ChemicalBook CAS DataBase List 1H-BENZOTRIAZOLE-1-ACETONITRILE

1H-BENZOTRIAZOLE-1-ACETONITRILE synthesis

7synthesis methods

Product Name:1H-BENZOTRIAZOLE-1-ACETONITRILE
CAS Number:111198-08-4
Molecular formula:C8H6N4
Molecular Weight:158.16

95-14-7 Synthesis

95-14-7
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590-17-0 Synthesis

590-17-0
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$5.00/5g

111198-08-4
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$80.00/1g

2-(2H-benzo[d][1,2,3]triazol-2-yl)acetonitrile

118521-81-6
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Yield: 75% ， 25%

Reaction Conditions:

with potassium carbonate in tetrahydrofuran at 50; for 2 h;Sonication;

Steps:

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].

References:

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,art. no. 109251]

95-14-7 Synthesis

95-14-7
857 suppliers
$6.00/100g

107-14-2 Synthesis