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Chemical Structure| 1446321-95-4 Chemical Structure| 1446321-95-4

Structure of 1446321-95-4

Chemical Structure| 1446321-95-4

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Product Details of [ 1446321-95-4 ]

CAS No. :1446321-95-4
Formula : C12H15Cl2N3
M.W : 272.17
SMILES Code : Cl.CC(C)N1N=CC=C1C1=NC=CC=C1CCl
MDL No. :MFCD29053762

Safety of [ 1446321-95-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501
Class:8
UN#:1759
Packing Group:

Application In Synthesis of [ 1446321-95-4 ]

* 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 [ 1446321-95-4 ]

[ 1446321-95-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 387-46-2 ]
  • [ 1446321-95-4 ]
  • [ 1446321-46-5 ]
YieldReaction ConditionsOperation in experiment
88% [0179] A mixture of 2,6-dihydroxybenzaldehyde (1.58 g, 11.47 mmol, 2 eq.) and K2C03 (2.4 g, 17.22 mmol, 3 eq.) in DMF (150 mL) was stirred at rt for 10 min. To this mixture was added 3-(chloromethyl)-2-(l-isopropyI-lH-pyrazol-5-yl)pyridine hydrochloride (1.56 g, 5.74 mmol, leq.) at rt. The mixture was heated at 50 C for 2 h, filtered, concentrated and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 2-hydroxy-6-((2-(l- isopropyl-lH-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde (1.71 g, 88%) as a pale yellow solid. NMR (400 MHz, CDC13) delta 11.96 (s, 1H), 10.40 (s, 1H), 8.77 (dd, J= 4.8, 1.5 Hz, 1H), 8.00 (d, J= 7.8 Hz, 1H), 7.63 (d, J= 1.8 Hz, 1H), 7.49 - 7.34 (m, 2H), 6.59 (d, J = 8.5 Hz, 1H), 6.37 (d, J= 1.8 Hz, 1H), 6.29 (d, J= 8.2 Hz, 1H), 5.10 (s, 2H), 4.67 (sep, J = 6.7 Hz, 1H), 1.50 (d, J= 6.6 Hz, 6H). LRMS (M+rf") m/z 338.1
37% [0178] A mixture of 2,6-dihydroxybenzaldehyde (1.96 g, 14.2 mmol, 2 eq.) and Cs2C03 (7.5 g, 21.3 mmol, 3 eq.) in DMF (180 mL) was stirred at rt for 30 min. To this mixture was added 3-(chloromethyl)-2-(l-isopropyl-lH-pyrazol-5-yl)pyridine hydrochloride (1.93 g, 7.1 mmol, leq.) at rt. The mixture was continued to stir at rt O/N, filtered, concentrated and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 2-hydroxy-6- ((2-(l-isopropyl-lH-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde (920 mg, 37%) as a pale yellow oil. NMR (400 MHz, CDCl3) delta 11.96 (s, 1H), 10.40 (s, 1H), 8.77 (dd, J= 4.8,7 1.5 Hz, 1H), 8.00 (d, J= 7.8 Hz, 1H), 7.63 (d, J= 1.8 Hz, 1H), 7.49 - 7.34 (m, 2H), 6.59 (d, J = 8.5 Hz, 1H), 6.37 (d, J= 1.8 Hz, 1H), 6.29 (d, J= 8.2 Hz, 1H), 5.10 (s, 2H), 4.67 (sep, J = 6.7 Hz, 1H), 1.50 (d, J= 6.6 Hz, 6H). LRMS (M+H+) m/z 338.1
  • 2
  • [ 867267-28-5 ]
  • [ 1446321-95-4 ]
  • 2-methoxy-5-[[2-(2-propan-2-ylpyrazol-3-yl)pyridin-3-yl]methoxy]pyridine-4-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate; In ethyl acetate; N,N-dimethyl-formamide; Step 3 A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (395 mg, 2.58 mmol, 1 eq.), 3-(chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride (700 mg, 2.58 mmol, 1 eq.), and K2CO3 (1.4 g, 10.32 mmol, 4 eq.) in DMF (10.0 mL) was heated at 70 C. for 2 h. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (590 mg, 65%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 10.41 (s, 1H), 8.76 (dd, J=4.7, 1.6 Hz, 1H), 8.04 (dd, J=7.9, 1.6 Hz, 1H), 7.90 (s, 1H), 7.61 (d, J=1.8 Hz, 1H), 7.44 (dd, J=7.9, 4.8 Hz, 1H), 7.10 (s, 1H), 6.37 (d, J=1.8 Hz, 1H), 5.14 (s, 2H), 4.65 (sep, J=6.6 Hz, 1H), 3.91 (s, 3H), 1.49 (d, J=6.6 Hz, 6H); MS (ESI) m/z 353.1 [M+H]+.
65% With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 2h; (00971 A mixture of 5-i dwx’-2-rnetho,i>isonicudnaldcla>de (395 mg. 2.58 nunol. I eq.). 3-(chloromah I i-2-j l-Isoprop) 1-11 I-p I ae’oI-5-3 I )p> ridine hydrochloride jlOO mg. 2.58 mmol, 1 eq.). and Kt’O3 (1.4 g 10.32 mnml. 4 eq.) n l)MF (10.0 ml.) S3s heated at 70k’ for 2 h. The minute as cooled. littered. coneenirazed. and purilied on silica gel using a mixture of Ft04.c and hexane’ as eiuait to give 5-((2-(I-isopropl-111-p>ra.’oI--ybpyndin- 3.L)mcthev)..2..metJio’ciopJcotinaldeh)de (Sto rug. 65.; as an off-white ofiJ. ‘II NMR (400 Mlii. t’lXi) wSlO.31 t 111), 8.76 (dd.J 47. 1.61k. lilt 804 (dd,J 7.9. 1.6 Ii’. 11l 7.90 (s. 110.7.61 d. 1 1.8 lii. lilt 7.44 (dd.J iS 4 8 II,. 111), 7.10 Cs. lIlt 6.37 (Li - 1.811,. lll).5.14s211).4.65sep. 1 6.611,. 111)351 (s,311), l.4Qtd.J 6.611,’.. 611). MS (ES1)m’z353.l IM’HI
65% With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 2h; Step 3 ;A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (395 mg, 2.58 mmol, 1 eq.), 3-(chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride (700 mg, 2.58 mmol, 1 eq.), and K2CO3 (1.4 g, 10.32 mmol, 4 eq.) in DMF (10.0 mL) was heated at 70 C. for 2 h. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (590 mg, 65%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 10.41 (s, 1H), 8.76 (dd, J=4.7, 1.6 Hz, 1H), 8.04 (dd, J=7.9, 1.6 Hz, 1H), 7.90 (s, 1H), 7.61 (d, J=1.8 Hz, 1H), 7.44 (dd, J=7.9, 4.8 Hz, 1H), 7.10 (s, 1H), 6.37 (d, J=1.8 Hz, 1H), 5.14 (s, 2H), 4.65 (sep, J=6.6 Hz, 1H), 3.91 (s, 3H), 1.49 (d, J=6.6 Hz, 6H). LRMS (M+H+) m/z 353.1.
65% With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 2h; Step 3:A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (395 mg, 2.58 mmol, 1 eq.), 3-(chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride (700 mg, 2.58 mmol, 1 eq.), and K2CO3 (1.4 g, 10.32 mmol, 4 eq.) in DMF (10.0 mL) was heated at 70 C. for 2 h. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (590 mg, 65%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 10.41 (s, 1H), 8.76 (dd, J=4.7, 1.6 Hz, 1H), 8.04 (dd, J=7.9, 1.6 Hz, 1H), 7.90 (s, 1H), 7.61 (d, J=1.8 Hz, 1H), 7.44 (dd, J=7.9, 4.8 Hz, 1H), 7.10 (s, 1H), 6.37 (d, J=1.8 Hz, 1H), 5.14 (s, 2H), 4.65 (sep, J=6.6 Hz, 1H), 3.91 (s, 3H), 1.49 (d, J=6.6 Hz, 6H); MS (ESI) m/z 353.1 [M+H]+.

  • 3
  • [ 1446321-95-4 ]
  • [ 1446321-46-5 ]
  • 4
  • [ 867267-28-5 ]
  • [ 1446321-95-4 ]
  • 5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-oxo-1,2-dihydropyridine-4-carbaldehyde [ No CAS ]
 

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