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[ CAS No. 40107-07-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 40107-07-1
Chemical Structure| 40107-07-1
Chemical Structure| 40107-07-1
Structure of 40107-07-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 40107-07-1 ]

CAS No. :40107-07-1 MDL No. :MFCD06808523
Formula : C9H5ClIN Boiling Point : -
Linear Structure Formula :- InChI Key :XPXHGYKMODLJBY-UHFFFAOYSA-N
M.W : 289.50 Pubchem ID :11173778
Synonyms :

Calculated chemistry of [ 40107-07-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 59.47
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.39
Log Po/w (XLOGP3) : 3.47
Log Po/w (WLOGP) : 3.49
Log Po/w (MLOGP) : 3.26
Log Po/w (SILICOS-IT) : 4.05
Consensus Log Po/w : 3.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.44
Solubility : 0.0106 mg/ml ; 0.0000365 mol/l
Class : Moderately soluble
Log S (Ali) : -3.42
Solubility : 0.109 mg/ml ; 0.000378 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.26
Solubility : 0.00159 mg/ml ; 0.0000055 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.82

Safety of [ 40107-07-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 40107-07-1 ]

* 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 [ 40107-07-1 ]
  • Downstream synthetic route of [ 40107-07-1 ]

[ 40107-07-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 342617-07-6 ]
  • [ 40107-07-1 ]
YieldReaction ConditionsOperation in experiment
92% at 20℃; for 1 h; 6-Iodo-4-quinolinol (100 g, 369 mmol) was suspended in POCl3 (340 mL, 3.7 mol) at rt.
After 1 hour it was concentrated, and the resulting residue was placed in an ice water bath and carefully neutralized using satd. aqueous Na2CO3.
The resulting brown suspension was filtered, and the solid was rinsed with water (2*500 mL) and dried under vacuum overnight.
4-chloro-6-iodoquinoline was obtained as a brown solid (103 g, 92percent).
1H NMR (400 MHz, DMSO-d6) δ 8.88 (d, J=4.8 Hz, 1H), 8.54 (d, J=1.8 Hz, 1H), 8.15 (dd, J=8.8, 2.0 Hz, 1H), 7.88 (d, J=8.8 Hz, 1H), 7.82 (d, J=4.8 Hz, 1H); MS (m/z) 289.9 (M+H+).
92% for 1 h; 4-Hydroxy-6-iodoquinoline (100 g, 369 mmol) was suspended in POCl3 (340 ml, 3.7 mol) at room temperature.
After 1 hour it was concentrated and the resulting residue was placed in an ice water bath and carefully neutralized using saturated aqueous Na2CO3.
The resulting brown suspension was filtered and the solid was rinsed with water (2 x 500 mL) and dried under vacuum overnight. 4-chloro-6-iodoquinoline was obtained as a brown solid (103 g, 92 percent).
1H NMR (400 MHz, DMSO-d6) δ 8.88 (d, J = 4.8 Hz, 1H), 8.54 (d, J = 1.8 Hz, 1H), 8.15 (dd, J = 8.8, 2.0 Hz, 1H), 7.88 (d, J = 8.8 Hz, 1H), 7.82 (d, J = 4.8 Hz, 1H); MS (m/z) 289.9 (M+H+).
66% for 2 h; Heating / reflux Compound 21-F (4.5 g) was dissolved in 50 mi of POCI3. The solution was heated to reflux for 2 hours. The excess amount of POCI3 was removed by evaporation under vacuum. The residue was neutralized with NH40H to pH-7 and extracted with EtOAc. The organic layer was concentrated and purified by chromatography on a silica gel column using hexane/ethylacetate (3: 1) to give 7.1 g (66percent yield) of 4-chloro-6-iodoquinoline 21-G as a yellow solid.
Reference: [1] Patent: US2012/41024, 2012, A1, . Location in patent: Page/Page column 8; 10; 16
[2] Patent: EP2566477, 2015, B1, . Location in patent: Paragraph 0157; 0160
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4867 - 4880
[4] Patent: WO2005/63739, 2005, A1, . Location in patent: Page/Page column 64
  • 2
  • [ 21873-51-8 ]
  • [ 40107-07-1 ]
YieldReaction ConditionsOperation in experiment
85% at 110℃; for 1 h; Intermediate 37 (4.9 g, 15.5 mmol) was combined with phosphorus oxychloride (14 mL, 15.5 mmol) and heated at 110° C. for 1 hour. The volatiles were removed in vacuo and the residue was treated with the biphasic mixture of saturated aqueous NaHCO3 and ethyl acetate. The layers were separated and the aqueous phase was extracted with ethyl acetate. The organic layers were combined, dried over solid Na2SO4, filtered and volatiles removed from the filtrate. The resulting residue was purified by silica gel column chromatography to afford the desired product (3.81 g, 85percent).
Reference: [1] Patent: US2008/234267, 2008, A1, . Location in patent: Page/Page column 24
  • 3
  • [ 540-37-4 ]
  • [ 40107-07-1 ]
Reference: [1] Patent: US2012/41024, 2012, A1,
[2] Patent: EP2566477, 2015, B1,
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4867 - 4880
  • 4
  • [ 909344-69-0 ]
  • [ 40107-07-1 ]
Reference: [1] Patent: US2012/41024, 2012, A1,
[2] Patent: EP2566477, 2015, B1,
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4867 - 4880
  • 5
  • [ 40107-07-1 ]
  • [ 81290-20-2 ]
  • [ 49713-56-6 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 16, p. 4268 - 4271
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