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[ CAS No. 121-92-6 ] {[proInfo.proName]}

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Chemical Structure| 121-92-6
Chemical Structure| 121-92-6
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Product Details of [ 121-92-6 ]

CAS No. :121-92-6 MDL No. :MFCD00007251
Formula : C7H5NO4 Boiling Point : -
Linear Structure Formula :(O2N)C6H4COOH InChI Key :AFPHTEQTJZKQAQ-UHFFFAOYSA-N
M.W : 167.12 Pubchem ID :8497
Synonyms :

Calculated chemistry of [ 121-92-6 ]      Expand+

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) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.77
Log Po/w (XLOGP3) : 1.83
Log Po/w (WLOGP) : 1.29
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : -0.93
Consensus Log Po/w : 0.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.27
Solubility : 0.904 mg/ml ; 0.00541 mol/l
Class : Soluble
Log S (Ali) : -3.2
Solubility : 0.106 mg/ml ; 0.000637 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 : 1.62

Safety of [ 121-92-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P273-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 121-92-6 ]

* 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 [ 121-92-6 ]
  • Downstream synthetic route of [ 121-92-6 ]

[ 121-92-6 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 121-92-6 ]
  • [ 97-02-9 ]
  • [ 13676-49-8 ]
Reference: [1] Patent: CN107474016, 2017, A,
  • 2
  • [ 121-92-6 ]
  • [ 334952-09-9 ]
Reference: [1] Patent: US2015/284327, 2015, A1,
  • 3
  • [ 79-19-6 ]
  • [ 121-92-6 ]
  • [ 833-47-6 ]
Reference: [1] Journal of Chemical Research, 2011, vol. 35, # 12, p. 703 - 706
[2] Medicinal Chemistry Research, 2012, vol. 21, # 6, p. 816 - 824
[3] Arzneimittel-Forschung/Drug Research, 1999, vol. 49, # 12, p. 1035 - 1038
[4] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 8, p. 2345 - 2350
[5] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 3, p. 1011 - 1016
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 8, p. 998 - 1001
[7] Pharmacy and Pharmacology Communications, 1998, vol. 4, # 2, p. 95 - 98
[8] Farmaco, 2003, vol. 58, # 10, p. 1023 - 1028
[9] Chinese Chemical Letters, 2010, vol. 21, # 3, p. 301 - 304
[10] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 211 - 221
[11] RSC Advances, 2014, vol. 4, # 27, p. 14248 - 14253
[12] Bioorganic Chemistry, 2018, vol. 81, p. 88 - 92
  • 4
  • [ 121-92-6 ]
  • [ 14192-26-8 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2015, vol. 58, # 7, p. 308 - 312
[2] Patent: US2015/284327, 2015, A1,
  • 5
  • [ 121-92-6 ]
  • [ 3958-57-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 413 - 421
  • 6
  • [ 859146-54-6 ]
  • [ 10035-10-6 ]
  • [ 3958-57-4 ]
  • [ 121-92-6 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1906, vol. 38, p. 513[2] Chem. Zentralbl., 1906, vol. 77, # II, p. 1554
  • 7
  • [ 121-92-6 ]
  • [ 6307-87-5 ]
Reference: [1] ChemMedChem, 2014, vol. 9, # 5, p. 973 - 983
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1556 - 1564
  • 8
  • [ 121-92-6 ]
  • [ 618-88-2 ]
Reference: [1] Patent: US5319134, 1994, A,
  • 9
  • [ 121-92-6 ]
  • [ 6307-83-1 ]
YieldReaction ConditionsOperation in experiment
72% at 50℃; for 19 h; Part G:
Preparation of 3-Bromo-5-nitrobenzoic Acid
A solution of 3-nitrobenzoic acid (16.7 g, 100 mmol) in trifluoroacetic acid (50 mL) and sulfuric acid (20 mL) at 50° C. N-Bromosuccinimide (26.7 g, 150 mmol) was added in three portions over 3 hours.
The mixture was stirred for 16 hours and then cooled to room temperature.
The mixture was poured into ice water (200 mL) and extracted three times with ethyl acetate.
The combined organic layers were combined, dried over sodium sulfate and concentrated under vacuum.
The residue was recrystallized from dichloromethane to provide a white solid (17.7 g, 72percent).
1H NMR (300 MHz, DMSO-d6) δ 13.8 (bs, 1H), 8.60 (s, 1H), 8.55 (s, 1H), 8.37 (s, 1H).
72% With N-Bromosuccinimide In sulfuric acid; trifluoroacetic acid at 50℃; for 19 h; A solution of 3-nitrobenzoic acid (16.7 g, 100 mmol) in trifluoroacetic acid (50 mL) and sulfuric acid (20 mL) was stirred at 50° C., and N-bromosuccinimide (26.7 g, 150 mmol) was added in three portions over 3 hours. The mixture was stirred for 16 hours and then cooled to room temperature. The mixture was then poured into ice water (200 mL) and extracted three times with ethyl acetate. The organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was recrystallized from dichloromethane to provide a white solid (17.7 g, 72percent). 1H NMR (300 MHz, DMSO-d6) δ13.8 (bs, 1H), 8.60 (s, 1H), 8.55 (s, 1H), 8.37 (s, 1H).
47% at 100℃; for 6 h; A mixture of 3-nitrobenzoic acid (10 g, 0.06 mols), concentrated sulphuric acid (120ml), silver sulphate (9.33 g, 0.03 mols) and bromine (3.68 ml, 0.07 mols) was stirred at 100°C for 6h. The mixture was poured on ice, and the solid filtered off and extracted with sodium carbonate solution. The title compound was precipitated on acidification from dilute alcohol giving 7.11 g (47percent). HPLC/MS (10 min) retention time 5.69 min LRMS: m/z 244 (M-1)
47%
Stage #1: at 100℃; for 6 h;
Stage #2: With sodium carbonate In waterCooling with ice
PREPARATION 20
3-bromo-5-nitrobenzoic acid
A mixture of 3-nitrobenzoic acid (10 g, 0.06 mols), concentrated sulphuric acid (120 mL), silver sulphate (9.33 g, 0.03 mols) and bromine (3.68 mL, 0.07 mols) was stirred at 100°C for 6h.
The mixture was poured on ice, and the solid filtered off and extracted with sodium carbonate solution.
The title compound was precipitated on acidification from dilute alcohol giving 7.11 g (47percent).

Reference: [1] ChemMedChem, 2014, vol. 9, # 5, p. 973 - 983
[2] Journal of the American Chemical Society, 2017, vol. 139, # 36, p. 12579 - 12590
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1556 - 1564
[4] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869
[5] Chemistry - A European Journal, 2011, vol. 17, # 10, p. 2987 - 2995
[6] Chemical Communications, 2013, vol. 49, # 2, p. 146 - 148
[7] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 576 - 585
[8] Patent: US2004/67935, 2004, A1, . Location in patent: Page/Page column 33
[9] Patent: US2005/197373, 2005, A1, . Location in patent: Page/Page column 20
[10] Chemical Communications, 2016, vol. 52, # 28, p. 4995 - 4998
[11] Patent: EP2196465, 2010, A1, . Location in patent: Page/Page column 42
[12] Patent: EP2394998, 2011, A1, . Location in patent: Page/Page column 22
[13] Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10479 - 10497
[14] Organic and Biomolecular Chemistry, 2005, vol. 3, # 20, p. 3757 - 3766
[15] Patent: WO2007/48771, 2007, A1, . Location in patent: Page/Page column 23; 57
[16] Patent: WO2007/47431, 2007, A2, . Location in patent: Page/Page column 34
[17] Patent: WO2005/48932, 2005, A2, . Location in patent: Page/Page column 179-180
[18] Patent: US2005/234046, 2005, A1, . Location in patent: Page/Page column 96
[19] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 3992 - 3996
[20] Patent: WO2005/48932, 2005, A2, . Location in patent: Page/Page column 179-180
  • 10
  • [ 128-08-5 ]
  • [ 121-92-6 ]
  • [ 6307-83-1 ]
Reference: [1] Patent: WO2004/24682, 2004, A2, . Location in patent: Page 15-16
  • 11
  • [ 1071-46-1 ]
  • [ 2414-98-4 ]
  • [ 121-92-6 ]
  • [ 52119-38-7 ]
Reference: [1] Patent: US4692447, 1987, A,
  • 12
  • [ 121-92-6 ]
  • [ 1877-77-6 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 1752[2] Chem. Zentralbl., 1906, vol. 77, # I, p. 615
  • 13
  • [ 7664-93-9 ]
  • [ 121-92-6 ]
  • [ 1877-77-6 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 1752[2] Chem. Zentralbl., 1906, vol. 77, # I, p. 615
  • 14
  • [ 50-00-0 ]
  • [ 121-92-6 ]
  • [ 99-64-9 ]
YieldReaction ConditionsOperation in experiment
93% With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; methanol; water at 64℃; In a 250 mL glass three-necked flask, 95 mL of methanol and 3 mL of tetrahydrofuran were added,16.7 g of m-nitrobenzoic acid, 0.2 g of 5percent palladium on carbon,A constant pressure dropping funnel was charged with 15.2 mL of 37percent aqueous formaldehyde solution.The reaction system in the air pump away, and then access to atmospheric hydrogen.The temperature was raised to 64oC and the reaction was stirred until no more hydrogen was absorbed.From the dropping funnel was added formaldehyde solution,Continue to hydrogenate at this temperature until no more hydrogen is absorbed.Stop stirring, filter recovery catalyst, the filtrate was concentrated, the product is precipitated.Collect the product by filtration, wash the product with a little water,Then 100 oC dry, the productM-dimethylaminobenzoic acid 15.3 g,The yield is 93percent.After the catalyst is recovered, it is washed with the reaction solvent before being used for the next reaction.
Reference: [1] Patent: CN107056633, 2017, A, . Location in patent: Paragraph 0013; 0014; 0015; 0016
[2] Journal of the Chemical Society, 1950, p. 1342,1345
  • 15
  • [ 7664-93-9 ]
  • [ 610-81-1 ]
  • [ 121-92-6 ]
Reference: [1] Chemische Berichte, 1906, vol. 39, p. 3794[2] Bulletin de la Societe Chimique de France, 1906, vol. <3>35, p. 1256[3] Chem. Zentralbl., 1907, vol. 78, # I, p. 104
  • 16
  • [ 121-92-6 ]
  • [ 140472-69-1 ]
Reference: [1] Patent: EP2394998, 2011, A1,
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10479 - 10497
  • 17
  • [ 121-92-6 ]
  • [ 42237-85-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 20, p. 3757 - 3766
[2] Patent: EP2394998, 2011, A1,
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10479 - 10497
  • 18
  • [ 121-92-6 ]
  • [ 690260-94-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 3992 - 3996
  • 19
  • [ 121-92-6 ]
  • [ 25900-61-2 ]
Reference: [1] Patent: EP2774918, 2014, A1,
  • 20
  • [ 121-92-6 ]
  • [ 706791-83-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1556 - 1564
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