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[ CAS No. 52010-97-6 ] {[proInfo.proName]}

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Chemical Structure| 52010-97-6
Chemical Structure| 52010-97-6
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Product Details of [ 52010-97-6 ]

CAS No. :52010-97-6 MDL No. :MFCD11870191
Formula : C8H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZFHUHPNDGVGXMS-UHFFFAOYSA-N
M.W : 136.15 Pubchem ID :556330
Synonyms :

Calculated chemistry of [ 52010-97-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.96
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : -0.08
Log Po/w (WLOGP) : 0.84
Log Po/w (MLOGP) : 0.85
Log Po/w (SILICOS-IT) : 1.83
Consensus Log Po/w : 0.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.95
Solubility : 15.4 mg/ml ; 0.113 mol/l
Class : Very soluble
Log S (Ali) : -0.25
Solubility : 76.3 mg/ml ; 0.56 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.14
Solubility : 0.977 mg/ml ; 0.00718 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 52010-97-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52010-97-6 ]

* 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 [ 52010-97-6 ]
  • Downstream synthetic route of [ 52010-97-6 ]

[ 52010-97-6 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
95% With hydrogen bromide In dichloromethane; acetic acid 1.3 4-(Bromomethyl)benza]dehyde, 3.3 Alcohol 2 (6.46 g, 47.5) was dissolved in DCM (100 ml) before HBr in acetic acid (33 wtpercent, 42 ml, 243, 5 eq) was added and stirred overnight. Water (100 ml) was added to the reaction mixture and the phases were separated and the organic phase obtained was washed with a NaOH solution (2 M, 2 χ 100 ml), dried over Na2S04, and evaporated. The residue was washed through a silica plug to yield 3 as a white solid (9.04 g, 45.4 mmol, 95percent). Rf = 0.77 (DCM); m.p. = 100°C (recrystallised from hexane); vmax = 1682, 1604, 1209, 1200, 830, 770, 726 cm'1; NMR (300 MHz, CDC ) δ = 10.02 (s, 1H, CHO), 7.87 (d, 3J(H,H) = 8.2 Hz, 2H, ArCH a to CHO), 7.56 (d, 3J(H,H) = 8.2 Hz, 2H, ArCH a to C3/4Br), 4.52 (s, 2Η, C1/2Br); 13C NMR (75 MHz, CDC13) δ = 191.5 (CHO), 144.2 (ArCCBr), 136.2 (ArCCHO), 130.2 (ArCH a to ArCCHO), 129.7 (ArCH a to ArCCH2Br), 31.9 (C3/4Br); HRMS (EST): m/z calculated for C83/4BrO [M - H]" : 196.9602, found 196.9602; elemental analysis calcd (percent) for C8H7BrO (199.04): C 48.27, H 3.54; found: C 47.40, H 3.53.
58% With N-Bromosuccinimide; triphenylphosphine In dichloromethane for 4.5 h; N-Bromosuccinimide (NBS, 19.6 g) was added to a solution of 2a or 2b (10.0 g) in dichloromethane(120 mL). Triphenylphosphine (2.0 equiv, 38.5 g, 0.146 mol) was divided into four equal aliquots andan aliquot was added to the reaction every 30 min. After the reaction was completed, the solution wasmixed with cold water (120 mL). The aqueous phase was extracted two times with dichloromethaneand the organic phase was washed with a saturated NaCl solution and dried over Na2SO4 for 8 h.The mixture was purified by silica gel chromatography with petroleum ether–ethyl acetate = 25:1 aseluent to give compound 3a 8.5 g (58.0percent yield) and 3b 6.8 g (46.8percent yield), respectively.
58% With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 3 h; Cooling with ice Take a 500mL eggplant-shaped bottle,Peeled 10.0 g of Intermediate II-1 (0.073 mol; 1.0 equiv)It was dissolved by adding 150 mL of methylene chloride, and 19.6 g of N-bromosuccinimide solid was added with stirring.Then under ice-cooling to the eggplant-shaped flask was added in four portions solid triphenylphosphine, a total of 38.5g (0.146mol; 2.0equiv), each batch half-hour intervals, until triphenyl phosphine addition was completed, the ice bath was removed ,The reaction was continued at room temperature for more than 3h, TLC TLC plate, UV analyzer (254nm) to monitor the progress of the reaction.After the raw material point II-1 disappears, the reaction is stopped and the reaction solution is poured into a beaker containing 150 ml of cold water,Then the aqueous phase was poured into the organic phase mixture separatory funnel extraction, the aqueous phase was extracted with 150ml of dichloromethane,The combined dichloromethane layers were washed with saturated aqueous sodium chloride solution. Then,The organic phase is dried over anhydrous sodium sulphate or anhydrous magnesium sulphate overnight. Filter out the desiccant,Weigh about 60-100 mesh size silica gel powder about 15g added to the filtrate, rotary evaporation to dry sand, silica gel column chromatography, the choice of elution system for petroleum ether: ethyl acetate = 99: 1, the resulting benzyl position Alcoholic hydroxyl brominated reaction products,A total of 8.5 g of a III-1 white solid was obtained in a yield of 58.0percent.
58% With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 3 h; Cooling with ice Take a 500mL eggplant-shaped bottle,10.0 g of Intermediate II-1 (0.073 mol; 1.0 equiv) was weighed by peeling.Add 150 mL of dichloromethane to dissolve it,19.6 g of N-bromosuccinimide solid was added with stirring.Then, triphenylphosphine was added to the eggplant flask in four batches under ice-cooling conditions.A total of 38.5g (0.146mol; 2.0equiv),Each batch is separated by half an hour.After triphenylphosphine is added,Remove the ice bath,Continue to react at room temperature for more than 3 hours,Thin layer TLC board,An ultraviolet analyzer (254 nm) monitors the progress of the reaction.After the material point of II-1 disappears,Stop the reaction, Pour the reaction solution into a beaker containing 150 ml of cold water.Then, the aqueous organic phase mixture is poured into a separatory funnel for extraction.The aqueous phase is extracted with 150 ml of dichloromethane.Combine the dichloromethane layer,Add saturated aqueous sodium chloride solution.Then,The organic phase was dried over anhydrous sodium sulfate or anhydrous magnesium sulfate overnight.Filter out the desiccant,Weigh about 15g of 60-100 mesh silica gel powder into the filtrate.Rotary to dry sand,Silica gel column chromatography separation,The elution system selected was petroleum ether:ethyl acetate = 99:1.The resulting benzylic hydroxyl alcohol bromo reaction product is collected,A total of 8.5 g of III-1 white solid was obtained.Yield: 58.0percent.

Reference: [1] Patent: WO2012/95628, 2012, A1, . Location in patent: Page/Page column 16
[2] Journal of the American Chemical Society, 1996, vol. 118, # 8, p. 1841 - 1855
[3] Chemical Communications, 2013, vol. 49, # 94, p. 11041 - 11043
[4] Journal of the American Chemical Society, 2005, vol. 127, # 3, p. 818 - 819
[5] Russian Chemical Bulletin, 2004, vol. 53, # 9, p. 2080 - 2085
[6] Molecules, 2016, vol. 21, # 7,
[7] Patent: CN107522647, 2017, A, . Location in patent: Paragraph 0050; 0051
[8] Patent: CN107522654, 2017, A, . Location in patent: Paragraph 0047; 0048
[9] Angewandte Chemie - International Edition, 2016, vol. 55, # 8, p. 2875 - 2878[10] Angew. Chem., 2016, vol. 128, p. 2925 - 2928,4
[11] Journal of the Chemical Society, 1956, p. 404,410
[12] Organic and Biomolecular Chemistry, 2010, vol. 8, # 5, p. 1181 - 1187
[13] ChemMedChem, 2010, vol. 5, # 8, p. 1272 - 1281
[14] Organic Letters, 2017, vol. 19, # 24, p. 6756 - 6759
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  • [ 623-27-8 ]
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  • [ 51359-78-5 ]
Reference: [1] Patent: US4733012, 1988, A,
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  • [ 52010-97-6 ]
  • [ 39895-56-2 ]
Reference: [1] Patent: WO2012/95628, 2012, A1,
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  • [ 123986-64-1 ]
Reference: [1] Patent: WO2012/95628, 2012, A1,
  • 5
  • [ 52010-97-6 ]
  • [ 156866-52-3 ]
Reference: [1] Patent: WO2012/95628, 2012, A1,
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