[ CAS No. 342636-66-2 ] {[proInfo.proName]}

Name: 342636-66-2|(4-Fluoro-3,5-dimethylphenyl)boronic acid|98%
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SKU: A714984
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Quality Control of [ 342636-66-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 342636-66-2 ]

Product Details of [ 342636-66-2 ]

CAS No. :	342636-66-2	MDL No. :	MFCD08706256
Formula :	C₈H₁₀BFO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PQIOZTCJOZUCMI-UHFFFAOYSA-N
M.W :	167.97	Pubchem ID :	17750045
Synonyms :

Safety of [ 342636-66-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 342636-66-2 ]

* 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 [ 342636-66-2 ]

[ 342636-66-2 ] Synthesis Path-Downstream 1~17

Yield	Reaction Conditions	Operation in experiment
22%		XXXVIII Methyl 5-Chloro-2-(3,5-dimethyl4-fluorophenyl)-1H-indolebutanoate The 3,5-dimethyl-4-fluorophenylboronic acid is obtained with a yield of 22% by a process analogous to the preparation of the phenylboronic derivatives, namely by successively reacting n-BuLi and then isopropyl borate with 5-bromo-2-fluoro-1,3-dimethylbenzene. NMR (300 MHz, DMSO) δ: 7.95 (s, 1H); 7.50 (d, 2H); 6.50 (s, 1H); 2.20 (s, 3H).

2
[ 342636-66-2 ]
[ 63328-49-4 ]
[ 1043890-88-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With oxygen; copper diacetate; triethylamine In dichloromethane at 20℃; for 87h; Molecular sieves 4Å;	4.a; 5.a To a suspension of (R)- 2-Amino-6-tert-butoxycarbonylamino-hexanoic acid methyl ester (3.000 g, 10.108 mmol), 3,5-dimethyl-4-fluorophenylboronic acid (3.398 g, 20.216 mmol), Cu(OAc)2 (2.019 g, 11.119 mmol), and molecular sieves 4A (7.591 g) in 45 mL of dichloromethane, triethylamine (2.8 mL, 20.216 mmol) was added. After stirring at room temperature under O2 for 87 h, the reaction mixture was filtered through a pad of Celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The product was isolated by Flash chromatography (silica gel) eluting with 0-30 % ethyl acetate/hexanes to give the title compound as colorless oil (3.084 g, 80% yield). LC-MS: tR = 9.8 min; m/z 383 (M+H)+.; (R)-6-tert-Butoxycarbonylamino-2-(4-fluoro-3,5-dimethyl-phenylamino)- hexanoic acid methyl ester (A5)To a suspension of (R)- 2-Amino-6-tert-butoxycarbonylamino-hexanoic acid methyl ester (3.000 g, 10.108 mmol), 3,5-dimethyl-4-fluorophenylboronic acid (3.398 g, 20.216 mmol), Cu(OAc)2 (2.019 g, 11.119 mmol), and molecular sieves 4A (7.591 g) in 45 mL of dichloromethane, was added triethylamine (2.8 mL, 20.216 mmol). After stirring at room temperature under O2 (1 arm) for 87 h, the reaction mixture was filtered through a pad of Celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The product was isolated by Flash column chromatography(silica gel column) eluting with 0-30 % ethyl acetate/hexanes to give the title compound as colorless oil (3.084 g, 80% yield). LC-MS: tR = 9.8 min; m/z 383 (M+H)+.
	With copper diacetate; triethylamine In dichloromethane at 20℃; Molecular sieve;

Reference： [1]Current Patent Assignee: PANTHERA BIOPHARNA; PAN THERA BIOPHARMA - WO2008/94592, 2008, A1 Location in patent: Page/Page column 39-40; 43-44
[2]Location in patent: scheme or table Jiao, Guan-Sheng; Kim, Seongjin; Moayeri, Mahtab; Cregar-Hernandez, Lynne; McKasson, Linda; Margosiak, Stephen A.; Leppla, Stephen H.; Johnson, Alan T. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 22, p. 6850 - 6853]

3
[ 342636-66-2 ]
[ 1043890-95-4 ]
[ 1043890-96-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With oxygen; copper diacetate; triethylamine In dichloromethane at 20℃; for 44h; Molecular sieves 4Å;	6.g To a suspension of crude (R)-methyl 6-(4-fluoro-3-methylbenzyloxy)-2- aminohexanoate (0.128 g, 0.453 mmol), 3,5-dimethyl-4-fluorophenylboronic acid (0.152 g, 0.906 mmol), Cu(OAc)2 (0.090 g, 0.498 mmol), and molecular sieves 4A (0.400 g) in 5 mL of dichloromethane, was added triethylamine (0.13 mL, 0.906 mmol). After stirring at room temperature under O2 (1 arm) for 44 h, the reaction mixture was filtered through a pad of Celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The product was isolated by Flash column chromatography(silica gel column) eluting with 0-30 % ethyl acetate/hexanes to give the title compound as light yellow oil (0.126 g, 68% yield). GC-MS: /R = 7.0 min; m/z 405 (M+).
	With oxygen; copper diacetate; triethylamine In dichloromethane at 20℃; Molecular sieve;

Reference： [1]Current Patent Assignee: PANTHERA BIOPHARNA; PAN THERA BIOPHARMA - WO2008/94592, 2008, A1 Location in patent: Page/Page column 47; 51-52
[2]Kim, Seongjin; Jiao, Guan-Sheng; Moayeri, Mahtab; Crown, Devorah; Cregar-Hernandez, Lynne; McKasson, Linda; Margosiak, Stephen A.; Leppla, Stephen H.; Johnson, Alan T. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 7, p. 2030 - 2033]

4
[ 342636-66-2 ]
D-alanine methyl ester [ No CAS ]
[ 1043890-87-4 ]

Yield	Reaction Conditions	Operation in experiment
38%	With oxygen; copper diacetate; triethylamine In dichloromethane at 20℃; for 39h; Molecular sieves 4Å;	3.a To a suspension of (R)-2-amino-propionic acid methyl ester (0.200 g, 1.940 mmol), 3,5-dimethyl-4-fluorophenylboronic acid (0.652 g, 3.880 mmol), Cu(OAc)2 (0.388 g, 2.134 mmol), and molecular sieves 4A (1.456 g) in 15 mL of dichloromethane, was added triethylamine (0.54 mL, 3.880 mmol). After stirring at room temperature under O2 for 39 h, the reaction mixture was filtered through a pad of Celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The product was isolated by Flash chromatography (silica gel) eluting with 0-30 % ethyl acetate/hexanes to give the title compound as brown oil (0.164 g, 38% yield). LC-MS: fe = 8.1 min; m/z 226 (M+H)+.

Reference： [1]Current Patent Assignee: PANTHERA BIOPHARNA; PAN THERA BIOPHARMA - WO2008/94592, 2008, A1 Location in patent: Page/Page column 37-38

5
[ 342636-66-2 ]
[ 1298130-59-2 ]
(R)-2-(4-fluoro-3,5-dimethylphenylamino)-8-(4-fluoro-3-methylphenyl)octanoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen; copper diacetate; triethylamine In dichloromethane at 20℃; Molecular sieve;

Reference： [1]Kim, Seongjin; Jiao, Guan-Sheng; Moayeri, Mahtab; Crown, Devorah; Cregar-Hernandez, Lynne; McKasson, Linda; Margosiak, Stephen A.; Leppla, Stephen H.; Johnson, Alan T. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 7, p. 2030 - 2033]

6
[ 7397-43-5 ]
[ 7732-18-5 ]
[ 99725-44-7 ]
[ 342636-66-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: 3,5-dimethyl-4-fluoro-1-bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: tri-(tert-butyl)borate In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #3: water With hydrogenchloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere;

Reference： [1]Cui, Lin-Song; Nomura, Hiroko; Geng, Yan; Kim, Jong U.k.; Nakanotani, Hajime; Adachi, Chihaya [Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1571 - 1575][Angew. Chem., 2017, vol. 129, # 6, p. 1593 - 1597]

7
[ 342636-66-2 ]
[ 3842-55-5 ]
2-(4-fluoro-3,5-dimethylphenyl)-4,6-diphenyl-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 60℃; for 8h; Inert atmosphere;

8
[ 342636-66-2 ]
[ 3842-55-5 ]
9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)-2,6-dimethylphenyl)-3,6-dimethyl-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 8 h / 60 °C / Inert atmosphere 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere 2.2: 12 h / 150 °C / Inert atmosphere

9
[ 342636-66-2 ]
[ 1043889-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: oxygen; copper diacetate; triethylamine / dichloromethane / 39 h / 20 °C / Molecular sieves 4Å 2: hydroxylamine; potassium cyanide / tetrahydrofuran; methanol; water / 68 h / 20 °C