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[ CAS No. 84102-69-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 84102-69-2
Chemical Structure| 84102-69-2
Chemical Structure| 84102-69-2
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Product Details of [ 84102-69-2 ]

CAS No. :84102-69-2 MDL No. :MFCD02667598
Formula : C11H9BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :XLJWAHXKBCDQNP-UHFFFAOYSA-N
M.W : 269.09 Pubchem ID :735184
Synonyms :

Calculated chemistry of [ 84102-69-2 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.18
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 60.0
TPSA : 39.44 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.98
Log Po/w (XLOGP3) : 3.74
Log Po/w (WLOGP) : 3.37
Log Po/w (MLOGP) : 2.36
Log Po/w (SILICOS-IT) : 3.24
Consensus Log Po/w : 3.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.11
Solubility : 0.0209 mg/ml ; 0.0000775 mol/l
Class : Moderately soluble
Log S (Ali) : -4.26
Solubility : 0.0148 mg/ml ; 0.0000549 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.62
Solubility : 0.00644 mg/ml ; 0.0000239 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.57

Safety of [ 84102-69-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 84102-69-2 ]

* 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 [ 84102-69-2 ]
  • Downstream synthetic route of [ 84102-69-2 ]

[ 84102-69-2 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 51336-47-1 ]
  • [ 84102-69-2 ]
YieldReaction ConditionsOperation in experiment
60% With 1,8-diazabicyclo[5.4.0]undec-7-ene In DMF (N,N-dimethyl-formamide) at 140℃; for 2 h; To a solution of 5-bromo-2-hydroxy-benzaldehyde (50.9 g, 253. 2 mmol) and ethyl bromoacetate (46.5 g, 278.5 mmol) in acetone (300 mL) is added K2CO3 (45.4 g, 329 mmol). The suspension is stirred for 16 h at RT, and the solid is filtered. The filtrate is concentrated to a residue and dissolved in DMF (100 mL), DBU (38.5 g, 253 mmol) is added and the solution is heated to 140 °C for 2 h. The reaction mixture is cooled down and poured into water (500 mL) and extracted with EtOAc (300 mL, 100 mL). The organic layer is dried over Na2S04, concentrated, purified on column chromatography (10percent EtOAc/Hex), to give the title compound as an oil (41.6 g, 60percent) H-NMR (ppm, CDC13) 8 : 7.81 (1 H, d, J=1. 8 Hz), 7.54 (1 H, dd, J=1.8, 8.8 Hz), 7.47 (1 H, d, J=9. 2 Hz), 7.44 (1 H, s), 4.47 (2 H, q, J=7. 0 Hz), 1. 44 (3 H, t, J=7. 0 Hz).
27%
Stage #1: With sodium ethanolate In ethanolHeating / reflux
Stage #2: With sulfuric acid In ethanol for 2 h; Heating / reflux
EXAMPLE 2 Preparation of ethyl 5-bromo-1-benzofuran-2-carboxylate; [0081] EMI299.0[0082] The compound was prepared according to a literature procedure.(Yoo et al., Bioorg. Med. Chem. 5:445, 1997). To ethyl (4-bromo-2-formylphenoxy)acetate (Example 1, 14.3 g, 49.7 mmol) was added, under Ar, 115 mL absolute EtOH. To this mixture was added 5.28 g (77.7 mmol) sodium ethoxide and the reaction allowed to reflux overnight. Sulfuric acid (conc., 2 mL) was then added, and the reaction allowed to reflux an additional 2 hours. The mixture was then cooled to rt, 50 mL water was added and the pH adjusted to neutrality with 1 N NaOH. The mixture was then extracted with 150 mL EtOAc, and the combined organic phase was washed with brine (2*150 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo. Purification by Biotage(R) separation using 5percent EtOAc/hexanes provided 3.62 g (27percent) of the desired compound. <1>H-NMR (CDCl3, [delta]): 1.43 (t, 3H), 4.45 (q, 2H), 7.46-7.57 (m, 3H), 7.82 (s, 1H); LRMS (GC/MS/ED) 268 [M]<+>.
Reference: [1] Synlett, 2001, # 5, p. 670 - 672
[2] Patent: WO2005/51938, 2005, A1, . Location in patent: Page/Page column 115
[3] Patent: US2003/195352, 2003, A1, . Location in patent: Page/Page column 31
[4] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 2, p. 445 - 459
[5] Patent: EP1849465, 2007, A1, . Location in patent: Page/Page column 86
  • 2
  • [ 105-36-2 ]
  • [ 1761-61-1 ]
  • [ 84102-69-2 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 5 h; Add to a 250 mL two-necked flask5-bromo-2-hydroxybenzaldehyde (15 g, 74.63 mmol)Ethyl bromoacetate (18.7g, 111.9mmol),Potassium carbonate (31 g, 223.9 mmol)And anhydrous DMF (80 mL),The reaction mixture was heated to 130 ° C for 5 hours to complete the reaction.Filtration, the filtrate is concentrated under reduced pressure,The residue was dissolved in ethyl acetate (100 mL)Washed with saturated brine (50 mL x 3)Dried over anhydrous sodium sulfate.Filtration, evaporation of the solvent under reduced pressure,The crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 20, V / V)A pale yellow solid of 16.6 g,Yield 83percent.
59.7% With caesium carbonate In N,N-dimethyl-formamide at 20 - 120℃; for 2.5 h; 5-bromosalicylaldehyde (0504-89) (5 g, 25 mmol, 1.0 eq.)And cesium carbonate (8.2 g, 25 mmol, 1.0 eq.)Mix in 80 ml DMF,Ethyl bromoacetate (8.3 g, 50 mmol, 2.0 eq.) was added dropwise.After the addition was completed, the reaction was performed at room temperature for half an hour.Warm up to 120°C for two hoursAfter the liquid detection reactionAll, cool to room temperature, pour it into ice water and stir for half an hour. Filter, filter cake washed with water,Drying gave a yellow powdered solid product, ethyl 5-bromobenzofuran-2-carboxylate (4 g, 59.7percent).
Reference: [1] Patent: CN106478564, 2017, A, . Location in patent: Paragraph 0216; 0217; 0218
[2] Patent: CN107383024, 2017, A, . Location in patent: Paragraph 0473
[3] Patent: US2004/209865, 2004, A1,
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5591 - 5593
  • 3
  • [ 624-61-3 ]
  • [ 84102-69-2 ]
YieldReaction ConditionsOperation in experiment
84% With sodium hexamethyldisilazane In tetrahydrofuran at -40℃; for 10 h; Compound 1 (1.0 mmol) and dibromoacetylene (1.2 mmol) were dissolved in THF at -40 °C.NaHMDS (2.0 mmol) was added, and the reaction was kept at -40 ° C for 10 hours (the compound 1 disappeared completely by TLC).After quenching the reaction with saturated ammonium chloride, the THF was evaporated under reduced pressure.After washing with saturated sodium chloride, the combined organic phases were dried over anhydrous sodium sulfateCompound 2 (226 mg, yield 84.0percent,The HPLC purity was 97.8percent and 1H NMR was consistent with known reports).
Reference: [1] Patent: CN108558802, 2018, A, . Location in patent: Paragraph 0011-0013
  • 4
  • [ 10242-11-2 ]
  • [ 84102-69-2 ]
YieldReaction ConditionsOperation in experiment
93% With sulfuric acid In ethanol 5C Ethyl 5-bromo-2-benzofurancarboxylate
A solution of 5-bromo-2-benzofurancarboxylic acid (5.01 g, 20.8 mmol) in absolute ethanol (150 ml) was added with concentrated sulfuric acid (15 ml) and the mixture was refluxed under stirring for 2 h.
After this time, the volatiles were evaporated off under reduced pressure and the resulting residue was neutralized with a sodium bicarbonate saturated solution and extracted with ethyl ether (4*100 ml).
The mixture was dried and the solvent was evaporated off under reduced pressure, to obtain 5.19 g of the title compound as a white solid with melting point 58-60° C. (93percent yield).
1 H N.M.R. (300 MHz, CDCl3) δ ppm: 1.34 (t, 3H); 4.35 (q, 2H); 7.39 (m, 3H); 7.71 (d, 1H).
Reference: [1] Patent: US5990142, 1999, A,
  • 5
  • [ 1761-61-1 ]
  • [ 84102-69-2 ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In butanone for 72 h; Heating / reflux A solution of 5-bromo-salicylaldehyde (5.0 g, 25 mmol) and bromo diethylmalonate (8.9 g, 37 mmol) in methyl ethyl ketone (50 ml) is treated with potassium carbonate (6.8 g, 50 mmol) and heated to reflux. The reaction is stirred over 3 days at reflux. The reaction is then concentrated to a crude solid that is purified by silica gel column chromatography (9:1 hexane / EtOAc) to afford 5.2 g (78 percent) of the desired product. 1H NMR (CDCl3) 7.81 (d, 1H), 7.26-7.55 (m, 3H), 4.44 (q, 2H), 1.42 (t, 3H)
Reference: [1] Patent: WO2004/26871, 2004, A1, . Location in patent: Page 47
  • 6
  • [ 685-87-0 ]
  • [ 78-93-3 ]
  • [ 1761-61-1 ]
  • [ 84102-69-2 ]
Reference: [1] Patent: US2001/56100, 2001, A1,
[2] Patent: US2002/169171, 2002, A1,
[3] Patent: US2002/165235, 2002, A1,
  • 7
  • [ 1761-61-1 ]
  • [ 84102-69-2 ]
Reference: [1] Synlett, 2001, # 5, p. 670 - 672
[2] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 2, p. 445 - 459
  • 8
  • [ 685-87-0 ]
  • [ 1761-61-1 ]
  • [ 84102-69-2 ]
Reference: [1] The Journal of pharmacy and pharmacology, 1999, vol. 51, # 4, p. 427 - 433
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