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[ CAS No. 144550-76-5 ] {[proInfo.proName]}

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Chemical Structure| 144550-76-5
Chemical Structure| 144550-76-5
Structure of 144550-76-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 144550-76-5 ]

CAS No. :144550-76-5 MDL No. :MFCD13182440
Formula : C8H8INO2 Boiling Point : -
Linear Structure Formula :- InChI Key :FSNRVHNXSYBHSI-UHFFFAOYSA-N
M.W : 277.06 Pubchem ID :18929930
Synonyms :

Calculated chemistry of [ 144550-76-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.84
TPSA : 52.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.02
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 1.67
Log Po/w (MLOGP) : 2.21
Log Po/w (SILICOS-IT) : 1.94
Consensus Log Po/w : 2.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.39
Solubility : 0.113 mg/ml ; 0.000408 mol/l
Class : Soluble
Log S (Ali) : -3.28
Solubility : 0.147 mg/ml ; 0.000531 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.06
Solubility : 0.24 mg/ml ; 0.000865 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.81

Safety of [ 144550-76-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 144550-76-5 ]

* 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 [ 144550-76-5 ]
  • Downstream synthetic route of [ 144550-76-5 ]

[ 144550-76-5 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 67-56-1 ]
  • [ 117324-10-4 ]
  • [ 144550-76-5 ]
YieldReaction ConditionsOperation in experiment
93% at 0 - 65℃; for 52 h; To 2-acetylamino-4-iodo-benzoic acid (13.8 g, 45.3 mmol) in 200 mL of dry methanol was added SOCl2 (32.7 mL, 453 mmol) dropwise at 0 °C. The reaction mixture was then heated at 65 °C for 2 h. The reaction was then cooled to 0 °C, an additional portion of SOCl2 (10 mL, 137 mmol) was added, and the reaction was heated at 65 0C for 2 h. The reaction was then cooled to 0 °C, a final portion of SOCl2 (10 mL, 137 mmol) was added, and the reaction was heated at 65 °C for 48 h. The reaction was then cooled to 22 °C and concentrated in vacuo The resulting residue was diluted with H2O and EPO <DP n="305"/>extracted with 3 x 150 mL CH2Cl2. The combined organic fractions were washed with brine and dried over Na2SO4 to give i-b (11.7 g, 93percent): MS m/z = 278 (M+H).
13.8 g at 0 - 20℃; for 39 h; A solution of 16.1 g of 2-acetylamino-4-iodobenzoic acid (m.p. 233° C.-235° C.; synthesized in accordance with U.S. Pat. No. 4,762,838) in 325 ml of absolute methanol is saturated at 0° C. with dry hydrogen chloride gas. The mixture is heated to the boil for 15 hours, cooled to room temperature, resaturated using dry hydrogen chloride gas, and allowed to stand at room temperature for 24 hours. The solvent is evaporated in vacuo, the residue is taken up in dichloromethane, and the organic phase is washed with a saturated aqueous sodium hydrogen carbonate solution until free from acid. The organic phase is dried over Na2 SO4, and evaporated in vacuo. This gives 13.8 g of methyl 2-amino-4-iodobenzoate of m.p. 63° C.-67° C.
Reference: [1] Patent: WO2006/41773, 2006, A2, . Location in patent: Page/Page column 303-304
[2] Patent: US2017/121294, 2017, A1, . Location in patent: Paragraph 0058
  • 2
  • [ 115081-94-2 ]
  • [ 144550-76-5 ]
YieldReaction ConditionsOperation in experiment
80% With sodium hydroxide In methanol d.
Methyl 2-amino-4-iodobenzoate
To a stirred solution of sodium hydroxide (0.048 g, 1.2 mM) in methanol (4.5 mL) was added 7-iodo-2H-3,1-benzoxazine-2,4(1H)-dione (2.6 g, 9.0 mM).
The mixture was heated at 60° C. for 7 hr and the resulting solution was cooled, poured into water and extracted with ethyl acetate.
The combined extracts were washed once with dilute sodium hydroxide, dried (MgSO4), filtered and concentrated to leave the title compound (2.0 g, 80percent) as a brown oil which slowly crystallized; MS(CI): 278 (M+H).
Reference: [1] Patent: US5599814, 1997, A,
  • 3
  • [ 117324-10-4 ]
  • [ 144550-76-5 ]
Reference: [1] Patent: US5463081, 1995, A,
  • 4
  • [ 186581-53-3 ]
  • [ 20776-54-9 ]
  • [ 144550-76-5 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 7033 - 7036
  • 5
  • [ 67-56-1 ]
  • [ 20776-54-9 ]
  • [ 144550-76-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 16, p. 7671 - 7690
  • 6
  • [ 144550-76-5 ]
  • [ 144550-36-7 ]
Reference: [1] Patent: US2017/121294, 2017, A1,
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