[ CAS No. 75927-49-0 ]

Name: 75927-49-0|Pinacol vinylboronate|97% (stablized with PTZ)
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SKU: A469455
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Product Details of [ 75927-49-0 ]

CAS No. :	75927-49-0	MDL No. :	MFCD00192492
Formula :	C₈H₁₅BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	154.01 g/mol	Pubchem ID :	5233012
Synonyms :

Safety of [ 75927-49-0 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P403+P235	UN#:	3272
Hazard Statements:	H225	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 75927-49-0 ]

Upstream synthesis route of [ 75927-49-0 ]
Downstream synthetic route of [ 75927-49-0 ]

[ 75927-49-0 ] Synthesis Path-Upstream 1~7

1
[ 76-09-5 ]
[ 151293-63-9 ]
[ 75927-49-0 ]

Yield	Reaction Conditions	Operation in experiment
252 g	at 85 - 90℃; Inert atmosphere	Under a nitrogen atmosphere, 193 g of pinacol and 14 g of 2,6-di-t-butyl-4-methylphenol were charged in a 1 L reaction flask,To 85-90 ° C, until the pinacol is completely melted, the slow trickle-down of the intermediate reaction, attention to control the dropping rate, then atmospheric steamDistillation device, the reaction of diisopropylamine separation, after the end of the reaction temperature to obtain colorless transparent liquid vinyl boronic acid which252 g of the alcohol ester, and GC: 99.1percent (excluding the polymerization inhibitor).

Reference： [1] Patent: CN105503926, 2016, A, . Location in patent: Paragraph 0018

2
[ 74-85-1 ]
[ 25015-63-8 ]
[ 82954-89-0 ]
[ 75927-49-0 ]

Reference： [1] Journal of the American Chemical Society, 2002, vol. 124, # 20, p. 5624 - 5625
[2] Journal of the American Chemical Society, 2002, vol. 124, # 20, p. 5624 - 5625

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

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

4
[ 623-73-4 ]
[ 75927-49-0 ]
[ 1215107-29-1 ]

Reference： [1] Patent: WO2010/30538, 2010, A2, . Location in patent: Page/Page column 212-213
[2] Patent: WO2011/112186, 2011, A1, . Location in patent: Page/Page column 211-212
[3] Patent: WO2015/52226, 2015, A1, . Location in patent: Paragraph 0187

5
[ 402-43-7 ]
[ 75927-49-0 ]
[ 1242770-50-8 ]

Reference： [1] New Journal of Chemistry, 2017, vol. 41, # 8, p. 3172 - 3176

6
[ 1813-97-4 ]
[ 75927-49-0 ]
[ 1242770-50-8 ]

Reference： [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3328 - 3333

7
[ 392-83-6 ]
[ 75927-49-0 ]
[ 1294009-25-8 ]

Reference： [1] New Journal of Chemistry, 2017, vol. 41, # 8, p. 3172 - 3176

[ 75927-49-0 ] Synthesis Path-Downstream 1~25

1
[ 736991-39-2 ]
[ 75927-49-0 ]
[ 1247002-63-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine;bis(tri-t-butylphosphine)palladium(0); In toluene; at 80℃; for 2h;Inert atmosphere; Autoclave; Microwave irradiation;	Exampel A51. Synthesis of (lR.2S)-(E)-5'-methoxy-2-(3-(4-(2-morpholinoethvnstyryl)- l Eta-indazol-6-yl)spiro[cyclopropane-K3'-indolinl-2'-one 2.2.2-trifluoroacetateA . (E)-4- (4- (2-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)vinyl) phenethyl)morpholineTo a mixture of <strong>[736991-39-2]4-(4-bromophenethyl)morpholine</strong> (731 mg, 2.71 mmol) and4,4,5, 5-tetramethyl-2-vinyl-l ,3,2-dioxaborolane (0.5 mL, 2.95 mmol, 1.1 eq.) and toluene (10 mL) in a 20 mL microwave vial was added Et3N (0.76 mL, 5.4 mmol, 2 eq.), followed by Pd(P'Bu3)2 (14 mg, 0.027 mmol, 1 mol%). The resulting mixture was purged with argon, then capped and heated at 80 0C (oil temp.) for 2 h. After cooling to rt, it was quenched with sat. NaHCO3 (10 mL), H2O (10 niL), extracted with EtOAc (30 mL x 2) and dried (Na2SO4). After evaporation of the solvents, the residue was purified by Biotage column system (EtOAc/hex gradient: 0-100%) to give (E)-4-(4-(2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)vinyl)phenethyl)mophiholine as a white solid (714 5 mg, 77%). 1 H NMR (400 MHz, CDCl3) delta 7.42 (d, J = 8.0 Hz, 2H), 7.38 (d, J = 19.0 Hz, I H), 7.19 (d, J = 7.8 Hz, 2H), 6.13 (d, J = 18.3 Hz, I H), 3.75 (t, J = 4.4 Hz, 4H), 2.84- 2.77 (m, 2H), 2.63-2.56 (m, 2H), 2.53 (br, pseudo s, 4H), 1.32 (s, 12H).
77%	With triethylamine;bis(tri-t-butylphosphine)palladium(0); In toluene; at 80℃; for 2h;Inert atmosphere; Microwave irradiation;	A. (E)-4-(4-(2-(4, 4, 5, 5-tetramethyl-l, 3,2-dioxaborolan-2-yl)vinyl) phenethyl)morpholine[00197] To a mixture of <strong>[736991-39-2]4-(4-bromophenethyl)morpholine</strong> (731 mg, 2.71 mmol) and 4,4,5,5-tetramethyl-2-vinyl-l,3,2-dioxaborolane (0.5 mL, 2.95 mmol, 1.1 eq.) and toluene (10 mL) in a 20 mL microwave vial was added Et3N (0.76 mL, 5.4 mmol, 2 eq.), followed by Pd(P'Bu3)2 (14 mg, 0.027 mmol, 1 mol%). The resulting mixture was purged with argon, then capped and heated at 80 C (oil temp.) for 2 h. After cooling to rt, it was quenched with sat. NaHC03 (10 mL), H20 (10 mL), extracted with EtOAc (30 mL x 2) and dried(Na2SC>4). After evaporation of the solvents, the residue was purified by Biotage column system (EtOAc hex gradient: 0-100%) to give (E)-4-(4-(2-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)vinyl)phenethyl)mo holine as a white solid (714 mg, 77%). NMR (400 MHz, CDC13) delta 7.42 (d, J = 8.0 Hz, 2H), 7.38 (d, J = 19.0 Hz, 1H), 7.19 (d, J = 7.8 Hz, 2H), 6.13 (d, J = 18.3 Hz, 1 H), 3.75 (t, J = 4.4 Hz, 4H), 2.84-2.77 (m, 2H), 2.63-2.56 (m, 2H), 2.53 (br, pseudo s, 4H), 1.32 (s, 12H).

Reference： [1]Patent: WO2010/115279,2010,A1 .Location in patent: Page/Page column 171-172
[2]Patent: WO2011/123946,2011,A1 .Location in patent: Page/Page column 81

2
[ 10386-27-3 ]
[ 75927-49-0 ]
[ 98436-74-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate; triphenylphosphine; In 1,4-dioxane; at 85℃; for 4h;Inert atmosphere;	Example A3. General experimental for the Suzuki coupling of aryl bromides or chlorides with boronic acidsGeneral Scheme:K2C03, Pd(OAc)2 Ph3P, dioxaneRepresentative SchePh3P, dioxaneA solution of the aryl bromide or aryl chloride (e.g., 6-bromonicotinonitrile, 1 equiv), 4,4,5,5-tetramethyl -2-vinyl-l,3,2- dioxaborolane (2 equiv), K2C03 (2 equiv), Pd(AcO)2 (0.4 equiv) and PI13P (0.8 equiv) in 1,4-dioxane was stirred under N2 at 85 °C until the reaction was complete (approximately 4 h). After cooling to room temperature, the mixture was quenched with water (50 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over Na2S04 and concentrated under reduced pressure. The crude vinyl-containing product (e.g., 2-vinylisonicotinonitrile) was purified by silica gel chromatography.

Reference： [1]Patent: WO2012/170845,2012,A2 .Location in patent: Page/Page column 80

3
[ 673-31-4 ]
[ 75927-49-0 ]
[ 1000376-26-0 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 5316 - 5319

4
[ 89892-22-8 ]
[ 75927-49-0 ]
[ 1305318-30-2 ]

Yield	Reaction Conditions	Operation in experiment
70.4%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 20 - 90℃;Sealed tube;	Synthesis of 7-vinylquinazoline [0574] To a stirred solution of <strong>[89892-22-8]7-bromoquinazoline</strong> (200 mg, 0.95 mmol) in Toluene: H20 (3 mL,(4:l)) was added 4,4,5,5-tetramethyl-2-vinyl-l,3,2- dioxaborolane (221 mg, 1.43 mmol), Na2CO3(304 mg,2.86 mmol),and Pd(PPh3)4 (55 mg,0.04 mmol) at RT. The reaction mixture was allowed to warm 90 °C stirred for 2h in seal tube. The reaction mixture was filtered, the solvent was evaporated, the crude material was purified by silica gel column chromatography to afford 7- vinylquinazoline (105 mg, 70.4percent) as a thick syrup. 1H-NMR (CDC13, 400 MHz): delta 9.31 (d, 2H), 7.95 (s, 1H), 7.86 (d, 1H), 6.98-6.85 (m, 1H), 6.05 (d, 1H), 5.55 (d, 1H); LC-MS: 98.77percent; 157.0 (M++l); (column; X-Bridge C-18, (50x3.0 mm, 3.5mu); RT 2.51 min. A: 5Mm NH4OAc in water, B: CH3CN, 0.8 ml/min); TLC: 30percent EtOAc/Hexane (Rf: 0.3).

Reference： [1]Patent: WO2013/142269,2013,A1 .Location in patent: Paragraph 0573; 0574

5
[ 22282-96-8 ]
[ 75927-49-0 ]
6-ethenyl-2-methyl-3-nitropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; XPhos; In 2-methyltetrahydrofuran; water; at 60℃; for 1h;Inert atmosphere;	Intermediate 19: 6-ethenvl-2-methvl-3-nitrolvridineA suspension/solution of <strong>[22282-96-8]6-bromo-2-methyl-3-nitropyridine</strong> (500 mg, 2.304 mmol), 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.782 mL, 4.61 mmol), palladium(II) acetate (25.9 mg,0.115 mmol), X-phos (110 mg, 0.230 mmol) and cesium carbonate (3.0 g, 9.22 mmol) in 2-methyltetrahydrofuran (2-MeTHF) (8 mL) and water (2 mL) was stirred under nitrogen at 60 C for1 hour. The reaction mixture was cooled then separated between ethyl acetate and water. Theorganic phase was washed with brine and dried over magnesium sulphate. The solvent was removed in vacuo and the residue was dissolved in DCM (5 mL). This was applied to a silica cartridge and eluted with a gradient of 0100% ethyl acetate in cyclohexane. This gave the crude product (440 mg) as a brown liquid which was used directly in the next step with no furtherpurification. LCMS (2 mm, formic) Rt 0.91 mi m/z (ESj 165 (M+H).1H NMR (400 MHz, CHLOROFORM-o) O ppm 8.28 (d, 1 H), 7.33 (d, 1 H), 6.85 (dd, 1 H), 6.40 (d, 1 H), 5.70 (d, 1 H), 2.89 (5, 3 H).
	With palladium diacetate; caesium carbonate; XPhos; In 2-methyltetrahydrofuran; water; at 60℃; for 1h;Inert atmosphere;	A suspension/solution of <strong>[22282-96-8]6-bromo-2-methyl-3-nitropyridine</strong> (500 mg, 2.304 mmol), 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.782 mL, 4.61 mmol), palladium(II) acetate (25.9 mg, 0.115 mmol), X-phos (110 mg, 0.230 mmol) and cesium carbonate (3.0 g, 9.22 mmol) in 2-methyltetrahydrofuran (2-MeTHF) (8 mL) and water (2 mL) was stirred under nitrogen at 60 C. for 1 hour. The reaction mixture was cooled then separated between ethyl acetate and water. The organic phase was washed with brine and dried over magnesium sulphate. The solvent was removed in vacuo and the residue was dissolved in DCM (5 mL). This was applied to a silica cartridge and eluted with a gradient of 0-100% ethyl acetate in cyclohexane. This gave the crude product (440 mg) as a brown liquid which was used directly in the next step with no further purification. LCMS (2 min, formic) Rt 0.91 min, m/z (ES+) 165 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.28 (d, 1H), 7.33 (d, 1H), 6.85 (dd, 1H), 6.40 (d, 1H), 5.70 (d, 1H), 2.89 (s, 3H).

Reference： [1]Organic Letters,2015,vol. 17,p. 2214 - 2217
[2]Patent: WO2013/160419,2013,A1 .Location in patent: Page/Page column 33; 34
[3]Patent: US2015/65507,2015,A1 .Location in patent: Paragraph 0171; 0172

6
[ 40381-90-6 ]
[ 75927-49-0 ]
2-chloro-6-vinylnicotinonitrile [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2214 - 2217

7
[ 75927-49-0 ]
[ 321436-06-0 ]
C₁₆H₂₀BNO₄ [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 3172 - 3176

8
[ 3066-75-9 ]
[ 1214264-88-6 ]
[ 75927-49-0 ]
(R)-2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-en-1-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine [ No CAS ]