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[ CAS No. 1428761-26-5 ]

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DV 2D 3D

3d Animation Molecule Structure of 1428761-26-5

Chemical Structure| 1428761-26-5

Chemical Structure| 1428761-26-5

Structure of 1428761-26-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1428761-26-5 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 1428761-26-5 ]

Product Details of [ 1428761-26-5 ]

CAS No. :	1428761-26-5	MDL No. :	N/A
Formula :	C₁₀H₁₀BrClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	277.54 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 1428761-26-5 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.98
TPSA :	26.3 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) :	-5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.51
Log Po/w (XLOGP3) :	3.39
Log Po/w (WLOGP) :	3.13
Log Po/w (MLOGP) :	3.53
Log Po/w (SILICOS-IT) :	3.85
Consensus Log Po/w :	3.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.82
Solubility :	0.0424 mg/ml ; 0.000153 mol/l
Class :	Soluble
Log S (Ali) :	-3.62
Solubility :	0.0664 mg/ml ; 0.000239 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.73
Solubility :	0.00514 mg/ml ; 0.0000185 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.09

Safety of [ 1428761-26-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P301+P312-P330	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1428761-26-5 ]

* 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 [ 1428761-26-5 ]

[ 1428761-26-5 ] Synthesis Path-Downstream 1~12

1
1-bromo-2-chloro-5-methyl-4-nitrobenzene [ No CAS ]
[ 1428761-26-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 16 h / 90 °C 2: sodium periodate; ruthenium(III) chloride monohydrate; tetra-(n-butyl)ammonium iodide / water; ethyl acetate / 0 - 20 °C 3: thionyl chloride / 4 h / 100 °C 4: sodium tetrahydroborate; nickel (II) chloride hexahydrate / methanol / 40 h / 0 - 20 °C 5: tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(I) bromide / acetonitrile / 20 °C
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 16 h / 90 °C 2.1: ruthenium(III) chloride trihydrate; tetra-(n-butyl)ammonium iodide / ethyl acetate / 0 °C 2.2: 2 h / 20 °C 3.1: thionyl chloride / 4.25 h / 100 °C 4.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / water; methanol / 0.67 h / 0 - 20 °C 5.1: copper(ll) bromide; tert.-butylnitrite; toluene-4-sulfonic acid; tetrabutylammomium bromide / acetonitrile / 4 h / 20 °C

Reference： [1]Current Patent Assignee: AFRAXIS INC - WO2013/43232, 2013, A2
[2]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; AFRAXIS INC - US2013/116263, 2013, A1

2
[ 57310-39-1 ]
[ 1428761-26-5 ]

Reference： [1]Patent: WO2013/43232,2013,A2
[2]Patent: US2013/116263,2013,A1

3
[ 1428761-23-2 ]
[ 1428761-26-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sodium periodate; ruthenium(III) chloride monohydrate; tetra-(n-butyl)ammonium iodide / water; ethyl acetate / 0 - 20 °C 2: thionyl chloride / 4 h / 100 °C 3: sodium tetrahydroborate; nickel (II) chloride hexahydrate / methanol / 40 h / 0 - 20 °C 4: tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(I) bromide / acetonitrile / 20 °C
	Multi-step reaction with 4 steps 1.1: ruthenium(III) chloride trihydrate; tetra-(n-butyl)ammonium iodide / ethyl acetate / 0 °C 1.2: 2 h / 20 °C 2.1: thionyl chloride / 4.25 h / 100 °C 3.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / water; methanol / 0.67 h / 0 - 20 °C 4.1: copper(ll) bromide; tert.-butylnitrite; toluene-4-sulfonic acid; tetrabutylammomium bromide / acetonitrile / 4 h / 20 °C

Reference： [1]Current Patent Assignee: AFRAXIS INC - WO2013/43232, 2013, A2
[2]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; AFRAXIS INC - US2013/116263, 2013, A1

4
[ 1428761-24-3 ]
[ 1428761-26-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / 4 h / 100 °C 2: sodium tetrahydroborate; nickel (II) chloride hexahydrate / methanol / 40 h / 0 - 20 °C 3: tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(I) bromide / acetonitrile / 20 °C
	Multi-step reaction with 3 steps 1: thionyl chloride / 4.25 h / 100 °C 2: nickel(II) chloride hexahydrate; sodium tetrahydroborate / water; methanol / 0.67 h / 0 - 20 °C 3: copper(ll) bromide; tert.-butylnitrite; toluene-4-sulfonic acid; tetrabutylammomium bromide / acetonitrile / 4 h / 20 °C

Reference： [1]Current Patent Assignee: AFRAXIS INC - WO2013/43232, 2013, A2
[2]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; AFRAXIS INC - US2013/116263, 2013, A1

5
[ 1428761-25-4 ]
[ 1428761-26-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium tetrahydroborate; nickel (II) chloride hexahydrate / methanol / 40 h / 0 - 20 °C 2: tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(I) bromide / acetonitrile / 20 °C
	Multi-step reaction with 2 steps 1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / water; methanol / 0.67 h / 0 - 20 °C 2: copper(ll) bromide; tert.-butylnitrite; toluene-4-sulfonic acid; tetrabutylammomium bromide / acetonitrile / 4 h / 20 °C

Reference： [1]Current Patent Assignee: AFRAXIS INC - WO2013/43232, 2013, A2
[2]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; AFRAXIS INC - US2013/116263, 2013, A1

6
[ 1428761-26-5 ]
[ 1432909-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene; tetrahydrofuran; water / 18 h / Reflux; Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene; tetrahydrofuran; water / 18 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; AFRAXIS INC - US2013/116263, 2013, A1

7
[ 1428761-26-5 ]
[ 1432909-88-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: zinc; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1.5 h / 120 °C / Inert atmosphere 2: hydroxylamine hydrochloride; sodium hydrogencarbonate / methanol / 4 h / 70 °C 3: 16 h / Reflux

Reference： [1]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; AFRAXIS INC - US2013/116263, 2013, A1

8
[ 1428761-26-5 ]
[ 1432909-86-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: zinc; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1.5 h / 120 °C / Inert atmosphere 2: hydroxylamine hydrochloride; sodium hydrogencarbonate / methanol / 4 h / 70 °C

Reference： [1]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; AFRAXIS INC - US2013/116263, 2013, A1

9
[ 1428761-26-5 ]
[ 73183-34-3 ]
[ 1432909-81-3 ]

Yield	Reaction Conditions	Operation in experiment
1.2 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In tetrahydrofuran; water; toluene for 18h; Reflux; Inert atmosphere;	7 Step 7: Synthesis of methyl 2-(2-chloro-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (14A) Step 7: Synthesis of methyl 2-(2-chloro-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (14A) A mixture of methyl 2-(4-bromo-2-chloro-5-methylphenyl)acetate (2.7 g, 9.78 mmol, 1 eq), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (3.23 g, 12.72 mmol, 1.3 eq), KOAc (1.92 g, 19.56 mmol, 2 eq) and Pd(dppf)C12 (500 mg) was refluxed in 30 mL of toluene/THF/H2O (0.5 ml/0.5 ml/0.25 ml) under N2 for 18 h. This mixture was filtered and the filtrate was diluted with water (50 mL) and extracted with EtOAc (50 mL*3). The organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give 1.2 g of 14A. 1H NMR (400 MHz, DMSO-d6) d ppm 7.74 (s, 1H), 7.06 (s, 1H), 3.73 (s, 2H), 3.69 (s, 3H), 2.47 (s, 3H), 1.33-1.32 (dd, 12H).

Reference： [1]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; AFRAXIS INC - US2013/116263, 2013, A1 Location in patent: Paragraph 0634

10
[ 1428761-26-5 ]
[ 1692-25-7 ]
[ 1428761-27-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In tetrahydrofuran; water; toluene at 90℃; for 4h; Inert atmosphere;	285.7 Step 7: Synthesis of methyl 2-(2-chloro-5-methyl-4-(pyridin-3-yl) phenyl) acetate (172) A mixture of methyl 2-(4-bromo-2-chloro-5-methylphenyl) acetate (280 mg, 1 mmol, 1.0 eq), pyridin-3-ylboronic acid (140 mg, 1.2 eq), K2C03 (276 mg, 2.0eq), and Pd(dppf)Cl2 in toluene/THF/H20 (5 mL, 2:2: 1 ) was stirred at 90 °C for 4h under N2. Water (30 mL) was added to the reaction mixture. The mixture was extracted with ethyl acetate (3x10ml), dried over Na2S04, filtered and concentrated. The crude material was purifed by silical gel column chromatography (PE: ethyl acetate=10: 1) to afford 172 (210 mg, 76%) as a white solid. LCMS: m/z 276 (M+l)+.

Reference： [1]Current Patent Assignee: AFRAXIS INC - WO2013/43232, 2013, A2 Location in patent: Paragraph 00659

11
[ 192650-79-6 ]
[ 1428761-26-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(I) bromide In acetonitrile at 20℃;	285.6 Step 6: Synthesis of methyl 2-(4-bromo-2-chloro-5-methylphenyl) acetate (171) To a solution of methyl 2-(4-amino-2-chloro-5-methylphenyl)acetate (2.0 g, 4.68 mmol, 1.0 eq), t-BuONO (580 mg, 1.2 eq), p-TsOH (972 mg, 1.2 eq), TBAB (3.0 g, 2.0 eq) in CH3CN (50 mL), was added CuBr (14.4 mg, lmol%). The reaction was stirred at room temperature for 3-4h, then concentrated. The mixture was dissolved in DCM (30 mL), washed with saturated aq NaHC03 (8x20 mL), H20 (2x10 mL), dried over Na2S04, filtered and concentrated to afford 171 (2.2 g), which was used the next step directly without further purification. Ή NMR (400 MHz, CDCb) ppm: 7.54 (s, 1 H), 7.13 (s, 1 H), 3.72 (s, 3H), 3.67 (s, 2H), 2.38 (s, 3H).
1 g	With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide In acetonitrile at 20℃; for 4h;	6 Step 6: Synthesis of methyl 2-(4-bromo-2-chloro-5-methylphenyl)acetate (13A) Step 6: Synthesis of methyl 2-(4-bromo-2-chloro-5-methylphenyl)acetate (13A) CuBr2 (10 mg) was added to a solution of methyl 2-(4-amino-2-chloro-5-methylphenyl)acetate (1.0 g, 4.68 mmol, 1.0 eq), t-BuONO (580 mg, 1.2 eq), p-TsOH (972 mg, 1.2 eq), TBAB (3.0 g, 2.0 eq) in CH3CN (50 ml) and stirred at room temperature for 4 h. The reaction mixture was concentrated, and then dissolved in dichloromethane (30 ml), washed with saturated aq NaHCO3 (20 ml8), H2O (10 ml2), dried over anhydrous Na2SO4, filtered and concentrated to afford 1 g of 13A which was used directly in the next step without further purification.

Reference： [1]Current Patent Assignee: AFRAXIS INC - WO2013/43232, 2013, A2 Location in patent: Paragraph 00658
[2]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; AFRAXIS INC - US2013/116263, 2013, A1 Location in patent: Paragraph 0633

12
[ 557-21-1 ]
[ 1428761-26-5 ]
[ 1432909-85-7 ]

Yield	Reaction Conditions	Operation in experiment
12%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; zinc In N,N-dimethyl-formamide at 120℃; for 1.5h; Inert atmosphere;	1 Step 1: Step 1: Synthesis of methyl 2-(2-chloro-4-cyano-5-methylphenyl)acetate (17A) A mixture of methyl 2-(4-bromo-2-chloro-5-methylphenyl)acetate 16A (4 g, 14.49 mmol, 1 eq), Zn(CN)2 (1.7 g, 14.49 mmol, 1 eq) and Zn (94.2 mg, 1.45 mmol, 0.1 eq) in anhydrous DMF (40 mL) was added Pd(dppf)Cl2 (500 mg) and Pd2(dba)3 (500 mg) under N2. The mixture was stirred at 120° C. for 1.5 h, then cooled to room temperature, diluted with water (50 mL) and extracted with EtOAc (350 mL). The organic layers were combined and washed with water (350 mL), brine (2*50 mL), dried over anhydrous Na2SO4, filtered and concentrated to give a crude product, which was purified by column chromatography with silica gel (PE/ethyl acetate=10:1 to 3:1) to afford 17A (0.4 g, 12%).

Reference： [1]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; AFRAXIS INC - US2013/116263, 2013, A1 Location in patent: Paragraph 0637

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Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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