15969-10-5|2-Bromo-4-chloro-6-nitrophenol| Ambeed

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Quality Control of [ 15969-10-5 ] Purity: 97% SDS Specification

COA

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NMR

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Product Details of [ 15969-10-5 ]

CAS No. :	15969-10-5
Formula :	C₆H₃BrClNO₃
M.W :	252.45
SMILES Code :	OC1=C([N+]([O-])=O)C=C(Cl)C=C1Br
MDL No. :	MFCD00024243
Boiling Point :	No data available
InChI Key :	POBOBTAMSJHELX-UHFFFAOYSA-N
Pubchem ID :	291871

Safety of [ 15969-10-5 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H315-H317-H318-H410
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501
Class:	9
UN#:	3077
Packing Group:	Ⅲ

Computational Chemistry of [ 15969-10-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	50.0
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.64
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	4.06
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.72
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.	1.64
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	0.58
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.27
Solubility	0.0137 mg/ml ; 0.0000541 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.	-5.15
Solubility	0.00178 mg/ml ; 0.00000706 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-2.68
Solubility	0.532 mg/ml ; 0.00211 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	No
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	Yes
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.	-4.96 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	0.0
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	2.0 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<1.0
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)	2.15

Application In Synthesis of [ 15969-10-5 ]

* 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 [ 15969-10-5 ]

[ 15969-10-5 ] Synthesis Path-Downstream 1~35

1
[ 695-96-5 ]
[ 15969-10-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium nitrate; sulfuric acid; acetic acid; In water; at 25 - 30℃;Large scale;	The reaction flask was successively added with acetic acid (7.5 L) 4-chloro-2-bromophenol (1500.0 g, 7.2 mol) was stirred well;Sodium nitrate was added dropwise at room temperature(1229.0 g, 14.5 mol)And concentrated sulfuric acid(1418.0 g, 14.5 mol) in water (1.4 L);After the drop, the temperature control 25-30C reaction about 20-30min;The reaction was stopped and poured into ice water (7.5 L) and stirred for 20 min.The filter cake was washed with water until the filtrate was near neutral (pH 6-7). The filter cake was dried to obtain a yellow solid: 1742 g, yield: 95%.
97.12 g (80.1%)	With nitric acid; In water; acetic acid;	(a) 2-bromo-4-chloro-6-nitro-phenol A solution of 2-bromo-4-chloro-phenol (99.24 g, 480 mmol) in acetic acid (110 ml) and acetic anhydride (125 ml) was cooled to -10C. Within 1 hour a solution containing 100% nitric acid (33 ml) and acetic acid (40 ml) was added between -10 and -5C, with stirring. The mixture was stirred for an additional 1.5 hours at 0-5 C, then the suspension poured onto 300 g of ice in 700 ml of water and stirred for a further 0.5 hour. The solid was collected, washed, and dried to give 97.12 g (80.1%) of the title compound (mp 121-2C).

References: [1]Patent: CN106146330,2016,A .Location in patent: Paragraph 0062-0064.
[2]Organic Letters,2019,vol. 21,p. 1315 - 1319.
[3]Journal of the American Chemical Society,1933,vol. 55,p. 2125,2129.
[4]Journal of Organic Chemistry,1946,vol. 11,p. 641,644.
[5]Patent: EP1160247,2001,A1 .

2
[ 89-64-5 ]
[ 15969-10-5 ]

Yield	Reaction Conditions	Operation in experiment
90.9%	With bromine; acetic acid; at 5 - 20℃;	Example 116; 1-[6-Chloro-8-(1H-pyrazol-4-yl)-3,4-dihydro-2H-benzo[1,4]oxazine-2-carbonyl]-4-(4-fluoro-benzyl)-piperidine-4-carbonitrile Step-1: 2-Bromo-4-chloro-6-nitro-phenolTo a solution of 4-chloro-2-nitrophenol (1 g, 5.76 mmol) in acetic acid was added bromine (0.32 ml, 6.3 mmol) at 5-10 C. and stirred at 10 C. for half an hour. The temperature of the reaction mixture was raised to room temperature and stireed at RT for 3 hours. The reaction mixture was diluted with ice-water and extracted with ethyl acetate. The organic layer was washed with ethyl acetate and dried over sodium sulfate. Concentration of organic layer was afforded 1.3 g (90.9%) of 2-Bromo-4-chloro-6-nitro-phenol. GCMS [m/z]: 253.0. 1H-NMR (400 MHz, DMSO-d6) delta (ppm): 11.1 (s, 1H), 8.10 (d, 1H), 8.04 (d, 1H).
84%	With bromine; acetic acid; at 5 - 20℃; for 3.5h;	[0054] A solution of 4-chloro-2-nitrophenol (4) (3.12 g, 18.0 mmol) in acetic acid (25 mL) was cooled to 5-10 C, and bromine (1.0 mL, 19.7 mmol) was added dropwise. The reaction mixture was stirred for half an hour at 10 C and then for 3 hours at room temperature. The mixture was then diluted with ice- water and extracted with dichloromethane (DCM) (3x30 mL). The combined organic extracts were washed with brine (30 mL) and dried over anhydrous Na2S04. The solvent was then evaporated to give the crude product which was recrystallized from 96 % ethanol to afford a yellow crystalline product (lb) (3.80 g, 84%, purity 99%, HPLC Method B). 1H NMR (600 MHz, DMSO-d6) delta: 8.02 (d, J= 2.6 Hz, 1H), 8.09 (d, J= 2.6 Hz, 1H) ppm; 1H NMR (300 MHz, CDC13) delta: 7.86 (d, J= 2.6 Hz, 1H), 8.11 (d, J= 2.6 Hz, 1H), 11.03 (1H, s, OH);13C NMR (150 MHz, DMSO-d6) delta: 114.90, 123,38, 123.97, 137.67, 137.77, 148.12 ppm; MS m/z [M-H]" 252.1.
76%	With bromine; acetic acid; at 20℃; for 4.0h;Cooling with ice;	Step 1: 4-chloro-2-nitrophenol (1.0 equiv.) was dissolved in Acetic Acid (0.64 M) and cooled in an ice-bath. To the mixture was then added bromine (1.1 equiv.) and the mixture agitated for 3 h while gradually warming to room temperature. Additional bromine (0.3 equiv.) was added. Then, after additional hour, almost complete conversion to the desired product is observed. At this stage, ice-cold water was added and immediately, a yellowish suspension was observed. The mixture was vigirously agitated and then filtered. The yellowish orange precipitate was washed with water and then with heptane and the yellow powder was placed under high-vacuum for 3 days to afford 2-bromo-4-chloro-6- nilrophenol in 76% yield. LCMS (rn/z) (M+H) = 291.9, Rt = 1.45 min.

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 7388 - 7397.
[2]Patent: US2010/152160,2010,A1 .Location in patent: Page/Page column 111.
[3]Patent: WO2013/49605,2013,A1 .Location in patent: Paragraph 0054.
[4]Patent: WO2016/38582,2016,A1 .Location in patent: Paragraph 00335.
[5]American Chemical Journal,1904,vol. 32,p. 15.

3
[ 88-87-9 ]
[ 15969-10-5 ]

References: [1]Chemical news and journal of industrial science,1891,vol. 63,p. 222.
Chemisches Zentralblatt,1891,vol. 62,p. 1031.

4
[ 5324-13-0 ]
[ 15969-10-5 ]

References: [1]Journal of the American Chemical Society,1933,vol. 55,p. 2125,2129.
[2]Journal of Organic Chemistry,1946,vol. 11,p. 641,644.

5
[ 15969-10-5 ]
[ 179314-60-4 ]

Yield	Reaction Conditions	Operation in experiment
85.1%	With hydrogen;Raney Ni; In ethyl acetate; for 4.0h;	Step-2: 2-Amino-6-bromo-4-chloro-phenol; To a solution of <strong>[15969-10-5]2-bromo-4-chloro-6-nitro-phenol</strong> (2.7 g, 10.6 mmol) in ethyl acetate was added raney Ni (1 g) and was hydrogenetaed at ballon pressure for 4 hours. The reaction mixture was filtered through celite bed and mother liquor was concentrated to afford 2 g (85.1%) of 2-Amino-6-bromo-4-chloro-phenol. LCMS [M+1]: 224.0. 1H-NMR (400 MHz, DMSO-d6) delta (ppm): 6.67 (s, 1H), 6.61 (s, 1H), 6.57 (s, 1H), 5.2 (bs, 2H).
64%	With iron; ammonium chloride; In ethanol; water; at 90℃; for 1.25h;	Step 2: <strong>[15969-10-5]2-bromo-4-chloro-6-nitrophenol</strong> (1.0 equiv.) was suspended in EtOH (0.5) and then iron powder (8.0 equiv.) followed by Ni l .C (8.0 equiv.) and Water (1/10 of EtOH volume) was added. The mixture was heated at 90 C for 75 min and then filtered hot through ceite. The filtrate was concentrated in vacuo and ther residue dissolved in EtOAc and washed with water and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give a dark brown residue. This material was suspended in DCM and titurated with heptane. The dark brown suspension was collected by filtration to afford 2- amino-6-bromo-4-chlorophenol in 64% yield. LCMS (m 'z) (M+H) = 223.8, Rt = 1.11 min

References: [1]Patent: US2010/152160,2010,A1 .Location in patent: Page/Page column 111.
[2]Patent: WO2016/38582,2016,A1 .Location in patent: Paragraph 00336.
[3]Bulletin de la Societe Chimique de France,1923,vol. <4>33,p. 1828.

6
[ 92044-52-5 ]
[ 15969-10-5 ]

References: [1]Journal of the American Chemical Society,1926,vol. 48,p. 2654.

7
[ 15969-10-5 ]
[ 541-41-3 ]
carbonic acid ethyl ester-(2-bromo-4-chloro-6-nitro-phenyl ester) [ No CAS ]

References: [1]American Chemical Journal,1904,vol. 32,p. 15.

8
[ 15969-10-5 ]
[ 108-24-7 ]
2-acetoxy-1-bromo-5-chloro-3-diacetylamino-benzene [ No CAS ]

References: [1]Journal of Organic Chemistry,1948,vol. 13,p. 329.

9
[ 88-87-9 ]
[ 7726-95-6 ]
[ 15969-10-5 ]

References: [1]Chemical news and journal of industrial science,1891,vol. 63,p. 222.
Chemisches Zentralblatt,1891,vol. 62,p. 1031.

10
[ 89-64-5 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 15969-10-5 ]

References: [1]American Chemical Journal,1904,vol. 32,p. 15.

11
[ 695-96-5 ]
[ 7697-37-2 ]
[ 64-19-7 ]
[ 15969-10-5 ]

References: [1]Journal of Organic Chemistry,1946,vol. 11,p. 641,644.

12
[ 5324-13-0 ]
[ 64-19-7 ]
NaNO₂ [ No CAS ]
[ 15969-10-5 ]

References: [1]Journal of the American Chemical Society,1933,vol. 55,p. 2125,2129.

13
[ 15969-10-5 ]
[ 7732-18-5 ]
[ 7726-95-6 ]
[ 488-48-2 ]

References: [1]Journal of the Chemical Society,1887,vol. 51,p. 786.
Journal of the Chemical Society,1892,vol. 61,p. 577.

14
[ 15969-10-5 ]
[ 7697-37-2 ]
[ 64-19-7 ]
[ 88-87-9 ]

References: [1]Journal of the Chemical Society,1889,vol. 55,p. 585,587.

15
[ 92044-52-5 ]
[ 7726-95-6 ]
[ 7553-56-2 ]
[ 15969-10-5 ]

References: [1]Journal of the American Chemical Society,1926,vol. 48,p. 2654.

16
6-bromo-2-nitro-4-diazonio-phenol betaine [ No CAS ]
[ 15969-10-5 ]

References: [1]Journal of the Chemical Society,1931,p. 2272.

17
[ 13073-25-1 ]
dichloropentamethylenetetramine [ No CAS ]
[ 15969-10-5 ]

References: [1]Zhurnal Obshchei Khimii,1935,vol. 5,p. 981,983.
Chemisches Zentralblatt,1936,vol. 107,p. 3669.

18
[ 15969-10-5 ]
[ 108-24-7 ]
[ 64-19-7 ]
zinc-powder [ No CAS ]
2-acetoxy-1-bromo-5-chloro-3-diacetylamino-benzene [ No CAS ]

References: [1]Journal of Organic Chemistry,1948,vol. 13,p. 329.

19
[ 573-56-8 ]
[ 15969-10-5 ]

References: [1]Chemical news and journal of industrial science,1891,vol. 63,p. 222.
Chemisches Zentralblatt,1891,vol. 62,p. 1031.

20
[ 15969-10-5 ]
carbonic acid ethyl ester-(2-amino-6-bromo-4-chloro-phenyl ester); hydrochloride [ No CAS ]

References: [1]American Chemical Journal,1904,vol. 32,p. 15.

Yield	Reaction Conditions	Operation in experiment
		A method of treating warm blooded animals to eradicate trematodes and nematodes; which method comprises administering to warm blooded animal in need of such treatment an effective amount of a compound selected from the group consisting of ... 2,4-dichloro-6-nitrophenol 2-chloro-4-fluoro-6-nitrophenol 2-bromo-4-fluoro-6-nitrophenol 2-iodo-4-fluoro-6-nitrophenol 2-bromo-4-chloro-6-nitrophenol

22
[ 15969-10-5 ]
[ 7440-02-0 ]
[ 179314-60-4 ]

Yield	Reaction Conditions	Operation in experiment
14.19 g (99.0%)	In ethyl acetate;	(b) 6-amino-2-bromo-4-chloro-phenol A solution of <strong>[15969-10-5]2-bromo-4-chloro-6-nitro-phenol</strong> (16.27 g, 64.4 mmol) in ethyl acetate (160 ml) was hydrogenated, at room temperature, with Raney-nickel (6 g). After hydrogen uptake (approx. 4.8 l) was complete, the nickel was removed by filtration and the filtrate evaporated in-vacuoto give 14.19 g (99.0%) of the title compound which was suitable for the next step.

References: [1]Patent: EP1160247,2001,A1 .

23
[ 25487-66-5 ]
[ 15969-10-5 ]
[ 376592-58-4 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; sodium carbonate; In water; at 50℃; for 3.5h;Inert atmosphere;	[0055] A mixture of Na2C03 (424 mg, 4 mmol), Pd(OAc)2 (22.4 mg, 5 mol %), PEG 2000 (7 g) and water (6 mL) was heated to 50 C under an inert atmosphere with stirring. Afterward, <strong>[15969-10-5]2-bromo-4-chloro-6-nitrophenol</strong> (Compound lb, 508 mg, 2 mmol) and 3- carboxyphenylboronic acid (Compound 3) (494 mg, 3 mmol) were added to the solution, and the mixture was heated at 50 C under an inert atmosphere. After 3.5 hrs the reaction mixture was cooled to room temperature, diluted with water (50 mL), treated with 5% aq. HC1 to adjust to pH = 2 and extracted with ethyl acetate (3x 20 mL). The combined ethyl acetate extracts were washed with water and brine (50 mL), dried over anhydrous Na2S04 and concentrated in vacuo. The crude product was obtained as a brown solid and was recrystallized from 60 % acetic acid/water to afford compound (2b) (340 mg, 58%, purity 92%, HPLC Method B).

References: [1]Patent: WO2013/49605,2013,A1 .Location in patent: Paragraph 0055.

24
[ 15969-10-5 ]
[ 376592-93-7 ]

References: [1]Patent: WO2013/49605,2013,A1 .
[2]Patent: CN106146330,2016,A .

25
[ 15969-10-5 ]
3'-amino-5-chloro-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid [ No CAS ]

References: [1]Patent: WO2013/49605,2013,A1 .

26
[ 15969-10-5 ]
Eltrombopag [ No CAS ]

References: [1]Patent: WO2013/49605,2013,A1 .

27
[ 106-48-9 ]
[ 15969-10-5 ]

References: [1]Organic Process Research and Development,2004,vol. 8,p. 568 - 570.

28
[ 15969-10-5 ]
8-bromo-6-chloro-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]