Structure of 121554-10-7
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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.
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| CAS No. : | 121554-10-7 |
| Formula : | C7H3BrIN |
| M.W : | 307.91 |
| SMILES Code : | N#CC1=CC(Br)=CC=C1I |
| MDL No. : | MFCD00672950 |
| InChI Key : | JIGKPMMZNMQXDL-UHFFFAOYSA-N |
| Pubchem ID : | 7020874 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H312-H332 |
| Precautionary Statements: | P280 |
| Num. heavy atoms | 10 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 0 |
| Num. H-bond acceptors | 1.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 51.57 |
| TPSA ? Topological Polar Surface Area: Calculated from |
23.79 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.17 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.98 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.93 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.08 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.44 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.92 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-4.07 |
| Solubility | 0.0262 mg/ml ; 0.000085 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-3.14 |
| Solubility | 0.221 mg/ml ; 0.000719 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.27 |
| Solubility | 0.0165 mg/ml ; 0.0000536 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) |
Yes |
| 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 |
-6.06 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<0.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.41 |
* 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.

[ 463-49-0 ]
[ 121554-10-7 ]
[ 121554-10-7 ]
[ 121554-10-7 ]
[ 121554-10-7 ]
[ 121554-10-7 ]
[ 121554-10-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| tetrakis(triphenylphosphine) palladium(0); at 20℃; for 48h; | Step E: 2- (2-Methylpropyl)-5-bromobenzonitrile; 5-Bromo-2-iodobenzonitrile (3.25 mmol) was combined with 6.5 mL of 0.5 M solution of iso-butylzinc bromide, the solution was degassed with argon, 100 mg of tetrakis (triphenylphosphine) palladium was added in one portion and the solution was stirred at rt under argon for 48 h. The solvents were removed under reduced pressure and the residual mixture was purified by column chromatogarphy using Biotage 40L cartridge to obtain the title compound : 1H NMR (500 MHZ, CDCl3) 8 0.97 (d, J = 8.5, 6H), 2.00 (m, 1H), 2.71 (d, J = 7.5, 2H), 7.19 (d, J = 8. 5, 1H), 7.65 (dd, J = 8. 5,2. 0, 1H), 7.76 (d, J = 2. 0, 1H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃; for 72h; | Reference Example 11 5-Bromo-2-iodobenzonitrile and 3-pyridylboric acid were dissolved in a mixture solution of aqueous 2 M sodium carbonate solution and toluene, then tetrakis(triphenylphosphine)palladium was added thereto, and the mixture was heated, stirred with heating in an argon atmosphere at 100C for 3 days to obtain 5-bromo-2-pyridin-3-ylbenzonitrile. EI: 258, 260. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With caesium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 80℃; for 1h; | 5-Bromo-2-iodobenzonitrile (0.30 g, 1.0 mmol), (1 -methyl -1 H-pyrazol -5- yl)boronic acid (188 mg, 1.5 mmol), dichloro[1 ,1 '- bis(diphenylphosphino)ferrocene] palladium(ll) dichoromethane adduct (26 mg, 0.05 mmol) and cesium carbonate (651 mg, 2.00 mmol) were stirred together at 80 degrees Celsius in a solvent mixture of 3:1 dioxane/water (5 ml_), respectively, for one hour. The reaction mixture was allowed to cool to room temperature and water (25 ml_) and 1 N HCI (5 ml_) were added. The product was extracted into methyene chloride. The organic mixture was concentrated by rotary evaporation to a small volume which was applied to a 40 g cartridge of silica gel. The cartridge was eluted with a 70:30 mixture of hexanes-acetone, respectively. The fractions containing the product were combined and concentrated to give a white solid as product. (210 mg, 80 %) |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| EXAMPLE 112a Preparation of intermediate 5-bromo-2-iodo-benzaldehyde To a solution of 5-bromo-2-iodo-benzomitrile (1.54 g, 5 mmol) in DCM (15 mL) was added a solution of DIBALH (6 mL, 6 mmol) dropwise at 0 C. After the addition, the reaction mixture was warmed to r.t. and stirred for 2 h. Then the mixture was poured into 20 g of ice and 20 mL of 1N HCl, filtered and extracted by DCM (40 mL), washed with aqueous sodium bicarbonate, dried over MgSO4 and concentrated to give crude product (Yield: 1.2 g). | ||
| Step 1: 5-Bromo-2-iodo-benzaldehyde To <strong>[121554-10-7]5-bromo-2-iodobenzonitrile</strong> (7.4 g, 24.2 mmol) in THF (40 mL) at -78 C. was added diisobutylaluminium hydride (1M in hexanes; 24.2 mL, 24.2 mmol) over 5 minutes, and the reaction was allowed to warm to room temperature and monitored by analytical tlc. After stirring overnight at room temperature, starting material was still present, so the mixture was cooled to 0 C. and additional diisobutylaluminium hydride (1M in hexanes; 10.0 mL, 10.0 mmol) was added. After stirring for 2 hours at room temperature, no starting material was seen by analytical tlc, so the mixture was carefully quenched with freshly saturated aqueous Na2SO4 and diluted with EtOAc. The mixture was stirred vigorously for 1 hour and then filtered through Celite. The filtrate was concentrated, and the resulting oil solidified on standing. The solid was stirred vigorously in CH2Cl2 and 1N aqueous HCl, and the aqueous layer was separated and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound. | ||
| T o a s o l u t i o n o f <strong>[121554-10-7]5-bromo-2-iodobenzonitrile</strong> (5.0Og, 16 00mmoles) in anhydrous tetrahydrofuran (80ml) at -8O0C is added diisobutyl aluminium hydride (16.0ml, 16.0mmoles, 1 M solution in toluene) dropwise over 10 minutes. The reaction mixture is stirred at -8O0C for a 1 hour, then allowed to warm to ambient temperature and stir overnight. Additional diisobutyl aluminium hydride (16.0ml, 16.0mmoles, 1 M solution in toluene) is next added dropwise at room temperature, and the reaction mixture further stirred for 1hour. After careful quenching with 2M hydrochloric acid (cooling in ice bath), the crude product is extracted with ethyl acetate (x 2), then all organics are combined and dried over magnesium sulfate and filtered. The filtrate is evaporated under reduced pressure then purified by flash column chromatography (isohexane to 10% ethyl acetate in isohexane eluant) to afford 5-bromo-2- iodobenzaldehyde (0.85g). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 20% | With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); XPhos; In 1,4-dioxane; at 80℃; for 8h;Inert atmosphere; | Preparation 3; Ethyl delta-^-bromo^-cyanophenyOaminol-i-methyl-^S-dihydro-IH-pyrazolo^S-hlquinazoline-S- carboxylate; To a solution of ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (207 mg, 0.753 mmol) in dioxane (6 mL), <strong>[121554-10-7]5-bromo-2-iodobenzonitrile</strong> (260 mg, 0.627 mmol) and cesium carbonate (290 mg, 0.753 mmol) were added and the flask was evacuated and backfilled with argon. [Pd2(dba)3] (13 mg, 0.014 mmol) andX-phos (19 mg, 0.033 mmol) were then charged and the mixture was heated at 800C under argon for 8 hours. After cooling to room temperature, the reaction mixture was concentrated, suspended in water (10 mL) and extracted with ethyl acetate. The organic phase was anidrified on Na2SU4, filtered and evaporated to dryness, the crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 98/2) to afford70 mg (20% yield) of the title compound.MS calc: 453.0669; MS found: 453.0659 |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; | To a sealed tube were added <strong>[121554-10-7]5-bromo-2-iodobenzonitrile</strong> 206-1 (500 mg, 1.6 mmol), 2-fluoropyridin-4-ylboronic acid 205-4 (229mg, 1.6 mmol), Pd(PPh3)4 (94 mg, 0.08 mmol), Na2CO3 ( 516 mg, 4.9 mmol), toluene (2 mL),H2O (2 mL) and ethanol (0.5 mL). The reaction mixture was stirred at 120 C overnight. After cooling to room temperature, the solvents were evaporated and the residue was redissolved in water (5 ml) and extracted with ethyl acetate (8 mL x 3). The combined organic phases were dried over Na2SO4, and concentrated. The residue was purified by silica gel flash chromatography and eluted with 15% ethyl acetate in hexane to give 5-bromo-2-(2-fluoropyridin-4-yl)benzonitrile 206-3. MS m/z 277 '.1 (M + 1). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In water; isopropyl alcohol; at 85℃;Inert atmosphere; | Example 5 ((S)-1-{(S)-2-[5-(2-Cyano-4-{2-[(S)-1-((S)-2-methoxycarbonylamino-3-methyl- butyryl)-pyrrolidin-2-yl]-1 H-benzoimidazol-5-yl}-phenyl)-1 H-benzoimidazol-2- yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl esterIntermediate 19 (103 mg, 0.22 mmol), <strong>[121554-10-7]5-bromo-2-iodo-benzonitrile</strong> (0.1 mmol, 0.1 mmol), 1M aq NaHCO3 solution (0.5 ml_, 0.5 mmol), and Pd(PPh3J4 (11.5 mg, 10 mol %) are suspended into 2.5 mL of isopropanol in a microwave vial. The mixture is purged with nitrogen, heated to 85 C, and stirred overnight. The mixture is concentrated under vacuum and the residue is purified by flash chromatography on silica gel (methanol/DCM, 0 to 6%) to give a white solid. This solid is further purified on reverse phase HPLC to give title compound (9.3 mg). 1H NMR (400 MHz, CD3OD): delta [ppm] 7.45-8.09 (m, 9H), 5.30 (m, 2H), 4.34 (d, 2H), 3.91 -4.02 (m, 4H), 3.64 (s, 6H), 2.03-2.40 (m, 10H), 0.86-0.98 (m, 12H).LC/MS : m/z 788.64 (M + H+). |
Tags: 121554-10-7 synthesis path| 121554-10-7 SDS| 121554-10-7 COA| 121554-10-7 purity| 121554-10-7 application| 121554-10-7 NMR| 121554-10-7 COA| 121554-10-7 structure

A143295 [1227311-09-2]
4-Iodo-3,5-dimethylbenzonitrile
Similarity: 0.75
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| 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 |
Sorry,this product has been discontinued.
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