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[ CAS No. 181765-86-6 ] {[proInfo.proName]}

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Chemical Structure| 181765-86-6
Chemical Structure| 181765-86-6
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Product Details of [ 181765-86-6 ]

CAS No. :181765-86-6 MDL No. :MFCD00144771
Formula : C8H6BrIO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CJRHLSZJEFJDLA-UHFFFAOYSA-N
M.W : 340.94 Pubchem ID :11078356
Synonyms :

Calculated chemistry of [ 181765-86-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.14
TPSA : 26.3 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) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.57
Log Po/w (XLOGP3) : 3.43
Log Po/w (WLOGP) : 2.84
Log Po/w (MLOGP) : 3.52
Log Po/w (SILICOS-IT) : 3.34
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) : -4.35
Solubility : 0.0151 mg/ml ; 0.0000444 mol/l
Class : Moderately soluble
Log S (Ali) : -3.66
Solubility : 0.0741 mg/ml ; 0.000217 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.24
Solubility : 0.0195 mg/ml ; 0.0000573 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.05

Safety of [ 181765-86-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 181765-86-6 ]

* 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 [ 181765-86-6 ]
  • Downstream synthetic route of [ 181765-86-6 ]

[ 181765-86-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 610-97-9 ]
  • [ 181765-86-6 ]
YieldReaction ConditionsOperation in experiment
77% With N-Bromosuccinimide; sulfuric acid In acetic acid at 20 - 50℃; for 92 h; To a stirred solution of methyl 2-iodobenzoate (5.0 g, 19.08 mmol, 1 equiv) and NBS (3.73 g, 20.99 mmol, 1 .1 equiv) in acetic acid (10 mL) was added H2S04 (10 mL) drop wise at 20-40°C. The reaction mixture was stirred for 88 h at room temperature and then heated to 50°C & stirred for 4 h. The reaction mixture was cooled to 10°C and quenched with cold water (40 mL) and extracted with DCM (3 x 50 mL). The organic layer was washed with 5percent sodium bicarbonate (2 x 50 mL), 10percent Na2S03 solution (50 mL), and water (50 mL), and then dried over sodium sulphate, and evaporated to obtain methyl 5-bromo-2- iodobenzoate as crude product which was purified over silica gel flash column chromatography. The compound eluted out in 10 percent ethyl acetate in hexanes. The pure fractions were evaporated to obtain methyl 5-bromo-2-iodobenzoate as off white solid (5 g, 77percent). NMR (400 MHz, CDCI3) δ ppm 3.94 (s, 3 H).7.26 - 7.29 (m, 1 H), 7.83 (d, J=8.4 Hz, 1 H), 7.93 (d, J=8.8 Hz, 1 H).
Reference: [1] Patent: WO2018/15879, 2018, A1, . Location in patent: Page/Page column 81
[2] Patent: US2004/92521, 2004, A1, . Location in patent: Page/Page column 16-20; 46
[3] Patent: US2005/256118, 2005, A1, . Location in patent: Page/Page column 18-19
[4] Patent: US2005/256309, 2005, A1, . Location in patent: Page/Page column 20-21; 36
[5] Patent: US2005/272728, 2005, A1, . Location in patent: Page/Page column 19-20
[6] Patent: US2005/272736, 2005, A1, . Location in patent: Page/Page column 20; 35-36
[7] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9442 - 9446
  • 2
  • [ 67-56-1 ]
  • [ 21740-00-1 ]
  • [ 181765-86-6 ]
YieldReaction ConditionsOperation in experiment
90% for 24 h; Reflux; Large scale Add 5-bromo-2-iodobenzoic acid (1998 g, 6.11 mol) portion wise to a 20 °C solution of sulfuric acid (100 mL) in methanol (13 L). Heat the suspension to reflux for 24 hours, then cool to 20 °C and remove the solvent under reduced pressure. Pour the residue into a 1 : 1 mixture of methyl-ieri-butyl ether and ice water (20 L) and separate the phases. Extract the aqueous phase with methyl-tert-butyl ether (1.5 L), combine the organic phases and wash with aqueous 0.2 M NaOH (5 L), wash with saturated aqueous sodium chloride, dry over sodium sulfate, filter, and evaporate under reduced pressure. Dissolve the crude product in 40-45 °C petroleum ether (10 L), filter through a pad of diatomaceous earth and evaporate under reduced pressure. Dissolve the residue in petroleum ether (5 L) and cool to -50 °C, filter the first crop solids, wash the solid with ice cold petroleum ether. Evaporate the mother liquor, redissolve the solid in petroleum ether (1 L), cool to -50 °C, and filter a second crop. Combine first and second crops and dry in open air to provide the title compound as a yellow solid (1880 g, 90percent).
Reference: [1] Organic Letters, 2008, vol. 10, # 14, p. 3001 - 3004
[2] Tetrahedron, 2011, vol. 67, # 1, p. 125 - 143
[3] Patent: WO2014/143601, 2014, A1, . Location in patent: Page/Page column 10
[4] Journal of the Chemical Society, 1937, p. 1096,1101
  • 3
  • [ 52727-57-8 ]
  • [ 181765-86-6 ]
Reference: [1] Chemistry Letters, 2017, vol. 46, # 6, p. 858 - 861
  • 4
  • [ 88-67-5 ]
  • [ 74-88-4 ]
  • [ 181765-86-6 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 4, p. 550 - 556
  • 5
  • [ 5794-88-7 ]
  • [ 181765-86-6 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 1, p. 125 - 143
[2] RSC Advances, 2013, vol. 3, # 38, p. 17271 - 17280
[3] Chemistry--A European Journal, 2014, vol. 20, # 36, p. 11336 - 11339,4
  • 6
  • [ 21740-00-1 ]
  • [ 181765-86-6 ]
Reference: [1] Journal of the Chemical Society, 1956, vol. 78, p. 6130,6134
[2] RSC Advances, 2013, vol. 3, # 38, p. 17271 - 17280
  • 7
  • [ 21740-00-1 ]
  • [ 77-78-1 ]
  • [ 181765-86-6 ]
Reference: [1] Chemistry--A European Journal, 2014, vol. 20, # 36, p. 11336 - 11339,4
  • 8
  • [ 118-92-3 ]
  • [ 181765-86-6 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 1, p. 125 - 143
  • 9
  • [ 67-56-1 ]
  • [ 293738-03-1 ]
  • [ 181765-86-6 ]
Reference: [1] RSC Advances, 2013, vol. 3, # 38, p. 17271 - 17280
  • 10
  • [ 88-67-5 ]
  • [ 181765-86-6 ]
Reference: [1] Patent: WO2018/15879, 2018, A1,
  • 11
  • [ 181765-86-6 ]
  • [ 199786-58-8 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With diisobutylaluminium hydride In tetrahydrofuran; dichloromethane at 0 - 20℃; Inert atmosphere
Stage #2: With citric acid In tetrahydrofuran; dichloromethane; water at 0℃; Inert atmosphere
To a solution of compound 10 (5.2 g, 0.015 mol) in dry CH2Cl2 (30 mL) was added DIBAL (30.5 mL, 1 M in THF, 30.5 mmol) at 0 °C; The mixture was slowly warmed up to rt and stirred overnight. The mixture was then cooled to 0 °C and quenched with citric acid (aq. 15percent) slowly. The resulting mixture was extracted with CH2Cl2. The organic layer was washed with brine and dried with MgSO4. After removal of CH2Cl2 under vacuum, the resulting crude product was purified by silica column flash chromatography (hexanes/CH2Cl2, 1:1) to give compound 11 as a white solid (4.79 g, 0.0153 mol, 100percent).
100% With sodium tetrahydroborate; ethanol In tetrahydrofuran at 5 - 20℃; for 40 h; Inert atmosphere To a stirred solution of sodium borohydride (1 .1 g, 14.7 mmol, 2 equiv) in ethanol (20 mL) was added methyl 5-bromo-2-iodobenzoate in THF (10 mL) at 5°C. The reaction mixture was warmed to room temperature and stirred for 18 h under nitrogen atmosphere. Additional quantity of sodium borohydride (0.84 g, 22 mmol, 1 .5 equiv) was added and the mixture was stirred for 22 h. The reaction mixture was cooled to 0°C, treated with 10 mL of 15percent citric acid slowly. The reaction mixture was extracted with DCM (2 x 75 mL). The organic layer was washed with 15percent of aq. NaCI (100 mL), and then dried over sodium sulphate and evaporated to obtain (5-bromo-2-iodophenyl)methanol (4.5 g, 100percent) as white solid. NMR (400 MHz, CDCI3) δ ppm 1 .83 - 1 .88 (m, 1 H), 4.63 (s, 2H), 7.12 (dd, J=2.8, 8.4 Hz, 1 H), 7.62- 7.66 (m, 2H).
Reference: [1] Organic Letters, 2008, vol. 10, # 14, p. 3001 - 3004
[2] Tetrahedron, 2011, vol. 67, # 1, p. 125 - 143
[3] Patent: WO2018/15879, 2018, A1, . Location in patent: Page/Page column 81
[4] Patent: US2004/92521, 2004, A1, . Location in patent: Page/Page column 19-20; 46
[5] Patent: US2005/256118, 2005, A1, . Location in patent: Page/Page column 18-19
[6] Patent: US2005/256309, 2005, A1, . Location in patent: Page/Page column 20; 21; 36
[7] Patent: US2005/272728, 2005, A1, . Location in patent: Page/Page column 19-20
[8] Patent: US2005/272736, 2005, A1, . Location in patent: Page/Page column 20; 36
  • 12
  • [ 181765-86-6 ]
  • [ 689291-89-2 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 1, p. 125 - 143
[2] Patent: WO2018/15879, 2018, A1,
  • 13
  • [ 680-15-9 ]
  • [ 181765-86-6 ]
  • [ 842136-32-7 ]
YieldReaction ConditionsOperation in experiment
75% With copper(I) bromide In 1-methyl-pyrrolidin-2-one at 120℃; for 15 h; A. 5-Bromo-2-(trifluoromethyl)benzoate. To a solution of methyl 5- bromo-2-iodobenzoate (4.65 g, 13.64 mmol) and methyl 2,2-difluoro-2- (fluorosulfonyl)acetate (2.6 mL, 20.44 mmol) in N-methyl-2-pyrrolidinone (10 mL) was added copper(I) bromide (235 mg, 1.638 mmol). The reaction mixture was stirred at 120°C for 15 h in a sealed tube. The reaction was partitioned between ethyl acetate and aqueous sodium chloride. The aqueous layer was extracted with ethyl acetate (3 x 25 mL), and the organic layers were combined and dried over magnesium sulfate. After filtration, the solvent was removed in vacuo. The residue was purified by silica gel chromatography (1-5percent ethyl acetate in hexanes) to give the title compound as an oil (2.9 g, 10.25 mmol, 75percent yield); 1H NMR (400 MHz, DMSOd6) δ 8.08 (s, IH), 8.01 (d, J= 8.20 Hz, IH), 7.83 (d, J= 8.20 Hz, IH), 3.90 (s, 3H).
Reference: [1] Patent: WO2009/89042, 2009, A1, . Location in patent: Page/Page column 101
  • 14
  • [ 1717-59-5 ]
  • [ 181765-86-6 ]
  • [ 842136-32-7 ]
YieldReaction ConditionsOperation in experiment
75% With copper(ll) bromide In 1-methyl-pyrrolidin-2-one at 120℃; Sealed tube Methyl 5-bromo-2-iodobenzoate (1.950 g, 5.72 mmol) was dissolved in NMP (4.0 ml). Methyl there2,2-difluoro2- (fluorosulfonyl)acetate(1.09 ml, 8.58 mmol), copper bromide (I) (99 mg, 0.69 mmol) was stirred 120. ° C. overnight sealed Tube added. After the reaction was extracted with ethyl acetate adding water. Dried with magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (SNAP 100 g, hexane / ethyl acetate) to give the title compound (1.214 g, 75.0percent) as a tan oil.
Reference: [1] Patent: JP2016/124812, 2016, A, . Location in patent: Paragraph 0275
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