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CAS No. : | 284030-57-5 | MDL No. : | MFCD08543937 |
Formula : | C7H4F2N2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WXXHOWQPFHXRDY-UHFFFAOYSA-N |
M.W : | 218.11 | Pubchem ID : | 16244088 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 46.54 |
TPSA : | 109.14 Ų |
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) : | -6.67 cm/s |
Log Po/w (iLOGP) : | 0.48 |
Log Po/w (XLOGP3) : | 1.35 |
Log Po/w (WLOGP) : | 2.0 |
Log Po/w (MLOGP) : | -0.28 |
Log Po/w (SILICOS-IT) : | -0.69 |
Consensus Log Po/w : | 0.57 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.21 |
Solubility : | 1.35 mg/ml ; 0.00621 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.24 |
Solubility : | 0.124 mg/ml ; 0.00057 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.36 |
Solubility : | 9.54 mg/ml ; 0.0438 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.11 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
95% | Stage #1: With ammonia In water at 0 - 20℃; for 2.5 h; Stage #2: With hydrogenchloride In water |
Step B: 4-Amino-2,3-difluoro-5-nitro-benzoic acid 3 [0122] Ammonium hydroxide solution (30percent in water) (35 mL, 271 mmol) is added to a solution of 2,3,4-trifluoro-5-nitro-benzoic acid 2 (15 g, 67.8 mmol) in 30 mL water at 0° C. with stirring. Upon completion of ammonium hydroxide addition the reaction mixture is warmed to room temperature with stirring. After 2.5 hours, the reaction mixture is cooled to 0° C. and concentrated HCl is carefully added until pH of reaction mixture is near 0. The reaction mixture is diluted with water (30 mL) and extracted with diethyl ether (3.x.50 mL). The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give 14 g (95percent) of pure desired product: MS APCI (-) m/z 217 (M-1) detected. |
95% | Stage #1: With ammonia In water at 0 - 20℃; for 2.5 h; Stage #2: With hydrogenchloride In water |
Ammonium hydroxide solution (-30percent in water) (35 ml, 271 mmol) was added to a solution of 2,3,4-trifluoro-5- nitro-benzoic acid (15 g, 67.8 mmol) in 30 ml water at 0 0C with stirring. Upon completion of the ammonium hydroxide addition, the reaction mixture was warmed to room temperature with stirring. After 2.5 hours, the reaction mixture was cooled to 0 0C and concentrated HCl was carefully added until pH of reaction mixture was 0. The reaction mixture was diluted <n="20"/>with water (30 ml) and extracted with diethyl ether (3 x 50 ml). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to give 14 g (95percent) of pure desired product: MS APCI (-) m/z 217 (M-I) detected. |
95% | Stage #1: With ammonium hydroxide In water at 0 - 20℃; for 2.5 h; Stage #2: With hydrogenchloride In water at 0℃; |
Ammonium hydroxide solution (30percent in water) (35 ml, 271 mmol) is added to a solution of 2,3,4-trifluoro-5-nitro-benzoic acid 2 (15 g, 67.8 mmol) in 30 ml water at 0° C. with stirring. Upon completion of ammonium hydroxide addition the reaction mixture is warmed to room temperature with stirring. After 2.5 h, the reaction mixture is cooled to 0° C. and concentrated HCl is carefully added until pH of reaction mixture is near 0. The reaction mixture is diluted with water (30 ml) and extracted with diethyl ether (3.x.50 ml). The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give 14 g (95percent) of pure desired product: MS APCI (-) m/z 217 (M-1) detected. |
95% | With ammonium hydroxide In water at 0 - 20℃; for 2.5 h; | 4-Amino-2, 3-difluoro-5-nitro-benzoic acid 3Ammonium hydroxide solution (—30percent in water) (35 ml, 271 mmol) is added to asolution of 2,3,4-trifluoro-5-nitro-benzoic acid 2 (15 g, 67.8 mmol) in 30 ml water at 0 °C with stirring. Upon completion of ammonium hydroxide addition the reaction mixture is warmed to room temperature with stirring. After 2.5 h, the reaction mixture is cooled to 0 °C andconcentrated HC1 is carefully added until pH of reaction mixture is near 0. The reaction mixture is diluted with water (30 ml) and extracted with diethyl ether (3 x 50 ml). combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give 14 g (95percent) of pure desired product: MS APCI (-) m/z 217 (M-1) detected. |
88% | Stage #1: With ammonia In water at 6 - 20℃; for 5 - 6.5 h; Stage #2: With hydrogenchloride In water at 0℃; for 1 h; |
Step B; 4-Amino-2.3-difluoro-5-nitrobenzoic acid; To a mixture of 2,3,4- trifluoro-5-nitrobenzoic acid (167.2 g, 0.756 mol, 1 equiv.) in 400 mL of distilled water was added concentrated ammonium hydroxide (28 percent NH3 solution; 340 g, 380 mL, 4.23 mol, 5.6 equiv), ensuring that internal temperature was below 6.0 °C over 2-2.5 hours. The mixture was stirred for 50 minutes and then warmed to room temperature for 3-4 hours. When the reaction was >90percent complete as determined by HPLC, the mixture was cooled in an ice-water bath, and concentrated HCl (350 mL) was then added dropwise to adjust pH = 2. The slurry was stirred for 1 hour with ice bath cooling and then filtered. The cake was rinsed with 1 L of distilled water and then with 350 mL of MTBE. The cake was oven-dried at 48 0C overnight to give 134.9 g of a yellow solid. HPLC was 83.6 apercent (220 nm) and 96.96 apercent (254 nm). The MTBE filtrate was concentrated on a rotary evaporator and pumped overnight to give 9.9 g of a second crop as a yellow solid: HPLC was 81.1 apercent (220 nm) and 95.40 apercent (254 nm). Combined yield of 4-amino-2,3-difluoro-5- nitrobenzoic acid was 144.8 g (88 percent). 1H NMR (400 MHz, DMSO-d6) δ 8.0 (2H, br s, NH2) 8.42 (IH, dd, J 1.5, 7.6, Ar-H); 19F NMR (376 MHz, DMSO- d6) δ -153.9, -129.0. 13C NMR (100 MHz, DMSO-d6) δ 106 (Q d, J 10), 126 (CH), 128 (C), 140 (C-F, dd, J241, 16), 140.8 (C, dd, J 12, 4), 153 (C-F, dd, J 263, 11), 164 (COOH). IR vmjcm~l 3494, 3383, 1697, 1641, 1280. MS APCI (-) m/z 217 (M-I) detected. EPO <DP n="52"/> |
88% | Stage #1: With ammonia In water at 6 - 20℃; for 5.83333 - 7.33333 h; Stage #2: With hydrogenchloride In water at 0℃; for 1 h; |
To a mixture of 2,3,4- trifluoro-5-nitrobenzoic acid (2) (167.2 g, 0.756 mol, 1 equiv) in 400 mL of distilled water EPO <DP n="65"/>was added concentrated ammonium hydroxide (28percent NH3 solution; 340 g, 380 mL, 4.23 mol, 5.6 equiv.) ensuring that internal temperature was below 6.0 0C over 2-2.5 hours. The mixture was stirred for 50 minutes and then warmed to room temperature for 3-4 hours. When the reaction was >90percent complete by HPLC, the reaction mixture was cooled in an ice- water bath and concentrated HCl (350 mL) was then added dropwise to adjust pH = 2. The slurry was stirred for 1 hour with ice bath cooling and filtered. The cake was rinsed with 1 L of distilled water and then with 350 mL of MTBE. The cake was oven-dried at 48 °C overnight to give 134.9 g of a yellow solid. HPLC was 83.6 apercent (220 nm) and 96.96 apercent (254 nm). The MTBE filtrate was concentrated on a rotary evaporator and pumped overnight to give 9.9 g of a second crop as a yellow solid: HPLC was 81.1 apercent (220 nm) and 95.40 apercent (254 nm). Combined yield of 4-amino-2,3-difluoro-5-nitrobenzoic acid (3) was 144.8 g (88percent). 1H NMR (400 MHz, d6 DMSO) δ 8.0 (2H5 br s, NH2) 8.42 (IH, dd, J 1.5, 7.6, Ar-H). 19F NMR (376 MHz, d6 DMSO) δ -153.9, -129.0. 13C NMR (100 MHz, d6 DMSO) δ 106 (C, d, J 10), 126 (CH), 128 (C), 140 (C-F, dd, J 241, 16), 140.8 (C, dd, J 12, 4), 153 (C-F, dd, J 263, 11), 164 (COOH). IR v^/cm"1 3494, 3383, 1697, 1641, 1280. MS APCI (-) m/z 217 (M-I) detected.; To a mixture of 2,3,4- trifluoro-5-nitrobenzoic acid (2) (167.2 g, 0.756 mol, 1 equiv) in 400 niL of distilled water was added concentrated ammonium hydroxide (28percent NH3 solution; 340 g, 380 mL, 4.23 mol, 5.6 equiv.) ensuring that internal temperature was below 6.0 °C over 2-2.5 hours. The mixture was stirred for 50 minutes and then warmed to room temperature for 3-4 hours. When the reaction was >90percent complete by HPLC, the reaction mixture was cooled in an ice- water bath and concentrated HCl (350 mL) was then added drop-wise to adjust pH = 2. The slurry was stirred for 1 hour with ice bath cooling and filtered. The cake was rinsed with 1 L of distilled water and then with 350 mL of MTBE. The cake was oven-dried at 48 °C overnight to give 134.9 g of a yellow solid. HPLC was 83.6 apercent (220 nm) and 96.96 apercent (254 nm). The MTBE filtrate was concentrated on a rotary evaporator and pumped overnight to give 9.9 g of a second crop as a yellow solid: HPLC was 81.1 apercent (220 nm) and 95.40 apercent (254 nm). Combined yield of 4-amino-2,3-difluoro-5-nitrobenzoic acid (3) was 144.8 g (88percent). 1H NMR (400 MHz, d6 DMSO) δ 8.0 (2H, br s, NH2) 8.42 (IH, dd, J 1.5, 7.6, Ar-H). 19F NMR (376 MHz, d6 DMSO) δ -153.9, -129.0. 13C NMR (100 MHz, d6 DMSO) δ 106 (C, d, J 10), 126 (CH), 128 (C), 140 (C-F5 dd, J241, 16), 140.8 (C, dd, J 12, 4), 153 (C-F, dd, J 263, 11), 164 (COOH). IR v^/cm"1 3494, 3383, 1697, 1641, 1280. MS APCI (-) m/z 217 (M-I) detected. |
64% | Stage #1: With ammonia In water for 0.0833333 h; Heating / reflux Stage #2: With hydrogenchloride In water |
Solid 5-nitro-2,3,4-trifluorobenzoic acid (0.75 g, 0.00339 mol) was dissolved in concentrated ammonium hydroxide (25 ml) to give instantly a yellow solution. A precipitate began to form within five minutes, after which time the mixture was acidified to pH 0 with concentrated aqueous hydrochloric acid. A yellow precipitate rapidly formed. The mixture was heated to boiling and was filtered hot. The yellow solids were washed with 10percent aqueous hydrochloric acid and were suction dried to afford 0.47 g of a yellow powder; 64percent yield; 1H-NMR (400 MHz; DMSO) δ 13.32 (s, 1H), 8.36 (d, 1H, J=7.6 Hz), 7.98 (s, 2H); 19F-NMR (376 MHz; DMSO) δ -128.69 to -128.76 (m), -153.60 (d). |
95% | With hydrogenchloride; ammonium hydroxide In water | Step B 4-Amino-2,3-difluoro-5-nitro-benzoic acid Ammonium hydroxide solution (~30percent in water) (35 ml, 271 mmol) is added to a solution of 2,3,4-trifluoro-5-nitro-benzoic acid (15 g, 67.8 mmol) in 30 ml water at 0° C. with stirring. Upon completion of ammonium hydroxide addition the reaction mixture is warmed to room temperature with stirring. After 2.5 h, the reaction mixture is cooled to 0° C. and concentrated HCl is carefully added until pH of reaction mixture is near 0. The reaction mixture is diluted with water (30 ml) and extracted with diethyl ether (3*50 ml). The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give 14 g (95percent) of pure desired product. |
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