[ CAS No. 89197-62-6 ] {[proInfo.proName]}

Name: 89197-62-6|5-Fluorobenzofuran-2-carboxylic acid|95%
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Quality Control of [ 89197-62-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 89197-62-6 ]

CAS No. :	89197-62-6	MDL No. :	MFCD09038172
Formula :	C₉H₅FO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HITUZQPFDWNUHA-UHFFFAOYSA-N
M.W :	180.13	Pubchem ID :	10986872
Synonyms :

Safety of [ 89197-62-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89197-62-6 ]

* 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 [ 89197-62-6 ]

[ 89197-62-6 ] Synthesis Path-Downstream 1~28

1
[ 89197-62-6 ]
[ 89197-63-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium amalgam In sodium hydroxide for 2.5h;
	With sodium hydroxide; sodium amalgam; sulfuric acid; sodium; mercury In water	1.b (b) (b) 5-Fluoro-2,3-dihydrobenzofuran-2-carboxylic acid 5-Fluorobenzofuran-2-carboxylic acid (2.4 g) was added to aqueous sodium hydroxide solution (3.3 g of sodium hydroxide in 50 ml of water). Sodium amalgam was added over 20 minutes (prepared from 1.1 g of sodium and 42 g of mercury). After a further 21/2 hours the solution was left to stand over the amalgam overnight. The mercury was separated and the solution filtered and then treated with excess 4 M sulphuric acid. The precipitated acid was filtered off and dried over P2 O5 in vacuo (1.5 g) I.R. νmax 1720 cm-1.

2
[ 93849-31-1 ]
[ 89197-62-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydroxide In methanol; water; N,N-dimethyl-formamide at 20℃;
	With potassium hydroxide In ethanol for 0.75h; Heating; Yield given;
	With sodium hydroxide In water; N,N-dimethyl-formamide at 60℃; for 0.5h;	General procedure: To a solution of intermediates 3a-3q (1mmol) in 10ml DMF, 2.0mL of 20% sodium hydroxide solution was dropped at 60°C to carry out the ester hydrolysis reaction for 30min. Afterwards, the mixture was cooled to room temperature, and the PH value of the solution was adjusted to 2 using 10% hydrochloric acid, then the mixture was extracted with ethyl acetate. The organic phase was combined and condensed by vacuum concentration to afford the crude product, which was purified by recrystallization to give the designed compounds (4a-4q).

Stage #1: ethyl 5-fluoro-1H-benzofuran-2-carboxylate With water; sodium hydroxide In ethanol for 1h; Heating; Stage #2: With hydrogenchloride In ethanol; water

Reference： [1]Wang, Yuqiang; Li, Lianfa; Ye, Wenqing; Tian, Zhiming; Jiang, Wei; Wang, Hong; Wright, Susan C.; Larrick, James W. [Journal of Medicinal Chemistry, 2003, vol. 46, # 4, p. 634 - 637]
[2]Chapleo, Christopher B.; Myers, Peter L.; Butler, Richard C. M.; Davis, John A.; Doxey, John C.; et al. [Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 570 - 576]
[3]Kong, Ling-Yi; Leng, Jia-Fu; Lian, Bao-Ping; Shao, Yu-Ying; Xia, Yuan-Zheng; Yin, Yong [European Journal of Medicinal Chemistry, 2020, vol. 190]
[4]Cao, Zhi-Ling; Liu, Shu-Hao; Liu, Wei-Wei; Liu, Xiu-Jian; Ren, Shu-Ting; Shi, Da-Hua; Wang, Lei; Wang, You-Xian; Wu, Yu-Ran [Heterocyclic Communications, 2019, vol. 25, # 1, p. 162 - 166]

3
[ 71086-99-2 ]
[ 89197-62-6 ]
[ 500536-57-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;

4
[ 89197-62-6 ]
[ 500536-61-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 60 percent / HBTU; diisopropylethylamine / acetonitrile / 20 °C 2: 44 percent / sodium hydroxide / dimethylformamide; methanol; H₂O / 20 °C

5
[ 89197-62-6 ]
5-fluoro-benzofuran-2-carboxylic acid [2-(1-chloromethyl-5-hydroxy-1,2-dihydro-benzo[<i>e</i>]indole-3-carbonyl)-1<i>H</i>-indol-5-yl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 60 percent / HBTU; diisopropylethylamine / acetonitrile / 20 °C 2.1: 44 percent / sodium hydroxide / dimethylformamide; methanol; H₂O / 20 °C 3.1: HCl / ethyl acetate / 20 °C 3.2: 68 percent / EDCI / dimethylformamide / 20 °C

6
[ 174775-48-5 ]
[ 89197-62-6 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 634 - 637

7
[ 347-54-6 ]
[ 89197-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃ / butan-2-one / 4 h / Heating 2: KOH / ethanol / 0.75 h / Heating
	Multi-step reaction with 3 steps 1.1: potassium iodide / N,N-dimethyl-formamide / 0.5 h / 10 °C 1.2: 2 h / 10 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 120 °C 3.1: sodium hydroxide / N,N-dimethyl-formamide; water / 0.5 h / 60 °C
	Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 8 h / Reflux 2.1: sodium hydroxide; water / ethanol / 1 h / Heating 2.2: pH 1

Reference： [1]Chapleo, Christopher B.; Myers, Peter L.; Butler, Richard C. M.; Davis, John A.; Doxey, John C.; et al. [Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 570 - 576]
[2]Kong, Ling-Yi; Leng, Jia-Fu; Lian, Bao-Ping; Shao, Yu-Ying; Xia, Yuan-Zheng; Yin, Yong [European Journal of Medicinal Chemistry, 2020, vol. 190]
[3]Cao, Zhi-Ling; Liu, Shu-Hao; Liu, Wei-Wei; Liu, Xiu-Jian; Ren, Shu-Ting; Shi, Da-Hua; Wang, Lei; Wang, You-Xian; Wu, Yu-Ran [Heterocyclic Communications, 2019, vol. 25, # 1, p. 162 - 166]

8
[ 89197-62-6 ]
[ 93885-40-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 62 percent / sodium amalgam / aq. NaOH / 2.5 h 2: thionyl chloride / benzene / 2.5 h / Heating 3: NH₃ / dioxane / 2 h / Ambient temperature 4: P₂O₅ / toluene / 2 h / Heating

Reference： [1]Chapleo, Christopher B.; Myers, Peter L.; Butler, Richard C. M.; Davis, John A.; Doxey, John C.; et al. [Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 570 - 576]

9
[ 89197-62-6 ]
[ 93885-39-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 62 percent / sodium amalgam / aq. NaOH / 2.5 h 2: thionyl chloride / benzene / 2.5 h / Heating 3: NH₃ / dioxane / 2 h / Ambient temperature

Reference： [1]Chapleo, Christopher B.; Myers, Peter L.; Butler, Richard C. M.; Davis, John A.; Doxey, John C.; et al. [Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 570 - 576]

10
[ 89197-62-6 ]
[ 93849-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 62 percent / sodium amalgam / aq. NaOH / 2.5 h 2: thionyl chloride / benzene / 2.5 h / Heating

Reference： [1]Chapleo, Christopher B.; Myers, Peter L.; Butler, Richard C. M.; Davis, John A.; Doxey, John C.; et al. [Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 570 - 576]

11
[ 89197-62-6 ]
[ 89197-42-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 62 percent / sodium amalgam / aq. NaOH / 2.5 h 2: thionyl chloride / benzene / 2.5 h / Heating 3: NH₃ / dioxane / 2 h / Ambient temperature 4: P₂O₅ / toluene / 2 h / Heating 5: 1.) NaOCH₃ / 1.) CH₃OH, 2 h, 2.) CH₃OH, 0 - 5 deg C, 0.25 h

Reference： [1]Chapleo, Christopher B.; Myers, Peter L.; Butler, Richard C. M.; Davis, John A.; Doxey, John C.; et al. [Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 570 - 576]

12
(S)-2-Amino-4-methyl-pentanoic acid-[3-hydroxy-1-(1-oxy-pyridine-2-sulfonyl)-azepan-4-yl]-amide [ No CAS ]
[ 89197-62-6 ]
5-Fluoro-benzofuran-2-carboxylic acid {(S)-3-methyl-1-[3-hydroxy-1-(1-oxy-pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethanolamine; benzotriazol-1-ol; 1,2-dichloro-ethane In dichloromethane	291.c c. c. 5-Fluoro-benzofuran-2-carboxylic acid {(S)-3-methyl-1-[3-hydroxy-1-(1-oxy-pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide To a solution of the compound of Example 291b (0.30 g) in CH2Cl2 was added 5-fluoro-benzofuran-2-carboxylic acid (0.11 g), EDC (0.13 g), HOBt (0.086 g), and TEA (0.22 mL). The reaction was stirred until complete as determined by LCMS whereupon it was diluted with ethyl acetate and washed with water, sat. K2CO3, 1N HCl, brine, dried (MgSO4), filtered and concentrated. Column chromatography (10% methanol:dichloromethane) of the residue provided 0.27 g of the title compound: MS(ES) 563 (M+H)+.
	With triethanolamine; benzotriazol-1-ol; 1,2-dichloro-ethane In dichloromethane	291.c c.) c.) 5-Fluoro-benzofuran-2-carboxylic acid {(S)-3-methyl-1-[3-hydroxy-1-(1-oxy-pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide To a solution of the compound of Example 291b (0.30 g) in CH2Cl2 was added 5-fluoro-benzofuran-2-carboxylic acid (0.11 g), EDC (0.13 g), HOBt (0.086 g), and TEA (0.22 mL). The reaction was stirred until complete as determined by LCMS whereupon it was diluted with ethyl acetate and washed with water, sat. K2CO3, 1N HCl, brine, dried (MgSO4), filtered and concentrated. Column chromatography (10% methanol:dichloromethane) of the residue provided 0.27 g of the title compound: MS(ES) 563 (M+H)+.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2003/144175, 2003, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2002/147188, 2002, A1

13
[ 89197-62-6 ]
5-fluorobenzofuran-2-carboxamidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		5 5-Fluorobenzofuran-2-carboxamidine EXAMPLE 5 5-Fluorobenzofuran-2-carboxamidine Analogously to Example 1d-f, starting from 5-fluorobenzo-furan-2-carboxylic acid there was obtained 5-fluorobenzofuran-2-carboxamidine hydrochloride as a white solid with m.p. >250°.
		5 5-Fluorobenzofuran-2-carboxamidine Example 5 5-Fluorobenzofuran-2-carboxamidine Analogously to Example 1d-f, starting from 5-fluorobenzofuran-2-carboxylic acid there was obtained 5-fluorobenzofuran-2-carboxamidine hydrochloride as a white solid with m.p. >250°.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US5955495, 1999, A
[2]Current Patent Assignee: ROCHE HOLDING AG - EP906301, 2002, B1

14
[ 347-54-6 ]
[ 685-87-0 ]
[ 89197-62-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 5-fluoro-2-hydroxybenzaldehyde; Diethyl 2-bromomalonate With tetrabutylammomium bromide; potassium carbonate; potassium iodide In toluene at 80℃; for 21h; Stage #2: With potassium hydroxide In ethanol; toluene at 80℃; for 25h;	40 Example 40:5-fluorobenzofuran-2-carboxylic acidOf the preparation To 100 mL of toluene was added sequentially5-fluorosalicylaldehyde (1 g, 7.3 mmol),Potassium carbonate (2 g, 15 mmol), tetrabutylammonium bromide (0.2 g, 0.7 mmol) andPotassium iodide (0.6 g, 3.7 mmol), stirred at 80 ° C,Then, diethyl bromo-malonate (2.6 g, 11 mmol) was added,After heating to reflux, 21 hours later, 3 mL of potassium hydroxide solution was added to the reaction solution,Stirring was continued for 24 hours, cooled to room temperature, the solvent was removed by a rotary evaporator,To the residue was added 1 g of potassium hydroxide and 100 mL of ethanol,The temperature was raised to 80 ° C. After 1 hour, the TLC test showed complete reaction,The solvent was removed using a rotary evaporator, 50 mL of water was added to the residue,Using 2M HCl solution adjusted to PH value of 3, a yellow solid,Filtered and washed with water to give 1.2 g of a pale yellow solid in 91% yield.
	With sulfuric acid; potassium carbonate In butanone	1.a (a) (a) 5-Fluorobenzofuran-2-carboxylic acid 5-Fluorosalicylaldehyde (4.4 g), diethylbromomalonate (11.3 g) and methyl ethyl ketone (35 ml) were stirred together. Anhydrous potassium carbonate (8.7 g) was added and the mixture was heated at reflux for 4 hours. Excess dilute sulphuric acid was added and the mixture was extracted with diethyl ether. The combined extracts were washed with water, dried and evaporated to leave an oil which was treated with 10% w/v ethanolic KOH (60 ml) and heated at reflux for 45 minutes. The solvent was evaporated and the residue treated with excess dilute sulphuric acid and heated briefly on a steam bath. After cooling the crude acid was filtered off. Recrystallisation from ethylacetate/ethanol gave a fawn coloured product (1.1 g), m.p. 261°-266° (decomp), I.R. νmax 1685 cm-1.

Reference： [1]Current Patent Assignee: FUDAN UNIVERSITY - CN107151255, 2017, A Location in patent: Paragraph 0295; 0296; 0297
[2]Current Patent Assignee: PIERRE FABRE PARCIPATIONS - US4411908, 1983, A

15
[ 110857-11-9 ]
[ 89197-62-6 ]
5-fluoro-benzofuran-2-carboxylic acid{(S)-3-methyl-1-[(4S,7R)-7-methyl-3-oxo-1-(1-oxy-pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		24 Preparation of 5-Fluoro-benzofuran-2-carboxylic acid {(S)-3-methyl-1-[(4S,7R)-7-methyl-3-oxo-1-(1-oxy-pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide Example 24 Preparation of 5-Fluoro-benzofuran-2-carboxylic acid {(S)-3-methyl-1-[(4S,7R)-7-methyl-3-oxo-1-(1-oxy-pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide Following the procedure of Example 12 (a-m), except substituting "1-oxy-pyridine-2-sulfonyl chloride" for "pyridine-2-sulfonyl chloride" and "5-Fluoro-benzofuran-2-carboxylic acid" for "quinoline-6-carboxylic acid" gave the title compound: 1H NMR: 8.22 (1H, d), 8.12 (1H, d), 7.32-7.46 (m, 7H), 7.13 (m, 1H), 6.98 (m, 1H), 5.05 (m, 1H), 4.76 (m, 1H), 4.36 (m, 1H), 2.11-2.28 (m, 2H), 1.51-1.78 (m, 3H), 0.99-1.02 (m, 12H); Liquid/Chromatgraphy/Electrospray mass spec: M+H+=575.16.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2004/44201, 2004, A1

16
[ 89197-62-6 ]
[ 174485-72-4 ]
5-fluoro-benzofuran-2-carboxylic acid{(S)-3-methyl-1-[(4S,7R)-7-methyl-3-oxo-1-(5-trifluoromethyl-pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		32 Preparation of 5-Fluoro-benzofuran-2-carboxylic acid {(S)-3-methyl-1-[(4S,7R)-7-methyl-3-oxo-1-(5-trifluoromethyl-pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide Example 32 Preparation of 5-Fluoro-benzofuran-2-carboxylic acid {(S)-3-methyl-1-[(4S,7R)-7-methyl-3-oxo-1-(5-trifluoromethyl-pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide Following the procedure of Example 12 (a-m), except substituting "5-trifluoromethyl-pyridine-2-sulfonyl chloride" for "pyridine-2-sulfonyl chloride" and "5-fluoro-benzofuran-2-carboxylic acid" for "quinoline-6-carboxylic acid" gave the title compound: 1H NMR: 9.0 (s, 1H), 8.20 (d, 1H), 8.12 (d, 1H), 7.40-7.50 (m, 2H), 7.30 (d, 1H), 7.20 (d, 1H), 6.90 (d, 1H), 5.05-5.15 (m, 1H), 4.65-5.75 (m, 2H), 4.40-4.50 (m, 1H), 3.90 (d, 1H), 2.00-2.30 (m, 2H), 1.50-1.80 (m, 5H), 0.95-1.10 (m, 9H); Electrospray mass spec: M+H+=627.2.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2004/44201, 2004, A1

17
[ 1210226-84-8 ]
[ 89197-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In dichloromethane at 0℃; for 3h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Gensini, Martina; Altamura, Maria; Dimoulas, Tula; Fedi, Valentina; Giannotti, Danilo; Giuliani, Sandro; Guidi, Antonio; Harmat, Nicholas J. S.; Meini, Stefania; Nannicini, Rossano; Pasqui, Franco; Tramontana, Manuela; Triolo, Antonio; Maggi, Carlo Alberto [ChemMedChem, 2010, vol. 5, # 1, p. 65 - 78]

18
[ 89197-62-6 ]
5-fluorobenzofuran-2-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Inert atmosphere;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Inert atmosphere;

Reference： [1]Almolhim, Hanan; Bremers, Emily K.; Butler, Joshua H.; Butschek, Grant J.; Carlier, Paul R.; Cassera, Maria B.; Ding, Sha; Merino, Emilio F.; Rizopoulos, Zaira; Slebodnick, Carla; Totrov, Maxim [ACS Medicinal Chemistry Letters, 2022, vol. 13, # 3, p. 371 - 376]
[2]Location in patent: experimental part Gensini, Martina; Altamura, Maria; Dimoulas, Tula; Fedi, Valentina; Giannotti, Danilo; Giuliani, Sandro; Guidi, Antonio; Harmat, Nicholas J. S.; Meini, Stefania; Nannicini, Rossano; Pasqui, Franco; Tramontana, Manuela; Triolo, Antonio; Maggi, Carlo Alberto [ChemMedChem, 2010, vol. 5, # 1, p. 65 - 78]

19
[ 1111942-06-3 ]
[ 89197-62-6 ]
[ 1408251-73-9 ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; Inert atmosphere;

Reference： [1]Mazurov, Anatoly A.; Kombo, David C.; Hauser, Terry A.; Miao, Lan; Dull, Gary; Genus, John F.; Fedorov, Nikolai B.; Benson, Lisa; Sidach, Serguei; Xiao, Yunde; Hammond, Philip S.; James, John W.; Miller, Craig H.; Yohannes, Daniel [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9793 - 9809]

20
[ 89197-62-6 ]
(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride [ No CAS ]
(R)-(1-(5-fluorobenzofuran-2-carboxamido)-3-methylbutyl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: 5-fluorobenzofuran-2-carboxylic acid With benzotriazol-1-ol In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 10h; Stage #3: With hydrogenchloride; Dihydroxy-isobutyl-boran In methanol; hexane; water at 20℃; for 5h;	40 (R) - (1- (5-fluorobenzofuran-2-carboxamido) -3-methylbutyl) boronic acid(Compound II-12) Under nitrogen protection conditions, 5 mL of anhydrous dichloromethane was added5-fluorobenzofuran-2-carboxylic acid (20 mg, 0.11 mmol)After stirring at room temperature, HOBt (18 mg, 0.13 mmol) was added,After stirring for 10 minutes, EDC · HCl (25 mg,0.13 mmol) followed by the addition of compound III-8-a of Example 6(50 mg, 0.17 mmol) and DIPEA (0.04 mL, 0.22 mmol)TLC after 10 hours showed complete reaction,The reaction solution was washed with 5% NaHCO3 solution, 10% citric acid solution,5% NaHCO3 solution and saturated brine,The organic phase was dried over anhydrous sodium sulfate,Drying after filtration, the use of rotary evaporator in addition to solvent,The resulting product was added directly to 5 mL of methanol and stirred at room temperature2-methylpropylboronic acid (22 mg, 0.22 mmol) and 5 mL of n-hexane, Followed by the addition of 1 M HCl solution (0.33 mL, 0.33 mmol)After 5 hours, the TLC assay showed complete reaction, the reaction solution was allowed to stand,The lower layer was washed with n-hexane, dried over anhydrous sodium sulfate,Drying after filtration, the use of rotary evaporator in addition to solvent,Column chromatography (dichloromethane: methanol = 50: 1) gave 17 mg of a yellow solid, The yield was 53%.

Reference： [1]Current Patent Assignee: FUDAN UNIVERSITY - CN107151255, 2017, A Location in patent: Paragraph 0298; 0299; 0300

21
[ 517-89-5 ]
[ 89197-62-6 ]
(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 5-fluorobenzofuran-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29.1%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 8h;	4.1.3 Synthesis of compounds 6a-6q General procedure: Shikonin (1mmol), benzofuran-2-carboxylic acid derivatives (4a-4q) (3mmol), 4-dimethyaminopyridine (0.5mmol), and N, N′- dicyclohexylcarbodiimide (0.5mmol) were suspended in the anhydrous DCM (10ml). The reaction mixture was stirred for 8h under 0°C. Afterwards, the targeted compounds 6a-6q were purified by column chromatography.

Reference： [1]Kong, Ling-Yi; Leng, Jia-Fu; Lian, Bao-Ping; Shao, Yu-Ying; Xia, Yuan-Zheng; Yin, Yong [European Journal of Medicinal Chemistry, 2020, vol. 190]

22
C₁₁H₁₁FO₄ [ No CAS ]
[ 89197-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 120 °C 2: sodium hydroxide / N,N-dimethyl-formamide; water / 0.5 h / 60 °C

Reference： [1]Kong, Ling-Yi; Leng, Jia-Fu; Lian, Bao-Ping; Shao, Yu-Ying; Xia, Yuan-Zheng; Yin, Yong [European Journal of Medicinal Chemistry, 2020, vol. 190]

23
[ 91703-57-0 ]
[ 199620-15-0 ]
[ 89197-62-6 ]

Yield	Reaction Conditions	Operation in experiment
73%	With [2,2]bipyridinyl; water; triethylamine; copper(ll) bromide In <i>tert</i>-butyl alcohol at 90℃; for 8h; Inert atmosphere; Sealed tube;

Reference： [1]Mo, Qinliang; Sun, Nan; Jin, Liqun; Hu, Baoxiang; Shen, Zhenlu; Hu, Xinquan [Journal of Organic Chemistry, 2020, vol. 85, # 17, p. 11490 - 11500]

24
[ 3416-24-8 ]
[ 89197-62-6 ]
5-fluoro-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 5-fluorobenzofuran-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In acetonitrile Stage #2: 2-amino-2-deoxyglucose In acetonitrile for 0.833333h; Heating;

Reference： [1]Cao, Zhi-Ling; Liu, Shu-Hao; Liu, Wei-Wei; Liu, Xiu-Jian; Ren, Shu-Ting; Shi, Da-Hua; Wang, Lei; Wang, You-Xian; Wu, Yu-Ran [Heterocyclic Communications, 2019, vol. 25, # 1, p. 162 - 166]

25
[ 89197-62-6 ]
5-fluoro-N-(4-(hydrazinecarbonyl)benzyl)benzofuran-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 0 °C 2: hydrazine hydrate / methanol / 24 h / Reflux

Reference： [1]Jiang, Yuqi; Xu, Jie; Yue, Kairui; Huang, Chao; Qin, Mengting; Chi, Dongyu; Yu, Qixin; Zhu, Yue; Hou, Xiaohan; Xu, Tongqiang; Li, Min; Chou, C. James; Li, Xiaoyang [Journal of Medicinal Chemistry, 2022, vol. 65, # 1, p. 285 - 302]

26
[ 89197-62-6 ]
5-fluoro-N-(4-(2-propylhydrazine-1-carbonyl)benzyl)-benzofuran-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 0 °C 2.1: hydrazine hydrate / methanol / 24 h / Reflux 3.1: ethanol 3.2: 20 h

27
[ 18469-52-8 ]
[ 89197-62-6 ]
methyl 4-((5-fluorobenzofuran-2-carboxamido)methyl)-benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In dichloromethane at 0℃;

28
[ 89197-62-6 ]
(R)-(1-(4-ethoxyphenyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)(5-fluorobenzofuran-2-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: dmap; triethylamine / dichloromethane / Inert atmosphere 2.2: 48 h / 0 - 20 °C / Inert atmosphere

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Code	Phrase
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P222	Do not allow contact with air.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
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Response
Code	Phrase
P301	IF SWALLOWED:
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P321
P322
P330	Rinse mouth.
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P370	In case of fire:
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P372	Explosion risk in case of fire.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
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P411
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
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P501	Dispose of contents/container to ...
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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) ]}	Inquiry {[ 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. 89197-62-6 ] {[proInfo.proName]}

Quality Control of [ 89197-62-6 ]

Related Doc. of [ 89197-62-6 ]

Product Details of [ 89197-62-6 ]

Safety of [ 89197-62-6 ]

Application In Synthesis of [ 89197-62-6 ]

[ 89197-62-6 ] Synthesis Path-Downstream 1~28

Related Functional Groups of [ 89197-62-6 ]

Fluorinated Building Blocks

Carboxylic Acids

Related Parent Nucleus of [ 89197-62-6 ]

Benzofurans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 89197-62-6 ]

Related Parent Nucleus of
[ 89197-62-6 ]