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Nitriles
2-(1H-Benzo[d][1,2,3]triazol-1-yl)acetonitrile
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[ CAS No. 111198-08-4 ] {[proInfo.proName]}

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Chemical Structure| 111198-08-4
Chemical Structure| 111198-08-4
Structure of 111198-08-4 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 111198-08-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
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Product Details of [ 111198-08-4 ]

CAS No. :111198-08-4 MDL No. :MFCD00082568
Formula : C8H6N4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 158.16 Pubchem ID :-
Synonyms :

Safety of [ 111198-08-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 111198-08-4 ]

* 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 [ 111198-08-4 ]

[ 111198-08-4 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 111198-08-4 ]
  • [ 69218-56-0 ]
YieldReaction ConditionsOperation in experiment
93% With dihydrogen peroxide; potassium carbonate In dimethyl sulfoxide
Reference： [1]Katritzky; Chen; Yang [Journal of Organic Chemistry, 1995, vol. 60, # 17, p. 5638 - 5642]
  • 2
  • [ 95-14-7 ]
  • [ 107-14-2 ]
  • [ 111198-08-4 ]
  • [ 118521-81-6 ]
YieldReaction ConditionsOperation in experiment
1: 73% 2: 21% With triethylamine In N,N-dimethyl-formamide at 110℃; for 12h;
1: 71.9% 2: 20% With triethylamine In N,N-dimethyl-formamide at 110℃; for 12h;
1: 12% 2: 55% With sodium methylate 1.) MeOH, DMF, 2.) DMF, heating;
With triethylamine In N,N-dimethyl-formamide at 110℃;
With triethylamine In N,N-dimethyl-formamide at 110℃;
In ethyl acetate Microwave irradiation; Reflux;

Reference： [1]Carta, Antonio; Palomba, Michele; Boatto, Gianpiero; Busonera, Bernardetta; Murreddu, Marta; Loddo, Roberta [Il Farmaco, 2004, vol. 59, # 8, p. 637 - 644]
[2]Sanna, Paolo; Carta, Antonio; Nikookar, Mohammad E. Rahbar [European Journal of Medicinal Chemistry, 2000, vol. 35, # 5, p. 535 - 543]
[3]Danan; Charon; Kirkiacharian; Bories; Loiseau [Il Farmaco, 1997, vol. 52, # 4, p. 227 - 229]
[4]Das, Jagattaran; Rao, C.V. Laxman; Sastry; Roshaiah; Sankar, P. Gowri; Khadeer, Abdul; Kumar, M. Sitaram; Mallik, Arundhuti; Selvakumar; Iqbal, Javed; Trehan, Sanjay [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 2, p. 337 - 343]
[5]Location in patent: experimental part Yu, Tianzhi; Zhang, Peng; Zhao, Yuling; Zhang, Hui; Meng, Jing; Fan, Duowang; Chen, Lili; Qiu, Yongqing [Organic electronics, 2010, vol. 11, # 1, p. 41 - 49]
[6]Li, Qiujing; Li, Zhulai; Liu, Guijun; Wang, Ningning; Yin, Huiyong [Journal of Heterocyclic Chemistry, 2019]
  • 3
  • [ 111198-08-4 ]
  • [ 4144-64-3 ]
YieldReaction ConditionsOperation in experiment
80% With sodium ethanolate; benzaldehyde In ethanol for 4h; Heating;
Reference： [1]Sanna, Paolo; Carta, Antonio; Nikookar, Mohammad E. Rahbar [European Journal of Medicinal Chemistry, 2000, vol. 35, # 5, p. 535 - 543]
  • 4
  • [ 14489-75-9 ]
  • [ 111198-08-4 ]
  • [ 468060-27-7 ]
  • [ 364333-50-6 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1939 - 1942
  • 5
  • [ 51639-59-9 ]
  • [ 111198-08-4 ]
  • [ 468060-22-2 ]
  • [ 364333-54-0 ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
Reference： [1]Henke, Brad R; Drewry, David H.; Jones, Stacey A.; Stewart, Eugene L.; Weaver, Susan L.; Wiethe, Robert W. [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 14, p. 1939 - 1942]
  • 6
  • [ 51639-59-9 ]
  • [ 111198-08-4 ]
  • [ 468060-25-5 ]
  • [ 364333-56-2 ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
Reference： [1]Henke, Brad R; Drewry, David H.; Jones, Stacey A.; Stewart, Eugene L.; Weaver, Susan L.; Wiethe, Robert W. [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 14, p. 1939 - 1942]
  • 7
  • [ 51639-59-9 ]
  • [ 111198-08-4 ]
  • [ 468060-27-7 ]
  • [ 364333-55-1 ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
Reference： [1]Henke, Brad R; Drewry, David H.; Jones, Stacey A.; Stewart, Eugene L.; Weaver, Susan L.; Wiethe, Robert W. [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 14, p. 1939 - 1942]
  • 8
  • [ 33403-97-3 ]
  • [ 111198-08-4 ]
  • [ 468060-27-7 ]
  • [ 364333-57-3 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1939 - 1942
  • 9
  • [ 872-85-5 ]
  • [ 111198-08-4 ]
  • [ 95-14-7 ]
  • [ 69218-56-0 ]
  • Z 3-(1H-benzotriazol-1-yl)-3-(pyridin-4-yl)acrylonitrile [ No CAS ]
  • E 3-(1H-benzotriazol-1-yl)-3-(pyridin-4-yl)acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 13.8% 2: 13.8% 3: 18% 4: 38.6% With triethylamine In toluene for 24h; Heating; Further byproducts given;
Reference： [1]Carta, Antonio; Sanna, Paolo; Bacchi, Alessia [Heterocycles, 2002, vol. 57, # 6, p. 1079 - 1090]
  • 10
  • [ 111198-08-4 ]
  • [ 59664-42-5 ]
  • (E)-2-Benzotriazol-1-yl-3-(2,4-bis-trifluoromethyl-phenyl)-acrylonitrile [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2002,vol. 37,p. 891 - 900
  • 11
  • [ 111198-08-4 ]
  • [ 26861-65-4 ]
YieldReaction ConditionsOperation in experiment
76% With lithium aluminium tetrahydride In tetrahydrofuran Reflux;
Reference： [1]Campora, Marta; Canale, Claudio; Gatta, Elena; Tasso, Bruno; Laurini, Erik; Relini, Annalisa; Pricl, Sabrina; Catto, Marco; Tonelli, Michele [ACS Chemical Neuroscience, 2021, vol. 12, # 3, p. 447 - 461]
  • 12
  • [ 95-14-7 ]
  • [ 590-17-0 ]
  • [ 111198-08-4 ]
  • [ 118521-81-6 ]
YieldReaction ConditionsOperation in experiment
1: 75% 2: 25% With potassium carbonate In tetrahydrofuran at 50℃; for 2h; Sonication; 4.1.1. Procedure for the synthesis of benzotriazolyl acetonitriles 3 and 4 Benzotriazole 1 (1 equiv), K2CO3 (2.2 equiv) and dry THF (30 mL)were combined in a 250 mL flask. Then, bromoacetonitrile 2 (1.2 equiv)was added dropwise and the reaction was left under an ultrasound bathfor 2 h. Reaction course was monitored by TLC analysis. After completion of the reaction, the solvent was removed, and the reaction mixture was washed with water and extracted with ethyl acetate (3 × 30 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Isolation of both isomer products was accomplished by column chromatography using a hexane/EtOAc (2:1) system. 4.1.1.1. 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetonitrile 3. (75%) Beige solid, mp 86-87 C; 1H NMR (400 MHz, CD3OD): δ 5.96 (s, 2H, CH2CN),7.44-7.48 (m, 1H, Harom), 7.59-7.63 (m, 1H, Harom), 7.82 (d, J = 8.4 Hz,1H, Harom), 8.01 (d, J = 8.4 Hz, 1H, Harom); 13C NMR (100 MHz, CD3OD): 36.4, 110.7, 114.9, 120.5, 126.1, 129.8, 133.9, 146.8. HRMS (ESI+)calcd for C8H7N4 [M+H]+ 159.06707, found 159.06712. Lit [63]. 4.1.1.2. 2-(2H-benzo[d][1,2,3]triazol-2-yl)acetonitrile 4. (25%) Beige solid, mp 78-80 °C; 1H NMR (500 MHz, CDCl3): δ 5.68 (s, 2H, CH2),7.44-7.46 (m, 2H, Harom), 7.87-7.89 (m, 2H, Harom); 13C NMR (125MHz, CDCl3): 43.6, 112.3, 118.2, 127.7, 145.1. HRMS (ESI+) calcd forC8H7N4 [M+H]+ 159.06707, found 159.06716. Lit [19,21].
Reference： [1]Hernández-Fernández, Eugenio; Ortega-Villarreal, Ana Sofia; García-López, Ma. Concepción; Chan-Navarro, Rodrigo; Garrard, Samuel; Valdivia-Berroeta, Gabriel A.; Smith, Stacey J.; Christensen, Kenneth A.; Michaelis, David J. [Dyes and Pigments, 2021, vol. 189]

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