[ CAS No. 202865-85-8 ] {[proInfo.proName]}

Name: 202865-85-8|1-Bromo-4-iodo-2-methylbenzene|98%
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Quality Control of [ 202865-85-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 202865-85-8 ]

CAS No. :	202865-85-8	MDL No. :	MFCD00070749
Formula :	C₇H₆BrI	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QSQOGKONVJDRNH-UHFFFAOYSA-N
M.W :	296.93	Pubchem ID :	2735574
Synonyms :

Calculated chemistry of [ 202865-85-8 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.83
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.53
Log Po/w (XLOGP3) :	3.63
Log Po/w (WLOGP) :	3.36
Log Po/w (MLOGP) :	4.25
Log Po/w (SILICOS-IT) :	3.95
Consensus Log Po/w :	3.54

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.46
Solubility :	0.0103 mg/ml ; 0.0000346 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.32
Solubility :	0.143 mg/ml ; 0.000481 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.58
Solubility :	0.00786 mg/ml ; 0.0000265 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.86

Safety of [ 202865-85-8 ]

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

Application In Synthesis of [ 202865-85-8 ]

* 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.

Downstream synthetic route of [ 202865-85-8 ]

[ 202865-85-8 ] Synthesis Path-Downstream 1~88

1
[ 6933-10-4 ]
[ 202865-85-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6764 - 6777
[2]Journal of the American Chemical Society,2000,vol. 122,p. 6871 - 6883
[3]Journal of Materials Chemistry,2004,vol. 14,p. 1731 - 1743

2
[ 202865-85-8 ]
[ 289617-98-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6764 - 6777
[2]Journal of the American Chemical Society,2000,vol. 122,p. 6871 - 6883

3
[ 627-19-0 ]
[ 202865-85-8 ]
1-bromo-2-methyl-4-pent-1-ynyl-benzene [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2004,vol. 14,p. 1731 - 1743

4
[ 616-45-5 ]
[ 202865-85-8 ]
1-(4-bromo-3-methylphenyl)pyrrolidin-2-one [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 2305 - 2308
[2]Organic Process Research and Development,1999,vol. 3,p. 248 - 252

5
[ 53937-02-3 ]
[ 202865-85-8 ]
[ 959960-95-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; N,N-dimethyl-formamide; at 180℃; for 0.25h;Microwave irradiation;	A mixture of 4-benzyloxy-2(lH)-pyridone (50 mg, 0.0025 mol), <strong>[202865-85-8]2-bromo-5-iodotoluene</strong> (1.13 g, 0.0038 mol), CuI (0.238 g, 0.0015 mol), N,N-dimethylethylenediamine (0.266 ml, 0.0025 mol), and K3PO4 (1.06 g, 0.005 mol) in dioxane/DMF 9:1 (75 ml) was stirred at 180 0C in a microwave for 15 minutes Then, DCM was added. The solid was filtered off through dicalite and the filtrate was washed with NH4OH 32 %. The organic layer was separated, dried over Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography (eluent: DCM). The desired product was collected and evaporated. The resulting product was precipitated with DIPE yielding 0.737 g of intermediate compound 1-11 (80 %).
70%		Al l. Preparation of intermediate I- 11; 1-11 A mixture of 4-benzyloxy-2(lH)-pyridone (0.100 g, 0.50 mmol), <strong>[202865-85-8]2-bromo-5-iodotoluene</strong> (0223 g, 0.75 mmol), CuI (0.048 g, 0.25 mmol), N,N'-dimethylethylenediamine (0.053 ml, 0.5 mmol) and K3PO4 (0.212 g, 1.0 mmol) in dioxane/DMF (4/1) was heated for 15 minutes at 180 0C in a microwave oven. Then DCM was added. The solid was filtered off through a CELITE pad and to the filtrate, a 32 % NH3 solution was added. The organic layer was separated, washed with brine, dried (Na2SO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: DCM). The product fractions were collected and the solvent was evaporated. The residue was treated with DIPE to yield intermediate compound 1-11 (0.130 g, 70 %).

Reference： [1]Patent: WO2008/68265,2008,A1 .Location in patent: Page/Page column 39
[2]Patent: WO2007/141200,2007,A1 .Location in patent: Page/Page column 33

6
[ 97674-02-7 ]
[ 202865-85-8 ]
C₁₁H₁₃BrO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 80℃; for 17h;Product distribution / selectivity;	PdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of <strong>[202865-85-8]1-bromo-4-iodo-2-methylbenzene</strong> (3.01 g, 10.13 mmol) and tri-n-butyl(1-ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 C. for 17 hours. The reaction mixture was treated with water (15 mL), cooled to 0 C. (ice/water), and then NBS (1.839 g, 10.3 mmol) was added in batches over 7 minutes. After about 25 minutes of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% ethyl acetate/hexanes)to provide bromide 121a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta=7.24, 400 MHz): 7.83 (s, 1H), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H).; PdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of <strong>[202865-85-8]1-bromo-4-iodo-2-methylbenzene</strong> (3.01 g, 10.13 mmol) and tri-n-butyl(1-ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 C. for 17 hr. The reaction mixture was treated with water (15 mL), cooled to 0 C. (ice/water), and then NBS (1.839 g, 10.3 mmol) was added in batches over 7 min. About 25 min of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% EtOAc/hexanes)to afford bromide 136a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta=7.24, 400 MHz): 7.83 (s, 1H), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H).
	bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 80℃; for 17h;	Example 121, Step a-bPdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of l-bromo-4-iodo-2-methylbenzene (3.01 g, 10.13 mmol) and tri-«-butyl(l- ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 0C for ~17 hours. The reaction mixture was treated with water (15 mL), cooled to ~0 0C (ice/water), and <n="130"/>then NBS (1.839 g, 10.3 mmol) was added in batches over 7 minutes. After about 25 minutes of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% ethyl acetate/hexanes)to provide bromide 121a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta = 7.24, 400 MHz): 7.83 (s, IH), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H).

Reference： [1]Patent: US2008/44380,2008,A1 .Location in patent: Page/Page column 80; 89
[2]Patent: WO2009/102318,2009,A1 .Location in patent: Page/Page column 128-129; 144

7
[ 97674-02-7 ]
[ 202865-85-8 ]
[ 3114-08-7 ]

Yield	Reaction Conditions	Operation in experiment
		Example N22, Step aA solution of l-bromo-4-iodo-2-methylbenzene (5.0 g, 16.83 mmol) in dioxane (75 mL) was purged with 2 for 10 minutes. Then PdCl2(Pli3P)2 (428 mg 0.609 mmol) and tri-n-butyl(l-ethoxyvinyl)stanane (5.94 mL, 17.59 mmol) was added, and the reaction mixture was purged with 2 for 10 minutes and heated at 80 C for overnight. Water (25 mL) was added to the reaction mixture and cooled to 0 C, NBS (3 g, 17.1 mmol) was added and the mixture was stirred for 30 minutes. The volatile component was removed under reduced pressure, and water was added to the resulting residue and it was extracted with DCM (3 x 100 mL). The combined organic extract was dried over Na2S04 and concentrated in vacuo. The crude was purified by flash chromatography (ISCO; EtOAc: petroleum ether, 2:98) to afford ketone N22a (2.6 g). ¾ NMR (CDCI3, delta = 7.26 ppm, 400 MHz): delta 7.84 (d, J = 0.8, 1H), 7.65-7.62 (m, 2H), 4.32 (s, 2H), 2.48 (s, 3H).
		PdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of <strong>[202865-85-8]1-bromo-4-iodo-2-methylbenzene</strong> (3.01 g, 10.13 mmol) and tri-n-butyl(1-ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 C. for 17 hours. The reaction mixture was treated with water (15 mL), cooled to 0 C. (ice/water), and then NBS (1.839 g, 10.3 mmol) was added in batches over 7 minutes. After about 25 minutes of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% ethyl acetate/hexanes) to provide bromide 121a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta=7.24, 400 MHz): 7.83 (s, 1H), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H).

Reference： [1]Patent: WO2012/39717,2012,A1 .Location in patent: Page/Page column 158-159
[2]Patent: US2008/50336,2008,A1 .Location in patent: Page/Page column 150

8
[ 202865-85-8 ]
[ 3114-08-7 ]

Yield	Reaction Conditions	Operation in experiment
		PdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of <strong>[202865-85-8]1-bromo-4-iodo-2-methylbenzene</strong> (3.01 g, 10.13 mmol) and tri-n-butyl(1-ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 C. for 17 hours. The reaction mixture was treated with water (15 mL), cooled to 0 C. (ice/water), and then NBS (1.839 g, 10.3 mmol) was added in batches over 7 minutes. After about 25 minutes of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% ethyl acetate/hexanes)to provide bromide 121a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta=7.24, 400 MHz): 7.83 (s, 1H), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H). Example 136 Step a and b PdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of <strong>[202865-85-8]1-bromo-4-iodo-2-methylbenzene</strong> (3.01 g, 10.13 mmol) and tri-n-butyl(1-ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 C. for 17 hr. The reaction mixture was treated with water (15 mL), cooled to 0 C. (ice/water), and then NBS (1.839 g, 10.3 mmol) was added in batches over 7 min. About 25 min of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% EtOAc/hexanes) to afford bromide 136a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta=7.24, 400 MHz): 7.83 (s, 1H), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H).

Reference： [1]Patent: US2008/44379,2008,A1 .Location in patent: Page/Page column 78; 88
[2]Patent: US2008/44380,2008,A1

9
[ 79887-14-2 ]
[ 202865-85-8 ]
2-methyl-4-(4-ethoxyphenylethynyl)bromobenzene [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals,2007,vol. 478,p. 259 - 269

10
[ 202865-85-8 ]
1-bromo-2-methyl-4-pentyl-benzene [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2004,vol. 14,p. 1731 - 1743

11
[ 202865-85-8 ]
C₁₄H₂₃BO₂ [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2004,vol. 14,p. 1731 - 1743

12
[ 202865-85-8 ]
C₁₂H₁₉BO₂ [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2004,vol. 14,p. 1731 - 1743

13
[ 202865-85-8 ]
2-cyano-6-(2-methyl-4-pentylphenyl)naphthalene [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2004,vol. 14,p. 1731 - 1743

14
[ 202865-85-8 ]
2-methyl-4-pentyl-4''-cyano-1,1':4',1''-terphenyl [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2004,vol. 14,p. 1731 - 1743

15
[ 202865-85-8 ]
[ 289617-99-8 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6871 - 6883

16
[ 202865-85-8 ]
[ 289618-00-4 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6871 - 6883

17
[ 202865-85-8 ]
[ 289618-03-7 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6871 - 6883

18
[ 79099-07-3 ]
[ 202865-85-8 ]
[ 227304-98-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With n-butyllithium; In tetrahydrofuran; hexane; pentane;	B. A 2.5M solution of n-butyllithium in hexane (38 ml, 94 mmol) was added over about 10 minutes to a stirred mixture of <strong>[202865-85-8]2-bromo-5-iodo-toluene</strong> (28 g, 94 mmol) in anhydrous ether (500 ml), under nitrogen, at about -75 C. After a further 15 minutes, a solution of t-butyl 4-oxopiperidine-1-carboxylate (17 g, 85 mmol) in anhydrous tetrahydrofuran (50 ml) was added at such a rate that the reaction temperature was maintained below -60 C. The reaction mixture was stirred at about -75 C. for 1 hour, allowed to warm to 0 C. and quenched with aqueous ammonium chloride solution. The organic phase was separated, washed with water, dried (MgSO4) and evaporated under reduced pressure. The residue was dissolved in pentane and the resulting solution cooled to 0 C., when the title compound crystallized. It was collected and dried to afford a colourless solid (20.1 g, 64%), identical with that obtained in Preparation 33A.

Reference： [1]Patent: US6387931,2002,B1

19
[ 444892-03-9 ]
[ 202865-85-8 ]
[ 1018829-32-7 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 1473 - 1476

20
[ 132871-12-6 ]
[ 202865-85-8 ]
[ 1018829-31-6 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 1473 - 1476

21
[ 204327-96-8 ]
[ 202865-85-8 ]
[ 1018829-33-8 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 1473 - 1476

22
[ 141-32-2 ]
[ 202865-85-8 ]
[ 1402975-31-8 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 1188 - 1195

23
[ 5419-55-6 ]
[ 202865-85-8 ]
C₁₃H₂₀BBrO₂ [ No CAS ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 8000 - 8005

24
[ 202865-85-8 ]
[ 1307795-20-5 ]

Reference： [1]Patent: WO2011/57382,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1953 - 1957

25
[ 202865-85-8 ]
[ 1307795-22-7 ]

Reference： [1]Patent: WO2011/57382,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1953 - 1957

26
[ 202865-85-8 ]
rac-tert-butyl (3S,4R)-4-[2-(1,3-dioxolan-2-yl)-4,5-difluorophenyl]-4-hydroxy-3-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1-piperidinecarboxylate [ No CAS ]

Reference： [1]Patent: WO2011/57382,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1953 - 1957

27
[ 202865-85-8 ]
rac-tert-butyl (1R,3'S)-5,6-difluoro-3-hydroxy-3'-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]

Reference： [1]Patent: WO2011/57382,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1953 - 1957

28
[ 202865-85-8 ]
rac-tert-butyl (3S,4R)-4-[4,5-difluoro-2-(hydroxymethyl)phenyl]-4-hydroxy-3-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1-piperidinecarboxylate [ No CAS ]

Reference： [1]Patent: WO2011/57382,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1953 - 1957

29
[ 202865-85-8 ]
rac-tert-butyl (1R,3'S)-5,6-difluoro-3'-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]