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Chemical Structure| 151414-76-5 Chemical Structure| 151414-76-5

Structure of 2-Allyloxyphenylboronic acid
CAS No.: 151414-76-5

Chemical Structure| 151414-76-5

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Product Details of [ 151414-76-5 ]

CAS No. :151414-76-5
Formula : C9H11BO3
M.W : 177.99
SMILES Code : OB(C1=CC=CC=C1OCC=C)O
MDL No. :MFCD11183169
InChI Key :IUALPRJAXOAGOF-UHFFFAOYSA-N
Pubchem ID :12035765

Safety of [ 151414-76-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 151414-76-5 ]

* 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 [ 151414-76-5 ]

[ 151414-76-5 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 33035-41-5 ]
  • [ 151414-76-5 ]
  • (2-(2-propenyloxy)phenyl)(2,4,6-trimethylphenyl)iodonium tetrafluoroborate [ No CAS ]
  • 2
  • [ 151414-76-5 ]
  • [ 73429-23-9 ]
  • 3
  • [ 151414-76-5 ]
  • [ 13524-73-7 ]
  • 4
  • [ 151414-76-5 ]
  • 3-(2-hydroxy-2-phenylethyl)-2,3-dihydrobenzofuran [ No CAS ]
  • 5
  • [ 5419-55-6 ]
  • [ 60333-75-7 ]
  • [ 151414-76-5 ]
  • 6
  • [ 1600-27-7 ]
  • [ 546-67-8 ]
  • [ 151414-76-5 ]
  • [ 151414-77-6 ]
  • 7
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 151414-76-5 ]
  • [ 1242412-59-4 ]
  • [ 6282-42-4 ]
  • [ 73429-23-9 ]
  • 8
  • [ 201230-82-2 ]
  • [ 107-18-6 ]
  • [ 151414-76-5 ]
  • [ 89844-08-6 ]
  • 9
  • [ 151414-76-5 ]
  • [ 68224-03-3 ]
  • 10
  • [ 151414-76-5 ]
  • potassium (2-(allyloxy)phenyl)trifluoroborate [ No CAS ]
  • 11
  • [ 151414-76-5 ]
  • [ 1334402-71-9 ]
  • [ 1334402-70-8 ]
  • 13
  • [ 61676-62-8 ]
  • [ 24892-63-5 ]
  • 2-(2-(allyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 151414-76-5 ]
  • 14
  • [ 6000-59-5 ]
  • [ 151414-76-5 ]
  • 2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonamide [ No CAS ]
  • 2-[2-(allyloxy)phenyl]-2-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In nitromethane; at 60℃; for 12.0h; General procedure: A 10-mL screw-cap glass tube with PP-cap was charged with a magnetic stirring bar, 2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonamide (1a; 68.0 mg, 0.25 mmol, 1.0 equiv), glyoxylic acid monohydrate (2; 30.0 mg, 0.33 mmol, 1.3 equiv), boronic acid 3 (0.5 mmol, 2.0 equiv), and nitromethane (1.5 mL, 0.17 M wrt sulfonamide) and firmly closed. The resulting mixture was stirred at 60 C for 12 h. After cooling to r.t., the mixture was diluted with acetone and filtered through a Celite/silica gel mixture and the filtrate was concentrated under reduced pressure. Purification of the crude residueby flash column chromatography afforded the product.
  • 15
  • C13H19BO3 [ No CAS ]
  • [ 151414-76-5 ]
YieldReaction ConditionsOperation in experiment
5.5 g With hydrogenchloride; In tetrahydrofuran; water;pH 3 - 4; 3-allyloxyphenylboronic acid (4): A solution of 3-allyloxybromobenzene (10.6 g, 50 mmol) in THF (30 mL) was added dropwise to stirred Mg (1.8 g, 74 mmol) suspended in THF (10 mL). The reaction started after addition of ca. 10 mL of the solution. The rest of 3-allyloxybromobenzene solution was dropped in 0.5 h to the stirred slurry (to maintain a gentle reflux, about 65 C). The reaction mixture was stirred for 1 h. A small amount of magnesium remained in the solution. The resultant slightly green slurry was diluted with THF (100 mL) and cooled to -68 C. B(OEt) 3 , (7.3 g, 50 mmol) was then added dropwise to the stirred mixture to give a colorless solution, which was stirred for 1 h. Then the cooling bath was removed and the mixture was allowed to warm to room temperature. The reaction mixture was acidified with 3 M aq. HCl until slightly acidic pH was reached (3-4). Total amount of 3 M aq. HCl added: 17 mL. After hydrolysis, 100 mL of water and 50 mL of diethyl ether was added. The clear yellowish organic layer was separated. The aqueous phase was extracted with diethyl ether (3 x 25 mL) and the extracts were added to the organic layer. Volatiles were evaporated from the organic phase (water bath, temp. about 50 C) under reduced pressure. This evaporation was continued until a thick slurry was obtained. After addition of water (100 mL) the residue was filtered and washed with water (3 x 25 mL) to give 8 g of crude, wet product which was washed using 25 mL of hexane. The product was filtered and dried to give 4 as a colorless powder. Yield 6.23 g (70%), mp 56-60 C; 1 H-NMR (300 MHz, DMSO-d 6 ): 8.00 (2H, br., OH), 7.38-7.36 (2H, m), 7.28-7.22 (1H, m), 7.00-6.96 (1H, m), 6.06 (1H, ddt, J = 18, J =12, J =6 Hz), 5.40 (1H, dq, J = 18 Hz, J = 3 Hz ), 5.25 (1H, ddt, J = 12 Hz, J = 3 Hz), 4.55 (2H, dt, J = 6 Hz, J = 3 Hz); 13 C{ 1 H} NMR (100.62 MHz, DMSO-d 6 ): 157.60, 136.77 (br), 133.98, 128.64, 126.60, 119.93, 117.29, 116.47, 67.98; 11 B NMR (96.32 MHz, DMSO-d 6 ) 30; δ HRMS (ESI) m/z calculated for C9H11BO3 ([M - H]) 177.07230, found 177.07245.
  • 16
  • [ 60333-75-7 ]
  • [ 151414-76-5 ]
  • 17
  • [ 423-39-2 ]
  • [ 151414-76-5 ]
  • 2-(2-iodo-4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)phenylboronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With 1,4-phenylene-bis-((1-methyl-1H-pyrazol-5-yl)borinic 8-oxyquinolinate); sodium L-ascorbate; In dimethyl sulfoxide; at 20℃;Irradiation; Potassium 2-allyloxyphenyltrifluoroborate (0.27 g, 1.5 mmol, 1 equiv.), perfluorobutyl iodide (0.69 g, 2.0 mmol, 1.33 equiv.), (+)-sodium L-ascorbate (0.10 g, 0.5 mmol, 0.33 equiv.) and 1 (8 mg, 15 μmol, 1.0 mol%) were dissolved in DMSO (6 mL) at RT. The reaction flask was placed approx. 2 cm from a blue LED light strip. After 48 h CH 2 Cl 2 (30 mL) was added and the mixture was filtered off. The organic layer was extracted with water (3x 25 mL). The combined organic phases were dried over anhydrous MgSO 4 , filtered off and allowed to evaporate under atmospheric pressure. The crude product was washed with diethyl ether and dried to give 2a as a yellowish powder. Yield 0.57 g (74%), mp = 95-97 C; 1 H-NMR (300 MHz, DMSO-d 6 ): 7.75 (2H, s, br) 7.55 (1H, dd, J = 6 Hz, J = 2 Hz ), 7.40-7.35 (1H,m), 7.00-6.95 (2H, m), 4.69-4.63 (1H, m), 4.34 (1H, dd, J = 15 Hz, J = 6 Hz), 4.27 (1H, dd, J = 15 Hz, J = 6 Hz), 3.46-3.29 (1H, m), 3.04-2.88 (1H, m); 13 C{ 1 H} NMR (100.62 MHz, DMSO-d 6 ): 161.35, 136.29, 131.41, 120.99, 111.52, 72.59, 36.01 (t, J = 20 Hz, C-CF 2 - ), 14.05; 19 F NMR (282.47 MHz, DMSO-d 6 ) -80.45- -80.54 (3F, m), -111.90- -114.51 (2F, m), -124.17 (2F, q, J = 8 Hz), -125.57 (2F, q, J = 8 Hz). 11 B NMR (96.32 MHz, DMSO-d 6 ) 28.1; HRMS (ESI) m/z calculated for C13H11BF9IO3 ([M - H]) 522.96240, found 522.96276.
  • 18
  • C39H34NiP2 [ No CAS ]
  • [ 151414-76-5 ]
  • [ 101383-96-4 ]
  • 19
  • [ 151414-76-5 ]
  • [ 3383-05-9 ]
  • [ 101383-96-4 ]
 

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[ 151414-76-5 ]

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