[ CAS No. 885523-43-3 ] {[proInfo.proName]}

Name: 885523-43-3|4-Bromo-1H-indazole-6-carboxylic acid|95%
Brand: Ambeed
SKU: A217122
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Quality Control of [ 885523-43-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 885523-43-3 ]

SDS Specification

Alternatived Products of [ 885523-43-3 ]

Product Details of [ 885523-43-3 ]

CAS No. :	885523-43-3	MDL No. :	MFCD07781800
Formula :	C₈H₅BrN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PTPANGLJLZZYNH-UHFFFAOYSA-N
M.W :	241.04	Pubchem ID :	24728402
Synonyms :

Calculated chemistry of [ 885523-43-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.75
TPSA :	65.98 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) :	-6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.76
Log Po/w (XLOGP3) :	1.77
Log Po/w (WLOGP) :	2.02
Log Po/w (MLOGP) :	1.46
Log Po/w (SILICOS-IT) :	2.04
Consensus Log Po/w :	1.61

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.9
Solubility :	0.306 mg/ml ; 0.00127 mol/l
Class :	Soluble
Log S (Ali) :	-2.77
Solubility :	0.406 mg/ml ; 0.00168 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.14
Solubility :	0.173 mg/ml ; 0.000719 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.62

Safety of [ 885523-43-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H317-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 885523-43-3 ]

* 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 [ 885523-43-3 ]
Downstream synthetic route of [ 885523-43-3 ]

[ 885523-43-3 ] Synthesis Path-Upstream 1~5

1
[ 885518-47-8 ]
[ 885523-43-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With water; sodium hydroxide In ethanol at 20℃; for 4 h;	4.2.2 4-Bromo-1H-indazole-6-carboxylic acid (14) A mixture of ester 13 (3.38 g, 13.3 mmol) and 15percent aqueous sodium hydroxide (15 mL) in ethanol (30 mL) was stirred at room temperature for 4 h and then concentrated under reduced pressure. The residue was diluted with water, acidified to pH 4 with 1 M hydrochloric acid, and the resulting orange precipitate was collected by filtration and dried in vacuo to give the acid 14 (2.64 g, 83percent) as a pale orange solid; R_f (10percent MeOH/CH₂Cl₂) 0.10; mp 294-296 °C (dec); δ_H (DMSO-d₆): 13.78 (1H, br s), 13.3 (1H, br s). 8.15 (2H, s), 7.80 (1H, d, J 0.5 Hz); δ_C (DMSO-d₆): 166.4, 139.9, 133.4, 129.9, 125.7, 123.0, 113.0, 111.8; m/z (ESI): 240.9 (M[⁷⁹Br]H⁺), 242.9 (M[⁸¹Br]H⁺); HRMS (ESI): M[⁷⁹Br]H⁺, found 240.9607. C₈H₆BrN₂O₂ requires 240.9613.
80%	Stage #1: With water; lithium hydroxide In ethanol at 20℃; for 20 h; Stage #2: With hydrogenchloride In water	A mixture of 4(3.1g,0.012mol) in 50 ml EtOH was treated with LiOH (0.43g,0.018mol)in 10ml water. The reaction mixture was stirred for 20 h at room temperature and then mixture was concentrated under reduced pressure. The residue was diluted with water and PH was adjusted to 4 by the addition of IN HC1. The precipitates was collected by filtration and dried over vacuum to give 5 (2.32g, 80percent)

Reference： [1] Tetrahedron, 2014, vol. 70, # 2, p. 318 - 326
[2] Patent: WO2011/38579, 2011, A1, . Location in patent: Page/Page column 35; 36

2
[ 96-98-0 ]
[ 885523-43-3 ]

Reference： [1] Patent: WO2011/38579, 2011, A1,
[2] Tetrahedron, 2014, vol. 70, # 2, p. 318 - 326

3
[ 34545-20-5 ]
[ 885523-43-3 ]

Reference： [1] Patent: WO2011/38579, 2011, A1,
[2] Tetrahedron, 2014, vol. 70, # 2, p. 318 - 326

4
[ 223519-08-2 ]
[ 885523-43-3 ]

Reference： [1] Patent: WO2011/38579, 2011, A1,
[2] Tetrahedron, 2014, vol. 70, # 2, p. 318 - 326

5
[ 223519-11-7 ]
[ 885523-43-3 ]

Reference： [1] Tetrahedron, 2014, vol. 70, # 2, p. 318 - 326

[ 885523-43-3 ] Synthesis Path-Downstream 1~19

1
[ 27578-60-5 ]
[ 885523-43-3 ]
[ 1285532-19-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20.0℃; for 2.0h;	A mixture of 5 (1.21g 0.005mol),CDI(0.82g 0.005mol), 2-(piperidin-l-yl)ethanamine (0.83g 0.005mol ) and DIPEA (0.65g 0.005mol) was dissolved in 20ml DMF and then stirred for 2 h at room temperature . The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography to give 6 (1.05g)

Reference： [1]Patent: WO2011/38579,2011,A1 .Location in patent: Page/Page column 35; 36

2
[ 96-98-0 ]
[ 885523-43-3 ]

Reference： [1]Patent: WO2011/38579,2011,A1
[2]Tetrahedron,2014,vol. 70,p. 318 - 326

3
[ 34545-20-5 ]
[ 885523-43-3 ]

Reference： [1]Patent: WO2011/38579,2011,A1
[2]Tetrahedron,2014,vol. 70,p. 318 - 326

4
[ 223519-08-2 ]
[ 885523-43-3 ]

Reference： [1]Patent: WO2011/38579,2011,A1
[2]Tetrahedron,2014,vol. 70,p. 318 - 326

5
[ 885518-47-8 ]
[ 885523-43-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With water; sodium hydroxide; In ethanol; at 20℃; for 4h;	4.2.2 4-Bromo-1H-indazole-6-carboxylic acid (14) A mixture of ester 13 (3.38 g, 13.3 mmol) and 15percent aqueous sodium hydroxide (15 mL) in ethanol (30 mL) was stirred at room temperature for 4 h and then concentrated under reduced pressure. The residue was diluted with water, acidified to pH 4 with 1 M hydrochloric acid, and the resulting orange precipitate was collected by filtration and dried in vacuo to give the acid 14 (2.64 g, 83percent) as a pale orange solid; Rf (10percent MeOH/CH2Cl2) 0.10; mp 294-296 °C (dec); deltaH (DMSO-d6): 13.78 (1H, br s), 13.3 (1H, br s). 8.15 (2H, s), 7.80 (1H, d, J 0.5 Hz); deltaC (DMSO-d6): 166.4, 139.9, 133.4, 129.9, 125.7, 123.0, 113.0, 111.8; m/z (ESI): 240.9 (M[79Br]H+), 242.9 (M[81Br]H+); HRMS (ESI): M[79Br]H+, found 240.9607. C8H6BrN2O2 requires 240.9613.
80%		A mixture of 4(3.1g,0.012mol) in 50 ml EtOH was treated with LiOH (0.43g,0.018mol)in 10ml water. The reaction mixture was stirred for 20 h at room temperature and then mixture was concentrated under reduced pressure. The residue was diluted with water and PH was adjusted to 4 by the addition of IN HC1. The precipitates was collected by filtration and dried over vacuum to give 5 (2.32g, 80percent)

Reference： [1]Tetrahedron,2014,vol. 70,p. 318 - 326
[2]Patent: WO2011/38579,2011,A1 .Location in patent: Page/Page column 35; 36

6
[ 885523-43-3 ]
[ 1285532-20-8 ]

Reference： [1]Patent: WO2011/38579,2011,A1

7
[ 885523-43-3 ]
[ 1285531-68-1 ]

Reference： [1]Patent: WO2011/38579,2011,A1

8
[ 223519-11-7 ]
[ 885523-43-3 ]