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Chemical Structure| 50670-55-8 Chemical Structure| 50670-55-8

Structure of 50670-55-8

Chemical Structure| 50670-55-8

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Product Details of [ 50670-55-8 ]

CAS No. :50670-55-8
Formula : C14H9NO
M.W : 207.23
SMILES Code : N#CC1=CC=C(C2=CC=C(C=O)C=C2)C=C1
MDL No. :MFCD04117353

Safety of [ 50670-55-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 50670-55-8 ]

* 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 [ 50670-55-8 ]

[ 50670-55-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 50670-58-1 ]
  • [ 50670-55-8 ]
YieldReaction ConditionsOperation in experiment
5.85 g (74%) With ammonia; In N-methyl-acetamide; water; a) 10.0 g of <strong>[50670-58-1]4'-bromo-4-biphenylcarboxaldehyde</strong> and 5.31 g of copper(I) cyanide were dissolved in 80 ml of dimethylformamide while gassing with argon and the solution was heated to reflux for 15 hours at 180 C. bath temperature. Thereafter, the reaction mixture was poured cautiously into 200 ml of 25 percent ammonia and extracted three times with 200 ml of methylene chloride each time. The organic phases were washed once with 200 ml of 25 percent ammonia and twice with 200 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the yellowish, crystalline residue (8.7 g) on silica gel gave 5.85 g (74%) of 4'-cyano-4-biphenylcarboxaldehyde as slightly yellowish crystals; Rf-value (toluene/ethyl acetate vol. 90:10) 0.27.
  • 2
  • [ 15862-94-9 ]
  • [ 50670-55-8 ]
  • 4'-(2-(4,5-dimethoxy-2-nitrophenyl)-1-hydroxyethyl)[1,1'-biphenyl]-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% General procedure: To a glass vessel capable of being sealed with Teflon cap (for microwave vials) were added 1 and benzaldehyde derivative (3 equiv.). The vessel was capped and then, evacuated and backfilled with N2 (process repeated 3X). Anhydrous DMF (3.5mL/mmol) was introduced and the solution was vigorously stirred for 20min at-20C. TDAE was added slowly and the mixture was stirred for 1h. Then, the reaction was stirred at room temperature overnight. After LC-MS analysis clearly showed that the chloride had been totally consumed, the reaction was hydrolysed with distilled water. The mixture was then extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered off and concentrated under reduced pressure to afford the corresponding crude product 3. (0029) 4.2.4.1. 4'-(2-(4,5-Dimethoxy-2-nitrophenyl)-1-hydroxyethyl)-[1,1'-biphenyl]-4-carbonitrile (3a). The crude product was prepared according to procedure B starting from 1 (112mg, 0.49mmol) and 4’-formyl-[1,1’-biphenyl]-4-carbonitrile (301mg, 1.45mmol). After purification by column chromatography on silica gel (CH2Cl2/EtOAc 9:1), the pure product (93mg, 0.23mmol) was obtained as a yellow solid. Yield, 48%. m.p: 185C; 1H NMR (400MHz, DMSO-d6) δ 7.91 (d, J=8.6Hz, 2H), 7.87 (d, J=8.6Hz, 2H), 7.72 (d, J=8.3Hz, 2H), 7.55 (s, 1H), 7.46 (d, J=8.3Hz, 2H), 6.87 (s, 1H), 5.47 (d, J=5.0Hz, 1H), 4.87-4.82 (m, 1H), 3.83 (s, 3H), 3.76 (s, 3H), 3.26 (dd, J=13.2, 4.6Hz, 1H), 3.18 (dd, J=13.2, 8.4Hz, 1H). 13C NMR (75MHz, DMSO-d6) δ 152.1, 147.0, 146.1, 144.5, 141.7, 136.9, 132.9 (2C), 128.3, 127.4 (2C), 126.8 (2C), 126.6 (2C), 118.9, 115.4, 109.9, 107.9, 72.3, 56.0 (2C), 42.3. Anal. Calcd. for C23H20N2O5 (%): C, 68.31; H, 4.98; N, 6.93. Found (%): C, 67.79; H, 4.89; N, 6.76.
 

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