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[ CAS No. 13423-60-4 ]

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2D
Chemical Structure| 13423-60-4
Chemical Structure| 13423-60-4
Structure of 13423-60-4 *Storage: {[proInfo.prStorage]}

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Product Details of [ 13423-60-4 ]

CAS No. :13423-60-4MDL No. :MFCD01076193
Formula : C8H7N3 Boiling Point : 292.3°C at 760 mmHg
Linear Structure Formula :C6H5C2H2N3InChI Key :CGRLXLHYYDSTKR-UHFFFAOYSA-N
M.W :145.16Pubchem ID :83432
Synonyms :

Computed Properties of [ 13423-60-4 ]

TPSA : 30.7 H-Bond Acceptor Count : 2
XLogP3 : 1.7 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 13423-60-4 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13423-60-4 ]

  • Upstream synthesis route of [ 13423-60-4 ]
  • Downstream synthetic route of [ 13423-60-4 ]

[ 13423-60-4 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 288-88-0 ]
  • [ 591-50-4 ]
  • [ 13423-60-4 ]
YieldReaction ConditionsOperation in experiment
96% With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 110℃; for 72.00 h; Inert atmosphere General procedure: A mixture of CuI (0.10 g, 0.50 mmol), the required azole(10 mmol), K3PO4 (4.4 g, 20 mmol), the required halide (12 mmol)and N,N0-dimethylethylenediamine (0.11 mL, 1.0 mmol) in DMF(5 mL) was degased and heated under argon at 110 C for 72 h.After filtration over celite (washing using AcOEt) and removal ofthe solvents, the crude product is purified by chromatography oversilica gel (the eluent is given in the product description). 4.3.1
1-Phenyl-1H-1,2,4-triazole (2a)
Compound 2a was prepared from 1,2,4-triazole (0.69 g) and iodobenzene (1.4 mL) using the general procedure 1, and was isolated (eluent: heptane/AcOEt 7:3) in 96percent yield as a yellow powder: mp 48 °C (lit.
28
46 °C); 1H NMR (CDCl3, 300 MHz) 7.42 (m, 1H), 7.53 (m, 2H), 7.71 (m, 2H), 8.15 (s, 1H), 8.74 (s, 1H); 13C NMR (CDCl3, 75 MHz) 120.1 (2CH), 128.3 (CH), 129.9 (2CH), 137.1 (C), 140.9 (CH), 152.7 (CH).
91% With caesium carbonate In DMF (N,N-dimethyl-formamide) at 50 - 82℃; for h; Example 1.17 [0636] Preparation of 1-phenyl-1H-1,2,41 triazole [0637] Operating protocol A (82 C., 48 hours) was followed using 117 mg of Chxn-Py-Al (0.4 mmoles), 336 ?l of iodobenzene (3 mmoles), 138 mg of 1,2,4-triazole (2 mmoles), 1.042 g of caesium carbonate (3.2 mmoles) and 1.2 ml of DMF. [0638] The degree of transformation and selectivity were 100percent and 98percent respectively. [0639] The residue obtained following treatment was purified by silica gel chromatography (eluent: hexane/dichloromethane, 100/0 to 50/50). [0640] 264 mg of a dark yellow solid was obtained in a yield of 91percent. [0641] Pale yellow needles were obtained after re-crystallisation from chloroform. [0642] The compound obtained had the following formula: [CHEMMOL-00056] [0643] The characteristics were as follows: [0644] MPt: 46 C. (CHCl3) (Lit: 46-47 C. given by Micetich, R G; Spevak, P; Hall, T W; Bains, B K; Heterocycles 1985, 23, 1645-1649); [0645] H NMR/CDCl3:? 8.52 (wide s, 1H, HI), 8.04 (wide s, 1H, H2), 7.53-7.65 (m, 2H, H4,8), 7.26-7.51 (m, 3H, H5,6,7); [0646] 13C NMR/CDCl3: ? 152.55 (C1), 140.88 (C2), 139.96 (C3), 129.73 (C5 and C7), 128.15 (C6), 119.99 (C4 and C8); [0647] GC/MS: Rt=14.02 min, M/Z=145, purity=100percent; [0648] Rf=0.21 (eluent: dichloromethane/ethyl acetate, 90/10). Example 1.18 [0649] Preparation of 1-phenyl-1H-[1,2,4]triazole [0650] Operating protocol A (82 C., 24 hours) was followed using 117 mg of Chxn-Py-Al (0.4 mmoles), 336 ?l of iodobenzene (3 mmoles), 138 mg of 1,2,4-triazole (2 mmoles), 1.042 g of caesium carbonate (3.2 mmoles) and 1.2 ml of DMF. [0651] The degree of transformation and selectivity were 79percent and 99percent respectively. [CHEMMOL-00057] Example 1.19 [0652] Preparation of 1-phenyl-1H-[1,2,4]triazole Example 1.18 was repeated, operating at 50 C. (72 hours). The degree of transformation and selectivity for 1-phenyl-1H-[1,2,4-triazole] were 75percent and 99percent respectively. [0653] [CHEMMOL-00058]
91%
Stage #1: at 100℃;
Stage #2: at 50 - 82℃; for h;
Operating protocol A (82° C., 48 hours) was followed using 117 mg of Chxn-Py-Al (0.4 mmoles), 336 μl of iodobenzene (3 mmoles), 138 mg of 1,2,4-triazole (2 mmoles), 1.042 g of caesium carbonate (3.2 mmoles) and 1.2 ml of DMF. The degree of transformation and selectivity were 100percent and 98percent respectively. The residue obtained following treatment was purified by silica gel chromatography (eluent: hexane/dichloromethane, 100/0 to 50/50). 264 mg of a dark yellow solid was obtained in a yield of 91percent. Pale yellow needles were obtained after re-crystallisation from chloroform. The compound obtained had the following formula: The characteristics were as follows: MPt: 46° C. (CHCl3) (Lit: 46-47° C. given by Micetich, R G; Spevak, P; Hall, T W; Bains, B K; Heterocycles 1985, 23, 1645-1649); 1H NMR/CDCl3: δ8.52 (wide s, 1H, H1), 8.04 (wide s, 1H, H2), 7.53-7.65 (m, 2H, H4,8), 7.26-7.51 (m, 3H, H5,6,7); 13C NMR/CDCl3: δ 152.55 (C1), 140.88 (C2), 139.96 (C3), 129.73 (C5 and C7), 128.15 (C6), 119.99 (C4 and C8); GC/MS: Rt=14.02 min, M/Z=145, purity=100percent; Rf=0.21 (eluent: dichloromethane/ethyl acetate, 90/10). Example 1.18; Preparation of 1-phenyl-1H-[1,2,4]triazole; Operating protocol A (82° C., 24 hours) was followed using 117 mg of Chxn-Py-Al (0.4 mmoles), 336 μl of iodobenzene (3 mmoles), 138 mg of 1,2,4-triazole (2 mmoles), 1.042 g of caesium carbonate (3.2 mmoles) and 1.2 ml of DMF. The degree of transformation and selectivity were 79percent and 99percent respectively. ; Example 1.19; Preparation of 1-phenyl-1H-[1,2,4]triazole; Example 1.18 was repeated, operating at 50° C. (72 hours). The degree of transformation and selectivity for 1-phenyl-1H-[1,2,4-triazole] were 75percent and 99percent respectively.
83% With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 30.00 h; sealed tube Preparation of 1-phenyl-1H-[1,2,4]triazole [0220] Following General Procedure A (90 0C, 30 hours), 1/-/-[1 ,2,4]triazole (104 mg, 1.5 mmol) is coupled with iodo-benzene (112 μL, 1.0 mmol). The crude brown oil is purified by flash chromatography on silica gel (eluent: dichloromethane/hexanes = 50/50) to provide 120 mg (83 percent isolated yield) of the desired product as a light yellow solid. <n="50"/>007/001836_ 49 -IdentificationMp: 460C.1H NMR (400 MHz, CDCI3): δ 8.49 (s, 1 H1 H8), 8.03 (s, 1H, H7), 7.58-7.61 (m, 2H, H2i6), 7.40-7.44 (t, 2H1 H3,5), 7.31-7.33 (t, 1 H, H4).13C NMR (100 MHz, CDCI3): δ 152.62 (C7), 140.91 (C8), 136.99 (C1), 129.77 (C3,5), 128.21 (C4), 120.04 (C2i6).IR (KBr) : v (cm'1) = 3105, 2924, 2852, 1600, 1514, 1416, 1359, 1278, 1223,1152, 1055, 981 , 876, 754, 681 , 671 , 503.GC/MS: rt = 15.28 min, M/Z = 145.HRMS: 146.0721 (M+H). Theoretical: 146.0718
71%
Stage #1: Inert atmosphere
Stage #2: at 120℃; for 64.00 h; Inert atmosphere
A flask was charged with K2CO3 (12.1689 g, 88 mmol), 1H-1,2,4-triazole (2.0042 g, 29 mmol), Cu2O(430 mg, 3 mmol) and 1,10-phenanthroline (1.0452 g, 5.8 mmol) and then evacuated and back-filled with N2. Then, anhydrous DMF (20 ml) and iodobenzene (8.9764 g, 4.92 ml, 44 mmol) were added and the resulting mixture was heated to 120 °C for 64 h and then diluted with CH2Cl2 (40 ml). The mixture was filtered through a pad of Celite and the residue washed with CH2Cl2 (20 ml). The resulting organic layer was washed with water (20 ml) and brine (20 ml), dried over MgSO4 and concentrated under reduced pressure. The crude mixture was purified by column chromatography (cyclohexane/ethyl acetate 8/0→2/0) to yield the product as a pale yellow solid (2.986 g, 71percent).
65%
Stage #1: With phenanthroline monohydrate; potassium carbonate In N,N-dimethyl-formamideInert atmosphere
Stage #2: at 100℃; for 48.00 h;
EXAMPLE 108
1-phenyltriazole 1 g (0.0145 mol) triazole 2, 0.21 g (0.00145 mol) copper(I)oxide, 0.29 g (0.00145 mol) phenantroline monohydrate and 6.01 g (0.044 mol) potassium carbonate are weighed into a Schlenk flask. After repeated evacuating and flushing with argon, 10 ml dry DMF is added. Evacuating and flushing with argon are repeated several times. Subsequently, 2.42 ml (4.43 g, 0.022 mol) of iodobenzene is added. The reaction mixture is stirred for 48 h at 100° C. under argon. After cooling 20 ml DCM is added and filtered. The solvent is removed in vacuum and the product is obtained after purification by column chromatography (KG 60, gradient petroleum ether/EtOAc 8:2 to EtOAc) as a yellowish-white solid.M 145.17 C8H7N3 Yield: 1.362 g (65percent)1H-NMR DM-94 (300 MHz/DMSO): (ppm)=7.41 (t, 1H, 6-H); 7.58 (t, 2H, 5/5'-H); 7.87 (d, 2H, 4-H); 8.25 (s, 1H, 1-H); 9.31 (s, 1H, 2-H)13C-NMR DM-94 (75.475 MHz/DMSO): (ppm)=119.37 (5/5'-C); 127.78 (6-C); 129.77 (4/4'-C); 136.74 (3-C); 142.27 (2-C); 152.39 (1-C)

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  • 2
  • [ 288-88-0 ]
  • [ 108-86-1 ]
  • [ 13423-60-4 ]
YieldReaction ConditionsOperation in experiment
93% With copper(I) 3-metthylsalicylate; potassium carbonate In dimethyl sulfoxide at 110℃; for 3.00 h; General procedure: A dry flask was charged with the nitrogen containing heterocycles (1.5 mmol), aryl halides (1 mmol), potassium carbonate(2 mmol) and CuMeSal (0.01 mmol) then anhydrous DMSO (5 ml) was added. The reaction mixture was stirred at 110°C, open to air, for 3h , cooled to room temperature, filtered, and the precipitate was washed with DMSO (2 ml) then stirred with ice water (30 ml) and extracted with ethyl acetate (3 × 50 ml),dried over sodium sulfate and the solvent was removed under reduced pressure.The residue was purified by chromatography or recrystallization as indicated with each compound.
6.32 g
Stage #1: With sodium methylate In methanol at 40℃; for 1.00 h;
Stage #2: at 90℃; for 16.00 h;
, adding 50 mmol of sodium methoxide into 50 mmol of 1, 2, 4-triazole (shown in the formula II)) and 50 mL of methanol solution, stirring for 60 minutes at 40 DEG c, and dropwise adding 60 mmol of bromobenzene, carrying out condensation reflux for 16 hours at the temperature of 90 DEG c, removing volatile matters in the reaction raffinate, washing the carbon tetrachloride, and filtering the solid impurities, and carrying out rotary evaporation to remove the washing solvent to obtain colorless liquid 1-phenyl -1,2,4-triazole 6.32g
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 22, p. 9121 - 9124
[2] Tetrahedron Letters, 2014, vol. 55, # 19, p. 3049 - 3051
[3] Green Chemistry, 2012, vol. 14, # 5, p. 1268 - 1271
[4] ChemCatChem, 2014, vol. 6, # 8, p. 2373 - 2383
[5] Journal of Organic Chemistry, 2007, vol. 72, # 22, p. 8535 - 8538
[6] Synthesis, 2008, # 11, p. 1707 - 1716
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[8] Dalton Transactions, 2015, vol. 44, # 18, p. 8433 - 8443
[9] Patent: CN108484654, 2018, A. Location in patent: Paragraph 0057; 0060
  • 3
  • [ 77287-34-4 ]
  • [ 100-63-0 ]
  • [ 13423-60-4 ]
YieldReaction ConditionsOperation in experiment
74% at 160℃; for 0.17 h; Microwave irradiation; Sealed tube To a dried microwave tube was added phenylhydrazine (108mg, 1 mmol) and formamide (0.82 mL, 20 mmol). The tube was sealed with a plastic microwave septum and then placed into the microwave cavity and irradiated at 160 °C, 250 psi, and 230W for 10 min. After completion of reaction (TLC), the mixture was cooled to r.t.; distilled H2O (10 mL) was added, and the mixture extracted with EtOAc (3 × 10 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using a mixture of n-hexane and EtOAc as eluent.
Reference: [1] Synlett, 2015, vol. 26, # 3, p. 404 - 407
[2] Heterocycles, 1985, vol. 23, # 7, p. 1645 - 1649
[3] Yakugaku Zasshi, 1958, vol. 78, p. 549[4] Chem.Abstr., 1958, p. 17244
  • 4
  • [ 59-88-1 ]
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  • [ 13423-60-4 ]
YieldReaction ConditionsOperation in experiment
1.2 g at 175℃; for 1.50 h; Sealed tube; Microwave irradiation To a 15 mL microwave vial 2 g (13.8 mmol) of phenyl hydrazinehydrochloride was added to 10 mL of formamide. The vial was sealedand heated at 175 °C for 1.5 h in a microwave reactor. The mixture waspoured into water and extracted 3 times with ethyl acetate. The organiclayers were combined and washed 3 times with water and once withbrine. The organic phase was dried over sodium sulfate and concentratedin vacuo. The crude material was purified by flash chromatography0–50percent EtOAc/Hexanes and a yellow oil was isolated thatsolidified upon standing, 1.2 g. ESI/MS: calculated C8H7N m/z=145.1found m/z=146.0 [M+1]. 1H NMR (CDCl3): 7.37–7.42 (m, 1H),7.47–7.53 (m, 2H), 7.66 (d, J=8.3 Hz, 2H), 8.10 (s, 1H), 8.54 (s, 1H).
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[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 15, p. 4441 - 4451
  • 5
  • [ 288-88-0 ]
  • [ 98-80-6 ]
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  • 6
  • [ 288-88-0 ]
  • [ 28899-97-0 ]
  • [ 13423-60-4 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 14, p. 2747 - 2748
  • 7
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  • 8
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  • 9
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  • [ 13423-60-4 ]
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  • 11
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  • 16
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Reference: [1] Gazzetta Chimica Italiana, 1894, vol. 24 II, p. 227
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