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[ CAS No. 672293-33-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 672293-33-3
Chemical Structure| 672293-33-3
Structure of 672293-33-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 672293-33-3 ]

CAS No. :672293-33-3 MDL No. :MFCD11112906
Formula : C9H10INO2 Boiling Point : -
Linear Structure Formula :- InChI Key :UEROLPZUGANXKB-UHFFFAOYSA-N
M.W : 291.09 Pubchem ID :44828937
Synonyms :

Calculated chemistry of [ 672293-33-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 59.81
TPSA : 52.32 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) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.19
Log Po/w (XLOGP3) : 2.11
Log Po/w (WLOGP) : 1.98
Log Po/w (MLOGP) : 2.5
Log Po/w (SILICOS-IT) : 2.42
Consensus Log Po/w : 2.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.18
Solubility : 0.191 mg/ml ; 0.000655 mol/l
Class : Soluble
Log S (Ali) : -2.84
Solubility : 0.421 mg/ml ; 0.00145 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.44
Solubility : 0.104 mg/ml ; 0.000359 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.85

Safety of [ 672293-33-3 ]

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 [ 672293-33-3 ]

* 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 [ 672293-33-3 ]
  • Downstream synthetic route of [ 672293-33-3 ]

[ 672293-33-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 6933-47-7 ]
  • [ 672293-33-3 ]
YieldReaction ConditionsOperation in experiment
85% With sodium periodate; iodine In N,N-dimethyl-formamide at 50℃; for 2 h; Intermediate 9; methyl 4-amino-5-iodo-2-methylbenzoate; To a solution of methyl 4-amino-2-methylbenzoate (Intermediate 7) (2.9 g, 16.6 mmol) in DMF (15 ml) was added sodium periodate (1.45 g, 6.6 mmol) and iodine (3.4 g, 13.3 mmol). The reaction mixture was stirred at 500C for 2 hours. The mixture was poured into cold water with NaHSO3 (0.5 g). After stirring, the mixture was left overnight. The precipitate was filtered, washed with water and diluted with dichloromethane. This solution was dried over Na2SO4, filtered and evaporated to give the title compound as orange solid (4.1 g, 85percent). NMR1H NMR (300 MHz), CDCI3 δ: 8.20 (s, 1 H), 6.47 (s, 1 H), 3.75 (s, 3H), 2.42 (s, 3H).
65%
Stage #1: With sodium periodate; iodine In N,N-dimethyl-formamide at 50℃; for 3 h;
Stage #2: With sodium hydrogen sulfite In water; N,N-dimethyl-formamide for 3 h;
To a mixture of 136   methyl 4-amino-2-methylbenzoate (15.0 g, 85.86 mmol) in 30   DMF (80 mL) was added 137   sodium periodate (7.36 g, 34.42 mmol) and 138   iodine (17.6. g, 68.84 mmol). The reaction mixture was stirred at 50° C. for 3 hours. The mixture was poured into a solution of 139   NaHSO3 (2.6 g) in 86   water (200 mL). After stirring for 3 h, the mixture was extracted with DCM (300 mL×3). The organic layer was dried over sodium sulfate, concentrated under reduced pressure and purified by chromatography on silica gel (2percent-30percent 32   EtOAc in 60   pet. ether) to give 18A (16.15 g, 65percent yield) as a yellow 140   solid: 1H NMR (400 MHz, CDCl3) δ 8.20 (s, 1H), 6.47 (s, 1H), 3.75 (s, 3H), 2.42 (s, 3H) ; ESI m/z 292.0 [M+H]+
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 942 - 945
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 946 - 949
[3] Patent: WO2009/47240, 2009, A1, . Location in patent: Page/Page column 30
[4] Patent: US2018/291002, 2018, A1, . Location in patent: Paragraph 0462; 0463
[5] Patent: US2004/142940, 2004, A1, . Location in patent: Page/Page column 42
[6] Patent: WO2006/7542, 2006, A1, . Location in patent: Page/Page column 24
  • 2
  • [ 67-56-1 ]
  • [ 90531-76-3 ]
  • [ 672293-33-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 11, p. 3349 - 3353
  • 3
  • [ 30459-70-2 ]
  • [ 672293-33-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 11, p. 3349 - 3353
  • 4
  • [ 1975-51-5 ]
  • [ 672293-33-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 11, p. 3349 - 3353
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