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[ CAS No. 535-87-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 535-87-5
Chemical Structure| 535-87-5
Chemical Structure| 535-87-5
Structure of 535-87-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 535-87-5 ]

CAS No. :535-87-5 MDL No. :MFCD00007807
Formula : C7H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :UENRXLSRMCSUSN-UHFFFAOYSA-N
M.W :152.15 Pubchem ID :12062
Synonyms :

Calculated chemistry of [ 535-87-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 3.0
Molar Refractivity : 42.21
TPSA : 89.34 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) : -7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.04
Log Po/w (XLOGP3) : 0.21
Log Po/w (WLOGP) : 0.57
Log Po/w (MLOGP) : -0.7
Log Po/w (SILICOS-IT) : -0.22
Consensus Log Po/w : -0.02

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.25
Solubility : 8.49 mg/ml ; 0.0558 mol/l
Class : Very soluble
Log S (Ali) : -1.65
Solubility : 3.44 mg/ml ; 0.0226 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.04
Solubility : 14.0 mg/ml ; 0.092 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.08

Safety of [ 535-87-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 535-87-5 ]

* 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.

  • Upstream synthesis route of [ 535-87-5 ]
  • Downstream synthetic route of [ 535-87-5 ]

[ 535-87-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 99-34-3 ]
  • [ 535-87-5 ]
YieldReaction ConditionsOperation in experiment
98.8% With sodium hydroxide In water at 25 - 30℃; M-Dinitrobenzoic acid 51 g (0.24 mol), 300 mL water added to 1L of Stainless steel high pressure reactor, after stirring it evely, the pH adjusted to 7-8 by using sodium hydroxide aqueous solution with a mass percentage concentration of 20percent, then 0.25g of Ni- Yb-Al three-way catalyst was added, after nitrogen replacement three times, controlled the hydrogen gas pressure at 0.2MPa, maintained the temperature at 25 ~ 30 degrees, reaction does not depressurize until the pressure is substantially reduced. Then recovered the catalyst through filtration, adjusted the filtrate to pH 3 with concentrated hydrochloric acid, precipitated the solid, filtration, washed with water and dried under vacuum to obtain the product 3,5-diamino benzoic acid 36.5g, The yield was 98.8percent and the HPLC purity was 98.9percent. The retention time was in accordance with the standard control.
75%
Stage #1: With sulfuric acid In water at 98℃;
Stage #2: With sodium carbonate In water
EXAMPLE 4 3,5-DI NITRO BENZOIC ACID TO 3,5-DI AMINO BENZOIC ACID Fresh cycle: In a 2-Liter-4-neck round bottom flask equipped with stirrer, condenser, thermometer, addition port arranged in suitable heating / cooling system was charged 700 ml water, heated to 80°C. Charged 20 ml 50percent H2S04 to get pH 2.0 and immediately charged 60 g G-CAT start up with continuous stirring at 80°C. First lot of 15.3 g Nitro 20 g G-CAT was charged to the reaction mass in 10 min. The reaction mass was maintained for 5-10 min at 98-100°C. Remaining lots of nitro G-CAT was charged in four equal lots in similar manner as followed for first lot. Reaction mass was maintained at 98-100°C for 60 min. Then 160.0 ml 25percent Na2C03 was charged to adjust pH 8.5 in 30 min to adjust pH 8.5. Then it is decanted collected in separate flask for further processing. 400 ml hot water wash given to solid inorganic by-product, remaining in the flask under stirring at 98°-100°C, to get 335 g of dry cake of solid inorganic by-product 0.34percent amine content, and appearance was black. The decanted mass is then cooled to 30-35°C and charged 49 ml 50percent Sulphuric acid (H2S04) slowly in 1.0 hrs to get pH 3.5 to 4.0. Liquid layer was then filtered and crystalline material was washed with 150 ml water to get 42 g off white with purity 98.56percent. with melting range 234°C. Total filtrate i.e. reaction medium and washings was collected recycled in subsequent batches.
75%
Stage #1: at 98℃;
EXAMPLE 4 3,5-DI NITRO BENZOIC ACID TO 3,5-DI AMINO BENZOIC ACIDFresh cycle: In a 2-Liter-4-neck round bottom flask equipped with stirrer, condenser, thermometer, addition port arranged in suitable heating/cooling system was charged 700 ml water, heated to 80° C. Charged 20 ml 50percent H2SO4 to get pH 2.0 and immediately charged 60 g G-CAT start up with continuous stirring at 80° C. First lot of 15.3 g Nitro 20 g G-CAT was charged to the reaction mass in 10 min. The reaction mass was maintained for 5-10 min at 98-100° C. Remaining lots of nitro G-CAT was charged in four equal lots in similar manner as followed for first lot. Reaction mass was maintained at 98-100° C. for 60 min. Then 160.0 ml 25percent Na2CO3 was charged to adjust pH 8.5 in 30 min to adjust pH 8.5. Then it is decanted collected in separate flask for further processing. 400 ml hot water wash given to solid inorganic by-product, remaining in the flask under stirring at 98°-100° C., to get 335 g of dry cake of solid inorganic by-product 0.34percent amine content, and appearance was black. The decanted mass is then cooled to 30-35° C. and charged 49 ml 50percent Sulphuric acid (H2SO4) slowly in 1.0 hrs to get pH 3.5 to 4.0. Liquid layer was then filtered and crystalline material was washed with 150 ml water to get 42 g off white with purity 98.56percent.with melting range 234° C. Total filtrate i.e. reaction medium and washings was collected recycled in subsequent batches.First recycle: In the same set up as described above, 700 ml reaction medium generated in fresh cycle was charged, heated to 90° C. Charged 20 ml 50percent H2SO4 to get pH 2.0 and immediately charged 60 g G-CAT start up with continuous stirring at 90-100° C. First lot of 15.3 g Nitro 20 g G-CAT was charged to the reaction mass in 10 min. The reaction mass was maintained for 5-10 min at 98-100° C. Remaining lots of nitro G-CAT was charged in four equal lots in similar manner as followed for first lot. Reaction mass was maintained at 98-100° C. for 60 min. Then 165.0 ml 25percent Na2CO3 was charged in 30 min to adjust pH 8.5. Then it is decanted collected in separate flask for further processing. 400 ml hot water wash given to solid inorganic by-product, remaining in the flask under stirring at 98°-100° C., to get 340 g of dry cake of solid inorganic by-product 0.34percent amine content, and appearance was black. The decanted mass is then cooled to 30-35° C. and charged 58 ml 50percent Sulphuric acid (H2SO4) slowly in 1.0 hrs to get pH 3.5 to 4.0. Liquid layer was then filtered and crystalline material was washed with 150 ml water to get 63 g off white with purity 98.26percent.with melting range 230° C. Total filtrate i.e. reaction medium and washings was collected recycled in subsequent batches.Fifth recycle: In the same set up as described above, 700 ml reaction medium generated in fourth cycle was charged, heated to 90° C. Charged 20 ml 50percent H2SO4 to get pH 2.0 and immediately charged 60 g G-CAT start up with continuous stirring at 90-100° C. First lot of 15.3 g Nitro 20 g G-CAT was charged to the reaction mass in 10 min. The reaction mass was maintained for 5-10 min at 98-100° C. Remaining lots of nitro G-CAT was charged in four equal lots in similar manner as followed for first lot. Reaction mass was maintained at 98-100° C. for 60 min. Then 170.0 ml 25percent Na2CO3 was charged in 30 min to adjust pH 8.5. Then it is decanted collected in separate flask for further processing. 400 ml hot water wash given to solid inorganic by-product, remaining in the flask under stirring at 98°-100° C., to get 370 g of dry cake of solid inorganic by-product 0.53percent amine content, and appearance was black. The decanted mass is then cooled to 30-35° C. and charged 53 ml 50percent Sulphuric acid (H2SO4) slowly in 1.0 hrs to get pH 3.5 to 4.0. Liquid layer was then filtered and crystalline material was washed with 150 ml water to get 70 g off white with purity 97.05percent.with melting range 233° C. Total filtrate i.e. reaction medium and washings was collected recycled in subsequent batches.Tenth recycle: In the same set up as described above, 700 ml reaction medium generated in ninth cycle was charged, heated to 90° C. Charged 20 ml 50percent H2SO4 to get pH 2.0 and immediately charged 60 g G-CAT start up with continuous stirring at 90-100° C. First lot of 15.3 g Nitro 20 g G-CAT was charged to the reaction mass in 10 min. The reaction mass was maintained for 5-10 min at 98-100° C. Remaining lots of nitro G-CAT was charged in four equal lots in similar manner as followed for first lot. Reaction mass was maintained at 98-100° C. for 60 min. Then 180.0 ml 25percent Na2CO3 was charged in 30 min to adjust pH 8.5. Then it is decanted collected in separate flask for further processing. 400 ml hot water wash given to solid inorganic by-product, remaining in the flask under stirring at 98°-100° C., to get 340 g of dry cake of solid inorganic by-product 0.65percent amine content, and appearance was black. The decanted mass is then cooled to 30-35° C. and charged 56 ml 50percent Sulphuric acid (H2SO4) slowly in 1.0 hrs to get pH 3.5 to 4.0. Liquid layer was then filtered and crystalline material was washed with 150 ml water to get 67 g off white with purity 92.65percent with melting range 230° C. Total filtrate i.e. reaction medium and washings was collected recycled in subsequent batches.Fifteenth recycle: In the same set up as described above, 700 ml reaction medium generated in fourteen Recycle was charged, heated to 90° C. Charged 20 ml 50percent H2SO4 to get pH 2.0 and immediately charged 60 g G-CAT start up with continuous stirring at 90-100° C. First lot of 15.3 g Nitro 20 g G-CAT was charged to the reaction mass in 10 min. The reaction mass was maintained for 5-10 min at 98-100° C. Remaining lots of nitro G-CAT was charged in four equal lots in similar manner as followed for first lot. Reaction mass was maintained at 98-100° C. for 60 min. Then 195.0 ml 25percent Na2CO3 was charged in 30 min to adjust pH 8.5. Then it is decanted collected in separate flask for further processing. 400 ml hot water wash given to solid inorganic by-product, remaining in the flask under stirring at 98°-100° C., to get 330 g of dry cake of solid inorganic by-product 0.66percent amine content, and appearance was black. The decanted mass is then cooled to 30-35° C. and charged 59 ml 50percent Sulphuric acid (H2SO4) slowly in 1.0 hrs to get pH 3.5 to 4.0. Liquid layer was then filtered and crystalline material was washed with 150 ml water to get 65 g off white with purity 95percent with melting range 232° C. Total filtrate i.e. reaction medium and washings was collected recycled in subsequent batches.Twentieth recycle: In the same set up as described above, 700 ml reaction medium generated in nineteen cycles was charged, heated to 90° C. Charged 20 ml 50percent H2SO4 to get pH 2.0 and immediately charged 60 g G-CAT start up with continuous stirring at 90-100° C. First lot of 15.3 g Nitro 20 g G-CAT was charged to the reaction mass in 10 min. The reaction mass was maintained for 5-10 min at 98-100° C. Remaining lots of nitro G-CAT was charged in four equal lots in similar manner as followed for first lot. Reaction mass was maintained at 98-100° C. for 60 min. Then 200.0 ml 25percent Na2CO3 was charged in 30 min to adjust pH 8.5. Then it is decanted collected in separate flask for further processing. 400 ml hot water wash given to solid inorganic by-product, remaining in the flask under stirring at 98°-100° C., to get 315 g of dry cake of solid inorganic by-product 0.68percent amine content, and appearance was black. The decanted mass is then cooled to 30-35° C. and charged 63 ml 50percent Sulphuric acid (H2SO4) slowly in 1.0 hrs to get pH 3.5 to 4.0. Liquid layer was then filtered and crystalline material was washed with 150 ml water to get 65 g off white with purity 98percent with melting range 230° C. Total filtrate i.e. reaction medium and washings was collected recycled in subsequent batches.Twenty-Fifth recycle: In the same set up as described above, 700 ml reaction medium generated in twenty-fourth cycles was charged, heated to 90° C. Charged 20 ml 50percent H2SO4 to get pH 2.0 and immediately charged 60 g G-CAT start up with continuous stirring at 90-100° C. First lot of 15.3 g Nitro 20 g G-CAT was charged to the reaction mass in 10 min. The reaction mass was maintained for 5-10 min at 98-100° C. Remaining lots of nitro G-CAT was charged in four equal lots in similar manner as followed for first lot. Reaction mass was maintained at 98-100° C. for 60 min. Then 195.0 ml 25percent Na2CO3 was charged in 30 min to adjust pH 8.5. Then it is decanted collected in separate flask for further processing. 400 ml hot water wash given to solid inorganic by-product, remaining in the flask under stirring at 98°-100° C., to get 330 g of dry cake of solid inorganic by-product 0.53percent amine content, and appearance was black. The decanted mass is then cooled to 30-35° C. and charged 68 ml 50percent Sulphuric acid (H2SO4) slowly in 1.0 hrs to get pH 3.5 to 4.0. Liquid layer was then filtered and crystalline material was washed with 150 ml water to get 66 g off white with purity 97.12percent with melting range 231° C. Total filtrate i.e. reaction medium and washings was collected recycled in subsequent batches.
Reference: [1] Patent: CN105949076, 2016, A, . Location in patent: Paragraph 0025; 0026; 0031; 0036; 0040; 0045; 0053
[2] Journal of the Iranian Chemical Society, 2014, vol. 11, # 6, p. 1587 - 1592
[3] Synthetic Communications, 2000, vol. 30, # 20, p. 3639 - 3644
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 9, p. 709 - 711
[5] Synthetic Communications, 2003, vol. 33, # 2, p. 281 - 289
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 9, p. 1315 - 1318
[7] Patent: WO2011/48535, 2011, A1, . Location in patent: Page/Page column 40-42
[8] Patent: US2012/203031, 2012, A1, . Location in patent: Page/Page column 12-14
[9] Justus Liebigs Annalen der Chemie, 1856, vol. 99, p. 104
[10] Zeitschrift fuer Chemie, 1865, p. 51
[11] Justus Liebigs Annalen der Chemie, 1870, vol. 154, p. 326 Anm. 2
[12] Justus Liebigs Annalen der Chemie, 1870, vol. 154, p. 326 Anm. 2
[13] Journal of the American Chemical Society, 1956, vol. 78, p. 3210,3215
[14] The Journal of biological chemistry, 1958, vol. 233, # 1, p. 184 - 188
[15] Journal and Proceedings of the Royal Society of New South Wales, 1940, vol. 74, p. 74,79, 373
[16] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2011, vol. 41, # 6, p. 590 - 597
  • 2
  • [ 99-34-3 ]
  • [ 618-84-8 ]
  • [ 535-87-5 ]
Reference: [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 8, p. 1306 - 1316
  • 3
  • [ 401-99-0 ]
  • [ 535-87-5 ]
Reference: [1] Photochemistry and Photobiology, 2005, vol. 81, # 6, p. 1539 - 1543
  • 4
  • [ 65-85-0 ]
  • [ 535-87-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1870, vol. 154, p. 326 Anm. 2
[2] Justus Liebigs Annalen der Chemie, 1856, vol. 99, p. 104
  • 5
  • [ 4277-02-5 ]
  • [ 535-87-5 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 2721
  • 6
  • [ 81417-03-0 ]
  • [ 535-87-5 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 2721
  • 7
  • [ 368-53-6 ]
  • [ 535-87-5 ]
Reference: [1] Photochemistry and Photobiology, 2005, vol. 81, # 6, p. 1539 - 1543
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