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[ CAS No. 6361-22-4 ] {[proInfo.proName]}

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Chemical Structure| 6361-22-4
Chemical Structure| 6361-22-4
Structure of 6361-22-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6361-22-4 ]

CAS No. :6361-22-4 MDL No. :MFCD00007204
Formula : C7H4ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :RZDOUWDCYULHJX-UHFFFAOYSA-N
M.W : 185.56 Pubchem ID :80701
Synonyms :

Calculated chemistry of [ 6361-22-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.66
TPSA : 62.89 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) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.01
Log Po/w (XLOGP3) : 1.88
Log Po/w (WLOGP) : 2.06
Log Po/w (MLOGP) : 0.86
Log Po/w (SILICOS-IT) : 0.48
Consensus Log Po/w : 1.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.41
Solubility : 0.717 mg/ml ; 0.00386 mol/l
Class : Soluble
Log S (Ali) : -2.82
Solubility : 0.279 mg/ml ; 0.0015 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.34
Solubility : 0.84 mg/ml ; 0.00453 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.71

Safety of [ 6361-22-4 ]

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

Application In Synthesis of [ 6361-22-4 ]

* 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.

  • Upstream synthesis route of [ 6361-22-4 ]
  • Downstream synthetic route of [ 6361-22-4 ]

[ 6361-22-4 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 76-09-5 ]
  • [ 6361-22-4 ]
  • [ 4964-69-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2216 - 2220
  • 2
  • [ 6361-22-4 ]
  • [ 23967-57-9 ]
Reference: [1] Patent: WO2016/191366, 2016, A1,
  • 3
  • [ 83-42-1 ]
  • [ 4637-24-5 ]
  • [ 6361-22-4 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: at 140℃; for 16 h;
Stage #2: With sodium periodate In water; N,N-dimethyl-formamide at 0 - 20℃; for 9 h;
Example 109; This example concerns the synthesis of Aldehyde 4: To a stirred solution of1 (18.53 g, 108.0 mmol) in dry DMF (240 mL) was added N,JV-dimethylformamide dimethyl acetal (DMF'DMA) (39.5 g, 44.0 mL, 331 mmol). After heating at 140°C for 16 h, the dark red solution was cooled to 0°C and added slowly, over 1 h via cannula, to a rapidly stirred solution OfNaIO4 (83.0 g, 388.0 mmol) in H2O (291 mL) and DMF (77 mL) at 0°C. The reaction flask was washed with DMF (20 mL) at 0°C and added to NaIO4 mixture. The reaction was stirred at 0°C for 2 h then allowed to warm to rt. After an additional 6 h, the orange solution was filtered and rinsed with PhMe/EtOAc (1 : 1 , 200 mL). The filtrate was then washed with H2O (3 x 150 mL) and sat. aq. NaCl (3 x 150 mL). The dried (MgSO4) extract was concentrated in vacuo to a dark red oil, and hexanes (40 mL) were added. Solids were isolated and recrystalized in PhMe to give the known aldehyde 4 (17.23 g, 92.88 mmol, 86percent). 1H NMR (400 MHz, CDCl3) δ 10.42 (s, IH), 8.01 (dd, J= 1.0, 8.2 Hz, IH), 7.79 (dd, J= 1.0, 8.1 Hz5 IH), 7.65 (t, J= 8.1 Hz, IH); 13C NMR (100 MHz, CDCl3) δ 188.6, 148.4, 138.6, 132.9, 132.4, 123.4, 121.9.
Reference: [1] Patent: WO2008/156656, 2008, A2, . Location in patent: Page/Page column 46; 177
  • 4
  • [ 83-42-1 ]
  • [ 6361-22-4 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 26, p. 9857 - 9865
[2] Gazzetta Chimica Italiana, 1990, vol. 120, # 7, p. 435 - 441
[3] Patent: DE107501, , ,
[4] Israel Journal of Chemistry, 1964, vol. 2, p. 25 - 28
  • 5
  • [ 50907-57-8 ]
  • [ 6361-22-4 ]
Reference: [1] Gazzetta Chimica Italiana, 1990, vol. 120, # 7, p. 435 - 441
[2] Patent: DE112400, , ,
[3] Israel Journal of Chemistry, 1964, vol. 2, p. 25 - 28
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 5, p. 406
  • 6
  • [ 56433-01-3 ]
  • [ 6361-22-4 ]
Reference: [1] Patent: DE107501, , ,
[2] Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 779 - 787
[3] Patent: DE112400, , ,
[4] Israel Journal of Chemistry, 1964, vol. 2, p. 25 - 28
  • 7
  • [ 95196-89-7 ]
  • [ 6361-22-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 19, p. 2751 - 2758
  • 8
  • [ 97301-33-2 ]
  • [ 6361-22-4 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 3807
  • 9
  • [ 97301-33-2 ]
  • [ 6361-22-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 19, p. 2751 - 2758
  • 10
  • [ 6361-22-4 ]
  • [ 50907-57-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 11, p. 2647 - 2666
[2] Green Chemistry, 2017, vol. 19, # 14, p. 3296 - 3301
[3] Patent: EP1227090, 2002, A1,
  • 11
  • [ 6361-22-4 ]
  • [ 35490-90-5 ]
YieldReaction ConditionsOperation in experiment
45 %Spectr. With vasicine In ethylene glycol at 80℃; for 48 h; General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80°C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product.
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 45, p. 5003 - 5008
  • 12
  • [ 6361-22-4 ]
  • [ 35490-90-5 ]
Reference: [1] Australian Journal of Chemistry, 1972, vol. 25, p. 639 - 646
[2] Patent: US2010/331306, 2010, A1, . Location in patent: Page/Page column 38; 39
  • 13
  • [ 6361-22-4 ]
  • [ 68050-37-3 ]
Reference: [1] Patent: US2003/144507, 2003, A1,
[2] Patent: EP1258252, 2002, A1,
[3] Patent: US2004/18192, 2004, A1,
  • 14
  • [ 6361-22-4 ]
  • [ 2365-48-2 ]
  • [ 35212-95-4 ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In N,N-dimethyl-formamide at 60℃; 2-chloro-6-nitrobenzaldehyde (556.5 mg, 3.0 mmol), methyl mercaptoacetate (274 uL, 3.0 mmol), K2C03 (414 mg, 3.0 mmol) and DMF (10 mL) were added to a 50 ml round bottom flask, and stirred at 60 °C overnight. The DMF was removed in vacuo, and the crude residue was dissolved in ethyl acetate (30 ml) and water (10 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2x). The combined organics were dried (MgSO4) and concentrated to give title compound (621 mg, 92percent). ‘H NMR (CDCI3, 400 MHz) ö 8.15 (d, IH, J 0.4 Hz), 7.68 (ddd, 1H, J 0.8, 1.6, 7.2 Hz), 7.357.31 (m, 2H), 3.89 (s, 3H).
Reference: [1] Patent: WO2016/191366, 2016, A1, . Location in patent: Page/Page column 34; 35
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 20, p. 4793 - 4807
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 12, p. 2998 - 3001
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