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[ CAS No. 25574-11-2 ] {[proInfo.proName]}

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Chemical Structure| 25574-11-2
Chemical Structure| 25574-11-2
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Product Details of [ 25574-11-2 ]

CAS No. :25574-11-2 MDL No. :MFCD09028724
Formula : C9H11BrO Boiling Point : -
Linear Structure Formula :- InChI Key :WODKXGCVVOOEIJ-UHFFFAOYSA-N
M.W : 215.09 Pubchem ID :10560614
Synonyms :

Calculated chemistry of [ 25574-11-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.88
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 2.3
Log Po/w (WLOGP) : 2.37
Log Po/w (MLOGP) : 2.91
Log Po/w (SILICOS-IT) : 3.01
Consensus Log Po/w : 2.59

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.83
Solubility : 0.319 mg/ml ; 0.00149 mol/l
Class : Soluble
Log S (Ali) : -2.36
Solubility : 0.933 mg/ml ; 0.00434 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.9
Solubility : 0.0273 mg/ml ; 0.000127 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.17

Safety of [ 25574-11-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 25574-11-2 ]

* 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.

  • Upstream synthesis route of [ 25574-11-2 ]
  • Downstream synthetic route of [ 25574-11-2 ]

[ 25574-11-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 25574-11-2 ]
  • [ 90562-10-0 ]
YieldReaction ConditionsOperation in experiment
66% With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 15.25 h; Example 138. l-Bromo-4-(3-bromo-propyD-benzene (79); [0322] To a solution of compound 78 described in Example 137 (4.0 g, 19 mmol) inTHF (30 mL) at 0 °C under the argon atmosphere was added PPh3 (6.3 g, 24 mmol) followed by CBr4 (8.0 g, 24 mmol). The mixture was stirred at the same temperature for 15 min and then stirred at room temperature for additional 15 h. Most of the solvent was removed and the residue purified by flash chromatography on silica gel (hexane) to afford the title compound (3.5 g, 66percent) as a colorless oil.[0323] 1H NMR (500 MHz, DMSO-d6): δ 2.03-2.12 (m, 2H), 2.68 (t, J= 7.5 Hz, 2H), 3.49 (t, J= 6.5 Hz, 2H), 7.19 (d, J= 8.3 Hz, 2H), 7.47 (d, J= 8.3 Hz, 2H).
66% With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 15.25 h; EXAMPLE 100. Synthesis of l-Broιtio-4-(3-Bromo-Propyl)-Benzene (Intermediate50150[02981 To a solution of intermediate 49 (Example 99) (4.0 g, 19 mmol) in THF (30 mL)O at 0 C under the argon atmosphere was added PPh3 (6.3 g, 24 mmol) followed by CBr4 (8.0 g, 24 mmol). The mixture was stirred at the same temperature for 15 min and then stirred at room temperature for additional 15 h. Most of the solvent was removed and the residue purified by flash chromatography on silica gel (hexane) to afford the title compound (3.5 g, 66percent) as a colorless oil.[0299] 1H NMR (500 MHz, DMSOd6): δ 2.03-2.12 (m, 2H), 2.68 (t, J= 7.5 Hz, 2H), 3.49 (t, J= 6.5 Hz, 2H), 7.19 (d, J= 8.3 Hz, 2H), 7.47 (d, J= 8.3 Hz, 2H).
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1546 - 1559
[2] Patent: WO2006/101977, 2006, A2, . Location in patent: Page/Page column 114
[3] Patent: WO2008/8234, 2008, A1, . Location in patent: Page/Page column 110
[4] Organic Letters, 2010, vol. 12, # 24, p. 5783 - 5785
[5] Tetrahedron, 1990, vol. 46, # 20, p. 7247 - 7262
[6] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4752 - 4756
[7] Patent: EP2168944, 2010, A1, . Location in patent: Page/Page column 94
[8] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3874 - 3883
  • 2
  • [ 25574-11-2 ]
  • [ 75567-84-9 ]
Reference: [1] Journal of Organometallic Chemistry, 2002, vol. 657, # 1-2, p. 129 - 135
  • 3
  • [ 25574-11-2 ]
  • [ 80793-25-5 ]
YieldReaction ConditionsOperation in experiment
96% With Dess-Martin periodane In dichloromethane at 20℃; for 2 h; Example A.4: Synthesis of 3-(4-bromophenyl)propanal (10*) Alcohol 4* (4.71g, 21.8mmol) was dissolved in DCM, treated with Dess-Martin periodinane (9.71g, 20.9mmol) and stirred at rt for 2h. The mixture was quenchedwith 2M NaOH, the phases were separated the aqueous layer extracted with DCM. The combined organic phases were dried on Mg504, filtered and evaporated in vacuo. The crude was purified by flash chromatography on silica gel using a gradient of DCM in cHex to yield the desired product 10* (4.46g, 96percent) as a colourless liquid.1H NMR (400MHz, CDCI3) 6 9.81 (5, 1H), 7.41 (d, 2H), 7.07 (d, 2H), 2.91 (t, 2H),2.79-2.74 (m, 2H).MS (ES) C9H9BrO requires: 211/213, (Mi-H) not found, 100percent.
86%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5 h;
Stage #2: With triethylamine In dichloromethane at -78 - 20℃; for 3 h;
Oxalyl chloride (0.599 mL, 6.973 mmol) was dissolved in DCM (15 mL), and DMSO (0.99 mL, 13.94 mmol)dissolved in DCM (10 mL) was slowly added thereto at -78°C. The mixture was stirred for 15 minutes, and 3-(4-bromophenyl)propan-1-ol (1.0 g, 4.64 mmol) dissolved in DCM (10 mL) was slowly added thereto at -78°C. The mixture was stirredfor 30 minutes, and TEA (1.96 mL) was slowly added thereto at -78°C. The temperature was slowly increased to roomtemperature, and the reaction solution was stirred for 3 hours. After termination of the reaction, the reaction solutionwas diluted with water and extracted with DCM. The organic layer was dried with anhydrous magnesiumsulfate andpurified by column chromatography (eluent, EtOAc/Hex = 1/5) to obtain the title compound (0.859 g, 86percent).NMR: 1H-NMR (CDCl3) δ 9.81(1H, s), 7.40 (2H, d), 7.07(2H, d), 2.91(2H, m), 2.77(2H, t)
76.9% With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 4 h; 3-(4-Bromophenyl) propan-1-ol (4 g, 18.5 mmol, 1.0 equiv) was dissolved into dichloromethane (60 mL) and cooled to 0°C. PCC (5.21 g, 24.1 mmol, 1.5 equiv) was added in portions and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered through celite bed and the filtrate was concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (10-20 percent diethyl ether/n-pentane) to afford the desired product 5.21a (3.05 g, 76.9 percent yield). 1H NMR (400 MHz, CDCI3) 69.83 (s, 1H), 7.43 (d, J = 8.3 Hz, 2H), 7.10 (d, J 8.2 Hz, 2H), 2.94 (t, J 7.3 Hz, 2H), 2.79 (t, J 7.4 Hz, 2H).
58.5% With sodium hydrogencarbonate; Dess-Martin periodane In dichloromethane at 0 - 20℃; To a 0° C. mixture of 26A (7 g, 32.5 mmol) and NaHCO3 (3.28 g, 39.1 mmol) in DCM (200 mL) was added Dess-Martin periodinane (16.56 g, 39.1 mmol) and the reaction was allowed to slowly warm to rt overnight. The reaction was diluted with sat. aq. NaHCO3 (150 mL) and extracted with DCM (50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed (SiO2; 80 g; A=Hex, B=EtOAc; 20 min gradient from 0percent B to 40percent B; flow rate=60 mL/min) to afford the title compound (4.06 g, 19.1 mmol, 58.5percent yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ 9.82 (t, J=1.2 Hz, 1H), 7.48-7.37 (m, 2H), 7.19-6.97 (m, 2H), 3.02-2.88 (m, 2H), 2.83-2.70 (m, 2H).

Reference: [1] Patent: WO2015/181272, 2015, A1, . Location in patent: Page/Page column 30
[2] Patent: EP3239143, 2017, A2, . Location in patent: Paragraph 0120
[3] Patent: WO2015/66413, 2015, A1, . Location in patent: Page/Page column 176; 177
[4] Patent: US2017/253554, 2017, A1, . Location in patent: Paragraph 0425; 0426
[5] Chemical Communications, 2011, vol. 47, # 27, p. 7875 - 7877
[6] Chinese Chemical Letters, 2016, vol. 27, # 4, p. 555 - 558
[7] Organic and Biomolecular Chemistry, 2018, vol. 16, # 34, p. 6187 - 6190
  • 4
  • [ 25574-11-2 ]
  • [ 109-89-7 ]
  • [ 83101-12-6 ]
YieldReaction ConditionsOperation in experiment
52% With 1-methyl-pyrrolidin-2-one In water 33B 3-(4-Cyanophenyl)propan-1-ol
A mixture of 3-(4-bromophenyl)propan-1-ol (2.0 g, 9.3 mmol), copper (I) cyanide (1.49 g, 16.7 mmol) and N-methylpyrrolidinone (13 ml) was stirred at 200°C for 2.5 hours.
After that the reaction mixture was cooled at room temperature, poured onto a solution of diethylamine (30 g) and water (80 ml) and extracted with ethyl acetate (3x40 ml).
The combined organic phases were dried and volatiles were removed, to obtain an oil from which N-methylpyrrolidinone was removed by distillation under high vacuum (0.5 torr, 85°C), thereby obtaining 0.78 g of the title compound (52percent yield).
1H N.M.R. (300 MHz, CDCL3) δ ppm: 1.85 (m, 2H); 2.42 (s broad, 1H); 2.76 (t, 2H); 3.64 (t, 2H); 7.29 (d, 2H); 7.53 (d, 2H).
Reference: [1] Patent: EP775133, 2001, B1,
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