150812-32-1|2-Amino-4-bromo-5-chlorobenzoic acid| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 150812-32-1 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 150812-32-1 ]

CAS No. :	150812-32-1
Formula :	C₇H₅BrClNO₂
M.W :	250.48
SMILES Code :	NC1=C(C(=O)O)C=C(C(=C1)Br)Cl
MDL No. :	MFCD10000554
InChI Key :	QLUCPCIKLHKGRW-UHFFFAOYSA-N
Pubchem ID :	15311388

Safety of [ 150812-32-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P280

Computational Chemistry of [ 150812-32-1 ] 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	2.0
Num. H-bond donors	2.0
Molar Refractivity	50.52
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	63.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.55
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	2.64
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.39
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.	1.22
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	1.84
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.93

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.36
Solubility	0.109 mg/ml ; 0.000436 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.62
Solubility	0.06 mg/ml ; 0.00024 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	-2.89
Solubility	0.326 mg/ml ; 0.0013 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	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	No
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.	-5.95 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.	0.56

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)	1.53

Application In Synthesis of [ 150812-32-1 ]

* 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 [ 150812-32-1 ]

[ 150812-32-1 ] Synthesis Path-Downstream 1~35

2
2,4-dibromo-5-chlorobenzoic acid [ No CAS ]
[ 150812-32-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With copper(I) oxide; ammonia; In water; at 30 - 40℃; for 0.5h;	To a mixture of 3-chlorotoluene (200 g, 1.58 mol), FeCl3 (9.4 g, 0.06 mol) and CH2Cl2 (1000 mL)stirred at 0~10 C, Br2 (500 g, 3.12 mol) was added slowly, during which the produced gas wasabsorbed by 15% NaOH aqueous solution (2000 mL). After 1 h of continued vigorous stirring, water(100 mL) was added and the mixture was adjusted to pH 8.0~10.0 with 10% aqueous NaOH (200 mL).The organic layer was separated and concentrated to dryness under vacuum to give a solid (95.7%, m.p.95~96 C), 426 g of which was added to a mixture of water (2000 mL), pyridine (200 mL) and KOH(112 g, 2.0 mol) and heated. When the interior temperature reached 80 C, KMnO4 (800 g, 5.0 mol) wasadded in portions, and the mixture was refluxed until complete consumption of the KMnO4. Then thesolution was filtered, the precipitate was washed with 10% KOH a.q. (1000 mL). The filtrates werecombined, and then vacuum evaporated to remove the pyridine and form a turbid solution, whichneeded to be filtered again. The fresh filtrate was acidified with concentrated HCl (360 mL) to pH 3~4.Then the precipitate was filtered, dried and crushed (80%, m.p. 170~171 C). A portion (340 g) wasdissolved in 25% NH3-H2O (1700 mL). To the solution, Cu2O was added in batches at 30~40 C. Afterabout 5 h of stirring, the solution without NH3 gas was diluted and acidified. Then the solid was filtered, washed, dried (yield 96%, m.p. 248~249 C) and 250 g was dissolved in 1500 mL of formamide,maintained at 150~170 C for 5 h. The solution was allowed to cool to R.T., and the precipitate wasfiltered and washed to give a white solid (92%, m.p. 306~307 C). Thus, 2 was succesfully obtained inan overall yield of 67%. IR (KBr), (cm1): 3188.6, 1643.4 (NH), 1680.3 (C=O); ESI-MS (m/z): 256.9[M - H]-, 258.9 [M + 2 - H]; 1H-NMR (300 MHz, DMSO-d6), delta (ppm): 12.50 (br, 1H), 8.15 (s, 1H),8.14 (s, 1H), 8.05 (s, 1H).
	In ammonium hydroxide; ammonia; ethyl acetate;	d 4-bromo-5-chloroanthranilic acid 2.8 g (0.0196 mol) of copper(I) oxide are suspended in 120 ml (corresponding to 1.6 mol of NH3) of 25% aqueous ammonia solution under nitrogen. To this is added dropwise, at 25 C. with stirring and over the course of 40 minutes, a suspension of 63.2 g (0.2 mol) of 5-chloro-2,4-dibromobenzoic acid, 160 ml (corresponding to 2.14 mol of NH3) of 25% strength aqueous ammonia solution and 180 ml of ethyl acetate, with the exclusion of oxygen. The temperature rises to about 35 C. during the addition. Stirring is continued for 21/4 hours at30 C. Finally, 11.6 g (0.04 mol) of ethylenediaminetetraacetic acidis added to the mixture and the pH is adjusted to 3.1 by acidifying with hydrochloric acid. The ethyl acetate is distilled off at 90 C., the suspension is stirred at room temperature, and the anthranilic acid isfiltered off under suction and washed. 48.2 g of 4-bromo-5-chloroanthranilic acid is obtained as a pale-brown powder, corresponding to 96.2% of theory relative to 5-chloro-2,4-dibromobenzoic acid.

References: [1]Molecules,2017,vol. 22.
[2]Patent: US5744638,1998,A .

3
[ 150812-32-1 ]
[ 1260847-61-7 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1033 - 1035.
[2]Patent: WO2015/54572,2015,A1 .
[3]Patent: WO2016/44772,2016,A1 .

4
[ 150812-32-1 ]
C₃₀H₃₁BrClN₃O₁₁ [ No CAS ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1033 - 1035.

5
[ 150812-32-1 ]
C₆₀H₆₂Cl₂N₆O₂₂ [ No CAS ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1033 - 1035.

6
[ 150812-32-1 ]
C₄₄H₄₆Cl₂N₆O₁₄ [ No CAS ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1033 - 1035.

7
[ 150812-32-1 ]
[ 122-51-0 ]
[ 17518-98-8 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1033 - 1035.

8
[ 150812-32-1 ]
4-bromo-5-chloro-2-hydrazinylbenzoic acid hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		Intermediate 29A: 4-Bromo-5-chloro-2-hydrazinylbenzoic acid hydrochloride A solution of sodium nitrite (3.03 g, 43.9 mmol) in water (14.8 mL) was added dropwise to a cooled (-10 C., NaCl-ice bath) suspension of <strong>[150812-32-1]2-amino-4-bromo-5-chlorobenzoic acid</strong> (10.0 g, 39.9 mmol) in 37% aqueous HCl (39.9 mL) and water (13.3 mL), at such rate that the temperature did not exceed 0 C. The resulting suspension was stirred at 0 C. for 15 min, then was treated with a solution of tin(II) chloride hydrate (22.7 g, 120 mmol) in 37% aqueous HCl (17 mL). The resulting mixture was warmed to room temperature and stirred for 60 min. The precipitate was collected by filtration, washed with water and air-dried overnight to give 4-bromo-5-chloro-2-hydrazinylbenzoic acid hydrochloride as an off-white solid (12.86 g, 96% yield). Mass spectrum m/z 365, 267 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta 9.05 (br. s., 1H), 7.95 (s, 1H), 7.55 (s, 1H).

References: [1]Patent: US2014/378475,2014,A1 .Location in patent: Paragraph 0469; 0470.
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 9173 - 9200.

9
[ 150812-32-1 ]
[ 3473-63-0 ]
[ 17518-98-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	In ethanol; for 16h;Reflux;	To a solution of <strong>[150812-32-1]2-amino-4-bromo-5-chlorobenzoic acid</strong> (500 mg,2mmol) in EtOH (20 mL) at RT, formamidine acetate (620 mg, 6 mmol) was added. The mixture was reflux for 16 hour. The mixture was concentrated in vacuo, and the residue was washed by saturated NaHCO3 aqueous solution, and a mixture of ethylacetate/petroleum ether = 1:2. The solid was dried in vacuo to get the product (520 mg, 100% yield) which was used directly in next step without further purification. ESI-MSm/z: 259.0 [M+H].
	In ethanol; for 16h;Reflux;	7-Bromo-6-chloroquinazolin-4-ol To a solution of <strong>[150812-32-1]2-amino-4-bromo-5-chlorobenzoic acid</strong> (500 mg, 2mmol) in EtOH (20 mL) at RT, formamidine acetate (620 mg, 6 mmol) was added. The mixture was reflux for 16 hour. The mixture was concentrated in vacuo, and the residue was washed by saturated NaHCO3 aqueous solution, and a mixture of ethyl acetate/petroleum ether = 1:2. The solid was dried in vacuo to get the product (520 mg, 100% yield) which was used directly in next step without further purification. ESI-MS m/z: 259.0 [M+H]+.

References: [1]Patent: WO2016/44772,2016,A1 .Location in patent: Page/Page column 291; 292.
[2]Patent: WO2015/54572,2015,A1 .Location in patent: Page/Page column 239.

10
[ 150812-32-1 ]
(2-amino-4-bromo-5-chlorophenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In diethyl ether; at 20℃; for 2h;	A suspension of <strong>[150812-32-1]2-amino-4-bromo-5-chlorobenzoic acid</strong> (4.97 g, 19.84 mmol) in dry ethyl ether (20 mL) was added dropwise to an ice cooled solution of lithium aluminum hydride (20 mmol) in dry ethyl ether (100 mL). The mixture was stirred at room temperature for 2 hours. Water (10 mL) was then added dropwise followed by aqueous sodium hydroxide solution (1M, 20 mL). After stirring at room temperature for one hour, the mixture was filtered. Solids were rinsed with EtOAc twice. The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure to afford 4.03 g of crude (2-amino-4-bromo-5-chlorophenyl)methanol (86% yield). 1H NMR (300 MHz, CDCl3): delta ppm 7.13 (s, 1H), 6.94 (br, 1H) 4.61 (s, 2H), 4.24 (br, 2H). LCMS (Method 1): Rt 1.92 min, m/z 237.87 [M+H]+.

References: [1]Patent: US2016/83365,2016,A1 .Location in patent: Paragraph 0655; 0656; 0657.

11
[ 150812-32-1 ]
2-amino-4-bromo-5-chlorobenzaldehyde [ No CAS ]

References: [1]Patent: US2016/83365,2016,A1 .

12
[ 150812-32-1 ]
3-acetyl-7-bromo-6-chloroquinolin-2(1H)-one [ No CAS ]

References: [1]Patent: US2016/83365,2016,A1 .

13
[ 150812-32-1 ]
C₁₅H₁₆BrClN₂O₂S [ No CAS ]

References: [1]Patent: US2016/83365,2016,A1 .

14
[ 150812-32-1 ]
(S)-N-((S)-1-(7-bromo-6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)-2-methylpropane-2-sulfinamide [ No CAS ]

References: [1]Patent: US2016/83365,2016,A1 .

15
[ 150812-32-1 ]
(S)-3-(1-aminoethyl)-7-bromo-6-chloroquinolin-2(1H)-one hydrochloride [ No CAS ]

References: [1]Patent: US2016/83365,2016,A1 .

16
[ 150812-32-1 ]
4-bromo-5-chloro-2-hydrazinylbenzoic acid hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		A solution of sodium nitrite (3.03 g, 43.9 mmol) in water (14.8 mL) was addeddropwise to a suspension of <strong>[150812-32-1]2-amino-4-bromo-5-chlorobenzoic acid</strong> (10.0 g, 39.9 mmol)in 37% aqueous HC1 (39.9 mL) and water (13.3 mL) which was stirred at -10 C on aNaC1-ice bath, at such rate that the temperature did not exceed 0 C. The resultingsuspension was stirred at 0 C for 15 mm, then was treated with a solution of tin(II)chloride hydrate (22.7 g, 120 mmol) in 37% aqueous HC1 (17 mL). The resulting mixture was warmed to room temperature and stirred for 60 mm. The precipitate was collected by filtration, washed with water and air-dried overnight to give 4-bromo-5-chloro-2- hydrazinylbenzoic acid hydrochloride as an off-white solid (12.86 g, 96% yield). Massspectrum m/z 365, 267 (M+H). ?H NMR (400 MHz, DMSO-d6) oe 9.05 (br. s., 1H), 7.95 (s, 1H), 7.55 (s, 1H).

References: [1]Patent: WO2016/65236,2016,A1 .Location in patent: Page/Page column 80.

17
[ 108-41-8 ]
[ 150812-32-1 ]