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Chemical Structure| 380430-49-9

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Product Details of (4-Boc-aminophenyl)boronic acid

CAS No. :380430-49-9
Formula : C11H16BNO4
M.W : 237.06
SMILES Code : C1=C(NC(OC(C)(C)C)=O)C=CC(=C1)B(O)O
MDL No. :MFCD02093054
InChI Key :UBVOLHQIEQVXGM-UHFFFAOYSA-N
Pubchem ID :3613184

Safety of (4-Boc-aminophenyl)boronic acid

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

Application In Synthesis of (4-Boc-aminophenyl)boronic acid

* 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 [ 380430-49-9 ]

[ 380430-49-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 180995-12-4 ]
  • [ 380430-49-9 ]
  • [4-(4-chloro-3-cyanopyrid-2-yl)phenyl]carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 2.0h; [4-(4-Chloro-3-cyanopyrid-2-yl)phenyl]carbamic acid tert-butyl ester To a solution of 519 mg of <strong>[180995-12-4]2,4-dichloronicotinonitrile</strong> in 25.5 ml of dioxane are added 782 mg of (4-boc-aminophenyl)boronic acid, 693 mg of sodium bicarbonate in 8.5 ml of water and 347 mg of tetrakis(triphenyl-phosphine)palladium. The suspension is stirred at 100 C. for 2 hours under argon. After cooling, the reaction mixture is poured into water and extracted three times with a 90/10 ethyl acetate/methanol solution. The combined organic phases are dried over magnesium sulfate and concentrated under reduced pressure. 1.58 g of crude product are chromatographed on a prepacked Biotage KP-Sil column of 60 A SiO2 32-63 mum (from 0.5/99.5 to 1/99 gradient of solution A in dichloromethane; solution A=38/17/2 dichloromethane/methanol/aqueous ammonia). 797 mg of [4-(4-chloro-3-cyanopyrid-2-yl)phenyl]carbamic acid tert-butyl ester are obtained, the characteristics of which are as follows: MS-EI: 329 (+) IR spectrum (CCl4): 3343; 2981; 2230; 1741; 1524; 1501; 1411; 1392; 1368; 1316; 1220; 1155; 1050 and 844 cm-1 1H NMR spectrum (400 MHz, (CD3)2SO, delta in ppm): 1.50 (s, 9H); 7.62 (d, J=9.0 Hz, 2H); from 7.78 to 7.84 (m, 3H); 8.83 (d, J=5.5 Hz, 1H); 9.67 (s, 1H).
  • 2
  • [ 709652-82-4 ]
  • [ 380430-49-9 ]
  • [ 1267853-94-0 ]
YieldReaction ConditionsOperation in experiment
71% To a microwave reaction vessel were added 4-(tert- butoxycarbonylamino)phenylboronic acid (180 mg, 0.759 mmol), 5-bromo-3-cyano- 2-aminopyridine (170.0 mg, 0.858 mmol), 1,4-dioxane (3.5 mL) and 2M aqueous sodium carbonate (0.94 mL, 1.88 mmol). Argon gas was bubbled through the solution for 5 min, then tetrakis(triphenylphosphine) palladium(O) (40.0 mg, 0.035 mmol) was <n="120"/>added and the vial was sealed and heated in a microwave reactor for 20 min at 170 C. The mixture was partitioned between EtOAc (10 mL) and saturated sodium bicarbonate (10 mL) The aqueous layer was separated and extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with brine (10 mL), dried over MgS04, filtered and concentrated under reduced pressure to give an oil which was purified by silica gel flash chromatography, eluting with 25-100% EtOAc in hexanes. The purified material was dissolved in DCM (4 mL), excess TFA (2 mL) added and the mixture was stirred at rt for 4 h. The mixture was concentrated to dryness, then EtOAc (8 mL), saturated NaHC03 (8 mL) and 1 M aqueous NaOH (1 mL) were added. After confirming basic pH, the layers were shaken and separated and the aqueous layer was extracted with EtOAc (2 x 5 mL). The combined extracts were dried over MgS04, filtered and concentrated under reduced pressure to give 2- amino-5-(4-aminophenyl)nicotinonitrile (113.9 mg, 71%) as a solid, which was sufficiently pure for the next step. LC-MS (ESI) m/z 2 (M +H)+.
  • 3
  • [ 709652-82-4 ]
  • [ 380430-49-9 ]
  • [ 1267849-53-5 ]
 

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