570391-20-7|3-Bromo-5-iodophenol| Ambeed

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Quality Control of [ 570391-20-7 ] Purity: 97% SDS Specification

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Product Details of [ 570391-20-7 ]

CAS No. :	570391-20-7
Formula :	C₆H₄BrIO
M.W :	298.90
SMILES Code :	OC1=CC(I)=CC(Br)=C1
MDL No. :	MFCD12405397
InChI Key :	IQYQJLWQIUGDTI-UHFFFAOYSA-N
Pubchem ID :	22630182

Safety of [ 570391-20-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 570391-20-7 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.94
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.91
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.76
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.15
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.03
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.76

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.02
Solubility	0.0286 mg/ml ; 0.0000955 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.0
Solubility	0.302 mg/ml ; 0.00101 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.61
Solubility	0.0727 mg/ml ; 0.000243 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.06 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.21

Application In Synthesis of [ 570391-20-7 ]

* 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.

Downstream synthetic route of [ 570391-20-7 ]

[ 570391-20-7 ] Synthesis Path-Downstream 1~35

1
5-bromo-3-amino-phenol [ No CAS ]
[ 570391-20-7 ]

References: [1]Journal of the Chemical Society,1926,p. 2078.

2
3-bromo-5-iodophenyl boronic acid pinacol ester [ No CAS ]
[ 570391-20-7 ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 7792 - 7793.

3
[ 591-18-4 ]
[ 570391-20-7 ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 7792 - 7793.
[2]Journal of the American Chemical Society,2015,vol. 137,p. 592 - 595.

Yield	Reaction Conditions	Operation in experiment
86%	With potassium hydrogen difluoride; dihydrogen peroxide; In water; N,N-dimethyl-formamide; at 20℃; for 16h;	General procedure: [00184] To C (79,3 mg, 0.189 mmol) in DMF (0.6 ml.) was added KHF2 (44.3 mg, 0.567 mmol, 3.0 equiv) and H202 (56 of 30percent w/w in H20, 0,49 mmol, 2.6 equiv), and the mixture was stirred at room temperature for 16 h and then partitioned between H20 and ethyl acetate (4 mL each). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (4 mL). The combined organic layer was washed with H20 (3 mL) and brine (2 mL), dried over MgS04, and concentrated. The residue was purified by flash column chromatography (0 -> 50percent ethyl acetate in hexanes) to afford the product as a colorless solid (35.3 mg, 87percent yield). : 1 NMR (500 MHz, CDCk) delta 7.62 (s, 1H), 7.46 - 7.42 (m, 1H), 7.25 (d, J= 0.9 Hz, IH), 6.55 (bs, IH), 2.59 (s, 3H). 13C MR (126 MHz, CDCI3) delta 197.94 (s), 157.18 (s), 139.47 (s), 124.30 (s), 123.89 (s), 123.30 (s), 113.94 (s), 26.96 (s). HRMS (ESI-) calcd for [C8H6Br02-] ( -H+): 212.9557, found: 212.9557.

5
[ 570391-20-7 ]
[ 824-94-2 ]
[ 915412-19-0 ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 44h;	<strong>[570391-20-7]3-Bromo-5-iodo-phenol</strong> (8.48 g, 28.37 mmol) was dissolved in DMF (50 mL) under dry argon and cooled to 0° C. Then potassium carbonate (3.92 g, 28.37 mmol) was added, followed by drop wise addition of 4-methoxybenzyl chloride (3.7 mL, 27.0 mmol). The mixture was slowly warmed to room temperature and stirred for 20 h. Additional 4-methoxybenzyl chloride (0.19 mL, 1.4 mmol) was added and the mixture was stirred for additional 24 h at room temperature. The reaction mixture was diluted with tert-butylmethyl ether (300 mL) and water (150 mL). The layers were separated and the aqueous one extracted with tert-butylmethyl ether (2.x.150 mL). The combined organics were washed with water and brine (150 mL), dried (Na2SO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (330 g, AcOEt/heptane 1:9). 1-Bromo-3-iodo-5-(4-methoxy-benzyloxy)-benzene (8.80 g, 59percent, purity 80percent, HPLC 220 nm) was obtained as a yellow oil.
59%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 44h;	1-Bromo-3-iodo-5-(4-methoxy-benzyloxy)-benzene<strong>[570391-20-7]3-Bromo-5-iodo-phenol</strong> (8.48 g, 28.37 mmol) was dissolved in DMF (50 mL) under dry argon and cooled to 0° C. Then potassium carbonate (3.92 g, 28.37 mmol) was added, followed by drop wise addition of 4-methoxybenzyl chloride (3.7 mL, 27.0 mmol). The mixture was slowly warmed to room temperature and stirred for 20 h. Additional 4-methoxybenzyl chloride (0.19 mL, 1.4 mmol) was added and the mixture was stirred for additional 24 h at room temperature. The reaction mixture was diluted with tert-butylmethyl ether (300 mL) and water (150 mL). The layers were separated and the aqueous one extracted with tert-butylmethyl ether (2.x.150 mL). The combined organics were washed with water and brine (150 mL), dried (Na2SO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (330 g, AcOEt/heptane 1:9). 1-Bromo-3-iodo-5-(4-methoxy-benzyloxy)-benzene (8.80 g, 59percent, purity 80percent, HPLC 220 nm) was obtained as a yellow oil.
59%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 44h;	[0357] 3-Bromo-5-iodo-rhohenol (8.48 g, 28.37 mmol) was dissolved in DMF(50 niL) under dry argon and cooled to 0°C. Then potassium carbonate (3.92 g, 28.37 mmol) was added, followed by drop wise addition of 4- methoxybenzyl chloride (3.7 mL, 27.0 mmol). The mixture was slowly warmed to room temperature and stirred for 20 h. Additional 4-methoxybenzyl chloride (0.19 mL, 1.4 mmol) was added and the mixture was stirred for additional 24 h at room temperature. The reaction mixture was diluted with fert-butylmethyl ether (300 mL) and water (150 mL). The layers were separated and the aqueous one extracted with tert-butylmethyl ether (2 x 150 mL). The combined organics were washed with water and brine (150 mL), dried (Na2SO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (330 g, AcOEt/heptane 1:9). 1-Bromo- 3-iodo-5-(4-methoxy-benzyloxy)-benzene (8.80 g, 59 percent, purity 80percent, HPLC 220 nm) was obtained as a yellow oil.

References: [1]Patent: US2006/270686,2006,A1 .Location in patent: Page/Page column 41.
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 179 - 200.
[3]Patent: US2008/280891,2008,A1 .Location in patent: Page/Page column 41.
[4]Patent: WO2008/8059,2008,A1 .Location in patent: Page/Page column 118.

6
[ 915412-18-9 ]
[ 570391-20-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogen bromide; acetic acid;tetrabutylammomium bromide; for 48h;Heating / reflux;	1-Bromo-3-iodo-5-methoxy-benzene (6.29 g, 20.1 mmol) was suspended in a solution of hydrogen bromide in acetic acid (33percent, 150 mL). Tetrabutylammonium bromide (0.5 g, 1.55 mmol) was added and the mixture was heated to reflux under vigorous stirring for 2 d. After cooling to room temperature the mixture was extracted with methylene chloride (3.x.100 mL). The combined organic layers were washed with water (50 mL), dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (300 g, AcOEt/heptane 1:9). 3-Bromo-5-iodo-phenol (21.2 g, 96percent) was obtained as pale brown solid.
96%	With tetrabutylammomium bromide; hydrogen bromide; acetic acid; for 48h;Heating / reflux;	3-Bromo-5-iodo-phenol1-Bromo-3-iodo-5-methoxy-benzene (6.29 g, 20.1 mmol) was suspended in a solution of hydrogen bromide in acetic acid (33percent, 150 mL). Tetrabutylammonium bromide (0.5 g, 1.55 mmol) was added and the mixture was heated to reflux under vigorous stirring for 2 d. After cooling to room temperature the mixture was extracted with methylene chloride (3.x.100 mL). The combined organic layers were washed with water (50 mL), dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (300 g, AcOEt/heptane 1:9). 3-Bromo-5-iodo-phenol (21.2 g, 96percent) was obtained as pale brown solid.
96%	With tetrabutylammomium bromide; hydrogen bromide; In acetic acid; for 48h;Heating / reflux;	[0355] l-Bromo-3-iodo-5-methoxy-benzene (6.29 g, 20.1 mmol) was suspended in a solution of hydrogen bromide in acetic acid (33 percent, 150 mL). Tetrabutylammonium bromide (0.5 g, 1.55 mmol) was added and the mixture was heated to reflux under vigorous stirring for 2 d. After cooling to room temperature the mixture was extracted with methylene chloride (3 x 100 mL). The combined organic layers were washed with water (50 mL), dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (300 g, AcOEt/heptane 1:9). 3-Bromo-5-iodo- phenol (21.2 g, 96 percent) was obtained as pale brown solid.

References: [1]Patent: US2006/270686,2006,A1 .Location in patent: Page/Page column 41.
[2]Patent: US2008/280891,2008,A1 .Location in patent: Page/Page column 41.
[3]Patent: WO2008/8059,2008,A1 .Location in patent: Page/Page column 117.

7
[ 570391-20-7 ]
[ 100-39-0 ]
[ 1215077-60-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 70℃; for 1h;Inert atmosphere;	Step 1: A mixture of <strong>[570391-20-7]3-bromo-5-iodophenol</strong> (1.40 g, 4.68 mmol), benzyl bromide (0.89 g, 5.20 mmol) and anhydrous K2CO3 (1.44 g, 10.4 mmol) in anhydrous NMP (8 mL) was stirred under argon at + 70 0C for 1 hour. The reaction mixture was partitioned between aqueous NH4Cl and hexanes. Aqueous layer was additionally extracted with hexanes and combined organic layers were washed with IN NaOH, brine, dried over anhydrous MgSO4 and concentrated under reduced pressure to give l-(benzyloxy)-3-bromo-5-iodobenzene as a colorless oil. Yield (2.14 g, 99percent); 1H NMR (400 MHz, <n="235"/>CDCl3) delta 7.45 (t, J = 1.4 Hz, IH), 7.32-7.40 (m, 5H), 7.26 (dd, J = 1.4, 2.2 Hz, IH), 7.09 (t, J= 2.0 Hz, IH), 5.00 (s, 2H).
99%	With potassium carbonate; In acetonitrile; for 18h;	Benzyl bromide (4.78 ml, 40.1 mmol) was added to a slurry of <strong>[570391-20-7]3-bromo-5-iodophenol</strong> (10.00g, 33.5 mmol) and potassium carbonate (13.87 g, 100 mmol) in acetonitrile (33.5ml). The resulting mixture was stirred for 18 h. Water and excess EtOAc was added. The organics were washed with water (2x) and brine (lx). The combined washes were back- extracted using EtOAc (2x). The combined organics were dried over Mg504, filtered, and concentrated to afford 1-(benzyloxy)-3-bromo-5-iodobenzene (14.06 g, 33.3 mmol, 99 percentyield) as an orange oil. MS (mlz) 388.9 (M+H).
50%		Step 1: 1 -(benzyloxy)-3-bromo-5-iodobenzene To a solution of <strong>[570391-20-7]3-bromo-5-iodophenol</strong> (1.5 g, 5 mmol) in DMF (10 ml) was added K2003 (0.83 g, 6 mmol). The reaction mixture was then heated at 50 C for 30 minutes before the addition of KI (0.08 g, 0.5 mmol) and (bromomethyl)benzene (0.93 g, 5.4 mmol). The reaction continued to stir for 18 hours at 65 00. The mixture was poured intowater and extracted with EtOAc (3 x 100 ml). The combined organic layers were washedwith water (3 x 50 ml), brine, dried over Na2504, filtered and concentrated in vacuo. Theresultant residue was purified via flash column chromatography (0-10 percent EtOAc:Hexane)to afford the title compound as a yellow oil (1.3 g, 50percent yield). MS (mlz) 391.3 (M+H).

50%

To a solution of <strong>[570391-20-7]3-bromo-5-iodophenol</strong> (1.5 g, 5 mmol) in DMF (10 ml) was added K2CO3 (0.83 g, 6 mmol). The reaction mixture was then heated at 50° C. for 30 minutes before the addition of KI (0.08 g, 0.5 mmol) and (bromomethyl)benzene (0.93 g, 5.4 mmol). The reaction continued to stir for 18 hours at 65° C. The mixture was poured into water and extracted with EtOAc (3*100 ml). The combined organic layers were washed with water (3*50 ml), brine, dried over Na2SO4, filtered and concentrated in vacuo. The resultant residue was purified via flash column chromatography (0-10percent EtOAc:Hexane) to afford the title compound as a yellow oil (1.3 g, 50percent yield). MS (m/z) 391.3 (M+H+).

References: [1]Patent: WO2010/48332,2010,A2 .Location in patent: Page/Page column 232-233.
[2]Patent: WO2017/6295,2017,A1 .Location in patent: Page/Page column 127.
[3]Patent: WO2015/104684,2015,A1 .Location in patent: Page/Page column 155.
[4]Patent: US2016/340328,2016,A1 .Location in patent: Paragraph 0631; 0632.

8
[ 570391-20-7 ]
3-(1H-indol-4-yl)-5-(pyridin-3-yl)phenol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 179 - 200.

9
[ 570391-20-7 ]
[ 915412-97-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 179 - 200.
[2]Patent: US2008/280891,2008,A1 .

10
[ 570391-20-7 ]
[ 1260030-02-1 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 179 - 200.

11
[ 570391-20-7 ]
C₂₈H₂₄N₂O₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 179 - 200.

12
[ 570391-20-7 ]
C₂₇H₂₂N₂O₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 179 - 200.

13
[ 570391-20-7 ]
[ 915412-20-3 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 179 - 200.
[2]Patent: US2008/280891,2008,A1 .

14
[ 570391-20-7 ]
[ 1260029-93-3 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 179 - 200.

15
[ 570391-20-7 ]
C₁₉H₂₇BrO₃Si [ No CAS ]