[ CAS No. 4363-34-2 ] {[proInfo.proName]}

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Quality Control of [ 4363-34-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4363-34-2 ]

Product Details of [ 4363-34-2 ]

CAS No. :	4363-34-2	MDL No. :	MFCD02258951
Formula :	C₂H₅BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	71.87	Pubchem ID :	-
Synonyms :

Safety of [ 4363-34-2 ]

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Application In Synthesis of [ 4363-34-2 ]

* 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.

Upstream synthesis route of [ 4363-34-2 ]
Downstream synthetic route of [ 4363-34-2 ]

[ 4363-34-2 ] Synthesis Path-Upstream 1~4

1
[ 123-91-1 ]
[ 2005-43-8 ]
[ 4363-34-2 ]
[ 772-03-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate In water	18.2 2-Vinylquinoline A mixture of 2-bromoquinoline (5.00 g, 24.03 mmol), vinylboronic acid (2.07 g, 28.83 mmol), K₂CO₃ (9.96 g, 72.08 mmol) and Pd(dppf)Cl₂ (1.96 g, 2.403 mmol) in water (10 mL) and 1,4-dioxane (30 mL) was stirred at 105° C. overnight. The mixture was diluted with EtOAc (100 mL) and washed with brine (30 mL*4). The organic layer was dried over Na₂SO₄, filtered and concentrated in vacuo. The residue was purified on a silica column (PE/EtOAc=20:1, v/v) to afford the title product as a light orange oil (2.25 g, yield 60percent). LCMS (ESI+): m/z 156 (M+H)⁺, R_t: 1.89 min.

Reference： [1] Patent: US2013/5705, 2013, A1,

2
[ 4363-34-2 ]
[ 6630-33-7 ]
[ 28272-96-0 ]

Reference： [1] European Journal of Organic Chemistry, 2004, # 5, p. 1075 - 1082

3
[ 76-09-5 ]
[ 4363-34-2 ]
[ 75927-49-0 ]

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 15, p. 6031 - 6034

4
[ 4363-34-2 ]
[ 4408-64-4 ]
[ 1104636-73-8 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 17, p. 5300 - 5303

[ 4363-34-2 ] Synthesis Path-Downstream 1~15

1
[ 4363-34-2 ]
[ 5111-65-9 ]
[ 63444-51-9 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 1075 - 1082

2
[ 4363-34-2 ]
[ 586-77-6 ]
[ 2039-80-7 ]

Yield	Reaction Conditions	Operation in experiment
89%	With cis,cis,cis-tetrakis[(diphenylphosphanyl)methyl]cyclopentane; potassium carbonate In xylene at 130℃; for 20h;

Reference： [1]Peyroux, Eugenie; Berthiol, Florian; Doucet, Henri; Santelli, Maurice [European Journal of Organic Chemistry, 2004, # 5, p. 1075 - 1082]

3
[ 4363-34-2 ]
[ 1122-91-4 ]
[ 1791-26-0 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 1075 - 1082

4
[ 573692-58-7 ]
[ 4363-34-2 ]
[ 943138-48-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2817 - 2822

5
[ 4363-34-2 ]
[ 107737-89-3 ]
[ 700870-27-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide;palladium diacetate; triphenylphosphine; In water; acetonitrile; at 70℃; for 20.0833h;	(i) - Vinyl boronate:To a dried Schlenk tube under a positive pressure of argon was added Pd(OAc)2 (4 mg, 0.018 mmol), PPh3 (10 mg, 0.038 mmol) and MeCN (0.5 mL). The mixture was stirred for 5min before the addition of NaOH (120 mg, 3.0 mmol), water (5 mL), MeCN (4.5 mL), 3 (225 mg, 0.85 mmol) and vinylboronate (0.300 mL, 1.7 mmol). The mixture was degassed using the freeze-pump-thaw method (3x) and the stirred mixture heated to 700C under argon. After 20hr the mixture was cooled, diluted with EtOAc (60 mL containing di-tert-butylphenol 0.05 mg/ml) and passed through Celite. The mixture was diluted with water (30 mL), separated, re-extracted with EtOAc (2x30 mL) and the combined organic phase evaporated without drying to give crude product as a viscous yellow oil. 1H NMR spectroscopy indicated 4 to be the major species along with a boronate ester. Purification by silica gel chromatography (EtO Ac/petroleum ether, 3:7) failed to separate the two species.

Reference： [1]Organic process research and development,2009,vol. 13,p. 434 - 441
[2]Patent: WO2007/93772,2007,A1 .Location in patent: Page/Page column 11; 14

6
[ 4363-34-2 ]
[ 22422-34-0 ]
B(OC(CH₃)CH(C(CH₃)2)CH₂CHCH₂CHO)(CHCH₂) [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1990,vol. 398,p. 53 - 57

7
[ 1104636-73-8 ]
[ 7732-18-5 ]
[ 4363-34-2 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963

8
[ 1104636-73-8 ]
[ 4363-34-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 7Synthesis of Boronate Ester 2hS-6 PhMe/DMSO 2h To a solution of S-6 (183 mg, 1 mmol) (Sigma-Aldrich product no. 704415) in THF(10 mL) was added 1 N NaOH (3 mL, 3 mmol) under ambient atmosphere and temperature and stirred vigorously for 15 min. The reaction was quenched with the addition of sat. NH4CI solution (10 mL). The mixture was stirred for 3 min, then transferred to a separatory funnel, rinsing with Et20 (10 mL). After phase separation, the organic phase was washed with another portion of sat. NH4CI solution (10 mL) and the combined aqueous phase extracted with 1 : 1 THF/Et20 (15 mL). The organic phase was dried over MgS04, filtered and concentrated in vacuo to give the boronic acid as a white solid. The solid was taken up in toluene (15 mL) and DMSO (0.75 mL) and la (404 mg, 1.5 mmol) was added. The reaction was heated to reflux with a Dean-Stark trap for 1.5 h. After cooling to room temperature, toluene was removed in vacuo. The residue was taken up in 2: 1EtOAc/acetone (15 mL) and washed twice with 1 : 1 H20/brine (10 mL). The aqueous layers were extracted with 2: 1 EtOAc/acetone (15 mL). The combined organic phase was dried over MgS04, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting first with Et20 then with 1 :4 acetone/Et20 to give a white solid as the pure product (153 mg, 55% over 2 steps).Results. TLC (Hexanes: acetone 3:2) Rf = 0.39, visualized by KMn04; 1H NMR (500 MHz, acetone-de) delta 6.15 (dd, J = 19, 13.5 Hz, 1H), 5.78 (app d, J = 12.5 Hz, 1H), 5.73 (dd, J = 19, 3.5 Hz, 1H), 4.24 (d, J = 18 Hz, 1H), 4.23 (d, J = 15.5 Hz, lH), 4.14 (d, J = 15.5 Hz, 1H), 4.00 (d, J = 18 Hz, 1H), 3.90 (dt, J = 10, 6.5 Hz, 1H), 2.58-2.52 (m, 1H), 2.50-2.41 (m, 2H), 2.00 (sept, J = 3.5 Hz, 1H), 1.92 (ddd, J = 6, 6, 2 Hz, 1H), 1.63 (ddd, J = 15, 6, 2.5 Hz, 1H), 1.35 (d, J = 7 Hz, 3H), 1.25 (s, 3H), 1.06 (d, J = 10 Hz, 1H), 0.98 (s, 1H); 13C NMR (125 MHz, acetone-d6) delta 170.2, 167.8, 130.1, 68.6, 61.0, 55.2, 50.2, 41.6, 39.6, 39.2, 32.3, 31.0, 27.4, 23.6; nB-NMR (100 MHz, acetone-d6) delta 11.3; HRMS (ESI+) Calculated for Ci6H25BN04: 306.1877, Found: 306.1872.

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963
[2]Journal of the American Chemical Society,2011,vol. 133,p. 13774 - 13777
[3]Patent: WO2012/149182,2012,A2 .Location in patent: Page/Page column 146

9
[ 4363-34-2 ]
[ 18995-35-2 ]
4-tert-butoxystyrene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963

10
[ 123-91-1 ]
[ 2005-43-8 ]
[ 4363-34-2 ]
[ 772-03-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate;Pd(dppf)Cl2; In water;	18.2 2-Vinylquinoline A mixture of 2-bromoquinoline (5.00 g, 24.03 mmol), vinylboronic acid (2.07 g, 28.83 mmol), K2CO3 (9.96 g, 72.08 mmol) and Pd(dppf)Cl2 (1.96 g, 2.403 mmol) in water (10 mL) and 1,4-dioxane (30 mL) was stirred at 105 C. overnight. The mixture was diluted with EtOAc (100 mL) and washed with brine (30 mL*4). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified on a silica column (PE/EtOAc=20:1, v/v) to afford the title product as a light orange oil (2.25 g, yield 60%). LCMS (ESI+): m/z 156 (M+H)+, Rt: 1.89 min.

Reference： [1]Patent: US2013/5705,2013,A1

11
[ 55304-75-1 ]
[ 4363-34-2 ]
[ 98-80-6 ]
C₁₄H₁₀F₃N [ No CAS ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1669 - 1672

12
[ 4363-34-2 ]
[ 1007882-59-8 ]
(S)-tert-butyl 2-(5-vinyl-1H-imidazol-2-yl)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; palladium diacetate; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere; Glovebox;

Reference： [1]Tan, Jiajing; Chen, Yonggang; Li, Hongmei; Yasuda, Nobuyoshi [Journal of Organic Chemistry, 2014, vol. 79, # 18, p. 8871 - 8876]

13
[ 16694-17-0 ]
[ 4363-34-2 ]
4-vinylthiophene-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere;	[96] Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed <strong>[16694-17-0]4-bromothiophene-3-carboxylic acid</strong> (900 mg, 4.35 mmol, 1.00 eq.), PdidppflC G bC (357 mg, 0.44 mmol, 0.10 eq.), potassium carbonate (1.8 g, 13.02 mmol, 3.00 eq.), 1,4-dioxane (40 mL),water (4 mL), and ethenylboronic acid (1.566 g, 21.75 mmol, 5.0 eq.). The resulting mixture was stirred overnight at 100 C and then cooled to room temperature. The solid was filtered out. The pH value of the filtrate was adjusted to 5-6 with HC1 (1 N). The resulting solution was extracted with dichloromethane (100 mL x2), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/petroleum ether (0-25%). The collected fraction was concentrated to give 240 mg (36%) of the title compound as a yellow solid. GCMS (ES, m/z): 154.

Reference： [1]Patent: WO2017/205296,2017,A1 .Location in patent: Paragraph 96

14
[ 4363-34-2 ]
[ 4408-64-4 ]
[ 1104636-73-8 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 5300 - 5303

15
[ 4363-34-2 ]
[ 35450-36-3 ]
[ 131001-91-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere;	A mixture of <strong>[35450-36-3]methyl 2-bromo-5-methoxybenzoate</strong> (3.0 g, 12.2 mmol), vinylboronic acid (2.26 g, 14.7 mmol), K2CC>3 (5.08 g, 36.72 mmol) and Pd(dppf)Cl2-DCM (500 mg, 0.61 mmol) in 1,4-dioxane/H2

Reference： [1]Patent: WO2020/2587,2020,A1 .Location in patent: Page/Page column 74

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[ CAS No. 4363-34-2 ] {[proInfo.proName]}

Quality Control of [ 4363-34-2 ]

Related Doc. of [ 4363-34-2 ]

Product Details of [ 4363-34-2 ]

Safety of [ 4363-34-2 ]

Application In Synthesis of [ 4363-34-2 ]

[ 4363-34-2 ] Synthesis Path-Upstream 1~4

[ 4363-34-2 ] Synthesis Path-Downstream 1~15

Precautionary Statements-General

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