl-5-pyrazolone and dissolved therein.The suspension of the diazonium salt is gradually added to the warm solution of the coupling component at 40 C. while the pH is maintained in the range from 6.0 to 6.5 by addition of aqueous sodium hydroxide solution. After coupling has ended, the yellow suspension is heated to 80 C. and 33.3 g of calcium chloride are added. The suspension is subsequently stirred at 80 C. for 2 hours, filtered, and the filter residue is washed, dried at 120 C. and ground to obtain 41.6 g of a yellow powder.
  • 27
  • [ 88-51-7 ]
  • [ 89-36-1 ]
  • C17H13ClN4O7S2(2-)*Sr(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
SYNTHESIS EXAMPLE 222.1 g (0.1 mol) of 2-amino-4-chloro-5-methylbenzene-1-sulfonic acid are introduced into 200 ml of water and dissolved with 9.1 ml of aqueous sodium hydroxide solution (33%) by heating, clarified and admixed with 25.0 ml of hydrochloric acid (31%). The suspension obtained is cooled to 15 C. and diazotized by addition of 13.3 ml of a 40% sodium nitrite solution.To 400 ml of water and 11.1 ml of aqueous sodium hydroxide solution (33%) are added 25.4 g (0.1 mol) of 1-(4'-sulfophenyl)-3-methyl-5-pyrazolone and dissolved therein.The suspension of the diazonium salt is gradually added to the warm solution of the coupling component at 40 C. while the pH is maintained in the range from 6.0 to 6.5 by addition of aqueous sodium hydroxide solution. After coupling has ended, the yellow suspension is heated to 80 C. and 53.3 g of strontium chloride are added. The suspension is subsequently stirred at 80 C. for 2 hours, filtered, and the filter residue is washed, dried at 120 C. and ground to obtain 52 g of a yellow powder.
  • 28
  • [ 100-01-6 ]
  • [ 89-36-1 ]
  • [ 741193-12-4 ]
  • 29
  • [ 1354703-76-6 ]
  • [ 89-36-1 ]
  • [ 1354703-98-2 ]
  • 30
  • bis(2-hydroxyethyl) 2-aminoterephthalate [ No CAS ]
  • [ 89-36-1 ]
  • C22H22N4O10S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In water; at 5℃; for 2h;pH 7; General procedure: BHET was nitrated and reduced in the general procedure (Scheme 2) [20]. A 500 mL three-necked round-bottom glass flask equipped with a magnetic stirrer, thermometer, and reflux condenser was charged with 10.00 g BHET. A mixture of 15 mL conc. sulfuric acid and 3 mL conc. nitric acid was added into the glass flask. The reaction was continued at 60 C for 1 h and at 80 C for 10 h successively. After the reaction, the mixture was refrigerated with ice water until the mixture reached room temperature. The precipitate was filtered with distilled water and ethanol 3 times successively. Then, the filtrate was dissolved in hot water to be recrystallized in the refrigerator. The formed crystal, nitro-bis(2-hydroxyethyl) terephthalate (NBHET), was dried in the oven at 60 C. A three-necked round-bottomed glass flask fitted with a stirrer, a reflux condenser, and a thermometer was charged with 26.65 g tin chloride dehydrate and 100 mL fuming hydrochloric acid. After the tin chloride dehydrate dissolved completely, 10.00 g of NBHET was added gradually into the glass flask. The reaction continued at 80 C for 3 h. After the reaction, the precipitate was filtered with distilled water and dried in an oven at 60 C for 2 h, then purified by recrystallization from ethanol and dried in an oven at 60 C for 2 h to form amino-bis(2-hydroxyethyl) terephthalate (ABHET). Five gram ABHET was added into 4.5 mL hydrochloric acid at 8 C with magnetic stirring. Then, 6.5 mL sodium nitrite aqueous solution (20% by weight ratio) was added slowly into the mixture and reacted at 5 C for 3 h to get diazonium salt (Scheme 3). The excess sodium nitrite was removed by carbamide. The resulting diazonium salt solution was used immediately in the coupling reaction with 1-(4-sulfophenyl)-3-methyl-5-pyrazo-lone (Scheme 4). 1-(4-Sulfophenyl)-3-methyl-5-pyrazolone (5 g) was added into 50 mL distilled water at 5 C, and the solution of the pH was maintained at 8.0 by sodium carbonate. Diazonium salt (6.23 g) was dissolved into the mixture, and the pH of the solution was maintained at 7.0 by sodium carbonate for 2 h. The bright yellow colored dyestuff was filtered, washed with distilled water, and dried at 60 C for2 h.
  • 31
  • [ 100-05-0 ]
  • [ 89-36-1 ]
  • 4-[3-methyl-4-((<i>Z</i>)-4-nitro-phenylhydrazono)-5-oxo-4,5-dihydro-pyrazol-1-yl]-benzenesulfonic acid ; sodium-salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
15.6 g MNODB was synthesized by the conventional diazo-coupling methods. p-Nitroaniline (6.9 g, 0.05 mol) was dissolved in a mixture of concentrated hydrochloric acid (10 mL, 37%) and water (50 ml). The solution was heated to 75 C for about 30 min and then cooled to 0-5 C. A 30% aqueous solution of sodium nitrite (3.52 g, 0.051 mol) was added to the p-nitroaniline solution and stirred for 30 min at 0-5 C. Further stirring at this temperature for 10 min resulted in a clear diazonium salt solution. The coupling reaction was carried out by adding the prepared diazonium salt solution to the coupling component (1-(4-sulfophenyl)-3-methyl-5-pyrazolone) solution (12.7 g, 0.05 mol) at 0-5 C, pH 8.5-9.0 for 3 h. The pH value of the coupling liquor was controlled by adding sodium carbonate powder. The dye was salted out by adding 2.0 g of sodium chloride. Crude yield: 19.5 g (91.8 %); FTIR (KBr, cm-1): 2927 (CH3), 1667 (C=O, pyrazolone), 1502, 1342 (NO2), 1155, 1043 (SO3Na); ESI MS (m/z, %): 402.1 (M-Na, 100). The crude dye MNODB was then purified by the N,N-dimethylformamide/ether (3:20 v/v) purification method [19]. Yield: 15.6 g (73.4%).
  • 32
  • [ 117-61-3 ]
  • [ 89-36-1 ]
  • C32H22N8O14S4(4-)*4Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% 2,2'-benzidinedisulfonic-acid 1g (2.9 mmol), 1ml of concentrated hydrochloric acid, 3ml of water and the mixture was stirred at internal temperature of 5 C and, 0.4g (5.8 mmol) of sodium nitrite was added over 5 minutes to a fraction was, stirring was continued for 30 minutes after the addition to form a diazonium salt. Separately, 4-(3-methyl-5-oxo-4 ,5-dihydro-1H-pyrazol-1-yl)benzenesulfonic acid 1.4g (5.5 mmol) in a 3-neck flask placed sodium acetate 5.9g (72.59 mmol), stirring by the addition of 5ml of DMF and 5ml EA and cooled so that the internal temperature is 5 C . Here and added over a diazonium salt prepared in a 10-minute, Additional stirring was continued for 1 hour. Collect the precipitate formed by the addition of 50ml of saturated aqueous sodium chloride solution to the reaction mixture by filtration by suction to give a pigment additive D, 1.7g (yield 67%)
  • 33
  • [ 32432-55-6 ]
  • [ 89-36-1 ]
  • C29H25N8O11S3(3-)*3Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% 3,5-diamino-2 ,4,6-trimethylbenzenesulfonic acid 1g (4.3 mmol), 1ml of concentrated hydrochloric acid, 3ml of water and the mixture was stirred at internal temperature 5 C and, 0.6g (8.6 mmol) of the Sodium nitrite fraction was added over 5 minutes,After the addition the stirring was continued for 30 minutes, forming a diazonium salt Separately, 4-(3-methyl-5-oxo-4 ,5-dihydro-1H-pyrazol-1-yl)benzenesulfonic acid 2.1g (8.2 mmol) in a 3-neck flask placed sodium acetate 8.9g (108.5 mmol), 7ml of stirring by the addition of EA and 7ml of DMF and cooled so that the internal temperature 5 C .Here and added over a diazonium salt prepared in a 10-minute,Addition was stirred for 1 hour.To the reaction mixture to collect the precipitate formed by the addition of 50ml of saturated aqueous sodium chloride solution by filtration by suction to give a pigment additive D, 1.9g (72% yield)
  • 34
  • bis(2-hydroxyethyl) 2-aminoterephthalate [ No CAS ]
  • [ 89-36-1 ]
  • C22H23N4O10S [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.8% The step (3) the resulting 1 parts by weight with ABHET 15% dilute hydrochloric acid 2 parts by weight of the 5 C mixed evenly under, add by 1 parts by weight of sodium nitrite and 2 parts by weight of 15% dilute hydrochloric acid mixed solution, fully stirring, reaction 3 hours to obtain salt, 5 C for storage. Excess nitrous acid can be used 20% the reaction to remove the ureas, reaction to produce nitrogen and carbon dioxide. (5) preparation of azo dye coupling reaction: In 5 C environment, the 3g of the 1 - (4-sulphonic acid-phenyl) - 3-methyl-5-pyrazolone in 50 ml water, and used for quality score 15% sodium carbonate solution to adjust the pH value to 8.0, to be solid completely dissolved, add 1g step (4) the resulting diazonium salt, re-used for quality score 15% sodium carbonate solution to adjust the solution to pH 6.8, reaction 2h. To the above-mentioned mixed solution by adding concentrated hydrochloric acid salting-out, concentrated hydrochloric acid to the adding amount of the volume of a mixed solution of 10% ; salting-out by the solid portion of the de-ionized water for washing and filtering 3 times, 60 drying 2h, decadent partner nitrogen disperse dye obtained, the purity of 94% or more, the yield 65.8%. This kind of dye suitable for pH3.5-5.0 under the acidic environment of the nylon fiber and its products dyeing, the dye-uptake different pH change with the staining solution
  • 35
  • [ 89-36-1 ]
  • C28H23N5O6S [ No CAS ]
  • 36
  • [ 89-36-1 ]
  • C27H20ClN5O6S [ No CAS ]
  • 37
  • [ 89-36-1 ]
  • C29H24ClN5O8S [ No CAS ]
  • 38
  • [ 89-36-1 ]
  • C29H25N5O7S [ No CAS ]
  • 39
  • [ 89-36-1 ]
  • C10H9N3O5S [ No CAS ]
  • 40
  • [ 89-36-1 ]
  • C27H25FeN5O9S [ No CAS ]
  • 41
  • [ 89-36-1 ]
  • C27H24FeN6O11S [ No CAS ]
  • 42
  • [ 89-36-1 ]
  • C28H27FeN5O9S [ No CAS ]
  • 43
  • [ 89-36-1 ]
  • C27H24ClFeN5O9S [ No CAS ]
  • 44
  • [ 89-36-1 ]
  • C29H28ClFeN5O11S [ No CAS ]
  • 45
  • [ 89-36-1 ]
  • C29H29FeN5O10S [ No CAS ]
  • 46
  • [ 89-36-1 ]
  • C27H25CuN5O9S [ No CAS ]
  • 47
  • [ 89-36-1 ]
  • C27H24CuN6O11S [ No CAS ]
  • 48
  • [ 89-36-1 ]
  • C28H27CuN5O9S [ No CAS ]
  • 49
  • [ 89-36-1 ]
  • 1-(p-sulphophenyl)-3-methyl-4-amino-5-pyrazolone [ No CAS ]
  • 50
  • [ 89-36-1 ]
  • C27H24ClCuN5O9S [ No CAS ]
  • 51
  • [ 89-36-1 ]
  • C29H28ClCuN5O11S [ No CAS ]
  • 52
  • [ 89-36-1 ]
  • C29H29CuN5O10S [ No CAS ]
  • 53
  • [ 89-36-1 ]
  • C54H38CrN10O12S2(1-) [ No CAS ]
  • 54
  • [ 89-36-1 ]
  • C54H36CrN12O16S2(1-) [ No CAS ]
  • 55
  • [ 89-36-1 ]
  • C56H42CrN10O12S2(1-) [ No CAS ]
  • 56
  • [ 89-36-1 ]
  • C54H36Cl2CrN10O12S2(1-) [ No CAS ]
  • 57
  • [ 89-36-1 ]
  • C58H46CrN10O14S2(1-) [ No CAS ]
  • 58
  • [ 89-36-1 ]
  • C27H21N5O6S [ No CAS ]
  • 59
  • [ 89-36-1 ]
  • C27H20N6O8S [ No CAS ]
  • 60
  • [ 89-36-1 ]
  • [ 573-58-0 ]
  • sodium 4-((E)-(3-methyl-5-oxo-1-(4-sulfonatophenyl)-4,5-dihydro-1H-pyrazol-4-yl)diazenyl)-3-((E)-(4'-((E)-(1-((E)-(3-methyl-5-oxo-1-(4-sulfonatophenyl)-4,5-dihydro-1H-pyrazol-4-yl)diazenyl)-4-sulfonatonaphthalen-2-yl)diazenyl)-[1,1'-biphenyl]-4-yl)diazenyl)naphthalene-1-sulfonate [ No CAS ]
  • 61
  • [ 56765-79-8 ]
  • [ 89-36-1 ]
  • 4-{(Z)-[5-hydroxy-3-methyl-1-(4-sulfophenyl)-1H-pyrazol-4-yl]diazenyl}phthalonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% General procedure: Diazotization of 0.6 g (0.0042 mol) of 4-aminophthalonitrile was performed as described in [8]. A solution of the resulting diazo salt was added dropwise with vigorous stirring to an alkaline solution of 0.0042 mol of azo component. Therewith, the temperature of the reaction mixture was maintained within 0-5. After the solution of the diazo compound had been added completely, stirring was continued for an additional 2 h. When the reaction had been complete (as established by the outflow test with a solution of disodium 2-hydroxynaphthalene-3,6-disulfonate), the reaction mixture was acidified with HCl. The precipitate that formed was filtered off, dried, and purified by column chromatography on silica gel 60, eluents DMF-water (1 : 1) (3) or water (4, 5). 4-{(Z)-[5-Hydroxy-3-methyl-1-sulfophenyl-1-pyrazol-4-yl]diazenyl}phthalonitrile (3) was obtained from 0.99 g of <strong>[89-36-1]3-methyl-1-(4-sulfophenyl)pyrazolin-5-one</strong>. Yield 1.11 g (65 %), mp 82C. IR spectrum, nu, cm-1: 3444 (OH), 2924 (CH3), 2233 (CN), 1631 (N=N), 1659 (N-N), 1066, 1132 (SO2), 1058 (CS). 1 NMR spectrum (DMSO-d6), delta, ppm: 13.18 s (SO3H), 8.30 br.s (OH), 8.36 d (1H, H1, JHH = 1.8 Hz), 8.17-8.15 d.d (1H, H2, 2, JHH = 8.8, 3JHH = 1.8 Hz), 7.87 d (2H, H4,7, JHH = 8.7 Hz), 7.96 d (1H, H3, JHH = 8.6 Hz), 7.69 d (H2, H6,5, JHH = 8.7 Hz), 2.54 m (3H, CH3). Mass spectrum, m/z: 407.57 [M -H ]+ (calculated: 408.39). Found, %: 51.6; H 3.21; N 20.92; S 7.99. C18H12N6O4S. Calculated, %: 52.94; H 2.96; N 20.58; S 7.85.
  • 62
  • [ 62-53-3 ]
  • [ 89-36-1 ]
  • C16H13N4O4S(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
98.73% (1) At room temperature (25C), take 0.930 g of aniline in a 100 mL beaker, add 15 mL of DMF (N,N-dimethylformamide), and 2.5 mL of concentrated hydrochloric acid (37%).32.5mL deionized water, stirring evenly to obtain feed solution A; (2) Take 0.731g of sodium nitrite solid in a 100mL beaker, add 15mL DMF (N, N-dimethylformamide), 35mL of deionized water, and stir until the solid sodium nitrite is completely dissolved to prepare a feed solution B; (3) At room temperature (25C), take 2.54 g of the coupling component 1-(4-sulfophenyl)-3-methyl-5-pyrazolone in a beaker and add 60 mL of water.After 30mLDMF (N, N-dimethylformamide) after shaking, adding sodium hydroxide solution to adjust the coupling component pH of 9.95-10.05, stirring until the coupling component is completely dissolved to prepare a feed solution C; (4) The microreactor used in this example consists of a micro-mixing module and a coil. At room temperature (25C), the feed liquid A and the feed liquid B are rapidly mixed by the first micro-mixing unit for diazotization.With a constant flow pump to control the flow of the reaction solution were 30mL/min, with the coil length to control the residence time of the reaction was 10s, to obtain diazonium salt solution D;(5) The feed liquid C and the diazonium salt solution D are rapidly mixed in the second micro-mixing unit at room temperature (25 C.).Coupling reaction occurs, and the flow rate of feed solution C and solution D is controlled by a constant flow pump to be 60 mL/min, and the residence time of the reaction is controlled by the coil length to be 7 s.The inner diameter of the coil used in the reaction was 2 mm to finally obtain an aqueous azo dye solution.The standard working curve of the dye was measured by a UV-visible spectrophotometer, and then based on the product at the maximum absorption wavelengthThe absorbance of the product was calculated by taking the long absorbance, and the azo dye product 1 (the structural formula is shown in Table 1) was calculated. The yield was 98.73%.
  • 63
  • [ 100-01-6 ]
  • [ 89-36-1 ]
  • C16H12N5O6S(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.71% (1) At room temperature (25C), 1.38 g of p-nitroaniline is taken in a 100 mL beaker and 15 mL of DMF (N,N-dimethylformamide) is added.2.5mL concentrated hydrochloric acid (37%), 32.5mL deionized water, stirring evenly to obtain the feed liquid A; (2) Take 0.731g of sodium nitrite solid in a 100mL beaker, add 15mL DMF (N, N-dimethylformamide), 35mL of deionized water, and stir until the solid sodium nitrite completely dissolved to prepare the feed solution B; (3) Take 2.54g of coupling component 1-(4-sulfophenyl)-3-methyl-5-pyrazolone in a beaker at room temperature (25C) and add 60mL of water.After 30mLDMF (N, N-dimethylformamide) after shaking, adding sodium hydroxide solution to adjust the coupling component pH of 9.95-10.05, stirring until the coupling component is completely dissolved to prepare a feed solution C; (4) This embodiment used micro-reactor for patents ZL00105779.0 introduced by the film distributed micro-reactor, at room temperature (25 C), in order to feed liquid A as disperse phase, feed liquid B as a continuous phase, the continuous phase and the dispersed phase in the continuous phase channel respectively flow channels with the dispersed phase, the dispersed phase channel pressure is greater than the continuous phase channel pressure, under the effect of differential pressure, the disperse phase in order to micro-droplets through the membrane in the form of dispersed in the continuous phase to, the diazotization reaction occurs, for constant flow pump control reaction liquid flow is 40 ml/min, control reaction time is 10 s, obtained D diazonium salt solution; (5) In order to feed liquid C as a continuous phase, in order to diazonium salt solution D as disperse phase, in a 2nd membrane dispersion type micro-reactor to carry out the mixing reaction; at room temperature (25 C), under the effect of differential pressure, the disperse phase in the form of tiny droplets D to disperse through the membrane to the continuous phase in the C, generating mass transfer coupling reaction, for constant flow pump control the feed liquid flow rate D C and solution to 80 ml/min, the control reaction time is 20 s, at the end of the azo dye aqueous solution. By UV-visible spectrophotometry the dye of the blood standard working curve, then according to the products under the maximum absorption wavelength of absorbance to calculate the concentration of the products, the calculated azo dye product 19 (structural formula shown in table 1), the yield rate thereof is 96.71%.
  • 64
  • [ 57597-64-5 ]
  • [ 89-36-1 ]
  • C24H23N3O6S [ No CAS ]
  • 66
  • [ 119-66-4 ]
  • [ 89-36-1 ]
  • C16H15N5O4S [ No CAS ]
  • 67
  • [ 119-66-4 ]
  • [ 89-36-1 ]
  • C16H13N5O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; at 0 - 5℃; for 2h;pH 7 - 8; General procedure: In the synthesis of D1, D2 and D3, the same coupling componentwas used, and the diazonium components of dyes D1, D2 and D3 wereprepared using ortho, meta and para-nitroaniline, respectively (seeFig. 1). For example, in the synthesis of D1, the o-nitroaniline wasblended with 40 mL water and 16 mL conc. hydrochloric acid. The resultingsolution was cooled to 0-5 C and was added to a solution of0.345 g sodium nitrite in 20 mL water over a period of 30 min. Theresulting mixture was stirred at 0-5 C for 30 min. Then urea was addedto solution until no blue color was apparent on starch/potassium iodidepaper in the range of 2 s. A solution of 0.07 mol of 4-(3-methyl-5-oxo-4,5-dihydropyrazol-1-yl) benzenesulfonic acid and 3 g NaOH in 200 mL water was filtered toremove the solid materials, and the diazo component was added indeionized water at 0-5 C, pH 8.0. After the resulting mixture wasstirred for 2 h, conc. HCl was added to acid out the coupling product,and the crystalline product was washed and then dried.
  • 68
  • [ 2028-76-4 ]
  • [ 89-36-1 ]
  • C16H15N5O4S [ No CAS ]
  • 69
  • [ 2028-76-4 ]
  • [ 89-36-1 ]
  • C16H13N5O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; at 0 - 5℃; for 2h;pH 7 - 8; General procedure: In the synthesis of D1, D2 and D3, the same coupling componentwas used, and the diazonium components of dyes D1, D2 and D3 wereprepared using ortho, meta and para-nitroaniline, respectively (seeFig. 1). For example, in the synthesis of D1, the o-nitroaniline wasblended with 40 mL water and 16 mL conc. hydrochloric acid. The resultingsolution was cooled to 0-5 C and was added to a solution of0.345 g sodium nitrite in 20 mL water over a period of 30 min. Theresulting mixture was stirred at 0-5 C for 30 min. Then urea was addedto solution until no blue color was apparent on starch/potassium iodidepaper in the range of 2 s. A solution of 0.07 mol of 4-(3-methyl-5-oxo-4,5-dihydropyrazol-1-yl) benzenesulfonic acid and 3 g NaOH in 200 mL water was filtered toremove the solid materials, and the diazo component was added indeionized water at 0-5 C, pH 8.0. After the resulting mixture wasstirred for 2 h, conc. HCl was added to acid out the coupling product,and the crystalline product was washed and then dried.
  • 70
  • [ 100-05-0 ]
  • [ 89-36-1 ]
  • C16H13N5O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; at 0 - 5℃; for 2h;pH 7 - 8; General procedure: In the synthesis of D1, D2 and D3, the same coupling componentwas used, and the diazonium components of dyes D1, D2 and D3 wereprepared using ortho, meta and para-nitroaniline, respectively (seeFig. 1). For example, in the synthesis of D1, the o-nitroaniline wasblended with 40 mL water and 16 mL conc. hydrochloric acid. The resultingsolution was cooled to 0-5 C and was added to a solution of0.345 g sodium nitrite in 20 mL water over a period of 30 min. Theresulting mixture was stirred at 0-5 C for 30 min. Then urea was addedto solution until no blue color was apparent on starch/potassium iodidepaper in the range of 2 s. A solution of 0.07 mol of 4-(3-methyl-5-oxo-4,5-dihydropyrazol-1-yl) benzenesulfonic acid and 3 g NaOH in 200 mL water was filtered toremove the solid materials, and the diazo component was added indeionized water at 0-5 C, pH 8.0. After the resulting mixture wasstirred for 2 h, conc. HCl was added to acid out the coupling product,and the crystalline product was washed and then dried.
  • 71
  • [ 100-05-0 ]
  • [ 89-36-1 ]
  • C16H15N5O4S [ No CAS ]
  • 72
  • [ 88-74-4 ]
  • [ 89-36-1 ]
  • C16H13N5O6S [ No CAS ]
  • 73
  • [ 88-74-4 ]
  • [ 89-36-1 ]
  • C16H15N5O4S [ No CAS ]
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