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CAS No. : | 41009-86-3 | MDL No. : | MFCD31555404 |
Formula : | C12H16Br2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MVJDECNMMQGXKW-UHFFFAOYSA-N |
M.W : | 320.06 | Pubchem ID : | 54072282 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 71.34 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.18 cm/s |
Log Po/w (iLOGP) : | 3.35 |
Log Po/w (XLOGP3) : | 5.73 |
Log Po/w (WLOGP) : | 4.34 |
Log Po/w (MLOGP) : | 4.93 |
Log Po/w (SILICOS-IT) : | 5.27 |
Consensus Log Po/w : | 4.72 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.36 |
Solubility : | 0.00141 mg/ml ; 0.00000441 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.5 |
Solubility : | 0.00102 mg/ml ; 0.00000318 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.51 |
Solubility : | 0.0000991 mg/ml ; 0.00000031 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.78 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
80% | With dibromotriphenylphosphorane In dichloromethane at 20℃; for 24h; | 5.D Step D To a stirred solution of the intermediate from Step C (2.5 g, 12.8 mmol) was added dibromotriphenylphosphorane (21.7 g, 51.5 mmol) in DCM (200 mL). The resulting mixture was stirred at ambient temperature overnight (24 hours) and then the mixture was concentrated under reduced pressure and hexane (200 mL) was added to the residue. The heterogeneous mixture was stirred rapidly for 30 minutes and then the hexane layer was decanted from the insoluble material. The organic layer was washed with water (2×100 mL), saturated NaCl (1×100 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford 3.14 g of the title intermediate (80% yield), which was used without further purification. |
With hydrogen bromide | ||
With sulfuric acid; sodium bromide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Reaktion ueber mehrere Stufen; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) NBS, (PhCO)2O2, AIBN, (ii) Zn-Cu; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) NaOEt, (ii) aq. HCl, (iii) (esterification); Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In methyl cyclohexane at 110 - 115℃; for 160h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In methyl cyclohexane; benzene at 110 - 115℃; for 160h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Rk.mit KCN; | ||
Rk.mit Malonester; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h 3: 85 percent / 2.5percent NaOH/H2O, (n-Bu)4NBr / toluene / 38 h / Heating 4: 79 percent / KOH / ethanol; H2O / 1.17 h / 85 - 90 °C 5: H2, boric acid / 10percent Pd/C / acetic acid / 20 °C / 760 Torr | ||
Multi-step reaction with 5 steps
1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C
2: t-BuOK / tetrahydrofuran / -78 °C
3: 85 percent / NaOH / |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h 3: 85 percent / 2.5percent NaOH/H2O, (n-Bu)4NBr / toluene / 38 h / Heating 4: 79 percent / KOH / ethanol; H2O / 1.17 h / 85 - 90 °C | ||
Multi-step reaction with 4 steps
1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C
2: t-BuOK / tetrahydrofuran / -78 °C
3: 85 percent / NaOH / |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h 3: 85 percent / 2.5percent NaOH/H2O, (n-Bu)4NBr / toluene / 38 h / Heating | ||
Multi-step reaction with 3 steps
1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C
2: t-BuOK / tetrahydrofuran / -78 °C
3: 85 percent / NaOH / |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h 3: 85 percent / 2.5percent NaOH/H2O, (n-Bu)4NBr / toluene / 38 h / Heating 4: 79 percent / KOH / ethanol; H2O / 1.17 h / 85 - 90 °C 5: H2, boric acid / 10percent Pd/C / acetic acid / 20 °C / 760 Torr 6: boric acid / acetic acid; acetic acid / 14 h / 55 - 60 °C | ||
Multi-step reaction with 6 steps
1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C
2: t-BuOK / tetrahydrofuran / -78 °C
3: 85 percent / NaOH / |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h | ||
Multi-step reaction with 2 steps 1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C 2: t-BuOK / tetrahydrofuran / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h | ||
Multi-step reaction with 2 steps 1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C 2: t-BuOK / tetrahydrofuran / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h 3: 85 percent / 2.5percent NaOH/H2O, (n-Bu)4NBr / toluene / 38 h / Heating 4: 76 percent / H2 / 10percent Pd/C / ethanol; acetic acid / 2 h / 20 °C / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Reaktion ueber mehrere Stufen 2: ethanol; sodium |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol; sodium 2: HBr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: (i) Py, (ii) (decarboxylation) 2: H2, aq. NaOH / Pd-C 3: (i) SOCl2, (ii) /BRN= 1098229/ 4: LiAlH4 / diethyl ether 5: NaBr, aq. H2SO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: H2, aq. NaOH / Pd-C 2: (i) SOCl2, (ii) /BRN= 1098229/ 3: LiAlH4 / diethyl ether 4: NaBr, aq. H2SO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: NaBr, aq. H2SO4 | ||
Multi-step reaction with 2 steps 1: LiAlH4 2: HBr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) NaOEt, (ii) aq. HCl, (iii) (esterification) 2: (i) KOtBu, xylene, (ii) (saponification), (iii) acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: (hydrolysis) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) NaOEt, (ii) aq. HCl, (iii) (esterification) 2: (saponification) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 2: (hydrolysis) 3: (esterification) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 2: (hydrolysis) 3: (esterification) 4: (i) KOtBu, xylene, (ii) (saponification), (iii) acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) NaOEt, (ii) aq. HCl, (iii) (esterification) 2: (i) KOtBu, xylene, (ii) (saponification), (iii) acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (i) SOCl2, (ii) /BRN= 1098229/ 2: LiAlH4 / diethyl ether 3: NaBr, aq. H2SO4 | ||
Multi-step reaction with 3 steps 1: H2SO4 2: LiAlH4 3: HBr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 1,3-bis(3-bromopropyl)benzene With potassium carbonate In acetonitrile at 20℃; for 18h; Stage #2: methylamine In tetrahydrofuran; acetonitrile at 20℃; for 18h; Stage #3: trifluoroacetic acid | 5.E Step E To a flask was added 2,2-diphenyl-2-(S)-pyrrolidin-3-ylacetamide (880 mg, 1.57 mmol), the intermediate from Step D (1.0 g, 1.57 mmol), ACN (2 mL) and potassium carbonate (1.4 g, 4.7 mmol) and the resulting mixture was stirred overnight (18 hours) at ambient temperature. Methylamine (2.0 M in THF, 7.8 mL, 15.7 mmol) was added and the resulting mixture was stirred at ambient temperature overnight (18 hours). The reaction mixture was concentrated under reduced pressure and a solution of 1:1 acetic acid/water (1.0 mL) was added to the residue. This mixture was chromatographed on reverse phase silica gel (gradient elution, 10-50% ACN/water) to afford 303 mg of the title compound (27% yield) as a bis(trifluoroacetate) salt. MS m/z: [M+H+] calc'd for C31H39N3O 470.3; found 470.6. Retention time=2.61 min (10-70% ACN: H2O, reverse phase HPLC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 1 h / -78 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: water; potassium hydroxide / ethanol / 4 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: Ethyl isobutyrate With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 1h; Inert atmosphere; Stage #2: 1,3-bis(3-bromopropyl)benzene With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; n-heptane; ethylbenzene at 20℃; Inert atmosphere; | 12 Dimethyl m-benzene-bis(2,2-dimethyl)pentanoate (D2) Under Ar-atmosphere, to a solution of ethyl isobutyrate (21.2 g, 24.4 mL, 183 mmol) in anhydrous THF (200 mL) was added dropwise lithium diisopropylamide (2.0 M in heptane/THF/ethylbenzene, 91.5 mL, 183 mmol) at -78° C. After 1 h, a solution of m-bis(3-bromopropyl)benzene (D1) (prepared according to Schimelpfenig, C. W. J. Org. Chem. 1975, 40, 1493-1494 and Effenberger, F.; Kurtz, W. Chem. Ber. 1973, 106, 511-524; 26.6 g, 83.1 mmol) in anhydrous THF (50 mL) was added dropwise, followed by the addition of DMPU (25 mL). The reaction mixture was allowed to warm to room temperature overnight, then cooled with an ice-bath, and hydrolyzed with saturated NH4Cl solution (100 mL). Deionized water (100 mL) was added and the layers were separated. The aqueous layer was extracted with ethyl acetate (3*100 mL). The combined organic layers were washed with saturated NaCl solution (100 mL), 1 N hydrochloric acid (2*100 mL), saturated NaHCO3 solution (100 mL), and saturated NaCl solution (100 mL). The combined organic phases were dried over MgSO4, concentrated in vacuo, and dried in high vacuo. The residue was purified by flash chromatography on silica (hexanes/ethyl acetate=95/5) to give diethyl 5,5'-(1,3-phenylene)bis(2,2-dimethylpentanoate) (15.7 g, 48%) as a yellowish oil. 1H NMR (CDCl3): δ=7.17 (t, 1 H, J=7.0 Hz), 6.97 (m, 3 H), 4.09 (q, 4 H, J=7.3 Hz), 2.55 (m, 4 H), 1.56 (m, 8 H), 1.22 (t, 6 H, J=7.3 Hz), 1.15 (s, 12 H). 13C NMR (CDCl3): δ=178.02, 142.37, 128.58, 128.32, 125.86, 60.31, 42.25, 40.52, 36.48, 27.03, 25.30, 14.39. |