[ CAS No. 570391-20-7 ] {[proInfo.proName]}

Name: 570391-20-7|3-Bromo-5-iodophenol|97%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 570391-20-7 ]

CAS No. :	570391-20-7	MDL No. :	MFCD12405397
Formula :	C₆H₄BrIO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IQYQJLWQIUGDTI-UHFFFAOYSA-N
M.W :	298.90	Pubchem ID :	22630182
Synonyms :

Calculated chemistry of [ 570391-20-7 ]

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 Å²

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) :	-6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.94
Log Po/w (XLOGP3) :	2.91
Log Po/w (WLOGP) :	2.76
Log Po/w (MLOGP) :	3.15
Log Po/w (SILICOS-IT) :	3.03
Consensus Log Po/w :	2.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.02
Solubility :	0.0286 mg/ml ; 0.0000955 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.0
Solubility :	0.302 mg/ml ; 0.00101 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 :	2.21

Safety of [ 570391-20-7 ]

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 [ 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.

Upstream synthesis route of [ 570391-20-7 ]
Downstream synthetic route of [ 570391-20-7 ]

[ 570391-20-7 ] Synthesis Path-Upstream 1~5

1
[ 915412-18-9 ]
[ 570391-20-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	for 48 h; 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%	for 48 h; 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 48 h; 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.

Reference： [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

2
[ 591-18-4 ]
[ 570391-20-7 ]

Reference： [1] Journal of the American Chemical Society, 2003, vol. 125, # 26, p. 7792 - 7793
[2] Journal of the American Chemical Society, 2015, vol. 137, # 2, p. 592 - 595

3
[ 6311-60-0 ]
[ 570391-20-7 ]

Reference： [1] Patent: US2008/280891, 2008, A1,
[2] Patent: WO2008/8059, 2008, A1,

4
[ 827-94-1 ]
[ 570391-20-7 ]

Reference： [1] Patent: US2008/280891, 2008, A1,
[2] Patent: WO2008/8059, 2008, A1,

5
[ 74137-36-3 ]
[ 570391-20-7 ]

Reference： [1] Patent: US2008/280891, 2008, A1,
[2] Patent: WO2008/8059, 2008, A1,

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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.

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).

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In acetonitrile; at 80℃;	Step 1: 1-bromo-3-ethoxy-5-iodobenzene To a 250 ml flask was added CH3CN (158 ml), <strong>[570391-20-7]3-bromo-5-iodophenol</strong> (12.1 g, 40.5 mmol), potassium carbonate (28.0 g, 202 mmol), and iodoethane (3.60 ml, 44.5mmol). The mixture was heated to 80 00 overnight and then cooled to room temperature. The reaction was filtered and the solids washed with CH3CN. The filtrate was concentrated and the residue was stirred with hexanes, then filtered and the solid washed with hexanes. The hexanes was concentrated to to give the title compound as a yellow oil (13.2 g, 100 percent yield). MS (mlz) 328.9 (M+2).
100%	With potassium carbonate; In acetonitrile; at 80℃;	To a 250 ml flask was added CH3CN (158 ml), <strong>[570391-20-7]3-bromo-5-iodophenol</strong> (12.1 g, 40.5 mmol), potassium carbonate (28.0 g, 202 mmol), and iodoethane (3.60 ml, 44.5 mmol). The mixture was heated to 80° C. overnight and then cooled to room temperature. The reaction was filtered and the solids washed with CH3CN. The filtrate was concentrated and the residue was stirred with hexanes, then filtered and the solid washed with hexanes. The hexanes was concentrated to give the title compound as a yellow oil (13.2 g, 100percent yield). MS (m/z) 328.9 (M+2+).
100%	With potassium carbonate; In acetonitrile; at 80℃;	To a 250 ml flask was added acetonitrile (158 ml), <strong>[570391-20-7]3-bromo-5-iodophenol</strong> (12.1 g,40.5 mmol), potassium carbonate (28.0 g, 202 mmol), and iodoethane (3.60 ml, 44.5 mmol).The reaction was heated at 80 00 overnight and then cooled to room temperature. The reaction was filtered and the solids washed with acetonitrile. The filtrate was concentrated and the residue was stirred with hexanes, then filtered and the solid washed with hexanes. The hexanes were concentrated to give the title compound as a yellow oil (13.2 g, 100 percentyield). MS (mlz) 328.9 (M+2).

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 80℃;Inert atmosphere;	Step 1: methyl 2-(3-bromo-5-iodophenoxy)acetate To a round bottom flask equipped with a teflon stir bar was added 3-bromo-5- iodophenol (2.06 g, 6.89 mmol), methyl 2-bromoacetate (0.979 ml, 10.34 mmol), acetonitrile (15.0 ml), and K2003 (4.76 g, 34.5 mmol). A water cooled-condenser, attached to a N2 outlet was attached to the flask and the reaction heated to 80 00 Thereaction was cooled to room temperature and quenched with water (40 ml). The solution was extracted with EtOAc (2 x 40 ml). The combined organic layers were washed with brine, dried over Na2504, filtered, and concentrated to afford the titled compound (2.0 g, 78 percent yield crude). MS (mlz) 372.7 (M+H).
	With potassium carbonate; In acetonitrile; at 80℃;	To a round bottom flask equipped with a teflon stir bar was added <strong>[570391-20-7]3-bromo-5-iodophenol</strong> (2.06 g, 6.89 mmol), methyl 2-bromoacetate (0.979 ml, 10.34 mmol), acetonitrile (15.0 ml), and K2CO3 (4.76 g, 34.5 mmol). A water cooled-condenser, attached to a N2 outlet was attached to the flask and the reaction heated to 80° C. The reaction was cooled to room temperature and quenched with water (40 ml). The solution was extracted with EtOAc (2*40 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to afford the titled compound (2.0 g, 78percent yield crude). MS (m/z) 372.7 (M+H+).

[ CAS No. 570391-20-7 ] {[proInfo.proName]}

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