[ CAS No. 1025113-78-3 ] {[proInfo.proName]}

Name: 1025113-78-3|Potassium trifluoro(5-formylthiophen-2-yl)borate|95%
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Quality Control of [ 1025113-78-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1025113-78-3 ]

CAS No. :	1025113-78-3	MDL No. :	MFCD09800740
Formula :	C₅H₃BF₃KOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XERVPXDMNWPUFB-UHFFFAOYSA-N
M.W :	218.05	Pubchem ID :	45479878
Synonyms :

Safety of [ 1025113-78-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1025113-78-3 ]

* 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 [ 1025113-78-3 ]

[ 1025113-78-3 ] Synthesis Path-Downstream 1~15

1
[ 1025113-78-3 ]
[ 108-91-8 ]
[ 1025113-79-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: potassium (5-formylthiophen-2-yl)trifluoroborate; cyclohexylamine With potassium hydrogen bifluoride In methanol at 20℃; for 2h; Stage #2: With borane pyridine complex In methanol for 16h; Further stages.;

Reference： [1]Molander, Gary A.; Cooper, David J. [Journal of Organic Chemistry, 2008, vol. 73, # 10, p. 3885 - 3891]

2
[ 1025113-78-3 ]
[ 36635-61-7 ]
potassium 5-(2-trifluoroboratothiophen-5-yl)-4-(toluene-4-sulfonyl)-4,5-dihydrooxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With polystyrene-bound 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 12h;

Reference： [1]Molander, Gary A.; Febo-Ayala, Wilma; Jean-Gerard, Ludivine [Organic Letters, 2009, vol. 11, # 17, p. 3830 - 3833]

3
(5-formylthiophen-2-yl)boronic acid [ No CAS ]
[ 1025113-78-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium hydrogenfluoride In methanol; water at 0℃; Inert atmosphere;
82%	With potassium hydrogenfluoride In methanol; water
	With potassium hydrogenfluoride In methanol; water at 12℃; for 20h;	1 [0134] Potassium trifluoro(5-formylthiophen-2-yl)borate [0135] 5-formyl-2-thienylboronic acids (7.6 g, 49 mmol) was dispersed in [MeOH:H20 (4: l)(250 mL)] then KHF2 (11.5 g, 147 mmol) was added. The reaction mixture was stirred for 12 hours at room temperature then concentrated in vacuo to provide a grey solid that was carried on directly to the next reaction.

Reference： [1]Molander, Gary A.; Febo-Ayala, Wilma; Jean-Gerard, Ludivine [Organic Letters, 2009, vol. 11, # 17, p. 3830 - 3833]
[2]Location in patent: experimental part Oliveira, Roberta A.; Silva, Ricardo O.; Molander, Gary A.; Menezes, Paulo H. [Magnetic Resonance in Chemistry, 2009, vol. 47, # 10, p. 873 - 878]
[3]Current Patent Assignee: INDIANA UNIVERSITY - WO2019/157233, 2019, A1 Location in patent: Paragraph 0134-0136

4
[ 1025113-78-3 ]
(5-formylthiophen-2-yl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With water; silica gel at 20℃; for 24h; Inert atmosphere;

Reference： [1]Molander, Gary A.; Cavalcanti, Livia N.; Canturk, Belgin; Pan, Po-Shen; Kennedy, Lauren E. [Journal of Organic Chemistry, 2009, vol. 74, # 19, p. 7364 - 7369]

5
[ 1025113-78-3 ]
[ 496-72-0 ]
[ 1393649-71-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium hydrogenfluoride; oxygen / ethanol; water; acetonitrile / 0.04 h / 760.05 Torr / Saturated solution 1.2: 24 h / 40 °C 2.1: palladium diacetate; triethylamine; XPhos / ethanol / 16 h / 85 °C / Inert atmosphere

Reference： [1]Molander, Gary A.; Ajayi, Kehinde [Organic Letters, 2012, vol. 14, # 16, p. 4242 - 4245]

6
[ 1025113-78-3 ]
[ 496-72-0 ]
C₁₂H₉BF₃N₂S^(1-)*K⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-methyl-1,2-diaminobenzene With potassium hydrogenfluoride; oxygen In ethanol; water; acetonitrile for 0.0388889h; Saturated solution; Stage #2: potassium (5-formylthiophen-2-yl)trifluoroborate In ethanol; water; acetonitrile at 40℃; for 24h;

Reference： [1]Molander, Gary A.; Ajayi, Kehinde [Organic Letters, 2012, vol. 14, # 16, p. 4242 - 4245]

7
potassium hydrogen difluoride [ No CAS ]
(5-formylthiophen-2-yl)boronic acid [ No CAS ]
[ 1025113-78-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	With water In methanol at 0 - 20℃; for 0.5h; Inert atmosphere;

Reference： [1]Petruzziello, Diego; Gualandi, Andrea; Jaffar, Hamza; Lopez-Carrillo, Veronica; Cozzi, Pier Giorgio [European Journal of Organic Chemistry, 2013, # 22, p. 4909 - 4917]

8
[ 53595-65-6 ]
[ 1025113-78-3 ]
[ 1620108-85-1 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 7243 - 7249

9
[ 1025113-78-3 ]
C₁₂H₁₄INO₂ [ No CAS ]
3-(6-(5-formylthiophen-2-yl)-3,4-dihydroquinolin-1(2H)-yl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate In ethanol
7.58 g	With palladium diacetate; caesium carbonate In ethanol Reflux;	1 [0136] 3-(6-(5-formylthiophen-2-yl)-3,4-dihydroquinolin-l(2//)-yl)propanoic acid (5) [0138] The following procedure was adapted from previously published literature (Shao et al. (2011)). To a solution of 4 (15.2 g, 44 mmol) in [THF :MeOH:H20 (2:2: l)(375 mL)] at 0 °C was added LiOHTT20 (2 g, 48 mmol). The reaction mixture was closely monitored by TLC, and upon consumption of starting material was immediately quenched by the addition of 0.5 M HC1 (100 mL) and the reaction solvents were removed in vacuo. The residue was re-constituted with EtOAc (200 mL) and the organic extract was washed with water (100 mL) and brine (100 mL) then dried over MgS04. The organic solution was concentrated in vacuo to a beige solid (13.5 g, 40 mmol, 92% yield) which was submitted directly to the next reaction. ESI MS m/z (M+H) found 332.0. To the potassium organotrifluoroborate salt was added the beige solid intermediate (13.5 g, 40 mmol) and EtOH (200 mL), followed by CS2CO3 (31.8 mL, 98 mmol) and Pd(OAc)2 (90 mg, 0.4 mmol). The reaction mixture was heated to reflux (120 °C) until the starting material was consumed, as indicated by TLC. The reaction mixture was concentrated in vacuo , diluted with CH2Cl2 (300 mL), and then slowly quenched by the addition of 8 M HC1 (150 mL). The organic layer was washed with water (200 mL), brine (200 mL), then dried over MgS04 and concentrated under reduced pressure. The residue was purified by flash column chromatography to provide an orange solid (7.58 g, 24 mmol, 60 % yield). 1H NMR (400 MHz, Chloroform-if) d 9.81 (s, 1H), 7.66 (d, J= 4.0 Hz, 1H), 7.39 (d, J = 8.9 Hz, 1H), 7.28 (s, 1H), 7.21 (d, = 4.0 Hz, 1H), 6.61 (d, J= 8.6 Hz, 1H), 4.15 (q, j = 7.1 Hz, 2H), 3.66 (t, J= 7.2 Hz, 2H), 3.36 (t, J= 5.6 Hz, 2H), 2.78 (t, J= 6.4 Hz, 2H), 2.61 (t, J= 7.1 Hz, 2H), 1.96 (p, J= 6.0 Hz, 2H), 1.27 (t, 3H); 13C NMR (126 MHz, DMSO) d 183.03, 173.18, 154.91, 145.82, 139.69, 139.04, 126.80, 125.52, 122.49, 121.80, 119.40, 110.43, 48.71, 46.47, 30.92, 27.35, 21.31. ESI MS [M+H] 316.1. Rf= 0.4 [Hexane: (EtOAc:EtOH(3: 1)2% AcOH}(2: l)]; TOF-HRMS (ES+) m/z (M+l) calculated for 316.0963, found: 316.1005.

Reference： [1]Hsu, Yen-Pang; Hall, Edward; Booher, Garrett; Murphy, Brennan; Radkov, Atanas D.; Yablonowski, Jacob; Mulcahey, Caitlyn; Alvarez, Laura; Cava, Felipe; Brun, Yves V.; Kuru, Erkin; VanNieuwenhze, Michael S. [Nature Chemistry, 2019, vol. 11, # 4, p. 335 - 341]
[2]Current Patent Assignee: INDIANA UNIVERSITY - WO2019/157233, 2019, A1 Location in patent: Paragraph 0136-0138

10
[ 1025113-78-3 ]
(E)-3-(6-(5-(3-(tert-butoxy)-2-cyano-3-oxoprop-1-en-1-yl)thiophen-2-yl)-3,4-dihydroquinolin-1(2H)-yl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; palladium diacetate / ethanol / Reflux 2: pyridine; piperidine / 18 h / 90 °C