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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 5445-17-0
*Storage: {[sel_prStorage]}
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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.
4.5
*For Research Use Only !
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 5445-17-0 |
Formula : | C4H7BrO2 |
M.W : | 167.00 |
SMILES Code : | CC(C(OC)=O)Br |
MDL No. : | MFCD00000143 |
InChI Key : | ACEONLNNWKIPTM-UHFFFAOYSA-N |
Pubchem ID : | 95576 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H314-H226 |
Precautionary Statements: | P210-P280-P370+P378-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310 |
Class: | 8(3) |
UN#: | 2920 |
Packing Group: | Ⅱ |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.75 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 30.5 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.79 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.31 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.94 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.09 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.81 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.19 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.57 |
Solubility | 4.51 mg/ml ; 0.027 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.46 |
Solubility | 5.75 mg/ml ; 0.0344 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.24 |
Solubility | 9.68 mg/ml ; 0.0579 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 |
-6.39 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 |
2.0 |
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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.91 |
* 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% | A mixture of methyl-2-bromopropionate (S7) (2.00 mL, 17.9 mmol, 1.10 eq) and triphenylphosphine (4.27 g,16.3 mmol, 1.00 eq) in water (18.0 mL) was stirred at 70 C for 2.5 h. Both the aqueousand the organic layer still contained PPh3. The temperature was raised to 80 C and themixture was stirred for further 2 h. According to TLC, there was still a considerableamount of PPh3. Therefore, the mixture was stirred at 75 C overnight. After totally 23 hthe mixture was allowed to cool to rt. Afterwards aqueous NaOH (38 mL 1 M, 2.3 eq) wasadded, which led to the immediate precipitation of a yellow solid. The suspension wasstirred for 5 min, then CH2Cl2 (50 mL) was added and the layers were separated. Theaqueous phase was extracted with CH2Cl2 (2×50 mL), washed with brine, dried overMgSO4 and concentrated under reduced pressure. The crude was obtained as a yellow oil,which turned into a solid upon addition of pentane. The solid was washed with hexane(3×20 mL) and dried in vacuo to afford phosphonium ylide 17 (5.48 g, 97%) as a slightlyyellow powder. | |
91% | With potassium iodide; In water; toluene; at 70℃; for 20h; | After dissolving 5 g (19.06 mmol) of triphenylphosphine in 15 ml of toluene, an aqueous solution of 0.32 g (1.90 mmol) of potassium iodide in 15 ml of distilled water and 3.2 ml (28.6 mmol) of methyl 2-bromopropionate were added thereto. And the mixture was stirred at 70 C for 20 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, basified (pH 9) with 10 N aqueous sodium hydroxide solution, and extracted with dichloromethane. The obtained organic layer was dried over anhydrous sodium sulfate, filtered under reduced pressure, and distilled under reduced pressure. The obtained solid was washed with hexane and then filtered under reduced pressure and dried under reduced pressure to give 6.0 g (yield: 91%) of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; | Intermediate Production Example 1 Production of 2-chloro-5-[1-(methoxycarbonyl)ethoxy]pyrimidine Used in Production Example 1 A mixture of 0.17 g of <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong>, 0.22 g of methyl 2-bromopropionate, 0.20 g of anhydrous potassium carbonate and 2.6 ml of N,N-dimethylformamide was stirred at 60° C. for 1 hour. The reaction solution was cooled to room temperature, then, poured into water, and extracted with t-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.17 g of 2-chloro-5-[1-(methoxycarbonyl)ethoxy]pyrimidine. 1H-NMR(CDCl3/300 MHz) delta(ppm): 1.68 (d, 3H, J=6.6 Hz),3.79(s, 3H), 4.82 (q, 1H, J=6.7 Hz), 8.27(s, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; | a. N(1'-methoxycarbonyl-ethyl)-N-(furan-(2")-carbonyl)-2,3,6-trimethylaniline. A suspension of 51.5 g (0.382 mole) of 2,3,6-trimethylaniline, 35.3 g of NaHCO3 and 126 ml (1.15 moles) of 2-bromopropionic acid methyl ester is stirred for 6 hours at a bath temperature of 130 C., then cooled, filtered from NaBr-salt and distilled. Yield: 67.3 g of α-(2,3,6-trimethylanilino)propionic acid methyl ester (b.p. 144-146 C./9 Torr.) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 3 Methyl 3-(4-methoxy-2-methylphenyl)-2-methyl-3-oxopropanoate Methyl 2-bromopropanoate (0.3 mL) was added to anhydrous tetrahydrofuran (100 mL) of zinc powder (11 g) under argon gas atmosphere, followed by refluxing by heat for 15 minutes. 4-methoxy-2-dimethylbenzonitrile (5.0 g) was added to the resultant reaction solution, and further methyl 2-bromopropanoate (15 mL) was dropped thereinto taking 40 minutes, followed by refluxing by heat for 1 hour. The resultant reaction solution was cooled into room temperature, and was diluted with tetrahydrofuran (50 mL) and 50% potassium carbonate solution (30 mL), followed by stirring for 30 minutes. The supernatant of the reaction solution was separated, and concentrated under reduced pressure. The residual was poured to water, and was extracted with ethyl acetate. The extracted solution was washed by a saturated saline solution, and concentrated under reduced pressure after drying with anhydrous magnesium sulfate. Methanol (110 mL) and IN hydrochloric acid (33 ml) were added to the residue, and stirred at room temperature for 15 hours. The resultant reaction solution was concentrated under reduced pressure, was poured to water, and was extracted with ethyl acetate. The extracted solution was washed by a saturated solution of sodium chloride, and concentrated under reduced pressure after drying with anhydrous magnesium sulfate. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0?71:29), to thereby obtain a title compound (5.4 g) having the following physical properties. TLC: Rf 0.55 (hexane:ethyl acetate=3:1); 1H-NMR(300 MHz, CDCl3): delta 7.72 (d, J=9.3 Hz, 1H), 6.81-6.73 (m, 2H), 3.85 (s, 3H), 3.68 (d, J=0.6 Hz, 3H), 2.54 (s, 3H), 1.56 (d, J=0.6 Hz, 3H), 1.45 (dd, J=7.2, 0.3 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | To a 0 C. solution of 5-chloro-2-methyl-indole (0.100 g, 0.6 mmol) in DMSO (6 mL) was added portionwise potassium hydroxide (0.33 g, 6 mmol). The resulting solution was stirred at room temperature for 15 minutes. To this was added methyl-2-bromo propionate (0.1 mL, 0.9 mmol) in a single portion. The reaction mixture was stirred at room temperature for 16 h. The solution was cooled to 0 C. and quenched with water (20 mL). The mixture was extracted with CH2Cl2 (50 mL). This solution was washed with a saturated solution of ammonium chloride (2×20 mL), brine (200 mL), and dried over sodium sulfate. The solution was concentrated and the residue was purified via silica gel chromatography using 15-40% CH2Cl2 in hexanes to obtain the methyl ester as a clear oil (0.05 g, 0.21 mmol, 35% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=238; tR=3.03 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a 50-mL two-neck round-bottom flask equipped with a cannula were added magnesium turnings (608 mg, 25 mmol), and the flask was heated at 80 C in vacuo for 1 h. A solution of the <strong>[2051-99-2]4-isobutylphenyl bromide</strong> (426 mg, 2.0 mmol) in THF (5 mL) was added dropwise over 3 min under argon. The mixture was heated at 50 C until the reaction was initiated. Additional <strong>[2051-99-2]4-isobutylphenyl bromide</strong> (1.71 g, 8.0 mmol) in THF (11.6 mL) was then added slowly via cannula over 15 min. The reaction mixture was heated at reflux for 3 h, after which a solution of 4-isobutylphenyl magnesium bromide 5 was obtained. To a separate 50-mL Schlenk tube was added anhydrous CoBr2 (21.9mg, 0.10mmol), and the tube was heated at 50C in vacuo for 2h. After cooling to room temperature, the cyclopropane-based bisoxazoline ligand 2 (0.12mmol) in THF (3mL) was added under argon. The resulting mixture was stirred for 1h at the same temperature, with 2-bromopropanoate 6 (1mmol) being added via syringe. The mixture solution was cooled to -80C, and the prepared Grignard reagent 5 (2.8mL, 0.5M in THF, 1.4mmol) was then added over 1h via syringe. The reaction mixture was stirred for another 6h at -80C and then quenched with saturated NH4Cl solution (5mL). The aqueous phase was extracted with diethyl ether (4×10mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate 100:1). 4.4.2 (S)-Methyl 2-(4-isobutylphenyl)propanoate 7b Colorless oil, 86% yield, 86:14 er. The enantiomeric ratio was determined by HPLC with a Daicel Chiralcel OJ-H column (0.5% 2-propanol in n-hexane, 0.5 mL/min, 220 nm, major tr = 16.75 min (S), minor tr = 20.48 min (R)). [alpha]D20 = +50.5 (c 1.0, CHCl3). Lit. 25 [alpha]D29 = +59.5 (c 1.1, CHCl3, 97:3 er). 1H NMR (300 MHz, CDCl3) delta: 7.21-7.18 (m, 2H), 7.09 (d, J = 8.1 Hz, 2H), 3.70 (q, J = 7.1 Hz, 1H), 3.66 (s, 3H), 2.45 (d, J = 7.2 Hz, 2H), 1.89-1.80 (m, 1H), 1.49 (d, J = 7.2 Hz, 3H), 0.90 (d, J = 6.6 Hz, 6H). 13C NMR (75 MHz, CDCl3) delta: 175.1, 140.5, 137.7, 129.3, 127.1, 51.9, 45.01, 45.00, 30.1, 22.3, 18.6. HRMS (APCI-TOF): calcd for C14H21O2 [M+H]+ 221.1542, found 221.1549. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With potassium carbonate; In acetonitrile; at 50℃; | General procedure: dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile was added.0.275 mmol of dimethyl butenedioate,The reaction was carried out under the conditions of Table 1. After the reaction was completed, it was cooled to room temperature.Add water and extract three times with ethyl acetate.Dried over anhydrous magnesium sulfate,The solvent was removed by filtration under reduced pressure.Separated and purified by column chromatography,Get the product,The column chromatography eluate used was a petroleum ether:ethyl acetate mixed solvent in a volume ratio of 10:1 to 5:1. |
Tags: 5445-17-0 synthesis path| 5445-17-0 SDS| 5445-17-0 COA| 5445-17-0 purity| 5445-17-0 application| 5445-17-0 NMR| 5445-17-0 COA| 5445-17-0 structure
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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 |
Sorry,this product has been discontinued.
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