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[ CAS No. 55304-73-9 ] {[proInfo.proName]}

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Chemical Structure| 55304-73-9
Chemical Structure| 55304-73-9
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Product Details of [ 55304-73-9 ]

CAS No. :55304-73-9 MDL No. :MFCD07369746
Formula : C6H3Cl2NO Boiling Point : -
Linear Structure Formula :- InChI Key :HWTMRGXKSANEDO-UHFFFAOYSA-N
M.W :176.00 Pubchem ID :12259383
Synonyms :

Calculated chemistry of [ 55304-73-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.64
TPSA : 29.96 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 1.0
Log Po/w (SILICOS-IT) : 2.79
Consensus Log Po/w : 1.82

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.32
Solubility : 0.848 mg/ml ; 0.00482 mol/l
Class : Soluble
Log S (Ali) : -1.84
Solubility : 2.54 mg/ml ; 0.0144 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.2
Solubility : 0.111 mg/ml ; 0.000628 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 55304-73-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 55304-73-9 ]

* 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.

  • Upstream synthesis route of [ 55304-73-9 ]
  • Downstream synthetic route of [ 55304-73-9 ]

[ 55304-73-9 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 2591-86-8 ]
  • [ 2402-78-0 ]
  • [ 113293-70-2 ]
  • [ 55304-73-9 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 15, p. 4793 - 4796
[2] Journal of Organic Chemistry, 1991, vol. 56, # 15, p. 4793 - 4796
  • 2
  • [ 55304-73-9 ]
  • [ 40381-90-6 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 1, p. 266 - 273
  • 3
  • [ 55304-73-9 ]
  • [ 63725-51-9 ]
YieldReaction ConditionsOperation in experiment
84% With hydrazine hydrate In butan-1-ol for 16.5 h; Reflux; Industrial scale In n-butanol (6 L), 2,6-dichloro-3-pyridinecarboxaldehyde (1056 g, 6.0 mol, 1 eq.) was added and hydrazine hydrate (1060g, 18.0mol, 3eq., 85percent), stirred at room temperature for 0.5h. The mixture was warmed to reflux overnight (16 h), filtered and evaporated. The crude product is then beaten with water/isopropyl alcohol (ν/ν = 7:1), filtered and dried. The product 6-chloro-1 hydrogen-pyrazolo[3,4-B]pyridine (774 g, 5.0 mol) was obtained as a yellow powdery solid. The yield was 84percent and the purity was 98percent.
Reference: [1] Patent: CN108570049, 2018, A, . Location in patent: Paragraph 0022; 0023; 0025-0036
[2] Patent: WO2013/169964, 2013, A1,
  • 4
  • [ 55304-90-0 ]
  • [ 55304-73-9 ]
YieldReaction ConditionsOperation in experiment
80% With Dess-Martin periodane In dichloromethane at 20 - 26℃; for 2 h; To a solution of (2,6-dichloropyridin-3-yl)methanol (1.0 g, 5.62 mmol) in CH2C12 (10 ml) was added Dess-Martin reagent (4.8 g, 11.24 mmol) at 26°C. After addition the mixture was stirred at room temperature for 2 h. Once the reaction was complete, the mixture was then quenched by adding 5percent aqueous Na2S203 and stirred for 30 min. The resulting mixture was extracted with CH2C12 (2x30 ml). The combined organic layers were washed with saturated Na2S203 solution (50 ml), brine (30 ml), dried over Na2S04 and concentrated to give the title compound which was used in next step without further purification. (800 mg, Yield 80percent). 1H NMR (400MHz, CDC13): 10.38 (s, 1H), 8.19 (d, J=8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H).
66% With pyridinium chlorochromate In dichloromethane for 2 h; Dissolve (2,6-dichloropyridin-3-yl)-methanol (876 mg, 4.92 mmol) in dichloromethane (20.mL). Add pyridium chlorochromate (2.12 g, 9.84 mmol). Stir for 2 hours. Add diethyl ether and stir for 20 minutes. Filter the mixture through a pad of Celite.(R). and silica gel and concentrate to give 2,6-dichloropyridine-3-carbaldehyde (575 mg, 66percent): 1H NMR (400 MHz5 CDCl3) δ 10.39 (s, IH)5 8.18 (d, IH, J = 8.0 Hz)5 7.43 (d, IH, J = 8.0 Hz).
Reference: [1] Patent: WO2014/100695, 2014, A1, . Location in patent: Paragraph 00409
[2] Journal of Organic Chemistry, 1982, vol. 47, # 14, p. 2800 - 2802
[3] Patent: WO2006/44454, 2006, A1, . Location in patent: Page/Page column 62
[4] Patent: US3974166, 1976, A,
  • 5
  • [ 2402-78-0 ]
  • [ 68-12-2 ]
  • [ 55304-73-9 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at -78℃; for 2 h;
Lithium diisopropylamide (2 M, 20.5 mL, 40.53 mmol, 1.2 eq.) was added into anhydrous tetrahydrofuran (20 mL) at -78 °C. Compound 1-1 (5.0 g, 33.78 mmol, 1.0 eq.) in tetrahydrofuran (20 mL) was added dropwise over 1 h at -78 °C. NN-Dimethylformamide (7.5 g, 101.35 mmol, 3.0 eq.) was added into the solution, and the mixture was stirred for another 2 hat -78 °C. Saturated ammonium chloride (60 mL) was added to the mixture to quench the reaction. The solution was evaporated to remove tetrahydrofuran and extracted with ethyl acetate (3 x 50 mL). The organic layer was collected, dried over sodium sulfate, and evaporated to give the crude product, which was purified by silica gel column chromatography (100percent petroleum ether to ethyl acetate : petroleum ether = 1:10) to give compound 1-2 as a white solid (3.5 g, yield: 59percent). MS (ESI) m/z 176.0 [M+H]+.
Reference: [1] Patent: WO2013/169964, 2013, A1, . Location in patent: Paragraph 00254; 00255
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3463 - 3468
  • 6
  • [ 2591-86-8 ]
  • [ 2402-78-0 ]
  • [ 55304-73-9 ]
YieldReaction ConditionsOperation in experiment
40%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5 h;
Stage #2: at -78℃; for 0.333333 h;
Under N2, to a solution of 2,6-dichloroyridine (6.00 g, 40.5 mmol) in anhydrous THF (75 mL) cooled at -78 0C was added LDA (2.0 M in heptane/THF/ethylbenzene, 20.5 mL, 41.0 mmol). After the mixture was stirred at -78 0C for 30 min, 1-formylpiperidine (4.64 g, 41.0 mmol) was added. The mixture was stirred at -78 0C for 20 min, and at -780C aqueous EPO <DP n="63"/>HCl (1 N, 60 mL) and Et2O (50 mL) were added. The organic layer was collected and the aqueous layer was extracted with Et2O (3 X 100 mL). The combined extracts were dried over anhydrous Na2SO4. After filtration the solvent was removed, and the residue was purified by flash chromatography on silica gel (CH2Cl2/hexanes, 1 :2 v/v) to afford 2,6-dichloro-pyridine- 3-carbaldehyde as a white solid (2.85 g, 40percent).
Reference: [1] Patent: WO2007/22371, 2007, A2, . Location in patent: Page/Page column 61-62
[2] Journal of Organometallic Chemistry, 1991, vol. 406, # 1+2, p. 49 - 56
  • 7
  • [ 68-12-2 ]
  • [ 55304-73-9 ]
YieldReaction ConditionsOperation in experiment
52%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -80℃; for 1.66667 h;
Stage #2: at -80℃; for 0.666667 h;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexanes
BuLi (2.5 M in hexanes, 36 mL, 90 mmol) was slowly added to diisopropylamine (12.5 mL, 89.2 mmol) in THF (80 mL) at O0C. The mixture was cooled to -80°C and 2,6-dichloropyridine (12.0 g, 81.1 mmol) in THF (80 mL) was added over 70 min at -800C. After 30 min, DMF (19 mL, 243 mmol) was added and the mixture was stirred for an additional 40 min at -8O0C. NH4Cl (aq, sat) was added and the mixture was extracted with EtOAc. The combined extracts were dried (Na2SO4), concentrated and crystallised from hexane to give the sub-title compound (7.43 g 52 percent).
Reference: [1] Patent: WO2006/77401, 2006, A1, . Location in patent: Page/Page column 63
  • 8
  • [ 70290-47-0 ]
  • [ 55304-73-9 ]
  • [ 130161-51-2 ]
Reference: [1] Heterocycles, 1990, vol. 31, # 6, p. 1097 - 1104
  • 9
  • [ 58584-86-4 ]
  • [ 55304-73-9 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 14, p. 2800 - 2802
  • 10
  • [ 38496-18-3 ]
  • [ 55304-73-9 ]
Reference: [1] Patent: WO2014/100695, 2014, A1,
  • 11
  • [ 2591-86-8 ]
  • [ 2402-78-0 ]
  • [ 113293-70-2 ]
  • [ 55304-73-9 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 15, p. 4793 - 4796
[2] Journal of Organic Chemistry, 1991, vol. 56, # 15, p. 4793 - 4796
  • 12
  • [ 55304-73-9 ]
  • [ 55304-90-0 ]
YieldReaction ConditionsOperation in experiment
3.01 g at 20℃; for 0.5 h; [1037] NaBH4 (808 mg, 21.3 mmol) was added to a solution of 514-1 (3.10 g, 17.7 mmol) in MeOH (22 niL), which had been pre-cooled to 0 °C. The mixture was allowed to reach r.t. and stirring was prolonged for 30 mins. 1 M aq. HC1 solution was added, and the organic solvent was removed under reduced pressure. The aqueous phase was extracted with DCM (3x). The combined organic portions were dried with and filtered. The volatiles were removed under reduced pressure to afford 514-2 (3.01 g). UPLC/MS(ES+): m/z 178.00 [M+H]+.
Reference: [1] Organic Letters, 2011, vol. 13, # 3, p. 526 - 529
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3463 - 3468
[3] Patent: WO2012/78608, 2012, A1, . Location in patent: Page/Page column 28
[4] Patent: WO2015/26792, 2015, A1, . Location in patent: Paragraph 1037
  • 13
  • [ 55304-73-9 ]
  • [ 124-41-4 ]
  • [ 95652-81-6 ]
YieldReaction ConditionsOperation in experiment
71.3% at 55℃; for 3 h; 2,6-Dichloronicotinaldehyde (1 g, 5.68 mmol) was diluted with sodium methoxide (11.4 mL, 5.68 mmol) (solution in methanol) and heated to 55°C. After stirring for 3 hours, the reaction was loaded directly onto a silica gel column and eluted with 5percent ethyl acetate/hexanes to 50percent ethyl acetate/hexanes to yield 6-chloro-2- methoxynicotinaldehyde (0.695 g, 4.05 mmol, 71.3 percent yield).
Reference: [1] Patent: WO2010/75200, 2010, A1, . Location in patent: Page/Page column 164
  • 14
  • [ 67-56-1 ]
  • [ 55304-73-9 ]
  • [ 95652-81-6 ]
Reference: [1] Synthesis, 2005, # 16, p. 2751 - 2757
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