Structure of 5-Bromo-2-nitrophenol
CAS No.: 27684-84-0
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 27684-84-0 |
Formula : | C6H4BrNO3 |
M.W : | 218.01 |
SMILES Code : | BrC1=CC(=C(C=C1)[N+](=O)[O-])O |
MDL No. : | MFCD03095027 |
InChI Key : | DTWHNSNSUBKGTC-UHFFFAOYSA-N |
Pubchem ID : | 13970496 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H315-H317-H318-H410 |
Precautionary Statements: | P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 44.99 |
TPSA ? Topological Polar Surface Area: Calculated from |
66.05 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.08 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.1 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.06 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.05 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.1 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.24 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.85 |
Solubility | 0.306 mg/ml ; 0.00141 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.12 |
Solubility | 0.166 mg/ml ; 0.000763 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.06 |
Solubility | 1.89 mg/ml ; 0.00867 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.14 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.92 |
* 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 |
---|---|---|
20%; 31% | With sodium nitrate; sulfuric acid; In water; at 20℃; for 2h; | 3-Bromophenol (32.9 g, 0.19 mol) was added slowly to a cold (10° C.) solution of sodium nitrate (29.0 g, 0.34 mol) in conc. sulfuric acid; (40.0 g) and water (70.0 mL) and the resulting mixture was allowed to stir at room temperature for 2 h. Water (200 mL) was added and the resulting mixture was extracted with diethyl ether and the extract was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (silica gel, 10percent ethyl acetate/hexanes) to afford first the title compound (8.1 g, 20percent), mp 40-42° C., then the undesired isomer, 3-bromo-4-nitrophenol, as a yellow solid (12.7 g, 31percent). mp 125-127° C. |
10%; 18% | With nitric acid; In acetic acid; at 0 - 20℃; for 1.08333h; | 3-bromo-4-nitrophenol and 3-bromo-6-nitrophenol. 3.8 ml of fuming nitric acid (89 mmole) in 12 ml glacial acetic acid was added over 35 minutes to a solution of 15.2 grams (87.9 mmole) of 3- bromophenol in 60 ml of glacial acetic acid in a flask with a surrounding ice bath. The reaction was stirred at room temperature for an additional 30 minutes and the reaction was then poured on ice. This was then concentrated in vacuo. Medium pressure chromatography on silica gel (1: 2 ethyl acetate: hexanes as eluent) allowed separation of products 3-bromo-4-nitrophenol (3.47 grams, 15.9 mmole, 18percent yield); m. p. 130-131C following recrystallization from ether/hexanes (reported m. p. 130- 131C (Wright, C et al., 1987) and 131 C (Hodgson, HH et al., 1926);'H NMR (DMSO-d6,500 MHz) 8 7.99 (d, 1H, J= 9 Hz), 7.18 (d, 1H, J= 3 Hz), 6.91 (dd, 1H, J= 9,3 Hz, ); and 3-bromo-6-nitrophenol (1.94 grams, 8.90 mmole, 10percent yield, following recrystallization from ether/hexanes); m. p. 41.5-42. 5C (reported m. p. 42-45 C (Hanzlik, RP et al., 1990) and 42 C (Hodson et al.,) ;'H NMR (CDCl3, 500 MHz) 8 10.60 (s, 1H), 7.95 (d, 1H, J= 9 Hz), 7.35 (d, 1H, J= 2 Hz), 7.11 (dd, 1H, J= 9,2 Hz, ) ; 13C NMR (CDCl3 ; assignments aided by HMQC) 8 122.9 (C-2), 123.8 (C-4), 126.0 (C-5), 132.2 (C-3), 132.7 (C-6), 155.2 (C-1) ; IR (KBr) 3450 (broad), 1612,1578, 1527,1475, 1311, 1235, 1186, 900 cm''). |
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