[ CAS No. 174672-06-1 ] {[proInfo.proName]}

Name: 174672-06-1|5-chlorobenzo[c][1,2]oxaborol-1(3H)-ol|98%
Brand: Ambeed
SKU: A672694
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Quality Control of [ 174672-06-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 174672-06-1 ]

CAS No. :	174672-06-1	MDL No. :	MFCD18633195
Formula :	C₇H₆BClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HMAFTPZYFJFEHK-UHFFFAOYSA-N
M.W :	168.39	Pubchem ID :	11845944
Synonyms :		Chemical Name :	5-chlorobenzo[c][1,2]oxaborol-1(3H)-ol

Safety of [ 174672-06-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P362+P364-P332+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 174672-06-1 ]

* 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 [ 174672-06-1 ]

[ 174672-06-1 ] Synthesis Path-Downstream 1~27

1
[ CAS Unavailable ]
[ 174672-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In tetrahydrofuran at 30℃;

Reference： [1]Baker, Stephen J.; Zhang, Yong-Kang; Akama, Tsutomu; Lau, Agnes; Zhou, Huchen; Hernandez, Vincent; Mao, Weimin; Alley; Sanders, Virginia; Plattner, Jacob J. [Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4447 - 4450]

2
[ 121-43-7 ]
[ 108-90-7 ]
[ 174672-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Trimethyl borate; chlorobenzene In tetrahydrofuran at -78℃; for 2.5h; Stage #2: With hydrogenchloride at 20℃; Stage #3: With water In hydrogenchloride; methanol Heating / reflux;	4.2.a To a solution of 4 (17.3 mmol) in anhydrous THF (80 mL) at -78° C. under nitrogen was added dropwise tert-BuLi or n-BuLi (11.7 mL) and the solution became brown colored. Then, B(OMe)3 (1.93 mL, 17.3 mmol) was injected in one portion and the cooling bath was removed. The mixture was warmed gradually with stirring for 30 min and then stirred with a water bath for 2 h. After addition of 6N HCl (6 mL), the mixture was stirred overnight at room temperature and about 50% hydrolysis has happened as shown by TLC analysis. The solution was rotary evaporated and the residue was dissolved in MeOH (50 mL) and 6N HCl (4 mL). The solution was refluxed for 1 h and the hydrolysis was completed as indicated by TLC analysis. Rotary evaporation gave a residue which was dissolved in EtOAc, washed with water, dried and then evaporated. The crude product was purified by flash column chromatography over silica gel to provide a solid with 80% purity. The solid was further purified by washing with hexane to afford 7.2 mmol of I.

Reference： [1]Current Patent Assignee: PFIZER INC - US2007/293457, 2007, A1 Location in patent: Page/Page column 41

3
[ 845301-97-5 ]
[ 174672-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C 1.2: (i-PrO)3B / tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C 1.3: aq. HCl / tetrahydrofuran; hexane 2.1: aq. HCl / tetrahydrofuran / 30 °C
	Stage #1: 2-bromo-5-chloro-1-(methoxymethoxymethyl)benzene With tert.-butyl lithium In tetrahydrofuran at -78℃; Stage #2: With Trimethyl borate In tetrahydrofuran for 2.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; methanol; water at 20℃; Heating / reflux;	4.4.2.4.2.a 5-chlorobenzo[c][1,2]oxaborol-1(3H)-ol (C1) To a solution of 4 (17.3 mmol) in anhydrous THF (80 mL) at -78° C. under nitrogen was added dropwise tert-BuLi or n-BuLi (11.7 mL) and the solution became brown colored. Then, B(OMe)3 (1.93 mL, 17.3 mmol) was injected in one portion and the cooling bath was removed. The mixture was warmed gradually with stirring for 30 min and then stirred with a water bath for 2 h. After addition of 6N HCl (6 mL), the mixture was stirred overnight at room temperature and about 50% hydrolysis has happened as shown by TLC analysis. The solution was rotary evaporated and the residue was dissolved in MeOH (50 mL) and 6N HCl (4 mL). The solution was refluxed for 1 h and the hydrolysis was completed as indicated by TLC analysis. Rotary evaporation gave a residue which was dissolved in EtOAc, washed with water, dried and then evaporated. The crude product was purified by flash column chromatography over silica gel to provide a solid with 80% purity. The solid was further purified by washing with hexane to afford 7.2 mmol of I. 5-chlorobenzo[c][1,2]oxaborol-1(3H)-ol (C1) M.p. 142-150° C. MS (ESI): m/z=169 (M+1, positive) and 167 (M-1, negative). HPLC (220 nm): 99% purity. 1H NMR (300 MHz, DMSO-d6): δ 9.30 (s, 1H), 7.71 (d, J=7.8 Hz, 1H), 7.49 (s, 1H), 7.38 (d, J=7.8 Hz, 1H) and 4.96 (s, 2H) ppm.

4
[ 21739-93-5 ]
5-chloro-1,3-dihydro-2,1-benzoxaborol-1-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4447 - 4450
[2]Patent: US2007/286822,2007,A1
[3]Patent: US2007/286822,2007,A1

5
[ 60666-70-8 ]
5-chloro-1,3-dihydro-2,1-benzoxaborol-1-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4447 - 4450
[2]Patent: US2007/286822,2007,A1
[3]Patent: US2007/286822,2007,A1

Yield	Reaction Conditions	Operation in experiment
		1.b b b Preparation of title compound A suspension of anhydrous ferric chloride catalyst (0.75 parts, Fisons) in dry dichloromethane (20 ml) was added at 20° to 25° C. simultaneously with boron tribromide (25 parts, 0.1M, Aldrich) in dry dichloromethane (100 mls) to a stirred suspension of the hydrazide from a) above (10.18 part, 0.033M) in dry dichloromethane (160 mls) under a nitrogen blanket. The reactants were then stirred under reflux and the evolved hydrogen bromide trapped under aqueous sodium hydroxide. After 3 hours stirring at reflux, the reactants were allowed to stand at 20°-25° C. for 48 hours and then stirred under reflux for a further 4 hours. The reaction mass was then cooled and the solvent removed by rotary evaporation. The solid obtained was then stirred under reflux with 2N sodium hydroxide solution (160 ml) for 3 hours.
	With hydrogenchloride In water	1 Step D: Preparation of Compound 1 General procedure: Water and hydrochloric acid (6M, 55 mL) were added to the above intermediate mixture, and the solvent was distilled under reduced pressure until the solvent was reduced by half.After the mixture was extracted with ethyl acetate and water, the organic layer was washed with saturated sodium chloride and dried over anhydrous sodium sulfate.After desolvation by distillation under reduced pressure, the residue was treated with isopropyl ether/hexane to obtain compound 1 (26.9 g, yield 60%) as a white powder,

7
[ 174672-06-1 ]
[ 1285533-36-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With nitric acid at -45℃;	Preparation of benzoxaborole 2h To fuming nitric acid (10 mL, 90%) at -45 °C was added 3H-5-chlorobenzo[c][1,2]oxaborol-1-ol (described in WO2006/089067, 1.4 g, 8.3 mmol) by portion. Stirring was kept for 40 minutes after addition, and then the mixture was poured onto ice/water in a beaker resulting in the product precipitation. The solid was filtered, washed with water until pH is about 7 and dried to give the desired nitro compound as white powder (1.7 g, yield 95%). 1H NMR (300 MHz, DMSO-d6): d 9.67 (s, 1H), 8.35 (s, 1H), 7.92 (s, 1H) and 5.12 (s, 2H).To the mixture of 3H-5-chloro-6-nitrobenzo[c][1,2]oxaborol-1-ol (1.5 g, 7 mmol) in methanol (50 mL) and Raney nickel (2 g) was added hydrazine (3 mL, aqueous solution) dropwise in 1 mL portion during 2h. The mixture was stirred overnight, filtered through Celite and concentrated to give light blue solid that was washed with small amount of ethyl acetate to provide compound 2h as off-white power (1.25 g, yield 97%). LC-MS (ESI) m/z 184 [M+1]+, (calcd MS 183.0). 1H NMR (300 MHz, DMSO-d6): d 9.07 (s, 1H), 7.24 (s, 1H), 7.09 (s, 1H), 5.26 (s, 2H) and 4.80 (s, 2H).

Reference： [1]Li, Xianfeng; Zhang, Suoming; Zhang, Yong-Kang; Liu, Yang; Ding, Charles Z.; Zhou, Yasheen; Plattner, Jacob J.; Baker, Stephen J.; Bu, Wei; Liu, Liang; Kazmierski, Wieslaw M.; Duan, Maosheng; Grimes, Richard M.; Wright, Lois L.; Smith, Gary K.; Jarvest, Richard L.; Ji, Jing-Jing; Cooper, Joel P.; Tallant, Matthew D.; Crosby, Renae M.; Creech, Katrina; Ni, Zhi-Jie; Zou, Wuxin; Wright, Jon [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 7, p. 2048 - 2054]

8
[ 174672-06-1 ]
[ 947165-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: nitric acid / -45 °C 2: hydrazine / methanol; water / 2 h

9
[ 174672-06-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: nitric acid / -45 °C 2: hydrazine / methanol; water / 2 h 3: 20 °C

10
[ 174672-06-1 ]
[ 1287702-36-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 22 h / 50 °C / Inert atmosphere

Reference： [1]Manabe, Kei; Ohba, Mai; Matsushima, Yuji [Organic Letters, 2011, vol. 13, # 9, p. 2436 - 2439]

11
[ 174672-06-1 ]
[ 1287702-38-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 22 h / 50 °C / Inert atmosphere 3: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 50 °C / Inert atmosphere

Reference： [1]Manabe, Kei; Ohba, Mai; Matsushima, Yuji [Organic Letters, 2011, vol. 13, # 9, p. 2436 - 2439]

12
[ 174672-06-1 ]
[ 1287702-40-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 22 h / 50 °C / Inert atmosphere

Reference： [1]Manabe, Kei; Ohba, Mai; Matsushima, Yuji [Organic Letters, 2011, vol. 13, # 9, p. 2436 - 2439]

13
[ 174672-06-1 ]
[ 1287702-42-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 22 h / 50 °C / Inert atmosphere 3: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 50 °C / Inert atmosphere

Reference： [1]Manabe, Kei; Ohba, Mai; Matsushima, Yuji [Organic Letters, 2011, vol. 13, # 9, p. 2436 - 2439]

14
[ 174672-06-1 ]
[ 1287702-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 50 °C / Inert atmosphere 2.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium fluoride; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 22 h / 50 °C / Inert atmosphere 2.2: 22 h / 50 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1.1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 20 °C / Inert atmosphere 2.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 22 h / 50 °C / Inert atmosphere 3.1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 50 °C / Inert atmosphere 4.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium fluoride; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 22 h / 50 °C / Inert atmosphere 4.2: 22 h / 50 °C / Inert atmosphere

Reference： [1]Manabe, Kei; Ohba, Mai; Matsushima, Yuji [Organic Letters, 2011, vol. 13, # 9, p. 2436 - 2439]
[2]Manabe, Kei; Ohba, Mai; Matsushima, Yuji [Organic Letters, 2011, vol. 13, # 9, p. 2436 - 2439]

15
[ 174672-06-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 50 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium fluoride; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 22 h / 50 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 22 h / 50 °C / Inert atmosphere 3: 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate / tetrahydrofuran / 22 h / 50 °C / Inert atmosphere 4: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium fluoride; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 22 h / 50 °C / Inert atmosphere

16
[ 174672-06-1 ]
[ 1287702-40-2 ]
[ 1287702-42-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate In tetrahydrofuran at 50℃; for 22h; Inert atmosphere; chemoselective reaction;

Reference： [1]Manabe, Kei; Ohba, Mai; Matsushima, Yuji [Organic Letters, 2011, vol. 13, # 9, p. 2436 - 2439]

17
[ 174672-06-1 ]
[ 1287702-42-4 ]
[ 1287702-12-8 ]
[ 1287702-43-5 ]

Yield	Reaction Conditions	Operation in experiment
34.5 mg	Stage #1: C₂₈H₂₃ClO₄; C₂₁H₁₂B₃F₉O₁₂S₃ With potassium fluoride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran; water at 50℃; for 22h; Inert atmosphere; Stage #2: 5-chloro-1,3-dihydro-2,1-benzoxaborol-1-ol With 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate In tetrahydrofuran at 50℃; for 22h; Inert atmosphere; chemoselective reaction;

Reference： [1]Manabe, Kei; Ohba, Mai; Matsushima, Yuji [Organic Letters, 2011, vol. 13, # 9, p. 2436 - 2439]

18
[ 174672-06-1 ]
[ 107658-28-6 ]
[ 1287702-32-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate In tetrahydrofuran at 20℃; for 22h; Inert atmosphere; chemoselective reaction;

Reference： [1]Manabe, Kei; Ohba, Mai; Matsushima, Yuji [Organic Letters, 2011, vol. 13, # 9, p. 2436 - 2439]

19
[ 913835-76-4 ]
[ 174672-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	Alkaline conditions;

Reference： [1]Current Patent Assignee: BORAGEN - WO2021/21932, 2021, A1 Location in patent: Paragraph 0114; 0115; 0120

20
[ 2596253-30-2 ]
[ 174672-06-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With n-butyllithium In tetrahydrofuran; hexane at -20 - 15℃; Inert atmosphere;	1; 4 Example 4: Continuous flow reaction for synthesis of 5-chlorobenzo[c][1 ,2]oxaborol- 1 (3H)-OI Feedstock A consisted of 2-bromo-5-chlorobenzyl diisopropyl borate dissolved in THF as a 0.3 M solution (601.98 mL, 1.0 eq) and was pumped at 4.0 mL/min.Feedstock B consisted of commercially available 2.5 M n-BuLi (144.48 mL) in hexane and was pumped at 0.96 mL/min. In order to make sure the reactants were sufficiently cooled before mixing, precooling loops were used for both Feedstock A and Feedstock B, which were cooled at -20 °C in PFA 1/8 tubing, and the loop volume was 9.4 ml. and 1 1 .3 mL, respectively. The feedstocks were maintained under an atmosphere of nitrogen, and the system pressure was maintained at 0.1 bar. The residence time for the lithiation step was set to 1 .89 min at -20 °C, and residence time for the borylation step was set to 2.27 min at 15 °C. The collected product stream was cooled to 0°C and adjust to pH = 1 with 2M HCI. The solution was extracted with ethyl acetate (500 ml. x 2) and the combined organic layer was washed with saturated NaCI solution (500 mL), dried with anhydrous Na2SO4 and concentrated under vacuum to give the crude product. The crude product was slurried in heptane (160 mL, 2V) for 5 h to give desired product as white solid (23.0 g, 98.9% purity, yield 75%), which was confirmed by HPLC, LCMS, and 1 HNMR. 1 H NMR (400 MHz, DMSO-d6) d (ppm): 9.30 (s, 1 H), 7.72 (d, J=8.0 Hz, 1 H), 7.51 (s, 1 H), 7.40 (d, J=8.0 Hz, 1 H), 4.98 (s, 2 H).

Reference： [1]Current Patent Assignee: BORAGEN - WO2021/21932, 2021, A1 Location in patent: Paragraph 0104; 0105; 0109-0111

21
[ 635-21-2 ]
[ 174672-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sulfuric acid; sodium nitrite / water / 0.5 h / 0 °C 1.2: 11.5 h / 0 - 90 °C 2.1: dimethylsulfide borane complex / tetrahydrofuran / 12 h / 0 - 25 °C 3.1: toluene / 1 h / 120 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / -20 - 15 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: BORAGEN - WO2021/21932, 2021, A1

22
[ 174672-06-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: Cs₂CO₃; triphenylphosphine; palladium diacetate; tetrabutylammonium bromide / toluene; lithium hydroxide monohydrate / 24 h / Reflux 2: 1H-imidazole / 10 h / 23 °C 3: triethylamine / dichloromethane / 2 h / 23 °C 4: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 2 h / 23 °C 5: triethylamine / dichloromethane / 2 h / 0 °C 6: potassium hydroxide; C₃₉H₃₇F₂N₂O₂⁽¹⁺⁾*Br^(1-) / lithium hydroxide monohydrate / 23 °C

Reference： [1]Du, Ji-Yuan; Balan, Tudor; Claridge, Tim D. W.; Smith, Martin D. [Journal of the American Chemical Society, 2022, vol. 144, # 32, p. 14790 - 14797]

23
[ 174672-06-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Cs₂CO₃; triphenylphosphine; palladium diacetate; tetrabutylammonium bromide / toluene; lithium hydroxide monohydrate / 24 h / Reflux 2: 1H-imidazole / 10 h / 23 °C

Reference： [1]Du, Ji-Yuan; Balan, Tudor; Claridge, Tim D. W.; Smith, Martin D. [Journal of the American Chemical Society, 2022, vol. 144, # 32, p. 14790 - 14797]

24
[ 174672-06-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Cs₂CO₃; triphenylphosphine; palladium diacetate; tetrabutylammonium bromide / toluene; lithium hydroxide monohydrate / 24 h / Reflux 2: 1H-imidazole / 10 h / 23 °C 3: triethylamine / dichloromethane / 2 h / 23 °C

Reference： [1]Du, Ji-Yuan; Balan, Tudor; Claridge, Tim D. W.; Smith, Martin D. [Journal of the American Chemical Society, 2022, vol. 144, # 32, p. 14790 - 14797]

25
[ 174672-06-1 ]
[ 2816110-03-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: Cs₂CO₃; triphenylphosphine; palladium diacetate; tetrabutylammonium bromide / toluene; lithium hydroxide monohydrate / 24 h / Reflux 2: 1H-imidazole / 10 h / 23 °C 3: triethylamine / dichloromethane / 2 h / 23 °C 4: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 2 h / 23 °C

Reference： [1]Du, Ji-Yuan; Balan, Tudor; Claridge, Tim D. W.; Smith, Martin D. [Journal of the American Chemical Society, 2022, vol. 144, # 32, p. 14790 - 14797]

26
[ 174672-06-1 ]
[ 2816109-76-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: Cs₂CO₃; triphenylphosphine; palladium diacetate; tetrabutylammonium bromide / toluene; lithium hydroxide monohydrate / 24 h / Reflux 2: 1H-imidazole / 10 h / 23 °C 3: triethylamine / dichloromethane / 2 h / 23 °C 4: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 2 h / 23 °C 5: triethylamine / dichloromethane / 2 h / 0 °C

Reference： [1]Du, Ji-Yuan; Balan, Tudor; Claridge, Tim D. W.; Smith, Martin D. [Journal of the American Chemical Society, 2022, vol. 144, # 32, p. 14790 - 14797]

27
[ 174672-06-1 ]
[ 57056-93-6 ]
[ 2816110-02-6 ]

Yield	Reaction Conditions	Operation in experiment
40.8%	With tetrabutylammonium bromide; palladium diacetate; Cs₂CO₃; triphenylphosphine In lithium hydroxide monohydrate; toluene for 24h; Reflux;

Reference： [1]Du, Ji-Yuan; Balan, Tudor; Claridge, Tim D. W.; Smith, Martin D. [Journal of the American Chemical Society, 2022, vol. 144, # 32, p. 14790 - 14797]

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P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
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.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
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.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
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
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
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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. 174672-06-1 ] {[proInfo.proName]}

Quality Control of [ 174672-06-1 ]

Related Doc. of [ 174672-06-1 ]

Product Details of [ 174672-06-1 ]

Safety of [ 174672-06-1 ]

Application In Synthesis of [ 174672-06-1 ]

[ 174672-06-1 ] Synthesis Path-Downstream 1~27

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry