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Chemistry
Organic Building Blocks
Aryls
fluorobenzene
3-Bromo-4-formylbenzonitrile
Chemistry
Organic Building Blocks
Aryls
Bromides Fluorinated Building Blocks Nitriles Aldehydes Benzene Compounds
fluorobenzene
benzonitrile formylbenzonitrile 3-bromobenzonitrile p-tolyl benzoyl benzyl

[ CAS No. 89891-69-0 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 89891-69-0
Chemical Structure| 89891-69-0
Chemical Structure| 89891-69-0
Structure of 89891-69-0 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 89891-69-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 89891-69-0 ]

SDS Specification
Alternatived Products of [ 89891-69-0 ]

Product Details of [ 89891-69-0 ]

CAS No. :89891-69-0 MDL No. :MFCD09261031
Formula : C8H4BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :ADHKMYHLJHBOKB-UHFFFAOYSA-N
M.W : 210.03 Pubchem ID :20510518
Synonyms :

Calculated chemistry of [ 89891-69-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.24
TPSA : 40.86 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) : -5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.57
Log Po/w (XLOGP3) : 2.38
Log Po/w (WLOGP) : 2.13
Log Po/w (MLOGP) : 1.51
Log Po/w (SILICOS-IT) : 2.63
Consensus Log Po/w : 2.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.98
Solubility : 0.22 mg/ml ; 0.00105 mol/l
Class : Soluble
Log S (Ali) : -2.88
Solubility : 0.278 mg/ml ; 0.00132 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.29
Solubility : 0.107 mg/ml ; 0.000512 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 89891-69-0 ]

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

Application In Synthesis of [ 89891-69-0 ]

* 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 [ 89891-69-0 ]
  • Downstream synthetic route of [ 89891-69-0 ]

[ 89891-69-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 1381846-22-5 ]
  • [ 89891-69-0 ]
YieldReaction ConditionsOperation in experiment
59.3% With dimethyl sulfoxide In water at 120℃; for 6 h; A solution of the product of Part 3A (8.80 g, 24.9 mmol) was dissolved in wet DMSO (83 mL) at ambient temperature then warmed to 120 °C and maintained 6 h. After cooling to ambient temperature, the resulting solution was diluted with H2O with transfer to a separatory funnel then washed EtOAc. The EtOAc solution was separated, washed with H2O and saturated aqueous NaCl then dried over Na2SO4, filtered and concentrated in vacuo to a yellow solid. Subsequent purification by chromatography on silica using 20: 1 hexanes/EtOAc afforded the title compound as a white solid (3.10 g, 14.8 mmol; 59.3percent).
Reference： [1] Patent: WO2013/36869, 2013, A2, . Location in patent: Page/Page column 226
  • 2
  • [ 105-07-7 ]
  • [ 89891-69-0 ]
Reference： [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 888 - 896
[2] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6414 - 6420
  • 3
  • [ 42872-74-2 ]
  • [ 89891-69-0 ]
Reference： [1] Journal of Organic Chemistry, 1964, vol. 29, p. 2034 - 2036
[2] Patent: WO2013/36869, 2013, A2,
  • 4
  • [ 33499-34-2 ]
  • [ 89891-69-0 ]
Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6414 - 6420
  • 5
  • [ 89892-39-7 ]
  • [ 89891-69-0 ]
Reference： [1] Journal of Organic Chemistry, 1964, vol. 29, p. 2034 - 2036
  • 6
  • [ 89891-69-0 ]
  • [ 90110-98-8 ]
YieldReaction ConditionsOperation in experiment
99% With sodium tetrahydroborate In methanol at 0 - 25℃; A solution of 3-bromo-4-formylbenzonitrile (1.0 g, 4.8 mmol) in CH3OH (30 niL) was cooled to 00C. NaBH4 (180 mg, 4.8 mmol) was added portionwise. The mixture was allowed to warm to room temperature and stirred at room temperature for 1 h. The mixture was qunched with IN HCl and concentrated under vacuum. The residue was extracted with ethyl acetate (25 mL*3). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and concentrated under vacuum to give a white solid of the desired compound (1.Og, 99percent). NMR (300 MHz, CDCl3): δ 7.82 (s, IH), 7.49-7.71 (m, 2H), 4.75 (s, 2H). LC-MS: 212 (M + I)+.
99% at 0 - 20℃; A solution of 3-bromo-4-formylbenzonitrile A (1.0 g, 4.8 mmol) in CH3OH(30 niL) was cooled to 00C. NaBH4 (180 mg, 4.8 mmol) was added portionwise. The mixture was allowed to warm to room temperature and stirr at room temperature for 1 h. The mixture was qunched with IN HCl and concentrated under vacuum. The residue was extracted with ethyl acetate (25 mL*3). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and concentrated under vacuum to give a white solid of the desired compound B (1.Og, 990Zo)-1H NMR (300 MHz, CDCl3): δ 7.82 (s, IH), 7.49-7.71 (m, 2H), 4.75 (s, 2H). LC-MS: 212 (M + I)+.
60.7% at 0℃; for 0.666667 h; A solution of the product of Part 3B (3.10 g, 14.7 mmol) was dissolved MeOH (74 mL) at ambient temperature then cooled to 0 °C using an ice bath. NaBH4 (0.279 g, 7.38 mmol) was then added in one portion and the resulting solution maintained 40 min at 0 °C. Dilute aqueous HCl was added to consume excess NaBH4 then all volatiles removed in vacuo. The residue was redissolved in EtOAc with transfer to a separatory funnel, successively washed with 5percent aqueous citric acid and H2O, then dried over Na2SO4, filtered and concentrated in vacuo. Purification by chromatography on silica using a step gradient from 9: 1 hexanes/EtOAc to 1 : 1 hexanes/EtOAc afforded the title compound as a white solid (1.90 g, 8.96 mmol; 60.7percent).
Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7317 - 7322
[2] Patent: WO2011/22337, 2011, A1, . Location in patent: Page/Page column 102
[3] Patent: WO2010/45503, 2010, A1, . Location in patent: Page/Page column 134
[4] Patent: WO2013/36869, 2013, A2, . Location in patent: Page/Page column 226
  • 7
  • [ 89891-69-0 ]
  • [ 91760-66-6 ]
Reference： [1] Journal of Organic Chemistry, 1964, vol. 29, p. 2034 - 2036
  • 8
  • [ 89891-69-0 ]
  • [ 90484-53-0 ]
Reference： [1] Journal of Organic Chemistry, 1964, vol. 29, p. 2034 - 2036

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Organic Building Blocks
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benzonitrile
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formylbenzonitrile
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formylbenzonitrile
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p-tolyl
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benzoyl
Chemistry
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benzyl
Chemistry
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