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[ CAS No. 42287-90-1 ] {[proInfo.proName]}

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Chemical Structure| 42287-90-1
Chemical Structure| 42287-90-1
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Product Details of [ 42287-90-1 ]

CAS No. :42287-90-1 MDL No. :MFCD01310792
Formula : C9H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DWKWMFSWLCIMKI-UHFFFAOYSA-N
M.W :229.07 Pubchem ID :2063862
Synonyms :

Calculated chemistry of [ 42287-90-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.49
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.91
Log Po/w (XLOGP3) : 2.37
Log Po/w (WLOGP) : 2.47
Log Po/w (MLOGP) : 2.7
Log Po/w (SILICOS-IT) : 2.56
Consensus Log Po/w : 2.4

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.93
Solubility : 0.272 mg/ml ; 0.00119 mol/l
Class : Soluble
Log S (Ali) : -2.79
Solubility : 0.368 mg/ml ; 0.00161 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.44
Solubility : 0.0832 mg/ml ; 0.000363 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 42287-90-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 42287-90-1 ]

* 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 [ 42287-90-1 ]
  • Downstream synthetic route of [ 42287-90-1 ]

[ 42287-90-1 ] Synthesis Path-Upstream   1~15

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Reference: [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1769 - 1774
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  • [ 65537-54-4 ]
YieldReaction ConditionsOperation in experiment
100% With borane-THF In tetrahydrofuran at 14℃; for 18 - 22 h; Heating / reflux To a solution of 3-(3-bromophenyl)propionic acid (10.0 g, 43.7 mmol) in anhydrous THF (150 mL) was added 1.0 M BH3.THF (150 mL, 150 mmol) via addition funnel. After BH3.THF was added, the reaction was refluxed for 18 hrs. The reaction was quenched with water (100 mL) and 1N HCl (300 mL). The solution was saturated with sodium chloride and extracted with ethyl acetate. The organic extract was washed with brine and dried over magnesium sulfate. The organic material was purified by chromatography on silica gel eluting with ethyl acetate in hexane to produce 9.39 g (100percent) of the desired alcohol as a colorless oil. NMR (CDCl3) δ 1.82-1.89 (m, 2H), 2.67 (t, 2H), 3.64 (t, 2H), 7.11 7.15 (m, 1H), 7.29-7.31 (m, 1H), 7.34 (s, 1H).Part A. Preparation of: To a solution of 3-(3-bromophenyl)propionic acid (15.0 g, 65.5 mmol) in anhydrous THF (200 mL) at 5° C. was added, via addition funnel, 1.0 M BH3-THF (200 mL, 200 mmol). The reaction temperature was kept below 14° C. during the addition of the BH3THF. After all the BH3THF was added, the reaction was refluxed for 22 hr and then quenched with water (100 mL) and 1N HCl (300 mL). The solution was saturated with sodium chloride and extracted with ethyl acetate (3.x.300 mL). The organic extract was washed with brine, dried over magnesium sulfate, and concentrated providing 14.4 g (100percent) of crude alcohol as a colorless oil. NMR(CDCl3) δ 1.82-1.89 (m, 2H), 2.67 (t, 2H), 3.64 (t, 2H), 7.11-7.15 (m, 1H), 7.29-7.31 (m, 1H), 7.34 (s, 1H).
98%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3 h;
Stage #2: With sodium hydroxide; water In tetrahydrofuran
Example 36. 3-(3-Bromo-plienvr)-propan-l-oI (23); [0173] 3-(3-Bromo-phenyl)-propionic acid (3.88 g, 16.9 mmol, 1 equiv) was diluted with THF (50 mL) and chilled to O0C. IM LAH solution added slowly so as to not allow internal reaction temperature to climb above 10-15°C. Once LAH addition was complete, reaction allowed to come to room temperature and stir for 3h. Reaction then quenched with sequential addition of water (0.5 mL), 15percent NaOH (0.5 mL) and water again(1.5 mL). This was then filtered and solvents evaporated to provide the product as a pale oil (2.75g, 98percent). Ri = 0.42 (30percent EtOAc/hexanes).
28% With borane-THF In tetrahydrofuran at 0 - 20℃; Inert atmosphere Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-(3-bromophenyl)propanoic acid (5 g, 21.83 mmol, 1.00 equiv) in THF (50 mL). This was followed by the addition of borane tetrahydrofuran complex solution (1 moL/L, 75 mL, 74.22 mmoL, 3.40 equiv) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The reaction mixture was poured into 150 mL of HCl (1 moL/L), extracted with 3×200 mL of DCM, washed with 300 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with DCM/MeOH (10:1). The collected fraction was concentrated to afford 3-(3-bromophenyl)propan-1-ol (1.3 g, 28percent) as colorless oil. 1H-NMR (DMSO, 400 MHz) δ(ppm): 7.41-7.20 (m, 4H), 4.51-4.48 (t, 1H), 3.41-3.34 (m, 2H), 2.67-2.59 (m, 2H), 1.73-1.66 (m, 2H).
9.8 g With borane-THF In tetrahydrofuran at 0℃; for 17 h; Inert atmosphere; Reflux To a cooied (ice bath) soiution of 3-(3-bromophenyi)propanoic acid (8.0 g,35 mmoi) in anhydrous THF (100 mL) was added BH3-THF (100 mL, 1.0 M) via addition funnei under a nitrogen atmosphere. The reaction was stirred at 0 °C for 1 h then at refiux for 16 h. The reaction was carefuiiy quenched with HCi (37 mL, 2 M) then concentrated to remove THF. The suspension was diiuted withDCM (300 mL) then fiitered to remove the soiids. The iayers were separatedand the organic phase was washed with water (50 mL) and brine (50 mL) then dried over anhydrous Na2SO4, filtered, and concentrated to give 3-(3-bromophenyl)propan-1-ol (9.8 g, >100percent) as a yellow oil, which was used for next step without further purification.

Reference: [1] Patent: US2004/10019, 2004, A1, . Location in patent: Page 160; 167
[2] Patent: WO2006/101977, 2006, A2, . Location in patent: Page/Page column 56
[3] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5178 - 5194
[4] Angewandte Chemie - International Edition, 2018, vol. 57, # 15, p. 4058 - 4062[5] Angew. Chem., 2018, vol. 130, p. 4122 - 4126,5
[6] Patent: US2016/264518, 2016, A1, . Location in patent: Paragraph 0969; 0970
[7] Patent: US2007/27141, 2007, A1, . Location in patent: Page/Page column 9
[8] Patent: WO2016/147144, 2016, A1, . Location in patent: Page/Page column 113; 114
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Reference: [1] Tetrahedron, 2007, vol. 63, # 2, p. 389 - 395
[2] Tetrahedron, 2007, vol. 63, # 2, p. 389 - 395
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Reference: [1] Bulletin de la Societe Chimique de France, 1983, vol. 2, # 3-4, p. 96 - 104
[2] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1769 - 1774
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Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2612 - 2621
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  • [ 125115-01-7 ]
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Reference: [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1769 - 1774
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Reference: [1] Tetrahedron, 2007, vol. 63, # 2, p. 389 - 395
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Reference: [1] Chemische Berichte, 1882, vol. 15, p. 2215
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2612 - 2621
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Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2612 - 2621
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Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2612 - 2621
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Reference: [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1769 - 1774
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Reference: [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1769 - 1774
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Reference: [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1769 - 1774
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  • [ 34598-49-7 ]
  • [ 125114-77-4 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 2, p. 389 - 395
[2] Tetrahedron, 2007, vol. 63, # 2, p. 389 - 395
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YieldReaction ConditionsOperation in experiment
100% for 3 h; Reflux Example 37A: methyl 3-(3-bromophenyl)propanoate j00412j 3-(3-bromophenyl)propanoic acid (1 g, 4.37 mmol) was dissolved in MeOH(17.46 mL). SOC12 (1.593 mL, 21.83 mmol) was added dropwise, and the reactionheated to reflux for 3 h. The reaction was concentrated in vacuo to yield Example 37A (1.08 g, 100percent). 1H NMR (400 MHz, CHLOROFORM-d) ö ppm 7.30 - 7.42 (2 H, m), 7.06 - 7.21 (2 H, m), 3.67 (3 H, s), 2.92 (2 H, t, J=7.78 Hz), 2.62 (2 H, t, J=7.65 Hz).
99% for 16 h; Reflux General procedure: In distinct reactors, solutions of the appropriate 3-(3-bromophenyl)-propionic acid or 3-(4-Bromophenyl)-propionic acid in MeOH were prepared and concentrated H2SO4 was added to each reactor. The resulting mixtures were stirred under reflux for 16h. Each crude mixture was reduced under vacuo and the residues were partitioned with dichloromethane (20 mL) and saturated NaHCO3 solution (20 mL). The organic layers of each reaction was dried with Na2SO4, filtered and evaporated. The resulting compounds were used in a further reaction without any further purification.
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 5, p. 2225 - 2235
[2] Patent: WO2014/201073, 2014, A1, . Location in patent: Paragraph 00412
[3] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 206 - 213
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