[ CAS No. 1315350-04-9 ]

Name: 1315350-04-9|4-Amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile|96%
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Product Details of [ 1315350-04-9 ]

CAS No. :	1315350-04-9	MDL No. :	MFCD12025487
Formula :	C₁₃H₁₇BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	244.10 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 1315350-04-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1315350-04-9 ]

Downstream synthetic route of [ 1315350-04-9 ]

[ 1315350-04-9 ] Synthesis Path-Downstream 1~15

1
[ 1315350-04-9 ]
[ 57486-69-8 ]
[ 1434044-06-0 ]

Yield	Reaction Conditions	Operation in experiment
89%		General procedure: To a 2-5 mL capacity microwave vial was charged <strong>[57486-69-8]methyl 2-(2-bromophenyl)acetate</strong> (0.100g, 0.43 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.115 g, 0.523 mmol)and cesium carbonate (0.280 g, 0.86 mmol) in anhydrous 1,2-dimethoxy ethane (4 mL). Themixture was stirred and degassed with argon for 5 min. To this mixture was added Pd(PPh3)4(25 mg, 0.021 mmol) under argon atmosphere, and purged for 2 min. The tube was sealedand irradiated in microwave at 125 C for 0.5 h (This is the internal temperature of reactionmixture and monitored on the screen through a sensor). The vial was cooled to 0C over aperiod of 15 min, followed by addition of 1M potassium tert-butoxide (0.65 mL, 0.65 mmol)solution in THF. The resulting mixture was stirred for 10 minutes and quenched withsaturated ammonium chloride solution. The mixture was diluted with ethyl acetate (30 mL)and washed with water and brine. The organic layer was dried over anhydrous sodiumsulfate, filtered and concentrated. The residue obtained was purified by flash columnchromatography by eluting with gradient of 2-20% ethyl acetate in hexane to afford the 5Hdibenzo[b,d]azepin-6(7H)-one (4) as off white solid (0.075 g, 82%).

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2916 - 2919

2
C₁₃H₁₇BN₂O₂ [ No CAS ]
[ 25015-63-8 ]
[ 1315350-04-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; N⁴,N⁴,N^4',N^4'-tetramethyl-[2,2'-bipyridine]-4,4'-diamine / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere; Glovebox 2: methanol / tetrahydrofuran / 20 °C / Inert atmosphere; Glovebox

3
[ 873-74-5 ]
[ 1315350-04-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Glovebox 2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; N⁴,N⁴,N^4',N^4'-tetramethyl-[2,2'-bipyridine]-4,4'-diamine / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere; Glovebox 3: methanol / tetrahydrofuran / 20 °C / Inert atmosphere; Glovebox
	Multi-step reaction with 2 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 0.17 h / 80 °C 1.2: 12 h / 80 °C 2.1: chloroform / 1 h / 20 °C

Reference： [1]Preshlock, Sean M.; Plattner, Donald L.; Maligres, Peter E.; Krska, Shane W.; Maleczka Jr., Robert E.; Smith III, Milton R. [Angewandte Chemie - International Edition, 2013, vol. 52, # 49, p. 12915 - 12919][Angew. Chem., 2013, vol. 125, # 49, p. 13153 - 13157,5]
[2]Smith, Milton R.; Bisht, Ranjana; Haldar, Chabush; Pandey, Gajanan; Dannatt, Jonathan E.; Ghaffari, Behnaz; Maleczka, Robert E.; Chattopadhyay, Buddhadeb [ACS Catalysis, 2018, vol. 8, # 7, p. 6216 - 6223]

4
C₁₉H₂₈B₂N₂O₄ [ No CAS ]
[ 1315350-04-9 ]

Yield	Reaction Conditions	Operation in experiment
146 mg	With methanol In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox;

5
[ 1315350-04-9 ]
[ 185739-14-4 ]
4-amino-3-(2,2-difluorovinyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 60℃; for 1h; Inert atmosphere;	1.5.2.ii Step ii): 4-Amino-3-(2,2-difluorovinyl)benzonitrile Step ii): 4-Amino-3-(2,2-difluorovinyl)benzonitrile 4-Amino-3-(4,4,5,5-tetramethyl[l,3,2]dioxaborolan-2-yl)benzonitrile (1 eq, 30.7 mmol) and toluene-4-sulfonic acid 2,2-difluorovinyl ester (1 eq, 7.2 g) are dissolved in a 4: 1 solution of dioxane and water (175 mL). Pd(dba)3 (0.05 eq, 1.4 g), HBF4PCy3 (0.1 eq, 1.1 g) and potassium phosphate (3 eq, 19.6 g) are added, after which the suspension is degassed under nitrogen atmosphere for 10 min and the reaction is brought to 60°C for 1 h. The suspension is then filtered over a Celite pad and concentrated in vacuo. The residue is dissolved in EtOAc and an aq. extraction with sat. NaHCOs and EtOAc (3 x 150 mL) is performed. The combined organics are washed with sat. brine, dried over Na2S04 and concentrated. Purification of the crude through column chromatography (silica, petroleum ether/EtOAc; 95:5 to 90: 10) yields the desired product.

Reference： [1]Current Patent Assignee: GALAPAGOS - WO2017/12647, 2017, A1 Location in patent: Paragraph 0238

6
[ 1315350-04-9 ]
4-amino-3-(2,2-difluoroethyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate; tricyclohexylphosphine tetrafluoroborate / 1,4-dioxane; water / 1 h / 60 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 50 °C / 3750.38 Torr / Inert atmosphere; Sealed tube

Reference： [1]Current Patent Assignee: GALAPAGOS - WO2017/12647, 2017, A1

7
[ 33348-34-4 ]
[ 73183-34-3 ]
[ 1315350-04-9 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 65℃; Inert atmosphere;	1.5.1.i 1.5.1. Step i): 4-Amino-3-(4,4,5,5-tetramethyl[l,3,2]dioxaborolan-2-yl)benzonitrile 1.5.1. Step i): 4-Amino-3-(4,4,5,5-tetramethyl[l,3,2]dioxaborolan-2-yl)benzonitrile PdCl2dppf (0.05 eq, 171 mg), potassium acetate (2 eq, 804 mg), bis(pinacolato)diboron (1.8 eq, 1.88 g) and 4-amino-3-iodobenzonitrile (1 eq, 1.0 g) are dissolved in anhydrous DMSO (10 mL) in a 20 mL microwave tube and the suspension is degassed under nitrogen atmosphere for 10 min. The reaction mixture is brought to 65°C and kept at this temperature under vigorous stirring overnight. After completion of the reaction as shown by LC-MS, the mixture is diluted with water and EtOAc. Extraction with EtOAc (3 x 50 mL) is performed. The combined organics are washed with sat. brine and dried over anhydrous Na2SO (. After concentration under reduced pressure, the crude is used as such in the following step.

Reference： [1]Current Patent Assignee: GALAPAGOS - WO2017/12647, 2017, A1 Location in patent: Paragraph 0237

8
[ 1315350-04-9 ]
C₁₇H₁₀Br₂O₂ [ No CAS ]
C₃₁H₁₆N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With bis-triphenylphosphine-palladium(II) chloride; sodium t-butanolate In toluene at 110℃; for 3h; Inert atmosphere;

Reference： [1]He, Congfa; Wang, Bin; Gao, Mingli; Gu, Zhenhua [Organometallics, 2017, vol. 36, # 5, p. 1073 - 1078]

9
[ 1315350-04-9 ]
3-chloro-5-(trifluoromethyl)-2-vinylpyridine [ No CAS ]
8-cyano-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; chloro(2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl)-palladium(II); potassium hydroxide; XPhos In 1,4-dioxane; water at 110℃; for 16h; Inert atmosphere; Sealed tube;

Reference： [1]Lam, Heather; Tsoung, Jennifer; Lautens, Mark [Journal of Organic Chemistry, 2017, vol. 82, # 12, p. 6089 - 6099]

10
[ 1315350-04-9 ]
2-phenyl-4,5-dihydro-3H-spiro[acenaphthylene-1,3'-indole]-7-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 80 °C / Sealed tube; Inert atmosphere 2.1: hydrogenchloride / water; acetonitrile / 0 °C / Inert atmosphere 2.2: 1 h / 0 - 5 °C / Inert atmosphere 2.3: 0 - 20 °C / Inert atmosphere 3.1: methanol; potassium hydroxide / 80 °C / Inert atmosphere 4.1: palladium diacetate; trifuran-2-yl-phosphane; potassium phosphate; norbornene / tetrahydrofuran; N,N-dimethyl-formamide / 10 h / 65 °C / Glovebox; Sealed tube; Inert atmosphere

Reference： [1]Bai, Lu; Liu, Jingjing; Hu, Wenjie; Li, Kunyu; Wang, Yaoyu; Luan, Xinjun [Angewandte Chemie - International Edition, 2018, vol. 57, # 18, p. 5151 - 5155][Angew. Chem., 2018, vol. 130, # 18]

11
[ 1315350-04-9 ]
C₂₂H₁₅IN₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 80 °C / Sealed tube; Inert atmosphere 2.1: hydrogenchloride / water; acetonitrile / 0 °C / Inert atmosphere 2.2: 1 h / 0 - 5 °C / Inert atmosphere 2.3: 0 - 20 °C / Inert atmosphere

12
[ 1315350-04-9 ]
3-(1H-indol-3-yl)-4-iodobenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 80 °C / Sealed tube; Inert atmosphere 2.1: hydrogenchloride / water; acetonitrile / 0 °C / Inert atmosphere 2.2: 1 h / 0 - 5 °C / Inert atmosphere 2.3: 0 - 20 °C / Inert atmosphere 3.1: methanol; potassium hydroxide / 80 °C / Inert atmosphere

13
[ 1315350-04-9 ]
[ 170456-80-1 ]
C₂₂H₁₇N₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,4-dioxane; water at 80℃; Sealed tube; Inert atmosphere;

14
C₁₁H₁₂B₂N₂O₄ [ No CAS ]
[ 73183-34-3 ]
[ 1315350-04-9 ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform at 20℃; for 1h; regioselective reaction;

Reference： [1]Smith, Milton R.; Bisht, Ranjana; Haldar, Chabush; Pandey, Gajanan; Dannatt, Jonathan E.; Ghaffari, Behnaz; Maleczka, Robert E.; Chattopadhyay, Buddhadeb [ACS Catalysis, 2018, vol. 8, # 7, p. 6216 - 6223]

15
[ 21803-75-8 ]
[ 73183-34-3 ]
[ 1315350-04-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; dichlorobis(trimethylphosphine)nickel; In tetrahydrofuran; at 100℃; for 2h;Inert atmosphere; Sealed tube;	Under an argon atmosphere,4.2 mg (0.015 mmol) of dichlorobis (trimethylphosphine) nickel,63.3 mg (0.5 mmol) of 2-chloro-4-cyanoaniline,152 mg (1.0 mmol) of cesium fluoride,140 mg (0.55 mmol) of 4,4,5,5,4 ', 4', 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2,2,2-trifluoroethoxy) silane and 0.5 mL of tetrahydrofuran were added and sealed,Followed by stirring at 100 C. for 2 hours.After cooling the reaction vessel to room temperature,1 mL of saturated aqueous ammonium chloride solution was added and the mixture was extracted three times with 8 mL of ethyl acetate, and the obtained organic phases were combined. By carrying out vacuum distillation (170-175 C., 3 mm Hg)101 mg (white solid, yield 83%) of 4-cyano-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline was obtained

Reference： [1]Patent: JP5699037,2015,B2 .Location in patent: Paragraph 0131; 0132

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P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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

[ CAS No. 1315350-04-9 ]

Quality Control of [ 1315350-04-9 ]

Related Doc. of [ 1315350-04-9 ]

Product Details of [ 1315350-04-9 ]

Safety of [ 1315350-04-9 ]

Application In Synthesis of [ 1315350-04-9 ]

[ 1315350-04-9 ] Synthesis Path-Downstream 1~15

Related Functional Groups of [ 1315350-04-9 ]

Nitriles

Organoboron

Amines

Aryls

Organoboron

Organoboron

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1315350-04-9 ]