[ CAS No. 1315692-91-1 ] {[proInfo.proName]}

Name: 1315692-91-1|2,6-Difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|97%
Brand: Ambeed
SKU: A1002457
Rating: 91 (40 reviews)

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2D 3D

Structure of 1315692-91-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1315692-91-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1315692-91-1 ]

SDS Specification

Alternatived Products of [ 1315692-91-1 ]

Product Details of [ 1315692-91-1 ]

CAS No. :	1315692-91-1	MDL No. :	MFCD22419270
Formula :	C₁₂H₁₆BF₂NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MQGLBRAIKSVSIT-UHFFFAOYSA-N
M.W :	255.07	Pubchem ID :	99738339
Synonyms :

Calculated chemistry of [ 1315692-91-1 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	67.24
TPSA :	44.48 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.43
Log Po/w (WLOGP) :	2.69
Log Po/w (MLOGP) :	1.94
Log Po/w (SILICOS-IT) :	1.95
Consensus Log Po/w :	1.8

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.13
Solubility :	0.188 mg/ml ; 0.000736 mol/l
Class :	Soluble
Log S (Ali) :	-3.01
Solubility :	0.251 mg/ml ; 0.000984 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.2
Solubility :	0.0161 mg/ml ; 0.0000631 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.05

Safety of [ 1315692-91-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1315692-91-1 ]

* 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 [ 1315692-91-1 ]

[ 1315692-91-1 ] Synthesis Path-Downstream 1~7

1
[ 1315692-85-3 ]
[ 1315692-91-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 2,2,6,6-tetramethylpiperidinyl-lithium / tetrahydrofuran; hexane / Inert atmosphere; Cooling 2.1: water; ammonium chloride / 0.5 h / 20 °C 3.1: potassium hydroxide / tert-butyl methyl ether; water / Inert atmosphere 3.2: 2 h / Inert atmosphere

Reference： [1]Zhichkin, Paul E.; Krasutsky, Sergiy G.; Beer, Catherine M.; Rennells, W. Martin; Lee, Seung H.; Xiong, Jin-Ming [Synthesis, 2011, # 10, p. 1604 - 1608]

2
[ 76-09-5 ]
C₁₂H₂₀BF₂NO₂Si₂ [ No CAS ]
[ 1315692-91-1 ]

Yield	Reaction Conditions	Operation in experiment
4.8 g	Stage #1: C₁₂H₂₀BF₂NO₂Si₂ With potassium hydroxide In tert-butyl methyl ether; water Inert atmosphere; Stage #2: 2,3-dimethyl-2,3-butane diol In water for 2h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Zhichkin, Paul E.; Krasutsky, Sergiy G.; Beer, Catherine M.; Rennells, W. Martin; Lee, Seung H.; Xiong, Jin-Ming [Synthesis, 2011, # 10, p. 1604 - 1608]

3
C₁₄H₂₆F₂N₂Si₂ [ No CAS ]
[ 1315692-91-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: Heating 2.1: 2,2,6,6-tetramethylpiperidinyl-lithium / tetrahydrofuran; hexane / Inert atmosphere; Cooling 3.1: water; ammonium chloride / 0.5 h / 20 °C 4.1: potassium hydroxide / tert-butyl methyl ether; water / Inert atmosphere 4.2: 2 h / Inert atmosphere

Reference： [1]Zhichkin, Paul E.; Krasutsky, Sergiy G.; Beer, Catherine M.; Rennells, W. Martin; Lee, Seung H.; Xiong, Jin-Ming [Synthesis, 2011, # 10, p. 1604 - 1608]

4
C₁₈H₃₂BF₂NO₂Si₂ [ No CAS ]
[ 1315692-91-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: water; ammonium chloride / 0.5 h / 20 °C 2.1: potassium hydroxide / tert-butyl methyl ether; water / Inert atmosphere 2.2: 2 h / Inert atmosphere

Reference： [1]Zhichkin, Paul E.; Krasutsky, Sergiy G.; Beer, Catherine M.; Rennells, W. Martin; Lee, Seung H.; Xiong, Jin-Ming [Synthesis, 2011, # 10, p. 1604 - 1608]

5
[ 5509-65-9 ]
[ 1315692-91-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: N,N-dimethylammonium chloride; zinc(II) iodide / Inert atmosphere; Heating 2.1: Heating 3.1: 2,2,6,6-tetramethylpiperidinyl-lithium / tetrahydrofuran; hexane / Inert atmosphere; Cooling 4.1: water; ammonium chloride / 0.5 h / 20 °C 5.1: potassium hydroxide / tert-butyl methyl ether; water / Inert atmosphere 5.2: 2 h / Inert atmosphere

Reference： [1]Zhichkin, Paul E.; Krasutsky, Sergiy G.; Beer, Catherine M.; Rennells, W. Martin; Lee, Seung H.; Xiong, Jin-Ming [Synthesis, 2011, # 10, p. 1604 - 1608]

Yield	Reaction Conditions	Operation in experiment
61%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 110℃; for 6h; Inert atmosphere;	A12 Example A1: 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline General procedure: A mixture of potassium acetate (14.4 g, 147 mmol), 5-bromo-2-fluoro-4-methylaniline (10.0 g, 49 mmol), and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (17.4 g, 69 mmol) in 1,4-dioxane (150 mL) was degassed with Ar for 10 min. PdCl2(dppf) (1.79 g, 2.5 mmol) was added and the reaction mixture was heated at 110 C for 6 h. The reaction was cooled to rt and filtered through a pad of celite. The filtrate was removed under reduced pressure and the residue was purified by silica gel column chromatography (0 to 50% EtOAc/hexanes and 1% EtOAc/DCM) to obtain 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (6.2 g, 50% yield) as a tan solid.1H NMR (500 MHz, DMSO-d6): δ 7.12 (d, J = 10.4 Hz, 1H), 6.78 (d, J = 12.8 Hz, 1H), 4.86 (s, 2H), 2.29 (s, 3H), 1.26 (s, 12H); MS (ESI) m/z: 252.2 (M+H+).
61%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 110℃; for 6h; Inert atmosphere;	A12 Example A1: 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline General procedure: A mixture of potassium acetate (14.4 g, 147 mmol), 5-bromo-2-fluoro-4-methylaniline (10.0 g, 49 mmol), and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (17.4 g, 69 mmol) in 1,4-dioxane (150 mL) was degassed with Ar for 10 min. PdCl2(dppf) (1.79 g, 2.5 mmol) was added and the reaction mixture was heated at 110 C for 6 h. The reaction was cooled to rt and filtered through a pad of celite. The filtrate was removed under reduced pressure and the residue was purified by silica gel column chromatography (0 to 50% EtOAc/hexanes and 1% EtOAc/DCM) to obtain 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (6.2 g, 50% yield) as a tan solid.1H NMR (500 MHz, DMSO-d6): δ 7.12 (d, J = 10.4 Hz, 1H), 6.78 (d, J = 12.8 Hz, 1H), 4.86 (s, 2H), 2.29 (s, 3H), 1.26 (s, 12H); MS (ESI) m/z: 252.2 (M+H+).

7
[ 1315692-91-1 ]
[ 1454682-77-9 ]
C₁₅H₁₃F₂N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; for 1h; Inert atmosphere;	D17 Example D1: 2,4-difluoro-5-(isoquinolin-7-yl)aniline General procedure: A solution of 7-chloro-2-methyl-1,6-naphthyridin-3-yl trifluoromethanesulfonate (B27, 3.0 g, 9.2 mmol), 2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A6, 2.2 g, 9.2 mmol) and K2CO3 (3.81 g, 28 mmol) in 1,4-dioxane (15 mL) and water (2.5 mL) was degassed with Ar for 5 min. PdCl2(dppf) (0.34 g, 0.46 mmol) was added and the reaction mixture was heated at 80 C for 1 h. The reaction mixture was cooled to rt and then the solution was filtered through a pad of celite. The filtrate was concentrated under reduced pressure and the crude was purified by silica gel column chromatography (0 to 100% EtOAc/hexanes) to afford 3-(7-chloro-2-methyl-1,6-naphthyridin-3-yl)- 2-fluoroaniline (2.0 g, 76% yield) as a brown solid.1H NMR (500 MHz, DMSO-d6): δ 9.27 (s, 1H), 8.45 (s, 1H), 8.02 (s, 1H), 7.03 (t, J = 7.7 Hz, 1H), 6.90 (t, J = 8.3 Hz, 1H), 6.56 (t, J = 6.9 Hz, 1H), 5.35 (s, 2H); MS (ESI) m/z: 288.0 (M+H+).
61%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; for 1h; Inert atmosphere;	D17 Example D1: 2,4-difluoro-5-(isoquinolin-7-yl)aniline General procedure: A solution of 7-chloro-2-methyl-1,6-naphthyridin-3-yl trifluoromethanesulfonate (B27, 3.0 g, 9.2 mmol), 2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A6, 2.2 g, 9.2 mmol) and K2CO3 (3.81 g, 28 mmol) in 1,4-dioxane (15 mL) and water (2.5 mL) was degassed with Ar for 5 min. PdCl2(dppf) (0.34 g, 0.46 mmol) was added and the reaction mixture was heated at 80 C for 1 h. The reaction mixture was cooled to rt and then the solution was filtered through a pad of celite. The filtrate was concentrated under reduced pressure and the crude was purified by silica gel column chromatography (0 to 100% EtOAc/hexanes) to afford 3-(7-chloro-2-methyl-1,6-naphthyridin-3-yl)- 2-fluoroaniline (2.0 g, 76% yield) as a brown solid.1H NMR (500 MHz, DMSO-d6): δ 9.27 (s, 1H), 8.45 (s, 1H), 8.02 (s, 1H), 7.03 (t, J = 7.7 Hz, 1H), 6.90 (t, J = 8.3 Hz, 1H), 6.56 (t, J = 6.9 Hz, 1H), 5.35 (s, 2H); MS (ESI) m/z: 288.0 (M+H+).

Reference： [1]Current Patent Assignee: DECIPHERA PHARMACEUTICALS LLC - WO2022/109001, 2022, A1 Location in patent: Paragraph 0294-0295
[2]Current Patent Assignee: DECIPHERA PHARMACEUTICALS LLC - WO2022/109001, 2022, A1 Location in patent: Paragraph 0294-0295

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H242	Heating may cause a fire
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H301	Toxic if swallowed
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H401	Toxic to aquatic life
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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. 1315692-91-1 ] {[proInfo.proName]}

Quality Control of [ 1315692-91-1 ]

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Product Details of [ 1315692-91-1 ]

Calculated chemistry of [ 1315692-91-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1315692-91-1 ]

Application In Synthesis of [ 1315692-91-1 ]

[ 1315692-91-1 ] Synthesis Path-Downstream 1~7

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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