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[ CAS No. 2377-81-3 ] {[proInfo.proName]}

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Chemical Structure| 2377-81-3
Chemical Structure| 2377-81-3
Structure of 2377-81-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2377-81-3 ]

CAS No. :2377-81-3 MDL No. :MFCD00013290
Formula : C8F4N2 Boiling Point : -
Linear Structure Formula :- InChI Key :WVHMPQKZPHOCRD-UHFFFAOYSA-N
M.W : 200.09 Pubchem ID :608182
Synonyms :

Calculated chemistry of [ 2377-81-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.7
TPSA : 47.58 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.09
Log Po/w (XLOGP3) : 1.76
Log Po/w (WLOGP) : 3.67
Log Po/w (MLOGP) : 2.46
Log Po/w (SILICOS-IT) : 3.51
Consensus Log Po/w : 2.5

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.623 mg/ml ; 0.00312 mol/l
Class : Soluble
Log S (Ali) : -2.38
Solubility : 0.84 mg/ml ; 0.0042 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.69
Solubility : 0.0407 mg/ml ; 0.000203 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 2377-81-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 UN#:2811
Hazard Statements:H301+H311+H331-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2377-81-3 ]

* 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 [ 2377-81-3 ]

[ 2377-81-3 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 86-74-8 ]
  • tetrafluoroisophthalonitrile [ No CAS ]
  • [ 1416881-52-1 ]
YieldReaction ConditionsOperation in experiment
93% General procedure: Carbazole (1670 mg,10.0 mmol) or diphenylamine (1.69 g, 10.0 mmol) in dry THF (20mL) was added slowly to a stirred solution of NaH (60% in oil, 600 mg, 15 mmol) dry THF (20 mL) under a nitrogen atmosphere at room temperature. After 30 min, tetrafluorophthalonitrile (400 mg, 2.0 mmol), tetrafluoroisophthalonitrile (400 mg, 2.0 mmol), pentafluorobenzonitrile (3470 mg, 1.8 mmol), 3,4,5-trifluorobenzonitrile (471mg, 3.0 mmol) or 4,5-difluorophthalonitrile (660 mg, 4.0 mmol) was added. After stirred at room temperature for 12 h, 2 mL water was added to the reaction mixture to quench the excess NaH. The resulting mixture was then concentrated under reduced pressure and washed by water and EtOH to yield the crude product, which was purified by recrystalization from hexane/CH2Cl2 or acetone/CHCl3 (in the cases of 3,4,5-3CzBN,and 4,5-2CzPN, column chromatography on silica gel (CH2Cl2: hexane, 4: 1 v/v) were used for further purification) to give 1434 mg (91%, 4CzPN), 1466 mg (93%, 4CzIPN), 1470 mg (97%, 5CzBN), 1.43 g (90%, 4DPAIPN), 1005 mg (56%, 3,4,5-3CzBN) and 1282 mg (70%, 4,5-2CzPN) corresponding products.
19.7% 480 mg (12.0 mmol) of 60% sodium hydride was placed in a 100-mE three-neck flask, the interior of the flask was substituted with nitrogen, and 40 mE, of N,N-dimethylformamide was added thereto, followed by stirring. 1.67 g (10.0 mmol) of 9H-carbazole was added to the mixture, which was stirred under a nitrogen stream at room temperature for 30 minutes. Afier stirring, 400 mg (2.00 mmol) of tetrafluoroisophthalonitrile was added to the mixture, and the mixture was stirred under a nitrogen atmosphere at 60 C. for 10 hours. Afier stirring, 5.0 mE of water was added to the mixture, which was then stirred. Afier stirring, N,Ndimethylformamide was removed from the mixture. After the removal, 200 mE of water was added to the mixture, to which ultrasonic waves were applied. Afier the application, the mixture was suction-filtered to provide a solid mattet The resulting solid matter was purified by silica gel colunmchromatography. In the column chromatography, a mixed solvent of chloroform and hexane (1/5) was firstly used as a developing solvent, and then a mixed solvent of chloroform and hexane (1/2) was used as a developing solvent. The resulting fraction was concentrated to provide a solid matter, which was then recrystallized from a mixed solvent of acetone, and hexane, thereby providing a yellow powdered solid matter in a yield amount of 311 mg and a yield of19.7%.
The reactor was evacuated and replaced with argon.Add carbazole 6, anhydrous THF and NaH in this orderAfter stirring at room temperature 30-40min, tetrafluoroisophthalonitrile 5 was added;After stirring for 12-13h at room temperature,Water is added to the reaction mixture to quench excess NaH,The resulting product is distilled under reduced pressure and washed with water and ethanol;The resulting crude product was subjected to silica gel column chromatography to give 4CzIPN.
8 mmol With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 4h;Inert atmosphere; 40 mmol of carbazole and 10 mmol of 1,3,4,5-tetrafluoro-2,6-dicyanobenzene were added in sequence into a 500 ml round-bottom flask under nitrogen protection and dissolved in 300 ml of DMF solvent, and then 50 mmol of NaH powder was added in batches at room temperature. After completion of the addition, the reaction was continued at room temperature for 4 hours. After completion of the reaction, the reaction was quenched by adding water, followed by suction filtration, rinsing, extraction with dichloromethane, and other steps in turn. Finally, the organic phase was combined, dried over anhydrous magnesium sulfate, filtered, and the organic solvent was evaporated under reduced pressure to give a yellow crude product, which was recrystallized with dichloromethane and methanol to give 8 mmol of the product HEU1. The product was dried in vacuo dried in vacuo for later use. MS (APCI)=789.1;

Reference: [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 1500 - 1505
    Angew. Chem.,2017,vol. 129,p. 1522 - 1527,6
[2]Journal of the American Chemical Society,2017,vol. 139,p. 9799 - 9802
[3]Angewandte Chemie - International Edition,2020,vol. 59,p. 5172 - 5177
    Angew. Chem.,2020,vol. 132,p. 5210 - 5215,6
[4]Organic Letters,2018,vol. 20,p. 5533 - 5536
[5]Chinese Chemical Letters,2019
[6]Chemistry - A European Journal,2020
[7]Journal of Organic Chemistry,2020,vol. 85,p. 3426 - 3439
[8]Nature,2012,vol. 492,p. 234 - 238
[9]Organic Syntheses,2019,vol. 96,p. 455 - 473
[10]Angewandte Chemie - International Edition,2018,vol. 57,p. 11278 - 11282
    Angew. Chem.,2018,vol. 130,p. 11448 - 11452,5
[11]Journal of Materials Chemistry A,2020,vol. 8,p. 3708 - 3716
[12]Angewandte Chemie - International Edition,2019,vol. 58,p. 1789 - 1793
    Angew. Chem.,2019,vol. 131,p. 1803 - 1807,5
[13]Angewandte Chemie - International Edition,2019,vol. 58,p. 9199 - 9203
    Angew. Chem.,2019,vol. 131,p. 9297 - 9301,5
[14]Advanced Synthesis and Catalysis,2020,vol. 362,p. 2254 - 2259
[15]Chemical Science,2018,vol. 9,p. 5883 - 5889
[16]Angewandte Chemie - International Edition,2019,vol. 58,p. 8182 - 8186
    Angew. Chem.,2019,vol. 131,p. 8266 - 8270,5
[17]Organic Letters,2019,vol. 21,p. 8957 - 8961
[18]Chemical Communications,2016,vol. 52,p. 9877 - 9880
[19]Chemical Communications,2018,vol. 54,p. 9337 - 9340
[20]Chemical Communications,2019,vol. 55,p. 466 - 469
[21]Journal of Organic Chemistry,2015,vol. 80,p. 9126 - 9131
[22]Advanced synthesis and catalysis,2020
[23]Chemical Communications,2018,vol. 54,p. 5606 - 5609
[24]Patent: US9502668,2016,B2 .Location in patent: Page/Page column 126; 127
[25]Patent: CN107382910,2017,A .Location in patent: Paragraph 0015; 0016
[26]Patent: US10323180,2019,B2 .Location in patent: Page/Page column 41; 42
[27]Chemical Communications,2020,vol. 56,p. 4240 - 4243
  • 2
  • [ 5599-71-3 ]
  • tetrafluoroisophthalonitrile [ No CAS ]
  • (2r,4s,5r)-2,4,5,6-Tetrakis(3,6-dichloro-9H-carbazol-9-yl)isophthalonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydride In tetrahydrofuran
87% Stage #1: 3,6-dichloro-9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil at 20℃; for 15h; Inert atmosphere;
87% Stage #1: 3,6-dichloro-9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil at 20℃; for 15h; Inert atmosphere;
87% Stage #1: 3,6-dichloro-9H-carbazole With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran at 20℃; for 15h;
79% Stage #1: 3,6-dichloro-9H-carbazole With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran at 20℃; for 1h;
68% Stage #1: 3,6-dichloro-9H-carbazole With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran for 120h; Inert atmosphere; Reflux;
Stage #1: 3,6-dichloro-9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil at 20℃; for 12h;

  • 3
  • [ 37500-95-1 ]
  • [ 2377-81-3 ]
  • [ 1630263-99-8 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 3,6-di(tert-butyl)-9H-carbazole With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;
87% Stage #1: 3,6-di(tert-butyl)-9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil at 20℃; for 15h; Inert atmosphere;
63% Stage #1: 3,6-di(tert-butyl)-9H-carbazole With sodium t-butanolate for 0.5h; Sealed tube; Milling; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran for 0.5h; Sealed tube; Milling;
54% Stage #1: 3,6-di(tert-butyl)-9H-carbazole With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran at 0 - 60℃;
Stage #1: 3,6-di(tert-butyl)-9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil at 20℃; for 12h;

  • 4
  • [ 56525-79-2 ]
  • tetrafluoroisophthalonitrile [ No CAS ]
  • 1,2,3,5-tetrakis(3,6-diphenylcarbazol-9-yl)-4,6-dicyanobenzene [ No CAS ]
  • 5
  • [ 2377-81-3 ]
  • [ 57103-01-2 ]
  • [ 1469703-62-5 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: 3,6-di-methoxy-9H-carbazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In N,N-dimethyl-formamide; mineral oil at 20℃; for 15h; Inert atmosphere;
87% Stage #1: 3,6-di-methoxy-9H-carbazole With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;
Stage #1: 3,6-di-methoxy-9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil at 20℃; for 12h;
  • 6
  • [ 6962-04-5 ]
  • tetrafluoroisophthalonitrile [ No CAS ]
  • 2,4,5,6-tetrakis(bis(4-chlorophenyl)amino)isophthalonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: bis(4-chlorophenyl)amine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In N,N-dimethyl-formamide; mineral oil at 20℃; for 15h; Inert atmosphere;
  • 7
  • [ 122-39-4 ]
  • [ 2377-81-3 ]
  • [ 1846598-27-3 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: diphenylamine With sodium hydride In tetrahydrofuran at 20℃; for 0.75h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
86% Stage #1: diphenylamine With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
66% Stage #1: diphenylamine With sodium hydride In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran at 40℃; Inert atmosphere;
62% Stage #1: diphenylamine With sodium hydride In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran at 40 - 60℃; Inert atmosphere;
62% Stage #1: diphenylamine With sodium hydride In N,N-dimethyl-formamide at 60℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile at 20 - 40℃; for 24h;
50% Stage #1: diphenylamine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In N,N-dimethyl-formamide; mineral oil at 20℃; for 15h; Inert atmosphere;
Stage #1: diphenylamine With sodium hydride In tetrahydrofuran at 20℃; for 0.75h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
Stage #1: diphenylamine With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil at 20℃; for 12h;
With sodium hydride In N,N-dimethyl-formamide at 50℃; for 5h; Inert atmosphere;
Stage #1: diphenylamine With sodium hydride In tetrahydrofuran; mineral oil Cooling with ice; Inert atmosphere; Schlenk technique; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil Cooling with ice; Inert atmosphere;
62 % Stage #1: diphenylamine With sodium hydride In tetrahydrofuran; mineral oil at 60℃; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil Inert atmosphere; Heating;
62 % Stage #1: diphenylamine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 60℃; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In N,N-dimethyl-formamide; mineral oil at 20 - 40℃; Inert atmosphere;

Reference: [1]Shee, Maniklal; Shah, Sk. Sheriff; Singh, N. D. Pradeep [Chemistry - A European Journal, 2020, vol. 26, # 62, p. 14070 - 14074]
[2]Li, Weiyu; Chen, Xiaofei; Zhou, Lei [Organic Letters, 2022, vol. 24, # 32, p. 5946 - 5950]
[3]Chernowsky, Colleen P.; Chmiel, Alyah F.; Wickens, Zachary K. [Angewandte Chemie - International Edition, 2021, vol. 60, # 39, p. 21418 - 21425][Angew. Chem., 2021, vol. 133, # 39, p. 21588 - 21595]
[4]Chernowsky, Colleen P.; Chmiel, Alyah F.; Wickens, Zachary K.; Williams, Oliver P.; Yeung, Charles S. [Journal of the American Chemical Society, 2021, vol. 143, # 29, p. 10882 - 10889]
[5]Alektiar, Sara N.; Wickens, Zachary K. [Journal of the American Chemical Society, 2021, vol. 143, # 33, p. 13022 - 13028]
[6]Garreau, Marion; Le Vaillant, Franck; Waser, Jerome [Angewandte Chemie - International Edition, 2019, vol. 58, # 24, p. 8182 - 8186][Angew. Chem., 2019, vol. 131, p. 8266 - 8270,5]
[7]Shah, Sk. Sheriff; Shee, Maniklal; Singh, N. D. Pradeep [Chemical Communications, 2020, vol. 56, # 30, p. 4240 - 4243]
[8]Liu, Yan; Chen, Xiao-Lan; Li, Xiao-Yun; Zhu, Shan-Shan; Li, Shi-Jun; Song, Yan; Qu, Ling-Bo; Yu, Bing [Journal of the American Chemical Society, 2021, vol. 143, # 2, p. 964 - 972]
[9]Zhou, Chao; Gan, Qi-Chao; Zhou, Tai-Ping; Lei, Tao; Ye, Chen; He, Xiao-Jun; Chen, Bin; Lu, Heng; Wan, Qian; Liao, Rong-Zhen; Tung, Chen-Ho; Wu, Li-Zhu [Angewandte Chemie - International Edition, 2022, vol. 61, # 10][Angew. Chem., 2022, vol. 134, # 10]
[10]Zeng, Liang; Qin, Jing-Hao; Lv, Gui-Fen; Hu, Ming; Sun, Qing; Ouyang, Xuan-Hui; He, De-Liang; Li, Jin-Heng [Chinese Journal of Chemistry, 2023, vol. 41, # 16, p. 1921 - 1930]
[11]Williams, Oliver P.; Chmiel, Alyah F.; Mikhael, Myriam; Bates, Desiree M.; Yeung, Charles S.; Wickens, Zachary K. [Angewandte Chemie - International Edition, 2023, vol. 62, # 18][Angew. Chem., 2023, vol. 135, # 18]
[12]Alektiar, Sara N.; Han, Jimin; Dang; Rubel, Camille Z.; Wickens, Zachary K. [Journal of the American Chemical Society, 2023, vol. 145, # 20, p. 10991 - 10997]
  • 8
  • [ 122-39-4 ]
  • [ 2377-81-3 ]
  • [ 2260543-73-3 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: diphenylamine With sodium hydride In tetrahydrofuran at 50℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;
80% Stage #1: diphenylamine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 2h; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil at 20℃;
80% Stage #1: diphenylamine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; Schlenk technique;
70% Stage #1: diphenylamine With sodium hydride In tetrahydrofuran; paraffin oil at 50℃; for 1h; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; paraffin oil at 20℃; for 24h;
Stage #1: diphenylamine With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 12.5h; Inert atmosphere;
80 % Stage #1: diphenylamine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Schlenk technique; Stage #2: tetrafluoroisophthalonitrile In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Schlenk technique; Darkness;

  • 9
  • [ 2377-81-3 ]
  • [ 122546-74-1 ]
YieldReaction ConditionsOperation in experiment
90% With H2SiEt2; C16H19BiN2O2 In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Sealed tube;
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