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[ CAS No. 36276-24-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 36276-24-1
Chemical Structure| 36276-24-1
Chemical Structure| 36276-24-1
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Product Details of [ 36276-24-1 ]

CAS No. :36276-24-1 MDL No. :MFCD04971197
Formula : C8H7BrO Boiling Point : -
Linear Structure Formula :- InChI Key :WTXXUAHMTVAQHW-UHFFFAOYSA-N
M.W : 199.05 Pubchem ID :816765
Synonyms :

Calculated chemistry of [ 36276-24-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.5
TPSA : 17.07 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) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 2.57
Log Po/w (MLOGP) : 2.52
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.204 mg/ml ; 0.00102 mol/l
Class : Soluble
Log S (Ali) : -2.44
Solubility : 0.72 mg/ml ; 0.00362 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.59
Solubility : 0.0512 mg/ml ; 0.000257 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.31

Safety of [ 36276-24-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 36276-24-1 ]

* 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 [ 36276-24-1 ]
  • Downstream synthetic route of [ 36276-24-1 ]

[ 36276-24-1 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 68120-35-4 ]
  • [ 36276-24-1 ]
YieldReaction ConditionsOperation in experiment
74% With manganese(IV) oxide In chloroform at 70℃; for 18 h; To a solution of the benzyl alcohol intermediate (4.5 g, 22.4 mmol) in chloroform (100 mL) was added manganese dioxide (15 g, 172 mmol). The reaction was refluxed with stirring in an oil bath at 70 °C for 18 h. Then it was filtered through celite and solvents were removed in vacuo to give a crude product that was purified by column chromatography (150 mL Si02, ethyl acetate.hexanes 1 :9) to give 35 (3.2974 g, 74percent) as a white crystalline solid: ? NMR (400 MHz, CDC13) ? 9.91 (s, 1H), 8.02 (d, J= 1.6, 1H), 7.70 (dd, J= 7.6, 1.6, 1H), 7.39 (d, J= 8.0, 1H), 2.47 (s, 3H); l3C NMR (100.6 MHz, CDC13) ? 190.4, 145.1, 135.8, 133.4, 131.3, 128.3, 125.6, 23.4; GC-MS (M)+ calcd for C8H7OBr 197.9680, found 197.9665.
Reference: [1] Patent: WO2013/40227, 2013, A2, . Location in patent: Page/Page column 37; 38
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8432 - 8454
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 3973 - 4001
[4] Patent: US2003/195259, 2003, A1,
  • 2
  • [ 104-87-0 ]
  • [ 36276-24-1 ]
YieldReaction ConditionsOperation in experiment
60.36%
Stage #1: With aluminum (III) chloride In dichloromethane at 0 - 40℃; for 0.5 h;
Stage #2: With bromine In dichloromethane at 0 - 20℃;
To a stirred solution of 4-methylbenzaldehyde (20.0 g, 166.5 mmol) in DCM (150 mL)at 0 00 AId3 (26.5 g, 198.7 mmol) was added portion wise. It was then heated at 4000 for 30 mm. , Br2 (31.9 g, 199.6 mmol) in DCM (50 mL) was then added to thereaction mixture drop wise at 0 00 and stirred at room temperature over night. The reaction mixture was diluted with ice water and extracted with DCM. The organic layer was washed with water and brine solution dried over anhydrous Na2SO4 and concentrated under vacuo. The crude product was purified by columnchromatography to yield the title compound (20 g, 60.36percent) as yellow oil.
Reference: [1] Dalton Transactions, 2004, # 2, p. 319 - 326
[2] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 77
[3] Journal of Organic Chemistry, 1958, vol. 23, p. 1412,1217
[4] Org. Synth. Coll. Vol., 1973, vol. V, p. 117,120
  • 3
  • [ 7726-95-6 ]
  • [ 104-87-0 ]
  • [ 36276-24-1 ]
YieldReaction ConditionsOperation in experiment
60.36%
Stage #1: With aluminum (III) chloride In dichloromethane at 0 - 40℃; for 0.5 h;
Stage #2: With (3-bromo-4-methyl-phenyl)-methanol In dichloromethane at 0 - 20℃;
To a stirred solution of 4-methylbenzaldehyde (20.0 g, 166.5 mmcl) in DCM (150 mL)at 000 AICI3 (26.5 g, 198.7 mmol) was added portion wise. It was heated at 40°C for30 mm, then Br2 (31.9 g, 199.6 mmol) in DCM (50 mL) was added drop wise at 000 and stirred at room temperature over night. The reaction mixture was diluted with ice water and extracted with DCM. The organic layer was washed with water and brine solution dried over anhydrous Na2SO4 and concentrated under vacuo. The crudeproduct was purified by column chromatography to yield the title compound (20 g,60.36percent) as yellow oil.
Reference: [1] Patent: WO2014/202528, 2014, A1, . Location in patent: Page/Page column 63
  • 4
  • [ 501420-55-9 ]
  • [ 36276-24-1 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 9, p. 3619 - 3628
[2] Tetrahedron Letters, 2015, vol. 56, # 5, p. 706 - 709
  • 5
  • [ 7697-26-9 ]
  • [ 36276-24-1 ]
Reference: [1] Patent: WO2013/40227, 2013, A2,
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8432 - 8454
[3] Patent: US2018/207126, 2018, A1, . Location in patent: Paragraph 0095
  • 6
  • [ 36276-24-1 ]
  • [ 68120-35-4 ]
YieldReaction ConditionsOperation in experiment
49.6% at 0 - 20℃; for 2 h; To a stirred solution of 3-bromo-4-methylbenzaldehyde (10.0 g, 50.2 mmol) in dry methanol (60 mL) at 0 00 NaBH4 (2.3 g, 36.0 mmol) was added portion wise and theresulting solution was stirred at room temperature for 2 h. The reaction mixture was quenched with ice water, extracted with ethyl acetate; the organic layer was washed with water and brine solution, dried over anhydrous Na2SO4 and concentrated. The product was purified by column chromatography to yield title compound (5.0 g, 49.60percent) as yellow oil.
49.6% at 0 - 20℃; for 2 h; To a stirred solution of 3-bromo-4-methylbenzaldehyde (10.0 g, 50.2 mmol) in drymethanol (60 mL) at 0°C, NaBH4 (2.3 g, 36.0 mmol) was added portion wise andstirred at room temperature for 2 h. The reaction mixture was quenched with ice water, extracted with ethyl acetate; the organic layer was washed with water and brine solution, dried over anhydrous Na2SO4 and concentrated. The product was purified by column chromatography to yield title compound (5.0 g, 49.60percent) as yellowoil.
Reference: [1] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 77; 78
[2] Patent: WO2014/202528, 2014, A1, . Location in patent: Page/Page column 63
  • 7
  • [ 36276-24-1 ]
  • [ 73183-34-3 ]
  • [ 847560-50-3 ]
YieldReaction ConditionsOperation in experiment
91.39%
Stage #1: With potassium acetate In 1,4-dioxane for 0.333333 h; Inert atmosphere
Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 90℃;
To a stirred solution of intermediate 4a (3.0 g, 15.1 mmol) in 1,4 dioxone (30 mL), bis(pinocolate)diboran (4.5 g, 17.7 mmol) and potassium acetate (2.98 g, 30.4 mmol) was added. The resultant was degasified with nitrogen for 20 mm. Then, Pd(dppf)C12 (0.62 g, 0.75 mmol) was added to it. It was heated at 90°C over night. The reaction mixture was diluted with water and extracted with ethyl acetate; the organic layer waswashed with water and brine solution and was then concentrated. The product was purified by combiflash to yield the title product (3.4 g, 91 .39percent) as a yellow semi solid.LCMS: (M+H) =247.2; 1H NMR: (ODd3, 300MHz) 69.99(s, 1H), 8.26 (5, 1H), 7.82- 7.85 (dd, 1H), 7.26-7.33 (m, 1H), 2.62 (5, 3H), 1.37 (5, 12H).
91.39%
Stage #1: With potassium acetate In 1,4-dioxane for 0.333333 h; Inert atmosphere
Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 90℃;
To a stirred solution of intermediate 4a (3.0 g, 15.1 mmol) in 1,4 dioxone (30 mL), bis(pinocolate)diboran (4.5 g, 17.7 mmol) and potassium acetate (2.98 g, 30.4 mmol)was added. The solution was then degasified with nitrogen for 20 mm. Then, Pd(dppf)C12 (0.62 g, 0.75 mmol) was added. It was heated at 90°C over night. The reaction mixture was diluted with water and extracted with ethyl acetate; the organic layer was washed with water, brine solution and concentrated. The product was purified by combif lash to yield the title product (3.4 g, 91 .39percent) as a yellow semi solid.LCMS: (M+H) =247.2; 1H NMR: (ODd3, 300MHz) 6 9.99 (5, 1 H), 8.26 (5, 1 H), 7.82-7.85 (dd, 1H), 7.26-7.33 (m, 1H), 2.62 (5, 3H), 1.37 (5, 12H).
85% With potassium acetate In DMF (N,N-dimethyl-formamide) at 85℃; for 2.5 h; Step 2 4-METHYL-3- (4, 4, 5, 5-TETRAMETHYL- [1, 3,2] dioxaborolan-2-yl)-benzaldehyde A mixture of 3-Bromo-4-methyl-benzaldehyde (3.105 g; 15.6 MMOL), bis (pinacolato) diboron (4.29 g; 16.86 MMOL) and Potassium acetate (4.59g ; 46.8 MMOL) in DIMETHYLFORMAMIDE (60 mL) was degassed by evacuation-nitrogen purge (3 cycles), followed by bubbling nitrogen gas through the stirred reaction mixture for 5 minutes. Palladium acetate (0.120 g; 0.536 MMOL) was added and reaction mixture was heated to 85 degrees C (oil-bath temperature) for 2.5 hours. Reaction mixture was allowed to cool to room temperature and DMF removed in vacuo. The residue was partitioned between ethyl acetate (150 mL) and water (150 mL) and the mixture was filtered through a pad of celite to remove black Pd solids. Filter cake was washed with ethyl acetate (2 x 50 mL) and combined filtrate phases were separated and the organic phase was washed with water (2 x 150 mL) then saturated sodium chloride solution (150 mL). Organic phase was dried over NA2SO4 and filtered, filtrate solvents removed in vacuo to afford a yellow oil which was purified by flash chromatography on silica gel (50g IST Flash ; eluting 0 to 10percent ethyl acetate in hexane) to afford product as a colourless solid Yield : 4.58 g; 85percent LC-MS retention time = 2.799 min; [M+H] + 247 1H NMR (400 MHz, CDCI3) 8 1.36 (s, 12H), 2.62 (s, 3H), 7.31 (d, 1H, J = 7.88 Hz), 7. 83 (dd, 1H, J = 7.88 and 1.9 Hz), 8.25 (d, 1H, J = 1.9 Hz), 9.98 (s, 1 H)
Reference: [1] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 79
[2] Patent: WO2014/202528, 2014, A1, . Location in patent: Page/Page column 65
[3] Patent: WO2005/21552, 2005, A1, . Location in patent: Page/Page column 62-63
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 3973 - 4001
  • 8
  • [ 36276-24-1 ]
  • [ 497224-12-1 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 8, p. 2789 - 2792
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