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[ CAS No. 52570-33-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 52570-33-9
Chemical Structure| 52570-33-9
Chemical Structure| 52570-33-9
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Product Details of [ 52570-33-9 ]

CAS No. :52570-33-9 MDL No. :MFCD12923250
Formula : C9H9IO2 Boiling Point : -
Linear Structure Formula :- InChI Key :IPPPZCXGKFWQEC-UHFFFAOYSA-N
M.W : 276.07 Pubchem ID :15656853
Synonyms :

Calculated chemistry of [ 52570-33-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.4
TPSA : 26.3 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) : -6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.45
Log Po/w (XLOGP3) : 2.79
Log Po/w (WLOGP) : 2.39
Log Po/w (MLOGP) : 3.11
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.55
Solubility : 0.0783 mg/ml ; 0.000284 mol/l
Class : Soluble
Log S (Ali) : -3.0
Solubility : 0.277 mg/ml ; 0.001 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.81
Solubility : 0.0428 mg/ml ; 0.000155 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.85

Safety of [ 52570-33-9 ]

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

Application In Synthesis of [ 52570-33-9 ]

* 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 [ 52570-33-9 ]
  • Downstream synthetic route of [ 52570-33-9 ]

[ 52570-33-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 18583-89-6 ]
  • [ 52570-33-9 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 38, p. 13148 - 13149
[2] Organic Letters, 2016, vol. 18, # 17, p. 4166 - 4169
  • 2
  • [ 133232-56-1 ]
  • [ 52570-33-9 ]
YieldReaction ConditionsOperation in experiment
92% at 0℃; for 3 h; Heating / reflux To a solution of compound 2 (63.0 g, 0.24 mol) in MeOH (300 mL) was added dropwise a freshly prepared solution of SOCI2 (52 mL, 0.72 mol) in MeOH (100 mL) at 0 0C. The mixture was heated to reflux for 3 hours. TLC (petroleum ether: ethyl acetate = 10:1) showed the reaction was complete, then the mixture was concentrated in vacuo. The residue was purified by column chromatography (petroleum ether) to afford compound 3 (60 g, 92percent) as brown oil. 1H NMR (400 MHz, CDCI3): δ 7.94-7.96 (d, J = 8.0 Hz, 1 H), 7.71-7.73 (d, J = 8.0 HzJ H), 6.87- 6.91 (t, J = 8.0 Hz, 1 H), 3.88 (s, 3H), 2.65 (s, 3H).
87.5% for 5 h; Heating / reflux 3-Iodo-2-methylbenzoic acid (10.00 g, 38.16 mmol), methanol (50 ml) and concentrated sulfuric acid (0.6 ml, 11.45 mmol) were mixed, and the mixture was stirred for 5 hours while heating to reflux. The reaction solution was concentrated, ethyl acetate (80 ml) and water (30 ml) were added to the residue. The organic layer was separated and washed three times with a saturated aqueous sodium bicarbonate solution (30 ml) and once with 10percent brine (30 ml) . The organic layer was concentrated, to yield the title compound (9.22 g) (yield 87.5percent) .1H-NMR (CDCl3, TMS, 300 MHz) δ (ppm) : 2.67 (3H, s) , 3.90 (3H, s), 6.92 (IH, t, J = 7.8 Hz), 7.74 (IH, dd, J = 1.2 Hz, 7.8 Hz) , 7.98 (IH, dd, J = 1.2 Hz, 7.9 Hz) .
80.4% at 0 - 80℃; for 16 h; [0469] To a solution of 3-iodo-2-methylbenzoic acid (2.0 g, 3.82 mmol) in dry MeOH (10 mL) at 0 °C was added thionyl chloride (681mg, 5.72 mmol). Then the reaction was heated to 80 °C for 16 hrs. TLC showed the starting material was consumed and one main spot was present. The reaction was cooled to rt and the solvent was removed. The residue was diluted with water (20 mL) and extracted with EA (40 mL) twice. The combined organic layers were washed with saturated sodium bicarbonate aqueous (30 mL), brine, dried over sodium sulfate, filtered and concentrated providing crude product, which was purified by column chromatography on silica-gel elution with petroleum ether:EA (from 0percent to 8percent) providing methyl 3-iodo-2-methylbenzoate (1.7 g, 80.4percent yield) as a colorless oil. MS (ESI) m/z 277.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.97 (dd, J = 1.2, 8.0 Hz, 1 H), 7.73 (dd, J = 0.8, 8.0 Hz, 1 H), 6.92 (t, J = 8.0 Hz, 1 H), 3.89 (s, 3 H), 2.66 (s, 3 H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6273 - 6278
[2] Patent: WO2006/117669, 2006, A1, . Location in patent: Page/Page column 41; 108
[3] Patent: WO2008/16184, 2008, A1, . Location in patent: Page/Page column 119-120
[4] Patent: WO2017/201069, 2017, A1, . Location in patent: Paragraph 0469
[5] Patent: WO2007/90068, 2007, A2, . Location in patent: Page/Page column 62
  • 3
  • [ 67-56-1 ]
  • [ 52107-91-2 ]
  • [ 52570-33-9 ]
Reference: [1] Patent: WO2008/16184, 2008, A1, . Location in patent: Page/Page column 120-121
  • 4
  • [ 52130-17-3 ]
  • [ 52570-33-9 ]
Reference: [1] Patent: WO2006/117669, 2006, A1,
  • 5
  • [ 680-15-9 ]
  • [ 52570-33-9 ]
  • [ 346603-63-2 ]
Reference: [1] Patent: US2003/216571, 2003, A1, . Location in patent: Page/Page column 62-63
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