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[ CAS No. 207115-22-8 ] {[proInfo.proName]}

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Chemical Structure| 207115-22-8
Chemical Structure| 207115-22-8
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Product Details of [ 207115-22-8 ]

CAS No. :207115-22-8 MDL No. :MFCD09029644
Formula : C6H4BrIO Boiling Point : -
Linear Structure Formula :- InChI Key :UXIULWIJWDJDQD-UHFFFAOYSA-N
M.W : 298.90 Pubchem ID :10924532
Synonyms :

Calculated chemistry of [ 207115-22-8 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.88
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.22
Log Po/w (XLOGP3) : 2.7
Log Po/w (WLOGP) : 2.76
Log Po/w (MLOGP) : 3.15
Log Po/w (SILICOS-IT) : 3.03
Consensus Log Po/w : 2.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.89
Solubility : 0.0387 mg/ml ; 0.00013 mol/l
Class : Soluble
Log S (Ali) : -2.78
Solubility : 0.499 mg/ml ; 0.00167 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.61
Solubility : 0.0727 mg/ml ; 0.000243 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.04

Safety of [ 207115-22-8 ]

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

Application In Synthesis of [ 207115-22-8 ]

* 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 [ 207115-22-8 ]
  • Downstream synthetic route of [ 207115-22-8 ]

[ 207115-22-8 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 533-58-4 ]
  • [ 207115-22-8 ]
YieldReaction ConditionsOperation in experiment
68% With tetra-N-butylammonium tribromide In methanol; dichloromethane at 20℃; for 2 h; 4-Bromo-2-iodophenol (4). 2-Iodophenol (11 g, 50 mmol) was dissolved in DCM (200 mL) and MeOH (100 mL). Tetrabutylammonium tribromide (TBATB) (25.31 g, 52.5 mmol) was then added portionwise over 10 min. The solution was stirred at room temperature for 2 h and then quenched with 1 N HCl (200 mL). The DCM layer was extracted and the aqueous layer was extracted another two times with DCM. The organic layers were then combined, washed with brine, dried, and concentrated. Purification of the residue with flash chromatography (silica, 50percent-100percent DCM/Hexanes) yielded 4-bromo-2-iodophenol (10.2 g, 68percent).
Reference: [1] Tetrahedron, 2015, vol. 71, # 35, p. 5946 - 5951
[2] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8680 - 8688
[3] Organic Letters, 2015, vol. 17, # 22, p. 5666 - 5669
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1931, vol. 192, p. 1037
[5] Canadian Journal of Chemistry, 1965, vol. 43, p. 650 - 658
  • 2
  • [ 106-41-2 ]
  • [ 207115-22-8 ]
YieldReaction ConditionsOperation in experiment
90% With N-iodo-succinimide; sulfuric acid In acetic acid at 22℃; 4-Bromophenol (51.9 g, 0.30 mol) and N-iodosuccinimide (67.5 g, 0.30 mol) were combined in acetic acid (360 ML).The mixture was stirred briefly, treated with concentrated sulfuric acid (5 ML, 0.09 mol) and stirred at about 22° C. overnight.The mixture was poured into water (about 800 ML) with stirring to precipitate the product.The suspension was stirred for about 1 hour and filtered.The wet cake was washed with water (50 ML, 2*) and dried under reduced pressure at about 50° C. (80.9 g, 90percent). MS-DEI (M+H)+ m/z at 298; 1H NMR (CDCl3 at 400 MHz) δ5.28 (s, 1H), 6.86 (d, 1H), 7.33 (dd, 1H), 7.75 (d, 1H); 13C NMR (CDCl3 at 100 MHz) δ86.0, 112.8, 116.0, 132.7, 139.4, 153.7.
77% With ammonia; iodine; potassium iodide In water at 20℃; for 2 h; Step A: To a solution of 4-bromophenol (25 g, 144.5 mmol) in 25percent aqueous ammonia solution (350 mL) was added a solution of potassium iodide (72 g, 433.5 mmol) and iodine (36.7 g, 144.5 mmol) in water (288 mL). The reaction mixture was stirred at ambient temperature for 2 h and quenched with 250 mL of water. The reaction was acidified by addition of concentrated HCl (350 mL) and extracted with dichloromethane. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude product which was purified by column chromatography (SiO2, 9:1 hexanes/ethyl acetate) providing 4-bromo-2-iodophenol (33 g, 77percent) as a pink solid: 1H NMR (CDCl3, 300 MHz) δ 7.78-7.75 (m, 1H), 7.37-7.31 (m, 1H), 6.88 (d, J=8.7 Hz, 1H).
67% With potassium hydrogensulfate; potassium iodide; isoquinolinium chlorochromate In water at 20℃; Sonication General procedure: The general method for ultrasonically assisted brominationreaction is almost similar to conventional reaction as mentionedabove. A centimolar (0.01 mol) organic substrate (phenols,anilines, or acetanilides), 0.001 mol potassium halide(KBr), about 50 mg of dilute KHSO4, and hypervalent Cr(VI) reagent (IQCC or IQDC) were suspended in about30 mL solvent (DCE or ACN) in a previously cleaned roundbottom(R.B) flask placed in a sonicator. The reaction mixtureis sonicated at room temperature about 30–40 min. Progressof the reaction was monitored by TLC technique. Workupprocedure after completion of the reaction mixture is similarto the one described previously.
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 21, p. 10634 - 10642
[2] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 1, p. 3 - 6
[3] Patent: US2004/54185, 2004, A1, . Location in patent: Page 10
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 38 - 55
[5] Tetrahedron Letters, 2007, vol. 48, # 1, p. 81 - 83
[6] Synthetic Communications, 2010, vol. 40, # 23, p. 3506 - 3513
[7] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2011, vol. 41, # 3, p. 258 - 261
[8] Synthetic Communications, 2008, vol. 38, # 17, p. 2881 - 2888
[9] Patent: US2012/184531, 2012, A1, . Location in patent: Page/Page column 53
[10] Tetrahedron, 2008, vol. 64, # 37, p. 8992 - 8996
[11] Journal of Medicinal Chemistry, 2008, vol. 51, # 18, p. 5650 - 5662
[12] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2016, vol. 46, # 6, p. 832 - 837
[13] Journal of the American Chemical Society, 2014, vol. 136, # 12, p. 4740 - 4745
[14] Tetrahedron Letters, 2010, vol. 51, # 16, p. 2170 - 2173
[15] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1981, vol. 20, # 2, p. 133 - 135
[16] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2559 - 2563
[17] Tetrahedron Letters, 2007, vol. 48, # 35, p. 6124 - 6128
[18] Synthetic Communications, 2008, vol. 38, # 22, p. 3894 - 3902
[19] Patent: WO2005/100301, 2005, A1, . Location in patent: Page/Page column 61
[20] Patent: WO2010/92043, 2010, A1, . Location in patent: Page/Page column 140
  • 3
  • [ 40925-68-6 ]
  • [ 207115-22-8 ]
YieldReaction ConditionsOperation in experiment
1.1 g
Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5 h;
Stage #2: With potassium iodide In water at 0 - 20℃;
To a solution of 2-amino-4-bromophenol (2 g, 8.9 mmol, 1.0 equiv) in HC1 (5 M, 12.5 mE, 7.0 equiv) was added drop-wise a solution of sodium nitrite (0.62 g, 8.9 mmol, 1.0 equiv) in water (5 mE) at 00 C. The mixture was stirred at this temperature for 30 mm afier which a cooled solution of KI (1.5 g, 8.9 mmol, 1.0 equiv) inH2O (14 mE) was slowly added at 00 C. The mixture was then allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate (200 mE) and the separated aqueous phase was extracted with ethyl acetate (100 mEx3). The combined organic fraction was washed with Na2S2O3 (10percent, 40 mE), water (100 mEx2) and brine (40 mE), dried over Na2SO4 and concentrated to dryness.11219] The residue was purified by flash silica gel chromatography (ethyl acetate/hexanes) to afford 1.1 g 4-bromo-2- iodo-pheno as a yellow solid.
Reference: [1] Patent: US2015/368278, 2015, A1, . Location in patent: Paragraph 1218; 1219
  • 4
  • [ 106-41-2 ]
  • [ 207115-22-8 ]
  • [ 15459-51-5 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 21, p. 2655 - 2657
  • 5
  • [ 15459-51-5 ]
  • [ 106-41-2 ]
  • [ 207115-22-8 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 12, p. 3911 - 3917
  • 6
  • [ 108-95-2 ]
  • [ 207115-22-8 ]
Reference: [1] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2016, vol. 46, # 6, p. 832 - 837
  • 7
  • [ 207115-22-8 ]
  • [ 74-88-4 ]
  • [ 98273-59-7 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In acetone at 20℃; for 16 h; Iodomethane (103 μL, 1.65 mmol) was added to a solution of 4-bromo-2-iodophenol (450 mg, 1.51 mmol) and potassium carbonate (271 mg, 1.96 mmol) in acetone (10 mL).
The resulting mixture was stirred at room temperature for 16 hours.
After concentration in vacuo, the mixture was partitioned between water (20 mL) and EtOAc (20 mL), and the aqueous layer extracted with EtOAc (2*15 mL).
The organics layers were combined and washed with brine (20 mL), dried over MgSO4 (s), and concentrated in vacuo, to afford the title compound as an orange oil in 93percent yield, 439 mg.
1H NMR (400 MHz, CDCl3): δ ppm 3.86 (s, 3H), 6.68 (d, 1H), 7.41 (dd, 1H), 7.88 (d, 1H).
Reference: [1] Patent: US2014/171435, 2014, A1, . Location in patent: Paragraph 0616; 0617; 0618; 0619
  • 8
  • [ 106-41-2 ]
  • [ 207115-22-8 ]
  • [ 15459-51-5 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 21, p. 2655 - 2657
  • 9
  • [ 207115-22-8 ]
  • [ 15459-51-5 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1931, vol. 192, p. 1037
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