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[ CAS No. 552-16-9 ] {[proInfo.proName]}

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Chemical Structure| 552-16-9
Chemical Structure| 552-16-9
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Product Details of [ 552-16-9 ]

CAS No. :552-16-9 MDL No. :MFCD00007137
Formula : C7H5NO4 Boiling Point : -
Linear Structure Formula :(O2N)C6H4COOH InChI Key :SLAMLWHELXOEJZ-UHFFFAOYSA-N
M.W : 167.12 Pubchem ID :11087
Synonyms :

Calculated chemistry of [ 552-16-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.22
TPSA : 83.12 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) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.83
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 1.29
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : -0.93
Consensus Log Po/w : 0.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.55 mg/ml ; 0.00925 mol/l
Class : Soluble
Log S (Ali) : -2.81
Solubility : 0.258 mg/ml ; 0.00154 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.15
Solubility : 12.0 mg/ml ; 0.0716 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.6

Safety of [ 552-16-9 ]

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 [ 552-16-9 ]

* 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 [ 552-16-9 ]
  • Downstream synthetic route of [ 552-16-9 ]

[ 552-16-9 ] Synthesis Path-Upstream   1~30

  • 1
  • [ 552-16-9 ]
  • [ 118-92-3 ]
  • [ 56-81-5 ]
  • [ 86-59-9 ]
Reference: [1] Chemistry of Natural Compounds, 1981, vol. 17, p. 149 - 152[2] Khimiya Prirodnykh Soedinenii, 1981, vol. 17, # 2, p. 192 - 195
  • 2
  • [ 552-16-9 ]
  • [ 34785-11-0 ]
Reference: [1] Patent: CN106187887, 2016, A,
  • 3
  • [ 109-04-6 ]
  • [ 552-16-9 ]
  • [ 4253-81-0 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 15, p. 4824 - 4833
  • 4
  • [ 552-16-9 ]
  • [ 6484-25-9 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 2709 - 2721
  • 5
  • [ 552-16-9 ]
  • [ 26892-90-0 ]
Reference: [1] Patent: CN106187887, 2016, A,
  • 6
  • [ 88-72-2 ]
  • [ 552-16-9 ]
  • [ 612-23-7 ]
Reference: [1] Synthetic Communications, 1999, vol. 29, # 13, p. 2211 - 2216
[2] Journal of the Chemical Society. Perkin Transactions 2, 1999, # 7, p. 1489 - 1495
  • 7
  • [ 552-16-9 ]
  • [ 4943-85-5 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 33, p. 27378 - 27387
  • 8
  • [ 552-16-9 ]
  • [ 13721-01-2 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3169 - 3173
  • 9
  • [ 552-16-9 ]
  • [ 28797-48-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 17, p. 4300 - 4315
  • 10
  • [ 552-16-9 ]
  • [ 885-70-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 17, p. 4300 - 4315
  • 11
  • [ 552-16-9 ]
  • [ 4141-08-6 ]
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 1, p. 111 - 117
[2] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 15, p. 3989 - 3996
[3] Patent: CN107235931, 2017, A,
[4] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 24, p. 6313 - 6321
  • 12
  • [ 552-16-9 ]
  • [ 610-71-9 ]
  • [ 603-78-1 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 1168,1170
[2] Chemische Berichte, 1881, vol. 14, p. 1168,1170
  • 13
  • [ 552-16-9 ]
  • [ 7732-18-5 ]
  • [ 7726-95-6 ]
  • [ 636-28-2 ]
  • [ 610-71-9 ]
  • [ 603-78-1 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 1168,1170
  • 14
  • [ 88-72-2 ]
  • [ 16968-19-7 ]
  • [ 552-16-9 ]
YieldReaction ConditionsOperation in experiment
24% With potassium hydroxide In methanol; water; anhydrous toluene (benzene) Example 1
Preparation of 2,2'-dinitrobibenzyl
A catalytic amount of a metal catalyst (0.01 g metal porfin or 0.005 g metal (AcAc)2 +0.01 g crown-ether) was added to a 33percent methanolic KOH-solution, (34 g KOH in 100 ml methanol).
The reaction mixture was cooled to 25° C., 2-nitrotoluene (13.7 g, 0.1 mol) was added and air was passed through the reaction mixture, the temperature of the reaction mixture being kept at 25° C.
After 12 hours the passsing through of air was interrupted and 150 ml water and 50 ml methanol was added.
The reaction mixture was filtered.
The filter layer was dissolved in boiling toluene (benzene), was filtered when hot, was cooled and was filtered again.
Recrystallisation from ethanol gave a product with m.p. 120°-121° C. Yield 24-27percent.
As a by-product o-nitrobenzoic acid was formed.
Reference: [1] Patent: US4721821, 1988, A,
  • 15
  • [ 552-16-9 ]
  • [ 610-29-7 ]
  • [ 603-11-2 ]
Reference: [1] Patent: US5319134, 1994, A,
  • 16
  • [ 552-89-6 ]
  • [ 552-16-9 ]
  • [ 612-25-9 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 2804
[2] Chemische Berichte, 1885, vol. 18, p. 2402
[3] Tetrahedron Letters, 2014, vol. 55, # 29, p. 3920 - 3922
[4] Oriental Journal of Chemistry, 2016, vol. 32, # 1, p. 359 - 365
  • 17
  • [ 552-16-9 ]
  • [ 612-25-9 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 23, p. 4395 - 4396
[2] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6994 - 6996
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1998, vol. 37, # 9, p. 945 - 947
  • 18
  • [ 88-72-2 ]
  • [ 552-16-9 ]
  • [ 612-25-9 ]
  • [ 552-89-6 ]
Reference: [1] Petroleum Chemistry, 2002, vol. 42, # 5, p. 314 - 317
[2] Tetrahedron Letters, 2002, vol. 43, # 5, p. 791 - 793
[3] Patent: CN105237317, 2016, A, . Location in patent: Paragraph 0089; 0090
  • 19
  • [ 5344-90-1 ]
  • [ 552-16-9 ]
  • [ 612-25-9 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 72, p. 38446 - 38449
  • 20
  • [ 67-56-1 ]
  • [ 56-23-5 ]
  • [ 552-89-6 ]
  • [ 552-16-9 ]
  • [ 612-25-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1947, vol. 558, p. 34,41
[2] Annales Academiae Scientiarum Fennicae, Series A, 1942, vol. 59, # 4, p. 3,4[3] Chem.Abstr., 1944, p. 6173
[4] Chemische Berichte, 1930, vol. 63, p. 855,865[5] Journal fuer Praktische Chemie (Leipzig), 1933, vol. <2>138, p. 51,54
  • 21
  • [ 88-72-2 ]
  • [ 127-09-3 ]
  • [ 552-16-9 ]
  • [ 65962-15-4 ]
  • [ 77376-01-3 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 22, p. 4925 - 4927
  • 22
  • [ 552-16-9 ]
  • [ 394-31-0 ]
YieldReaction ConditionsOperation in experiment
30% by weight With sulfuric acid In water EXAMPLE I
Preparation of 2-amino-5-hydroxybenzoic acid (II) from (A)
4.5 g of ortho-nitrobenzoic acid are added to 100 ml of a 10percent by weight of 10 N sulfuric acid in water solution.
To the solution is then added 0.5 g of 5percent platinum-on-carbon hydrogenation catalyst.
The slurry is then stirred and hydrogenated at a hydrogen pressure of 20 psi about 80 to 100° C. for a period of about 20 hours.
After hydrogenation, the catalyst is removed by filtration and the filtrate evaporated in vacuo to give a mixture containing about 30percent by weight of the desired product of formula (II) which may be purified by chromatography, for example column chromatography with silica gel.
Reference: [1] Patent: US4314078, 1982, A,
  • 23
  • [ 552-16-9 ]
  • [ 394-31-0 ]
Reference: [1] Chemische Berichte, 1894, vol. 27, p. 1930
  • 24
  • [ 552-16-9 ]
  • [ 64113-91-3 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 18, p. 8966 - 8979
[2] Patent: WO2008/122667, 2008, A2,
  • 25
  • [ 552-16-9 ]
  • [ 601-99-0 ]
  • [ 88-75-5 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 47, p. 13171 - 13180
  • 26
  • [ 75-09-2 ]
  • [ 552-16-9 ]
  • [ 39549-79-6 ]
Reference: [1] Molecules, 2018, vol. 23, # 11,
  • 27
  • [ 552-16-9 ]
  • [ 610-71-9 ]
  • [ 603-78-1 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 1168,1170
[2] Chemische Berichte, 1881, vol. 14, p. 1168,1170
  • 28
  • [ 552-16-9 ]
  • [ 7732-18-5 ]
  • [ 7726-95-6 ]
  • [ 636-28-2 ]
  • [ 610-71-9 ]
  • [ 603-78-1 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 1168,1170
  • 29
  • [ 552-16-9 ]
  • [ 130627-09-7 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1990, vol. 332, # 3, p. 336 - 344
  • 30
  • [ 552-16-9 ]
  • [ 1253452-78-6 ]
Reference: [1] ChemMedChem, 2013, vol. 8, # 1, p. 125 - 135
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