Structure of 284030-58-6
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
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
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 284030-58-6 |
Formula : | C8H6F2N2O4 |
M.W : | 232.14 |
SMILES Code : | O=C(OC)C1=CC([N+]([O-])=O)=C(N)C(F)=C1F |
MDL No. : | MFCD06201870 |
Boiling Point : | No data available |
InChI Key : | HOJFIOHGPQOQBF-UHFFFAOYSA-N |
Pubchem ID : | 2759749 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H320-H335 |
Precautionary Statements: | P264-P270-P301+P312-P330 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 50.86 |
TPSA ? Topological Polar Surface Area: Calculated from |
98.14 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.22 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.67 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.09 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.15 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.22 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.18 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.41 |
Solubility | 0.901 mg/ml ; 0.00388 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.35 |
Solubility | 0.105 mg/ml ; 0.000452 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.06 |
Solubility | 2.01 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 |
No |
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 |
-6.53 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 |
3.0 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) |
2.26 |
* 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 |
---|---|---|
92% | With methanol; In tetrahydrofuran; at 0 - 20℃; for 0.5h; | Step C: 4-Amino-2,3-difluoro-5-nitro-benzoic acid methyl ester 4. A 2 M solution of TMS diazomethane in hexanes (6.88 mL, 13.75 mmol) is added to a suspension of <strong>[284030-57-5]4-amino-2,3-difluoro-5-nitro-benzoic acid</strong> 3 (2.00 g, 9.17 mmol) in 25 mL of 4:1 THF:MeOH at 0 C. under nitrogen atmosphere. Upon completion of addition, reaction mixture is warmed to room temperature. After 0.5 hours, excess TMS diazomethane is destroyed by the careful addition of acetic acid. The reaction is then concentrated under reduced pressure and dried in vacuo to give 1.95 g (92%) of pure desired product: MS APCI (-) m/z 231 (M-1) detected. |
92% | A 2 M solution of TMS diazomethane in hexanes (6.88 ml, 13.75 mmol) is added to a suspension of <strong>[284030-57-5]4-amino-2,3-difluoro-5-nitro-benzoic acid</strong> 3 (2.00 g, 9.17 mmol) in 25 ml of 4:1 THF:MeOH at 0 C. under nitrogen atmosphere. Upon completion of addition, reaction mixture is warmed to room temperature. After 0.5 h, excess TMS diazomethane is destroyed by the careful addition of acetic acid. The reaction is then concentrated under reduced pressure and dried in vacuo to give 1.95 g (92%) of pure desired product: MS APCI (-) m/z 231 (M-1) detected. | |
92% | In tetrahydrofuran; methanol; hexane; at 0 - 20℃; for 0.5h;Inert atmosphere; | 4-Amino-2, 3-difluoro-5-nitro-benzoic acid methyl ester 4A 2 M solution of TMS diazomethane in hexanes (6.88 ml, 13.75 mmol) is added to a suspension of <strong>[284030-57-5]4-amino-2,3-difluoro-5-nitro-benzoic acid</strong> 3 (2.00 g, 9.17 mmol) in 25 ml of 4:1 THF:MeOH at 0 C under nitrogen atmosphere. Upon completion of addition, reaction mixture is warmed to room temperature. After 0.5 h, excess TMS diazomethane is destroyed by the careful addition of acetic acid. The reaction is then concentrated under reduced pressure anddried in vacuo to give 1.95 g (92%) of pure desired product: MS APCI (-) m/z 231 (M-1) detected. |
84% | In methanol; at 0℃; for 1h; | Trimethylsilylated diazomethane (1.26 g, 11.02 mmol) was slowly added dropwise to a solution of compound 3 (2.0 g, 9.17 mmol) in methanol at 0 C, and the reaction was continued for 1 h. The reaction was quenched by the addition of a few drops of acetic acid, and then the mixture was evaporated. EtOAc (EtOAc) Methanol (10 ml) was beaten to obtain a pure product of 1.8 g in a yield of 84%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.95 g (92%) | With acetic acid; In tetrahydrofuran; methanol; | Step C 4-Amino-2,3-difluoro-5-nitro-benzoic acid methyl ester A 2 M solution of TMS diazomethane in hexanes (6.88 ml, 13.75 mmol) is added to a suspension of <strong>[284030-57-5]4-amino-2,3-difluoro-5-nitro-benzoic acid</strong> (2.00 g, 9.17 mmol) in 25 ml of 4:1 THF:MeOH at 0 C. under nitrogen atmosphere. Upon completion of addition, reaction mixture is warmed to room temperature. After 0.5 h, excess TMS diazomethane is destroyed by the careful addition of acetic acid. The reaction is then concentrated under reduced pressure and dried in vacuo to give 1.95 g (92%) of pure desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With diazomethyl-trimethyl-silane; In tetrahydrofuran; methanol; hexane; at 0 - 20℃; for 0.5h; | A 2 M solution of tetramethylsilane (TMS) diazomethane in hexanes (6.88 ml, 13.75 mmol) was added to a suspension of <strong>[284030-57-5]4-amino-2,3-difluoro-5-nitrobenzoic acid</strong> (2.00 g, 9.17 mmol) in 25 ml of 4: 1 Tetrahydrofuran (THF):MeOH at 0 0C under nitrogen atmosphere. Upon completion of addition, reaction mixture was warmed to room temperature. After 0.5 hours, excess TMS diazomethane was destroyed by the careful addition of acetic acid. The reaction was then concentrated under reduced pressure and dried in vacuo 1.95 g (92%) of pure desired product: MS APCI (-) m/z 231 (M-I) detected. |
70% | With hydrogenchloride; In methanol; | Step c Preparation of methyl 4-amino-2,3-difluoro-5-nitrobenzoate Hydrogen chloride gas was dissolved in anhydrous methanol (30 ml) until the solution was warm. The solid <strong>[284030-57-5]4-amino-2,3-difluoro-5-nitrobenzoic acid</strong> (0.47 g; 0.00215 mol) was dissolved in this solution and the reaction mixture was brought to reflux with vigorous stirring for 23 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool slowly on the bench. A yellow precipitate formed and was collected by vacuum filtration and dried with suction to afford 0.35 g of yellow microfilaments; 70% yield; m.p. 183.5-184 C.; 1H-NMR (400 MHz; DMSO) delta8.36 (dd, 1H, J=7.3, 1.7 Hz), 8.06 (s, 2H), 3.78 (s, 3H); 19F-NMR (376 MHz; DMSO) delta-128.85 to -128.92 (m), -153.29 (d); MS (APCl-) 231 (M-1, 100); IR (KBr) 3433, 3322, 1700, 1650, 1549, 1343, 1285 cm-1; Anal. calcd/found for: C8H6F2N2O4 C, 41.39/41.40; H, 2.61/2.50; N, 12.07/11.98; F, 16.37/16.58. |
70% | With hydrogenchloride; In methanol; for 23h;Heating / reflux; | Hydrogen chloride gas was dissolved in anhydrous methanol (30 ml) until the solution was warm. The solid <strong>[284030-57-5]4-amino-2,3-difluoro-5-nitrobenzoic acid</strong> (0.47 g; 0.00215 mol) was dissolved in this solution and the reaction mixture was brought to reflux with vigorous stirring for 23 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool slowly on the bench. A yellow precipitate formed and was collected by vacuum filtration and dried with suction to afford 0.35 g of yellow microfilaments; 70% yield; m.p. 183.5-184 C.; 1H-NMR (400 MHz; DMSO) delta 8.36 (dd, 1H, J=7.3, 1.7 Hz), 8.06 (s, 2H), 3.78 (s, 3H); 19F-NMR (376 MHz; DMSO) delta -128.85 to -128.92 (m), -153.29 (d); MS (APCl-) 231 (M-1, 100); IR (KBr) 3433, 3322, 1700, 1650, 1549, 1343, 1285 cm-1; Anal. calcd/found for: C8H6F2N2O4 C, 41.39/41.40; H, 2.61/2.50; N, 12.07/11.98; F, 16.37/16.58. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With chloro-trimethyl-silane; for 15.0833h;Heating / reflux; | Step C; 4-Amino-2,3-difluoro-5-nitrobenzoic acid methyl ester; TMSCl (132 g, 1.21 mol, 2.0 equiv) was added over 5 minutes to a slurry of 4-amino-2,3- difluoro-5-nitrobenzoic acid (132.3 g, 0.607 mol, 1 equiv.) in 325 mL of MeOH. The mixture was heated at reflux for 15 hours. When the reaction was complete as determined by HPLC, the mixture was cooled in an ice-water bath for 45 minutes. The reaction mixture was then filtered and the cake was washed with 65 mL of MeOH. The wet cake was dried overnight at 55 0C under high vacuum to give 128.8 g (92%) of 4-amino-2,3-difluoro-5- nitrobenzoic acid methyl ester. HPLC was 97.9 a% (220 n?i) and 99.2 a % (254 nm). 1H NMR (400 MHz, DMSO-d6) delta 3.84 (3H, s, OMe), 8.1 (2H, br s, NH2), 8.43 (IH, apparent dd, J 1.9, 7.2, Ar-H). 19F NMR (376 MHz, D6 DMSO) delta -153.6, -129.2. 13C NMR (100 MHz, DMSO-d6) delta 52 (CH3O), 105 (C, d, J 10), 125 (CH, t, J 2.7,), 128 (CH, d, J 5), 140 (C-F, dd, J 244, 15,), 141 (C, dd, J 14, 5), 152 (C-F, dd, J263, 11), 162 (COO, t, J3). IR vmjcm l 3433, 3322, 1699, 1637, 1548, 1342, 1234. MS APCI (-) m/z 231 (M-I) detected. |
92% | With chloro-trimethyl-silane; for 15h;Heating / reflux; | TMSCl (132 g,1.21 mol, 2.0 equiv) was added over 5 minutes to a slurry of 4-amino-2,3-difluoro-5- nitrobenzoic acid (3) (132.3 g, 0.607 mol, 1 equiv) in 325 mL of MeOH. The mixture was heated at reflux for 15 hours. Once the reaction was complete by HPLC, the reaction mixture was cooled in an ice- water bath for 45 minutes. Then the reaction mixture was filtered and the cake was washed with 65 mL of MeOH. The wet cake was dried overnight at 55 C under high vacuum to provide 128.8 g (92%) of <strong>[284030-57-5]4-amino-2,3-difluoro-5-nitrobenzoic acid</strong> methyl ester (4). HPLC was 97.9 a% (220 nm) and 99.2 a % (254 nm). 1H NMR (400 MHz, d6 DMSO) delta 3.84 (3H, s, OMe)5 8.1 (2H, br s, NH2), 8.43 (IH, apparent dd, J 1.9, 7.2, Ar-H). 19F NMR (376 MHz, d6 DMSO) delta -153.6, -129.2. 13C NMR (100 MHz, d6 DMSO) delta 52 (CH3O), 105 (C, d, J 10), 125 (CH, t, J2.7,), 128 (CH5 d, J 5), 140 (C-F5 dd, J244, 15,), 141 EPO <DP n="66"/>(C, dd, J 14, 5), 152 (C-F, dd, J263, 11), 162 (COO, t, J 3). IR vmax/cm'' 3433, 3322, 1699, 1637, 1548, 1342, 1234. MS APCI (-) m/z 23.1 (M-I) detected.; TMSCl (132 g,1.21 mol, 2.0 equiv) was added over 5 minutes to a slurry of 4-amino-2,3-difluoro-5- nitrobenzoic acid (3) (132.3 g, 0.607 mol, 1 equiv) in 325 mL of MeOH. The mixture was EPO <DP n="78"/>heated at reflux for 15 hours. Once the reaction was complete by HPLC, the reaction mixture was cooled in an ice-water bath for 45 minutes. Then the reaction mixture was filtered and the cake was washed with 65 mL of MeOH. The wet cake was dried overnight at 55 C under high vacuum to provide 128.8 g (92%) of <strong>[284030-57-5]4-amino-2,3-difluoro-5-nitrobenzoic acid</strong> methyl ester (4). HPLC was 97.9 a% (220 nm) and 99.2 a % (254 nm). 1H NMR (400 MHz, d6 DMSO) delta 3.84 (3H, s, OMe), 8.1 (2H, br s, NH2), 8.43 (IH, apparent dd, J 1.9, 7.2, Ar-H). 19F NMR (376 MHz, d6 DMSO) delta -153.6, -129.2. 13C NMR (100 MHz, d6 DMSO) delta 52 (CH3O), 105 (C, d, J 10), 125 (CH, t, J2.7,), 128 (CH, d, J5), 140 (C-F, dd, J244, 15,), 141 (C, dd, J 14, 5), 152 (C-F, dd, J263, 11), 162 (COO, t, J 3). IR vmjcra l 3433, 3322, 1699, 1637, 1548, 1342, 1234. MS APCI (-) m/z 231 (M-I) detected. |