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Type | HazMat fee for 500 gram (Estimated) |
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Structure of 700381-18-6
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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.
4.5
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CAS No. : | 700381-18-6 |
Formula : | C8H8BrFO |
M.W : | 219.05 |
SMILES Code : | COC1=CC=C(F)C=C1CBr |
MDL No. : | MFCD00671769 |
Boiling Point : | No data available |
InChI Key : | LXUGHXUXEMUEKR-UHFFFAOYSA-N |
Pubchem ID : | 20111745 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H314 |
Precautionary Statements: | P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 |
Class: | 8 |
UN#: | 1759 |
Packing Group: | Ⅱ |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 45.73 |
TPSA ? Topological Polar Surface Area: Calculated from |
9.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.41 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.55 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.0 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.24 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.84 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.08 |
Solubility | 0.184 mg/ml ; 0.000839 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.39 |
Solubility | 0.89 mg/ml ; 0.00406 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.07 |
Solubility | 0.0187 mg/ml ; 0.0000855 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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 |
-5.83 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 |
1.0 |
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 |
1.0 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) |
1.61 |
* 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 |
---|---|---|
With hydrogen bromide; In chloroform; water; at 20℃; for 1h; | This intermediate is synthesised as follows: Add Sodium borohydride (540 mg, 13.95 mmol) in portions to a solution of 5-Fluoro-2- methoxy-benzaldehyde (2.15g, 13.94 mmol) in absolute EtOH (20 ml) and stir at room temperature. After lh, evaporate the solvent, dilute the residue in CH2Cl2 and treat with aqueous 3M HCI. Separate the phases, wash the organic one twice with H2O, dry over Na2S04 and concentrate at vacuum to obtain pure (5-Fluoro-2-methoxy-phenyl)-methanol as white solid. Add aqueous concentrated HBr (15 ml) to a solution of (5-Fluoro-2- methoxy-phenyl)-methanol (1.9g, 12.17 mmol) in CHC13 (10 ml) and stir at room temperature. After 1h, separate the phases, wash the aqueous one with CH2C12, combine organic phases, wash with H2O, dry over Na2SO4 and concentrate at vacuum to obtain a residue. Purify the residue by column chromatography on silica gel eluting with hexane to afford 2-Bromomethyl-4-fluoro-1-methoxy-benzene as white solid.'H-NMR (CDCl3, 200 MHz) : 8 7.06 (dd, J=3.0 and 8.6 Hz, 1H), 6.98 (m, 1H), 6.81 (dd, J= 4.4 and 9.0 Hz, 1H), 4.50 (s, 2H), 3.87 (s, 3H). | |
With hydrogen bromide; In chloroform; at 20℃; for 2h; | Step 2: To 43 (1 eq, 17.9 mmol, 2.8 g) in CHCU (18 ml_) at room temperature, added HBr (22 mL) and the reaction mixture was stirred 2h, then diluted with dichloromethan, washed with water then brine, dried over sodium sulfate, and concentrated in vacuo to give 44 (3.3 g) as an off-white solid. | |
With phosphorus tribromide; In dichloromethane; for 0.5h; | b) Preparation of 2-bromomethyl-4-fluoro-1-methoxy-benzenePhosphorus tribromide (0.312 mL, 3.28 mmol) is added to a solution of (5-fluoro-2- methoxy-phenyl)-methanol (1.03 g, 6.56 mmol) in DCM (10 mL). After 30 minutes, the reaction mixture is poured directly on to a silica gel column and eluted with DCM to afford 2-bromomethyl-4-fluoro-1-methoxy-benzene. |
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