Structure of 79456-30-7
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CAS No. : | 79456-30-7 |
Formula : | C6H4BrF3N2 |
M.W : | 241.01 |
SMILES Code : | NC1=NC=C(C=C1Br)C(F)(F)F |
MDL No. : | MFCD07375382 |
InChI Key : | KBNACDZKKVMULE-UHFFFAOYSA-N |
Pubchem ID : | 13064155 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 41.34 |
TPSA ? Topological Polar Surface Area: Calculated from |
38.91 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.78 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.08 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.61 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.08 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.36 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.38 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.95 |
Solubility | 0.271 mg/ml ; 0.00113 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.53 |
Solubility | 0.717 mg/ml ; 0.00297 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.41 |
Solubility | 0.0935 mg/ml ; 0.000388 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 |
-6.29 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 |
0.0 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) |
1.85 |
* 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 |
---|---|---|
96 g | With N-Bromosuccinimide In chloroform at 20 - 80℃; for 1.5 h; Cooling with ice | Production Example 59-1 71 g of N-bromosuccinimide was added to a mixture of 65 g of 5-trifluoromethyl-pyridine-2-ylamine and 100 mL of chloroform by being divided into 5 portions under ice water-cooling, The temperature was elevated to room temperature and the mixture was stirred for 1 hour. Then, the mixture was heated to 80°C and was heated and stirred for 3C minutes. After allowing the mixture to cool to room temperature, a saturated aqueous sodium thiosulfate solution and a saturated aqueous sodium hydrogen carbonate solution were added to the mixture, which was then subjected to extraction using chloroform. A combined organic layer was dried using sodium sulfate, and then, was condensed under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 96 g of 3-bromo-5-trifluoromethyl-pyridin-2-ylamine. 3-bromo-5-trifluoromethyl-pyridin-2-ylamine 1H-NMR (CDCl3) δ: 8.27 (1H, d), 7.86 (1H, d), 5.38 (2H, brs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of 2-amino-3-(4-methylthio)phenyl-5-trifluoromethylpyridine (9.7 g), OsO4 (2 mL of a 4% solution in water) and NMO (13 g) in acetone/water (60 mL:5 mL) was stirred at r.t. overnight. Saturated aqueous Na2SO3 was then added and the resulting mixture was stirred for 30 min. The acetone was evaporated and the resulting mixture was extracted with ether and ethyl acetate. The combined organics were washed with Na2SO3, water, brine and then concentrated. The solid residue was stirred vigorously in hexane and ether for 1 h and then filtered to provide the title compound as a pale yellow solid (9.9 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of <strong>[79456-30-7]2-amino-3-bromo-5-trifluoromethylpyridine</strong> from Example 1 (15 g) in dioxane/water/12N HCl (75 mL:75 mL:15.5 mL) at 0C was added a solution of sodium nitrite (10.54 g). The mixture was stirred for 3 h at r.t.. The mixture was poured into an ice bath and then neutralized with 10 N NaOH. The resulting solid was filtered and azeotroped with toluene. The resulting solid and POCl3 (14.5 mL) was heated at 80C for 3 h. The mixture was cooled to r.t., poured into an ice bath and then neutralized, first by the addition of 3 N NaOH followed by the addition of saturated sodium carbonate. The resulting mixture was extracted with CH2Cl2 and the combined organics were washed with brine, dried and concentrated. The title compound was obtained as a volatile liquid that was used without further purification in the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; di(1-adamantyl)benzylphosphonium hydrobromide; In dimethyl sulfoxide; at 100℃; for 1h;Schlenk technique; Inert atmosphere; | General procedure: In a flame-dried Schlenk tube under nitrogen atmosphere, 3-bromopyridine-2-amine (1a; 173 mg,1.00 mmol), Pd(PPh3)2Cl2 (17.5 mg, 0.025 mmol), and (1-Ad)2PBn*HBr (22.6 mg, 0.050 mmol) were dissolved in anhyd DMSO (1.50 mL). Phenylacetylene (2a; 122 mg, 1.20 mmol) and DBU (457 mg, 3.00 mmol) were added via syringe and the reaction mixture was stirred in a preheated oil bath at 100 C until complete conversion of compound 1a (monitored by TLC). Then, KOt-Bu (281 mg, 2.5 mmol) and anhyd DMSO (1.00 mL) were added and the mixture was stirred at 100 C until completion of the reaction (monitored by TLC). After cooling to r.t., de-ionized H2O (2.00 mL) was added and the aqueous layer was extracted three times with EtOAc. The combined organic phases were first washed twice with de-ionized H2O and then dried with anhyd Na2SO4. The solvents were removed under reduced pressure.The residue was adsorbed onto Celite and purified by column chromatography on a SNAP 100 g cartridge (EtOAc-n-hexane33%) using a Biotage SP-1 flash chromatography purification system to give pure compound 4a as a colorless solid. | |
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(ll) bromide; at 60℃; | Under an atmosphere of argon, to a solution of <strong>[79456-30-7]3-bromo-5-(trifluoromethyl)pyridin-2-amine</strong> (the compound described in Bio. Org. Med. Chem., 9, 1715 (1999)) (163 mg) in triethylamine (1.5 mL), ethynylbenzene (82 muL), bis(triphenylphosphine)palladium dichloride (43 mg) and copper bromide(14 mg) were added. The reaction mixture was stirred for overnight at 60C. To the reaction mixture, water was added and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried with anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 5: 1) to give the title compound (26 mg) having the following physical data. TLC: Rf 0.42 (hexane: ethyl acetate = 3:1); NMR (d6-DMSO): delta 7.13, 7.42, 7.68, 7.90, 8.28. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; sodium thiosulfate; acetic acid; In water; | EXAMPLE 4 Preparation of 2-Amino-3-bromo-5-trifluoromethylpyridine In a 100 ml four necked flask equipped with the same equipments as those used in Example 3 were placed 3 g of 2-amino-5-trifluoromethylpyridine and 30 ml of acetic acid to provide a homogeneous solution. 4.4 g of bromine was dropwise added thereto while cooling the flask with ice water at 10 to 20 C., and after completion of the dropwise addition, the mixture was reacted for 1 hour. The reaction product was poured into 200 ml of water, washed with an aqueous solution of sodium thiosulfate and extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate, and the solvent was evaporated off. The solid thus obtained was washed with n-hexane to obtain 3.5 g of the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,2-dimethoxyethane; at 20℃; for 18h;Reflux; | To a solution of <strong>[79456-30-7]2-amino-3-bromo-5-(trifluoromethyl)pyridine</strong> (10.0 g, 41.5 mmol) in 1,2 dimethoxyethane (300 rnL) at room temperature was added ethyl bromopyruvate (9.889 g, 45.64 mmol) dropwise. The reaction mixture was heated to reflux for 18 h. The 1,2- dimethoxyethane was removed under reduced pressure and the residual solid was recrystalized from 1-chlorobutane. The solid was isolated by filtration and dried to afford an off-white solid, 8-bromo-6-(trifluoromethyl)imidazo[l,2-alpha]pyridine-2-carboxylic acid, ethyl ester (11.044 g).The solid obtained above was dissolved in tetrahydrofuran (150 mL) and a solution of LiOH (2.353 g, 98.29 mmol) in water (100 mL) was added. The reaction mixture was stirred at room temperature for 4 h. The tetrahydrofuran was removed under reduced pressure to provide an aqueous solution which was cooled to 5 0C. Dilute HCl was added dropwise until a pH < 5.0 was achieved. After several minutes a solid began to precipitate from the solution. The solid was collected by filtration, washed once with water (50 mL), and dried in a vacuum oven for 18 h at 80 0C to afford 8.632 g of the title compound as a solid. 1H NMR (dmso-d6) delta 13.17 (br s, IH), 9.31 (s, IH), 8.69 (s, IH), 8.03 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.65 g | With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); In N,N-dimethyl-formamide; at 120℃; for 0.5h; | Production Example 17 (1) [0787] A mixture of 5.22 g of <strong>[79456-30-7]2-amino-3-bromo-5-trifluoromethylpyridine</strong>, 3.80 g of zinc cyanide, 600 mg of tris(dibenzylideneacetone)dipalladium(O), 720 g of 1,1'-bis (diphenylphosphino) ferrocene and 20 ml of DMF was stirred at 120C for 30 minutes. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered. The aqueous layer of the filtrate was extracted with ethyl acetate, then combined with the organic layer of the filtrate and washed with water, and dried over anhydrous magnesium sulfate. The mixture was concentrated under reduced pressure, and then the resulting residue was applied to a silica gel column chromatography to obtain 3.65 g of 2-amino-3-cyano-5-trifluoromethylpyridinepyridine. 2-Amino-3-cyano-5-trifluoromethylpyridinepyridine 1H-NMR (CDCl3) delta: 8.50(1H, d), 7.93(1H, d), 5.60(2H, brs) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15 g | With copper acetylacetonate; ammonia; caesium carbonate; acetylacetone; In 1-methyl-pyrrolidin-2-one; water; at 110℃; for 12h;Autoclave; Cooling with ice; | Production Example 59-2 40 g of <strong>[79456-30-7]3-bromo-5-trifluoromethyl-pyridin-2-ylamine</strong>, 2.2 g of copper (II) acetylacetone, 6.6 g of acetylacetone, 59 g cf cesium carbonate, and 105 mL of NMP were added to an autoclave reactor, and 25 mL of a 28percent ammonia water solution was added thereto under ice-cooling. After sealing the reactor, the temperature was elevated to 110°C and the mixture was heated and stirred for 12 hours. After ice-cooling to room temperature, the reaction mixture was diluted with water and was subjected to extraction using ethyl acetate. A combined organic layer was dried using sodium sulfate, and then, was condensed under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 15 g of 5-trifluoromethyl-pyridine-2,3-diamine. 5-trifluoromethyl-pyridine-2,3-diamine 1H-NMR (CDC13) delta: 7.93 (1H, d), 7.04 (1H, d), 4.71 (2H, brs), 3.46 (2H, brs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.6 g | With sulfuric acid; In ethanol; at 90℃; | A mixture of <strong>[79456-30-7]3-bromo-5-(trifluoromethyl)pyridin-2-amine</strong> (3.0 g), potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate (5.4 g), sulfuric acid (0.80 mL) and ethanol (60 mL) was stirred overnight at 90 C. The reaction mixture was diluted with ethyl acetate, and washed with water. The aqueous layer was neutralized with 1N sodium hydroxide, and extracted with ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was suspended in a mixed solvent of IPE and hexane, and the obtained solid was collected by filtration to give the title compound (2.6 g). MS (APCI+). found: 337.1, 339.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37.7% | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; at 130℃; for 12h;Sealed tube; Inert atmosphere; | Step 1: In a sealed tube, 2-amino-3-bromo-5-trifluoromethyl pyridine (2.0 g, 8.2 mmol), 4-iodo benzotrifluoride (2.25 g, 8.2 mmol), Xant-phos (0.425 g, 0.82 mmol) and cesium carbonate (4.0 g, 12.3 mmol) were mixed in anisole (30 mL). The resulting mixture was purged with argon, added Pd(OAc)2 (0.276 g, 1.23mmol) and heated at 130 C for 12 h. After completion of the reaction, the reaction mixture was filtered through celite bed and concentrated under vacuum. The residue obtained was diluted with ethyl acetate (200 mL), washed with water, brine solution and dried over anhydrous Na2S04. The organic phase was concentrated and purified by the column chromatography (230-400 size mesh) to get the yellow solid 3-bromo- 5-(trifluoromethyl)-N-(4-(trifluoromethyl)phenyl)pyridin-2-amine ( .2 g, 37.7%). LCMS: (Method B) 385 (M+H), RT. 4.02 min, 1H MR (400 MHz, DMSO-d6) : delta 8.47 (d, J = 0.80 Hz, 1 H), 8.00 (d, J = 0.40 Hz, 1 H), 7.80 (d, J = 8.4 Hz, 2H), 7.63 (d, J = 8.4 Hz, 2H), 7.42 (s, 1 H). |
Tags: 79456-30-7 synthesis path| 79456-30-7 SDS| 79456-30-7 COA| 79456-30-7 purity| 79456-30-7 application| 79456-30-7 NMR| 79456-30-7 COA| 79456-30-7 structure
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P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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