[ CAS No. 1544739-25-4 ]

Name: 1544739-25-4|2-(3-(Bromomethyl)-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|97%
Brand: Ambeed
SKU: A534764
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Quality Control of [ 1544739-25-4 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 1544739-25-4 ]

Product Details of [ 1544739-25-4 ]

CAS No. :	1544739-25-4	MDL No. :	MFCD23098825
Formula :	C₁₃H₁₇BBrFO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	314.99	Pubchem ID :	-
Synonyms :

Computed Properties of [ 1544739-25-4 ]

TPSA :Topological Polar Surface Area	-	H-Bond Acceptor Count :	-
XLogP3 :	-	H-Bond Donor Count :	-
SP3 :	-	Rotatable Bond Count :	-

Safety of [ 1544739-25-4 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501	UN#:	1759
Hazard Statements:	H302-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1544739-25-4 ]

Downstream synthetic route of [ 1544739-25-4 ]

[ 1544739-25-4 ] Synthesis Path-Downstream 1~6

1
[ 1544739-07-2 ]
[ 1544739-25-4 ]
[ 1544739-24-3 ]

Yield	Reaction Conditions	Operation in experiment
	With silver carbonate In toluene at 110℃; Inert atmosphere;	2-4.C Step C: 4- [2-Fluoro-5 -(4,4,5,5 -tetramethyl- [1,3,21 dioxaborolan-2-yl)-benzyloxyl -1,1 a,6,6a- tetrahydro-3-aza -cyclopropa[alindene-1-carboxylic acid ethyl ester (2-4) Step C: 4- [2-Fluoro-5 -(4,4,5,5 -tetramethyl- [1,3,21 dioxaborolan-2-yl)-benzyloxyl -1,1 a,6,6a- tetrahydro-3-aza -cyclopropa[alindene-1-carboxylic acid ethyl ester (2-4)To a stirred solution of compound 2-3 (863 mg, 2.74 mmol) and 1-9 (500 mg, 2.28 mmol) intoluene (35 mL), was added Ag2CO3 (1.30 g, 4.56 mmol) in one portion. The resulting mixture was heated to 110°C under N2 protection overnight. TLC showed compound 2-3 was consumed.The mixture was filtered, the filtrate was concentrated to afford crude product which waspurified b by column chromatography on silica gel (PE:EA=5:1) to give 2-4. MS (ESI) mlz: 454 (M+Hj. ‘H-NMR (400 MHz, CDC13) ö: 8.10 (s, 1H), 7.93 (d, 1H, J4.0 Hz), 7.72 (t, 1H, J4.0 Hz), 7.06 (t, 1H, J=2.8 Hz), 6.61 (s, 1H), 5.36 (s, 2H), 4.12 (dd, 2H, J=2.0 and 7.2 Hz), 3.23 (dd, 1H, J=6.0 and 12.0 Hz), 2.98 (d, 1H, J=8.8 Hz), 2.88 (d, 1H, J2.8 Hz), 2.43-2.39 (m, 1H), 1.33(s, 12H), 1.26-1.23 (m, 4H).
	With silver carbonate In toluene at 110℃; Inert atmosphere;	2.4.C Step C: 4-[2-Fluoro-5-( 4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-L 1a,6,6atetrahydro-3-aza -cyclopropa[a]indene-1-carboxylic acid ethyl ester (2-4) To a stirred solution of compound 2-3 (863 mg, 2.74 mmol) and 1-9 (500 mg, 2.28 mmol) intoluene (35 mL), was added Ag2C03 (1.30 g, 4.56 mmol) in one portion. The resulting mixturewas heated to 11 0°C under N2 protection overnight. TLC showed compound 2-3 was consumed.5 The mixture was filtered, the filtrate was concentrated to afford crude product which was purifiedb by column chromatography on silica gel (PE:EA=5: 1) to give 2-4. MS (ESI) m/z: 454 (M+H+).1H-NMR (400 MHz, CDCh) 8: 8.10 (s, 1H), 7.93 (d, 1H, J=4.0 Hz), 7.72 (t, 1H, J=4.0 Hz),7.06 (t, 1H, J=2.8 Hz), 6.61 (s, 1H), 5.36 (s, 2H), 4.12 (dd, 2H, J=2.0 and 7.2 Hz), 3.23 (dd, 1H,J=6.0 and 12.0 Hz), 2.98 (d, 1H, J=8.8 Hz), 2.88 (d, 1H, J=2.8 Hz), 2.43-2.39 (m, 1H), 1.33 (s,10 12H), 1.26-1.23 (m, 4H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2014/22528, 2014, A1 Location in patent: Page/Page column 90; 91
[2]Current Patent Assignee: MERCK & CO INC - WO2014/19186, 2014, A1 Location in patent: Page/Page column 76; 77

2
[ 99725-13-0 ]
[ 1544739-25-4 ]

Reference： [1]Patent: WO2014/19186,2014,A1

3
[ 73183-34-3 ]
[ 1544739-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 110 °C / Inert atmosphere 2: phosphorus tribromide / tetrahydrofuran / 1 h / 0 °C

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2014/19186, 2014, A1 Current Patent Assignee: MERCK & CO INC - WO2014/22528, 2014, A1

4
[ 1352733-99-3 ]
[ 1544739-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus tribromide In tetrahydrofuran at 0℃; for 1h;	2-4.B Step B: 2-(3 -Bromomethyl-4-fluoro-phenyl)-4,4,5 ,5 -tetramethyl- [1,3 ,2ldioxaborolane (2-3) Step B: 2-(3 -Bromomethyl-4-fluoro-phenyl)-4,4,5 ,5 -tetramethyl- [1,3 ,2ldioxaborolane (2-3)To a stirred solution of compound 2-2 (7 g, 28 mmol) in THF (80 mL), was added PBr3 (7.6 g,28 mmol) dropwise at 0 °C. The resulting mixture was stirred at 0 °C for lh. H20 (50 mL) was added to the mixture and the resulting mixture was extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to afford crude product, which was purified b by column chromatography on silica gel (PE:EA=20: 1) to give compound 2-3. MS (ESI) mlz: 315, 316 (M+Hj.
	With phosphorus tribromide In tetrahydrofuran at 0℃; for 1h;	2.4.B Step B: 2-(3-Bromomethyl-4-fluoro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2-3) To a stirred solution of compound 2-2 (7 g, 28 mmol) in THF (80 mL), was added PBr3 (7.6 g,15 28 mmol) dropwise at 0 °C. The resulting mixture was stirred at 0 °C for 1h. H20 (50 mL) wasadded to the mixture and the resulting mixture was extracted with EtOAc (50 mL x 3). Thecombined organic layers were washed with brine, dried over Na2S04, and concentrated to affordcrude product, which was purified b by column chromatography on silica gel (PE:EA=20:1) togive compound 2-3. MS (ESI) m/z: 315, 316 (M+H+).
	With bromine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere;	55.A Step A. 2-(3-(bromomethyl)-4-fluorophenyl)-4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolane Step A. 2-(3-(bromomethyl)-4-fluorophenyl)-4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolane A methylene chloride solution of bromine (0.698 M, 3 ml, 2.094 mmol) was added slowly to a solution of (2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)methanol (250 mg, 0.992 mmol), triethylamine (0.15 ml, 1.076 mmol) and triphenylphosphine (547 mg, 2.086 mmol) in dichloromethane (2 ml) at 0°C under N2- The mixture was stirred at RT overnight. The solvent was evaporated. The residue was purified on silica gel using hexane and EtOAc to obtain the title compound. -NMR (500 MHz, CDCI3) δ: 7.84 (dd, 1H), 7.75 (ddd, 1H), 7.06 (dd, 1H), 4.5 (s, 3H), 1.34 (s, 12H).

With bromine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere;

55.A Step A. 2-(3-(bromomethyl)-4-fluorophenyl)-4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolane Step A. 2-(3-(bromomethyl)-4-fluorophenyl)-4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolane A methylene chloride solution of bromine (0.698 M, 3 ml, 2.094 mmol) was added slowly to a solution of (2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)methanol (250 mg, 0.992 mmol), triethylamine (0.15 ml, 1.076 mmol) and triphenylphosphine (547 mg, 2.086 mmol) in dichloromethane (2 ml) at 0°C under N2- The mixture was stirred at RT overnight. The solvent was evaporated. The residue was purified on silica gel using hexane and EtOAc to obtain the title compound. -NMR (500 MHz, CDCI3) δ: 7.84 (dd, 1H), 7.75 (ddd, 1H), 7.06 (dd, 1H), 4.5 (s, 3H), 1.34 (s, 12H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2014/22528, 2014, A1 Location in patent: Page/Page column 90
[2]Current Patent Assignee: MERCK & CO INC - WO2014/19186, 2014, A1 Location in patent: Page/Page column 76
[3]Current Patent Assignee: MERCK & CO INC - WO2015/89809, 2015, A1 Location in patent: Page/Page column 95; 96
[4]Current Patent Assignee: MERCK & CO INC - WO2015/95256, 2015, A1 Location in patent: Page/Page column 96

5
[ 1544739-25-4 ]
[ 1544739-49-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine / water; 1,4-dioxane / 0.17 h / 130 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine / water; 1,4-dioxane / 0.17 h / 130 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2014/22528, 2014, A1
[2]Current Patent Assignee: MERCK & CO INC - WO2014/19186, 2014, A1

6
[ 1544739-25-4 ]
[ 1544739-47-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine / water; 1,4-dioxane / 0.17 h / 130 °C / Inert atmosphere; Microwave irradiation 3: sodium hydroxide; water / methanol / 0.5 h / 50 °C
	Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine / water; 1,4-dioxane / 0.17 h / 130 °C / Inert atmosphere; Microwave irradiation 3: water; sodium hydroxide / methanol / 0.5 h / 50 °C

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2014/22528, 2014, A1
[2]Current Patent Assignee: MERCK & CO INC - WO2014/19186, 2014, A1

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H200	Unstable explosive
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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

[ CAS No. 1544739-25-4 ]

Quality Control of [ 1544739-25-4 ]

Related Doc. of [ 1544739-25-4 ]

Product Details of [ 1544739-25-4 ]

Computed Properties of [ 1544739-25-4 ]

Safety of [ 1544739-25-4 ]

Application In Synthesis of [ 1544739-25-4 ]

[ 1544739-25-4 ] Synthesis Path-Downstream 1~6

Related Functional Groups of [ 1544739-25-4 ]

Fluorinated Building Blocks

Bromides

Organoboron

Benzyl bromides

Aryls

Organoboron

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1544739-25-4 ]