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Search for reports by entering the product batch number.
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CAS No. : | 161796-10-7 |
Formula : | C9H7BrO4 |
M.W : | 259.05 |
SMILES Code : | COC(=O)C1=CC(=CC(Br)=C1)C(O)=O |
MDL No. : | MFCD06797598 |
Boiling Point : | No data available |
InChI Key : | QIXJVAGZPJKDGY-UHFFFAOYSA-N |
Pubchem ID : | 22593641 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.11 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 52.38 |
TPSA ? Topological Polar Surface Area: Calculated from |
63.6 ?2 |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.91 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.52 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.93 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.23 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.8 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.08 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.15 |
Solubility | 0.182 mg/ml ; 0.000703 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.5 |
Solubility | 0.0816 mg/ml ; 0.000315 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.7 |
Solubility | 0.513 mg/ml ; 0.00198 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 |
-6.09 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 |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.8 |
* 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 |
---|---|---|
97% | With n-Butyl nitrite; copper(ll) bromide; In acetonitrile; at 0 - 20℃; for 3.5h; | Step G (2): 3-bromo-5-(methoxycarbonyl)benzoic acid.; To a mixture of copper (II) bromide (5.5 g, 24.6 mmol), 7-butyl nitrite (3.17g, 30.75 mmol) and acetonitrile (300 mL) was added <strong>[28179-47-7]3-amino-5-(methoxycarbonyl)benzoic acid</strong> (Step G (1), 4.0 g, 20.5 mmol) in aceonitrile (300 mL) over 30 min at 0 0C and the mixture was warmed up and stirred at rt for 3 h. H2O was added and acetonitrile was removed. Ethyl acetate (600 mL) was added and the mixture was washed with 3N HCl, H2O, dried over Na2SO4, and concentrated in vacuo to give the title compound (97% yield): 1H NMR (CDCl3, 500 MHz) delta ppm 3.96 (3H, s), 8.41 (IH, s), 8.41 (IH, s), 8.67 (IH, m). MS (ESI) (M-HX 259.02. |
68% | Step 2: Preparation of 3-bromo-5-(methoxycarbonyl)benzoic acid[00143] 3-Amino-5-(methoxycarbonyl)benzoic acid (1.0 g, 5.12 mmol, 1 eq.) was dissolved in 15% HBr (22.5 mL) at RT, then cooled to 0 0C with stirring. A 2.5 M aqueous solution OfNaNO2 (2.3 mL, 5.64 mmol, 1.1 eq.) was added slowly via an addition funnel to generate the diazonium salt. In a separate flask, CuBr was partially dissolved in 15% HBr (9 mL) and cooled to 0 0C with stirring, to which the <n="89"/>diazonium salt solution was subsequently added. A slight exotherm was observed. The reaction was stirred at RT for 30 minutes then carefully heated at 70 0C for 1 hour. The reaction was worked up by filtering off insoluble material as crude product. The solids were dissolved in water/EtOAc and the layers separated. The aqueous layer was extracted again with EtOAc. The organic layers were combined, dried over sodium sulfate and concentrated to give an off-white solid. The product was purified over silica gel in 1 : 1 hexanes/EtOAc to 100% EtOAc to 4: 1 methylene chloride/MeOH to yield 3-bromo-5-(methoxycarbonyl)benzoic acid (0.90 g, 3.47 mmol, 68% yield) as a white solid. MS found: (M - H)+ = 257/259. | |
34% | With n-Butyl nitrite; copper(ll) bromide; In acetonitrile; at 0 - 30℃; for 1.5h; | 14.0 g (62.7 mmol) copper-(II)-bromide and 12.0 ml (102.6 mmol) n-butylnitrite in 300 ml acetonitrile were combined with 10.0 g (51.2 mmol) 6.3-a, suspended in 300 ml acetonitrile, while cooling with an ice bath. The reaction solution was stirred for 1.5 hours at 30 C., then evaporated to dryness i. vac. Then the residue was combined with dichloromethane and washed with 3N HCl and water. The organic phase was dried and evaporated to dryness using the rotary evaporator. The residue was combined with diethyl ether and the precipitate was filtered off. Yield 4.5 g (34%) 6.3-b. ES-MS (M+H)+=257/259 (bromine isotopes) RT(HPLC-MS)=2.87 min |
With n-Butyl nitrite; copper(ll) bromide; In acetonitrile; at 0 - 20℃; for 1.41667h; | A mixture of copper (II) bromide (5.55 g, 24.9 mmol), n-butyl nitrite (3.21 g, 31.2 mmol) and acetonitrile (90 mL) was stirred in a round bottom flask at 0 C. 3-Amino-5-(methoxycarbonyl)benzoic acid (4.05 g, 20.77 mmol) was added as a slurry in warm aceonitrile (210 mL) over 25 min. and the mixture was stirred at room temeprature for 1 h. The mixture was concentrated and partitioned between dichloromethane and 3N hydrochloric acid. The organic layer was separated, dried over MgSO4, and concentrated in vacuo to give the title compound (5.3 g): 1H NMR (CD3OD, 500 MHz) delta ppm 3.97 (3H, s), 8.34-8.36 (2H, m), 8.58 (1H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 60℃; for 12.5h; | Method 125; Methyl 3-bromo-5-(hydroxymethyl)benzoate; A solution of 3-bromo-5-(methoxycarbonyl)benzoic acid (Method 97; 1.2 g, 4.6 5 mmol) in anhydrous THF (20 ml) was treated with BH3-dimethyl sulfide (2.0 M in THF, 3.5 ml, 6.9 mmol) dropwise under nitrogen at 0 C. The mixture was stirred at 0 C for 30 min then heated up to 60 C for 12 hours. The reaction mixture was quenched with H2O-acetic acid (1 :2) (3 ml) and then diluted with EtOAc. The organics were washed with NaHCO3 (sat) and then dried with NaCl (sat) followed by Na2SO4 (s). The solvents were removed under 10 reduced pressure to give the desired product. |
Tags: 161796-10-7 synthesis path| 161796-10-7 SDS| 161796-10-7 COA| 161796-10-7 purity| 161796-10-7 application| 161796-10-7 NMR| 161796-10-7 COA| 161796-10-7 structure
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