[ CAS No. 89465-97-4 ] {[proInfo.proName]}

Name: 89465-97-4|4-Bromo-2-chloro-1-nitrobenzene|95%
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SKU: A789979
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Quality Control of [ 89465-97-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 89465-97-4 ]

CAS No. :	89465-97-4	MDL No. :	MFCD11848538
Formula :	C₆H₃BrClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QWRNVDWDFCINEY-UHFFFAOYSA-N
M.W :	236.45	Pubchem ID :	22280606
Synonyms :

Calculated chemistry of [ 89465-97-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.97
TPSA :	45.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.7
Log Po/w (XLOGP3) :	3.13
Log Po/w (WLOGP) :	3.01
Log Po/w (MLOGP) :	3.04
Log Po/w (SILICOS-IT) :	1.02
Consensus Log Po/w :	2.38

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.62
Solubility :	0.0573 mg/ml ; 0.000242 mol/l
Class :	Soluble
Log S (Ali) :	-3.76
Solubility :	0.041 mg/ml ; 0.000173 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.25
Solubility :	0.132 mg/ml ; 0.000558 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.93

Safety of [ 89465-97-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302+H312+H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89465-97-4 ]

* 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 [ 89465-97-4 ]
Downstream synthetic route of [ 89465-97-4 ]

[ 89465-97-4 ] Synthesis Path-Upstream 1~3

1
[ 108-37-2 ]
[ 63860-31-1 ]
[ 89465-97-4 ]

Reference： [1] Patent: US2002/173490, 2002, A1,

2
[ 108-37-2 ]
[ 7697-37-2 ]
[ 63860-31-1 ]
[ 89465-97-4 ]

Reference： [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
[3] Journal of the Chemical Society, 1928, p. 693

3
[ 89465-97-4 ]
[ 38762-41-3 ]

Reference： [1] Synlett, 2010, # 20, p. 3019 - 3022
[2] , 1967, vol. 3, p. 1795 - 1799[3] Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 10, p. 1839 - 1843
[4] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 4, p. 175 - 179

[ 89465-97-4 ] Synthesis Path-Downstream 1~43

1
[ 5228-61-5 ]
[ 89465-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine

Reference： [1]Koerner; Contardi [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1908, vol. <5> 17 I, p. 473]

2
[ 872266-26-7 ]
[ 89465-97-4 ]

Reference： [1]Koerner; Contardi [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1908, vol. <5> 17 I, p. 473]

3
[ 64-17-5 ]
[ 89465-97-4 ]
[ 124-40-3 ]
5-bromo-N,N-dimethyl-2-nitroaniline [ No CAS ]

Reference： [1]Hodgson; Kershaw [Journal of the Chemical Society, 1930, p. 497,500]

4
[ 89465-97-4 ]
[ 124-40-3 ]
5-bromo-N,N-dimethyl-2-nitroaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol

Reference： [1]Hodgson; Kershaw [Journal of the Chemical Society, 1930, p. 497,500]

5
[ 825-41-2 ]
[ 89465-97-4 ]

Reference： [1]Journal of the American Chemical Society,1962,vol. 84,p. 1026 - 1032
[2]Journal of Organic Chemistry USSR (English Translation),1967,vol. 3,p. 1795 - 1799
Zhurnal Organicheskoi Khimii,1967,vol. 3,p. 1839 - 1843

6
[ 89465-97-4 ]
[ 38762-41-3 ]

Reference： [1]Synlett,2010,p. 3019 - 3022
[2]Journal of Organic Chemistry USSR (English Translation),1967,vol. 3,p. 1795 - 1799
Zhurnal Organicheskoi Khimii,1967,vol. 3,p. 1839 - 1843
[3]ACS Medicinal Chemistry Letters,2010,vol. 1,p. 175 - 179

7
[ 89465-97-4 ]
[ 180516-87-4 ]
3'-Chloro-4'-nitro-biphenyl-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; trifluoroacetic acid; Wang resin Multistep reaction;

Reference： [1]Hajduk, Philip J.; Dinges, Jürgen; Miknis, Gregory F.; Merlock, Megan; Middleton, Tim; Kempf, Dale J.; Egan, David A.; Walter, Karl A.; Robins, Terry S.; Shuker, Suzy B.; Holzman, Thomas F.; Fesik, Stephen W. [Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3144 - 3150]

8
[ 108-37-2 ]
[ 7697-37-2 ]
[ 63860-31-1 ]
[ 89465-97-4 ]

9
m-chloro-bromobenzene [ No CAS ]
[ 63860-31-1 ]
[ 89465-97-4 ]

Reference： [1]Gazzetta Chimica Italiana,1874,vol. 4,p. 341
Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften,1875,p. 317
[2]Gazzetta Chimica Italiana,1874,vol. 4,p. 341
Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften,1875,p. 317

Yield	Reaction Conditions	Operation in experiment
	Rk. m. Natrium-thiophenolat/MeOH b. 15.0grad, 25.0grad, 35.0grad;
	Kinetik d. Rk. m. Natriumthiophenolat/MeOH zu 5-Brom-2-nitro-diphenylsulfid: Aktivierungsenergie: E= 17.0 kcal/mol, Aktivierungsentropie: ΔS(excit)= -16.4 e.u. 35grad;
	Rk. m. Piperidin/Benzol;

	Red. <SnCl2> --> 2-Chlor-4-brom-anilin;
	With piperidine In benzene at 30 - 60℃;

11
[ 89465-97-4 ]
2,5-bis(tri-n-butylstannyl)furan [ No CAS ]
2,5-bis-(3-chloro-4-nitro-phenyl)-furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane

Reference： [1]Stephens, Chad E.; Brun, Reto; Salem, Manar M.; Werbovetz, Karl A.; Tanious, Farial; Wilson, W. David; Boykin, David W. [Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 12, p. 2065 - 2069]

12
[ 89465-97-4 ]
[ 292638-85-8 ]
[ 863202-54-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: 4-bromo-2-chloro-1-nitrobenzene; acrylic acid methyl ester With tributyl-amine; potassium carbonate In N,N-dimethyl-formamide at 150℃; for 0.166667h; microwave irradiation; Stage #2: With sodium hydroxide; water In N,N-dimethyl-formamide at 130℃; for 0.0833333h; microwave irradiation; Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide	1 (E)-3-Chloro-4-nitro-cinnamic acid A solution of 4-bromo-2-chloro-1-nitrobenzene (237 mg, 1.0 mmol), acrylic acid methyl ester (108 μL, 1.2 mmol), potassium carbonate (150 mg, 1.1 mmol), tributylamine (263 μL, 1.1 mmol) and a catalytic amount of bis(triphenylphosphino)palladium(II) dichloride (0.005 eq.) in DMF (5 mL) was heated at 150° C. for 10 minutes in a microwave oven. 1M aqueous sodium hydroxide (1 mL) and water (4 mL) were added and the mixture was heated for 5 minutes at 130° C. in the microwave oven. The solution was acidified with 1N hydrochloric acid and the aqueous layer was extracted with ethyl acetate. The organic solvents were removed in vacuo and the residue was submitted to flash column chromatography to give the title compound in 40% yield. 1H NMR: δ(CDCl3) 7.94 (d, 1H), 7.72 (d, 1H), 7719 (d, 1H), 7.57 (dd, 2H), 6.56 (d, 1H)

Reference： [1]Current Patent Assignee: ACTIVE BIOTECH AB - US2005/192289, 2005, A1 Location in patent: Page/Page column 9

13
[ 38762-41-3 ]
[ 89465-97-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 24h;Heating / reflux;	EXAMPLE 1 (E)-3-Chloro-4-nitro-cinnamic acid A mixture of <strong>[38762-41-3]2-chloro-4-bromo-aniline</strong> (413 mg, 2.0 mmol) and m-chloro-peroxybenzoic acid (60%, 1.72 g, 6 mmol) in dichloromethane (30 mL) was refluxed for 24 h. After cooling, the solution was washed with sodium carbonate (3*10 mL) and water (20 mL). The organic phase was evaporated and the residue was submitted to flash column chromatography to give 355 mg of 4-bromo-2-chloro-1-nitro-benzene (yield 75%).

Reference： [1]Patent: US2005/192289,2005,A1 .Location in patent: Page/Page column 9
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6224 - 6229
[3]Advanced Synthesis and Catalysis,2007,vol. 349,p. 2286 - 2300

14
[ 635-22-3 ]
[ 89465-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid; NaOBr / man verwandelt in die Acetylderivate, trennt diese durch fraktionierte Krystallisation aus Alkohol und verseift durch konz.Schwefelsaeure bei 120grad
	Multi-step reaction with 2 steps 1: acetic acid; NaOBr / man verwandelt in die Acetylderivate und trennt diese durch fraktionierte Krystallisation aus Alkohol

Reference： [1]Koerner; Contardi [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1908, vol. <5> 17 I, p. 473]
[2]Koerner; Contardi [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1908, vol. <5> 17 I, p. 473]

15
[ 588-07-8 ]
[ 89465-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (i) HNO₃, H₂SO₄, (ii) aq. HCl 2: (i) aq. HBr, NaNO₂, (ii) aq. CuBr

Reference： [1]Frankovskii,Ch.S. et al. [Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1795 - 1799][Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 10, p. 1839 - 1843]

16
[ 89465-97-4 ]
[ 16604-87-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SnCl₂, aq. HCl 2: (i) NaNO₂, aq. HCl, (ii) /BRN= 969616/, aq. NaOH, aq. Na₂CO₃

Reference： [1]Frankovskii,Ch.S. et al. [Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1795 - 1799][Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 10, p. 1839 - 1843]

17
[ 109-01-3 ]
[ 89465-97-4 ]
[ 1059705-52-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tert-pentoxide In tetrahydrofuran at 100℃; for 3h;	1 An oven-dried vial was charged subsequently with 0.05 eq. PdCl2(dppf), 0.15 eq. dppf, 1.0 eq. 4-bromo-2-chloro-1-nitro-benzene and 1.25 eq. sodium tert-pentoxide. The vial was evacuated and purged with argon, and THF and piperazine of general formula A (1.1 eq.) were added. THF was added in a quantity to obtain a 0.5 M solution of 4-bromo-2-chloro-1-nitro-benzene. The vial was sealed and heated to 100°C for 3 h. The reaction mixture was taken up in half-saturated brine and extracted three times with ethyl acetate. The volume of the combined organic phases was reduced in vacuo and extracted with 5% hydrochloric acid in water. The acidic aqueous phase was concentrated and the product was isolated by preparative HPLC. In order to remove any ammonium formate derivative formed during preparative HPLC on RP18, the resulting product was taken up in chloroform, extracted twice with saturated aqueous NaHCO3, the combined aqueous phases were re-extracted with chloroform, and the combined organic phases were dried over MgSO4 and concentrated in vacuo to obtain the desired product.
	With sodium tert-pentoxide In tetrahydrofuran at 100℃; for 3h;	3a.1 An oven-dried vial was charged subsequently with 0.05 eq. PdCI2(dppf), 0.15 eq. dppf, 1.0 eq. 4-bromo-2-chloro-1 -nitro-benzene and 1.25 eq. sodium te/t-pentoxide. The tube was evacuated and purged with argon, and THF and 1 -methyl-piperazine (1.1 eq.) were added. THF was added in a quantity to obtain a 0.5 M solution of 4- bromo-2-chloro-1 -nitro-benzene. The vial was sealed and heated to 1000C for 3 h. The reaction mixture was taken up in half -saturated brine and extracted three times with ethyl acetate. The volume of the combined organic phases was reduced in vacuo and extracted with 5% hydrochloric acid in H2O. The acidic aqueous phase was concentrated and the product was isolated by preparative HPLC. In order to remove any ammonium formate derivative formed during preparative HPLC, the resulting product was taken up in chloroform, extracted twice with saturated aqueous NaHCO3, the combined aqueous phases were re-extracted with chloroform, and the combined organic phases were dried over MgSO4 and concentrated in vacuo to obtain the desired product.

Reference： [1]Current Patent Assignee: Corporacion Quimico Farmaceutica Esteve SA - EP1676842, 2006, A1 Location in patent: Page/Page column 67-68
[2]Current Patent Assignee: Corporacion Quimico Farmaceutica Esteve SA - WO2006/69807, 2006, A1 Location in patent: Page/Page column 104

18
[ 108-37-2 ]
[ 63860-31-1 ]
[ 89465-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; nitric acid;	Step A. To a solution of 1 mmol of 3-bromo chlorobenzene in 2 mL of con. H2SO4 was added 1.5 mmol of 79% HNO3 at -10 C. After it was stirred for 30 min. the mixture was poured onto ice/water mixture. The yellow precipitate was filtered and dried to give a mixture of 2-chloro-4-bromo nitrobenzene (desired) and 4-chloro-2-bromo nitrobenzene.

Reference： [1]Patent: US2002/173490,2002,A1

19
[ 89465-97-4 ]
2-Amino-6-ethyl-4-phosphonomethoxybenzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		42.B Step B. Step B. 2-Chloro-4-bromo nitrobenzene was subjected to Step A of Example 34, Step B of Example 32, Step B of Example 29, and Step D of Example 27 to give 2-Amino-6-ethyl-4-phosphonomethoxybenzothiazole (42.1) mp. >220° C.(dec.). Anal. calcd. for C10H13N2O4PS+0.3HBr: C: 38.43; H: 4.29; N: 8.96. Found: C: 38.35; H: 4.44; N: 8.75.

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2002/173490, 2002, A1

20
[ 109-01-3 ]
[ 89465-97-4 ]
[ 14593-46-5 ]
[ 1059705-52-0 ]
C₁₁H₁₄ClNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With 1,1'-bis-(diphenylphosphino)ferrocene In tetrahydrofuran at 100℃; for 4h;

Reference： [1]Tasler, Stefan; Mies, Jan; Lang, Martin [Advanced Synthesis and Catalysis, 2007, vol. 349, # 14-15, p. 2286 - 2300]

21
[ 5610-49-1 ]
[ 89465-97-4 ]
[ 1059705-53-1 ]

Yield	Reaction Conditions	Operation in experiment
36%	With 1,1'-bis-(diphenylphosphino)ferrocene In tetrahydrofuran at 100℃; for 4h;

Reference： [1]Tasler, Stefan; Mies, Jan; Lang, Martin [Advanced Synthesis and Catalysis, 2007, vol. 349, # 14-15, p. 2286 - 2300]

22
[ 34803-66-2 ]
[ 89465-97-4 ]
[ 1059705-54-2 ]

Yield	Reaction Conditions	Operation in experiment
38%	With 1,1'-bis-(diphenylphosphino)ferrocene In tetrahydrofuran at 100℃; for 4h;

Reference： [1]Tasler, Stefan; Mies, Jan; Lang, Martin [Advanced Synthesis and Catalysis, 2007, vol. 349, # 14-15, p. 2286 - 2300]

23
[ 110-89-4 ]
[ 89465-97-4 ]
[ 861199-86-2 ]

Yield	Reaction Conditions	Operation in experiment
	at 20℃;

Reference： [1]Illig, Carl R.; Chen, Jinsheng; Wall, Mark J.; Wilson, Kenneth J.; Ballentine, Shelley K.; Rudolph, M. Jonathan; DesJarlais, Renee L.; Chen, Yanmin; Schubert, Carsten; Petrounia, Ioanna; Crysler, Carl S.; Molloy, Christopher J.; Chaikin, Margery A.; Manthey, Carl L.; Player, Mark R.; Tomczuk, Bruce E.; Meegalla, Sanath K. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 5, p. 1642 - 1648]

24
[ 89465-97-4 ]
N-(3-chloro-4'-((1-methylpiperidin-4-yl)oxy)-[1,1'-biphenyl]-4-yl)-3',6-dimethoxy-[1,1'-biphenyl]-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 12 h / 110 °C 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 20 °C 3: hydrogen; palladium 10% on activated carbon / methanol / 2 h / 20 °C 4: pyridine / dichloromethane / 4 h / 20 °C / Cooling with ice
	Multi-step reaction with 4 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 110 °C / Reflux 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 20 °C 3: palladium 10% on activated carbon; hydrogen / methanol 4: pyridine / dichloromethane / 4 h / 20 °C / Cooling with ice

Reference： [1]Zhao, Huiping; Garg, Gaurav; Zhao, Jinbo; Moroni, Elisabetta; Girgis, Antwan; Franco, Lucas S.; Singh, Swapnil; Colombo, Giorgio; Blagg, Brian S.J. [European Journal of Medicinal Chemistry, 2015, vol. 89, p. 442 - 466]
[2]Current Patent Assignee: UNIVERSITY OF KANSAS - WO2015/70091, 2015, A1

25
[ 89465-97-4 ]
C₁₈H₂₁ClN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 12 h / 110 °C 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 20 °C 3: hydrogen; palladium 10% on activated carbon / methanol / 2 h / 20 °C
	Multi-step reaction with 3 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 110 °C / Reflux 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 20 °C 3: palladium 10% on activated carbon; hydrogen / methanol

26
[ 89465-97-4 ]
4-((3′-chloro-4′-nitro[1,1′-biphenyl]-4-yl)oxy)-1-methylpiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 12 h / 110 °C 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 20 °C
	Multi-step reaction with 2 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 110 °C / Reflux 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 20 °C

27
[ 89465-97-4 ]
[ 71597-85-8 ]
3'-chloro-4'-nitro-[1,1'-biphenyl]-4-ol [ No CAS ]