[ CAS No. 1159511-89-3 ] {[proInfo.proName]}

Name: 1159511-89-3|5-Bromo-2,4-dimethyl-2H-indazole|95%
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SKU: A205855
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3d Animation Molecule Structure of 1159511-89-3

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Quality Control of [ 1159511-89-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1159511-89-3 ]

SDS Specification

Alternatived Products of [ 1159511-89-3 ]

Product Details of [ 1159511-89-3 ]

CAS No. :	1159511-89-3	MDL No. :	MFCD12028635
Formula :	C₉H₉BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CJUCAYMTGYRYEH-UHFFFAOYSA-N
M.W :	225.09	Pubchem ID :	44119467
Synonyms :

Calculated chemistry of [ 1159511-89-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	53.66
TPSA :	17.82 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) :	-5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.29
Log Po/w (XLOGP3) :	2.63
Log Po/w (WLOGP) :	2.64
Log Po/w (MLOGP) :	2.49
Log Po/w (SILICOS-IT) :	2.54
Consensus Log Po/w :	2.52

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.45
Solubility :	0.0803 mg/ml ; 0.000357 mol/l
Class :	Soluble
Log S (Ali) :	-2.65
Solubility :	0.499 mg/ml ; 0.00222 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.72
Solubility :	0.0429 mg/ml ; 0.000191 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.63

Safety of [ 1159511-89-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1159511-89-3 ]

* 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.

Downstream synthetic route of [ 1159511-89-3 ]

[ 1159511-89-3 ] Synthesis Path-Downstream 1~8

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate at 20℃; for 14.5h;	Preparation 33: 5-Bromo-4-fluoro-2-methyl-2H-indazole General procedure: To a suspension of 5-bromo-4-fluoro-1H-indazole (1.0 g, 4.7 mmol) in EtOAc (20 mL) was added trimethyloxonium tetrafluoroborate (1 .0 g, 7.0 mmol) at room temperature. After stirring at the same temperature for 14.5 h, the mixture was quenched with sat. NaHCO3 aq. and extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Theresidue was purified by column chromatography on silica gel (gradient elution, 0-60% EtOAc/hexane) to give the title compound (0.91 g), MS: [M+H] = 230.

2
[ 1082041-34-6 ]
[ 74-88-4 ]
[ 1159511-80-4 ]
[ 1159511-89-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 37.8% 2: 21.3%	With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 16h;

Reference： [1]Glogowski, Michal P.; Matthews, Jay M.; Lawhorn, Brian G.; Minbiole, Kevin P. C. [Journal of Organic Chemistry, 2021, vol. 86, # 4, p. 3120 - 3137]

3
[ 22364-25-6 ]
[ 1159511-80-4 ]
[ 1159511-89-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium acetate; 18-crown-6 ether; tert.-butylnitrite; acetic anhydride / chloroform / 16 h / 75 °C 1.2: 2 h / 50 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 16 h / 0 - 20 °C

Reference： [1]Glogowski, Michal P.; Matthews, Jay M.; Lawhorn, Brian G.; Minbiole, Kevin P. C. [Journal of Organic Chemistry, 2021, vol. 86, # 4, p. 3120 - 3137]

4
[ 1159511-89-3 ]
[ 2845125-54-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 1 h / 120 °C / Inert atmosphere; Microwave irradiation 2: potassium carbonate; Brettphos Pd G₃ / 1,4-dioxane; water / 100 °C / Sealed tube; Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 1 h / 120 °C / Inert atmosphere; Microwave irradiation; Sealed tube 2: potassium carbonate; BrettPhos Pd G₃ / 1,4-dioxane; water / 100 °C / Sealed tube; Inert atmosphere

Reference： [1]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2022/212819, 2022, A1
[2]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2022/212819, 2022, A1

5
[ 1159511-89-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 1 h / 120 °C / Inert atmosphere; Microwave irradiation 2: potassium carbonate; Brettphos Pd G₃ / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 1 h / 120 °C / Inert atmosphere; Microwave irradiation; Sealed tube 2: potassium carbonate; BrettPhos Pd G₃ / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2022/212819, 2022, A1
[2]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2022/212819, 2022, A1

6
[ 1159511-89-3 ]
[ 2845125-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 1 h / 120 °C / Inert atmosphere; Microwave irradiation 2: potassium carbonate; Brettphos Pd G₃ / 1,4-dioxane; water / 3 h / 100 °C / Sealed tube; Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 1 h / 120 °C / Inert atmosphere; Microwave irradiation; Sealed tube 2: potassium carbonate; BrettPhos Pd G₃ / 1,4-dioxane; water / 3 h / 100 °C / Sealed tube; Inert atmosphere

Reference： [1]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2022/212819, 2022, A1
[2]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2022/212819, 2022, A1

7
[ 1159511-89-3 ]
[ 2845125-25-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 1 h / 120 °C / Inert atmosphere; Microwave irradiation 2: potassium carbonate; Brettphos Pd G₃ / 1,4-dioxane; water / 3 h / 100 °C / Sealed tube; Inert atmosphere 3: lithium aluminium deuteride / tetrahydrofuran / 0.25 h / 20 °C
	Multi-step reaction with 3 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 1 h / 120 °C / Inert atmosphere; Microwave irradiation; Sealed tube 2: potassium carbonate; BrettPhos Pd G₃ / 1,4-dioxane; water / 3 h / 100 °C / Sealed tube; Inert atmosphere 3: lithium aluminium deuteride / tetrahydrofuran / 15 min / 20 °C

Reference： [1]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2022/212819, 2022, A1
[2]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2022/212819, 2022, A1

8
[ 1159511-89-3 ]
[ 73183-34-3 ]
[ 1315335-61-5 ]

Yield	Reaction Conditions	Operation in experiment
34%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 120℃; for 1h; Inert atmosphere; Microwave irradiation;	25 2,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole. 5-Bromo-2,4-dimethyl-2H-indazole (2.00 g, 8.89 mmol, 1 eq), potassium acetate (2.61 g, 26.7 mmol, 3 eq), Pd(dppf)Cl2^DCM (727 mg, 0.89 mmol, 0.1 eq) and bis(pinacolato)diboron (3.38 g, 13.3 mmol, 1.5 eq) were combined in a vial, which was sealed and placed under an inert atmosphere. 1,4-Dioxane (30 mL) was then added via syringe, and the resulting reaction mixture was stirred at 120 °C under microwave irradiation for 1 h, after which time the reaction mixture was filtered through a pad of Celite with DCM, and solvents were concentrated. The crude residue was purified by column chromatography (3-80% EtOAc in hexanes) to give the product, which co-elutes with de-brominated indazole by column chromatography (819 mg, 34%). The product may be purified by recrystallizing from EtOH. ES-MS [M+H]+= 273.2.
34%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 120℃; for 1h; Inert atmosphere; Microwave irradiation;	25 2,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole. 5-Bromo-2,4-dimethyl-2H-indazole (2.00 g, 8.89 mmol, 1 eq), potassium acetate (2.61 g, 26.7 mmol, 3 eq), Pd(dppf)Cl2^DCM (727 mg, 0.89 mmol, 0.1 eq) and bis(pinacolato)diboron (3.38 g, 13.3 mmol, 1.5 eq) were combined in a vial, which was sealed and placed under an inert atmosphere. 1,4-Dioxane (30 mL) was then added via syringe, and the resulting reaction mixture was stirred at 120 °C under microwave irradiation for 1 h, after which time the reaction mixture was filtered through a pad of Celite with DCM, and solvents were concentrated. The crude residue was purified by column chromatography (3-80% EtOAc in hexanes) to give the product, which co-elutes with de-brominated indazole by column chromatography (819 mg, 34%). The product may be purified by recrystallizing from EtOH. ES-MS [M+H]+= 273.2.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 120℃; Inert atmosphere; Microwave irradiation; Sealed tube;	25 2,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole. 5-Bromo-2,4-dimethyl-2H-indazole (2.00 g, 8.89 mmol, 1 eq), potassium acetate (2.61 g, 26.7 mmol, 3 eq), Pd(dppf)Cl2^DCM (727 mg, 0.89 mmol, 0.1 eq) and bis(pinacolato)diboron (3.38 g, 13.3 mmol, 1.5 eq) were combined in a vial, which was sealed and placed under an inert atmosphere. 1,4-Dioxane (30 mL) was then added via syringe, and the resulting reaction mixture was stirred at 120 °C under microwave irradiation for 1 h, after which time the reaction mixture was filtered through a pad of Celite with DCM, and solvents were concentrated. The crude residue was purified by column chromatography (3-80% EtOAc in hexanes) to give the product, which co-elutes with de-brominated indazole by column chromatography (819 mg, 34%). The product may be purified by recrystallizing from EtOH. ES-MS [M+H]+= 273.2.

Reference： [1]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2022/212819, 2022, A1 Location in patent: Paragraph 00354
[2]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2022/212819, 2022, A1 Location in patent: Paragraph 00354
[3]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2022/212819, 2022, A1 Location in patent: Paragraph 00354

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1159511-89-3 ] {[proInfo.proName]}

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[ 1159511-89-3 ] Synthesis Path-Downstream 1~8

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Bromides

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Indazoles

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