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[ CAS No. 54073-94-8 ] {[proInfo.proName]}

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Chemical Structure| 54073-94-8
Chemical Structure| 54073-94-8
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Product Details of [ 54073-94-8 ]

CAS No. :54073-94-8 MDL No. :MFCD00016423
Formula : C9H8I2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :AVFDHVCJEMRWFS-UHFFFAOYSA-N
M.W : 417.97 Pubchem ID :634500
Synonyms :

Calculated chemistry of [ 54073-94-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 69.99
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.64
Log Po/w (XLOGP3) : 3.09
Log Po/w (WLOGP) : 2.78
Log Po/w (MLOGP) : 3.32
Log Po/w (SILICOS-IT) : 3.52
Consensus Log Po/w : 3.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.5
Solubility : 0.0133 mg/ml ; 0.0000318 mol/l
Class : Moderately soluble
Log S (Ali) : -3.73
Solubility : 0.077 mg/ml ; 0.000184 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.11
Solubility : 0.0324 mg/ml ; 0.0000776 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.04

Safety of [ 54073-94-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 54073-94-8 ]

* 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.

  • Downstream synthetic route of [ 54073-94-8 ]

[ 54073-94-8 ] Synthesis Path-Downstream   1~38

  • 1
  • [ 120-47-8 ]
  • [ 54073-94-8 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydrogencarbonate; N,N,N-trimethylbenzenemethanaminium dichloroiodate In methanol; dichloromethane for 7h; Ambient temperature;
With potassium iodate; ethanol; iodine
  • 2
  • [ 64-17-5 ]
  • [ 618-76-8 ]
  • [ 54073-94-8 ]
  • 3
  • [ 54073-94-8 ]
  • [ 141-52-6 ]
  • 4-ethoxycarbonylmethoxy-3,5-diiodo-benzoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethanol anschliessend Erwaermen mit Chloressigsaeure-aethylester;
With ethanol anschliessend Erwaermen mit Chloressigsaeure-aethylester;
  • 4
  • [ 54073-94-8 ]
  • [ 89011-17-6 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate
  • 5
  • [ 54073-94-8 ]
  • [ 100-44-7 ]
  • 4-benzyloxy-3,5-diiodo-benzoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide
  • 6
  • [ 54073-94-8 ]
  • [ 19231-06-2 ]
  • [ 189156-59-0 ]
YieldReaction ConditionsOperation in experiment
at 37℃; Hydrolysis;
YieldReaction ConditionsOperation in experiment
Herstellung von 4-Hydroxy-3,5-di-<131<i>I</i>>jod-benzoesaeure-aethylester;
  • 9
  • [ 5720-05-8 ]
  • [ 54073-94-8 ]
  • 2'-hydroxy-4,4''-dimethyl-[1,1';3',1'']terphenyl-5'-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tris(dibenzylideneacetone)dipalladium (0); potassium carbonate In water; acetone at 60℃; for 19h;
  • 10
  • [ 5720-07-0 ]
  • [ 54073-94-8 ]
  • ethyl 3,5-di(4-methoxyphenyl)-4-hydroxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tris(dibenzylideneacetone)dipalladium (0); potassium carbonate In water; acetone at 60℃;
  • 11
  • [ 54073-94-8 ]
  • [ 271242-03-6 ]
  • [ 271242-06-9 ]
YieldReaction ConditionsOperation in experiment
81% With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate In water; acetone at 65℃; for 18h;
  • 12
  • [ 54073-94-8 ]
  • [ 536-74-3 ]
  • 3-phenyl-7-phenylethynyl-benzofuran-5-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 20℃;
  • 13
  • [ 54073-94-8 ]
  • [ 108-24-7 ]
  • ethyl 4-(acetyloxy)-3,5-diiodobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; dmap
  • 14
  • [ 3970-21-6 ]
  • [ 54073-94-8 ]
  • [ 1025941-72-3 ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydride In tetrahydrofuran at 60℃;
  • 15
  • [ 54073-94-8 ]
  • [ 100-52-7 ]
  • 4-hydroxy-3-(hydroxy-phenyl-methyl)-5-iodo-benzoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 4-hydroxy-3,5-diiodo-benzoic acid ethyl ester With methylmagnesium chloride; lithium chloride In tetrahydrofuran at -30℃; for 0.666667h; Stage #2: With isopropylmagnesium chloride In tetrahydrofuran at -30℃; for 0.5h; Stage #3: benzaldehyde In tetrahydrofuran at -30℃;
  • 16
  • [ 54073-94-8 ]
  • [ 106-95-6 ]
  • 3-allyl-4-hydroxy-5-iodo-benzoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% Multistep reaction;
  • 17
  • [ 54073-94-8 ]
  • ethyl 6-(acetyloxy)-4'-formyl-5-iodobiphenyl-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: pyridine; DMAP 2.1: Li(acac); s-Bu2Zn / 1-methyl-pyrrolidin-2-one; diethyl ether; cyclohexane / 10 h / 0 °C 2.2: 83 percent / Pd(PPh3)4 / various solvents / 12 h / 20 °C
  • 18
  • [ 54073-94-8 ]
  • [ 271242-07-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / Pd2(dba)3; Cs2CO3 / acetone; H2O / 18 h / 65 °C 2: 99 percent / n-Bu4NF / tetrahydrofuran / 2 h / 20 °C
  • 19
  • [ 54073-94-8 ]
  • 3-<i>p</i>-tolyl-7-<i>p</i>-tolylethynyl-benzofuran-5-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 72 percent / NaH / tetrahydrofuran; various solvent(s) / 60 °C 2: 10 percent Spectr. / Pd(PPh3)2Cl2; CuI; piperidine
  • 20
  • [ 54073-94-8 ]
  • 3-(4-bromo-phenyl)-7-(4-bromo-phenylethynyl)-benzofuran-5-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 72 percent / NaH / tetrahydrofuran; various solvent(s) / 60 °C 2: 10 percent Spectr. / Pd(PPh3)2Cl2; CuI; piperidine
  • 21
  • [ 54073-94-8 ]
  • 4-(2-methoxy-ethoxymethoxy)-3,5-bis-<i>p</i>-tolylethynyl-benzoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 72 percent / NaH / tetrahydrofuran; various solvent(s) / 60 °C 2: Pd(PPh3)2Cl2; CuI; piperidine
  • 22
  • [ 54073-94-8 ]
  • 3,5-bis-(4-bromo-phenylethynyl)-4-(2-methoxy-ethoxymethoxy)-benzoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 72 percent / NaH / tetrahydrofuran; various solvent(s) / 60 °C 2: Pd(PPh3)2Cl2; CuI; piperidine
  • 23
  • [ 54073-94-8 ]
  • ethyl 3,5-di[4-(4-nitrophenylethynyl)phenyl]-4-hydroxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 81 percent / Pd2(dba)3; Cs2CO3 / acetone; H2O / 18 h / 65 °C 2: 99 percent / n-Bu4NF / tetrahydrofuran / 2 h / 20 °C 3: 80 percent / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran / 16 h / 20 °C
  • 24
  • [ 54073-94-8 ]
  • [ 271242-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 81 percent / Pd2(dba)3; Cs2CO3 / acetone; H2O / 18 h / 65 °C 2: 99 percent / n-Bu4NF / tetrahydrofuran / 2 h / 20 °C 3: 81 percent / Pd(PPh3)2Cl2; CuI; piperidine / 16 h / 20 °C
  • 25
  • [ 54073-94-8 ]
  • [ 69240-57-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cu; Et3N 2: DIBAL 3: PCC
  • 26
  • [ 54073-94-8 ]
  • [ 250129-95-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cu; Et3N 2: DIBAL
  • 27
  • [ 54073-94-8 ]
  • 5-[1-[3,5-Diiodo-4-(4-methoxy-phenoxy)-phenyl]-meth-(Z)-ylidene]-thiazolidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Cu; Et3N 2: DIBAL 3: PCC 4: TiCl4; pyridine
  • 28
  • [ 54073-94-8 ]
  • 5-[1-[4-(4-Hydroxy-phenoxy)-3,5-diiodo-phenyl]-meth-(Z)-ylidene]-thiazolidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Cu; Et3N 2: DIBAL 3: PCC 4: TiCl4; pyridine 5: BBr3
  • 29
  • [ 54073-94-8 ]
  • 5-[1-[4-(4-Hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]-meth-(Z)-ylidene]-thiazolidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: Cu; Et3N 2: DIBAL 3: PCC 4: TiCl4; pyridine 5: BBr3 6: I2; KI; NH4OH
  • 30
  • [ 54073-94-8 ]
  • 5-[1-[4-(4-Hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-meth-(Z)-ylidene]-thiazolidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: Cu; Et3N 2: DIBAL 3: PCC 4: TiCl4; pyridine 5: BBr3 6: I2; KI; NH4OH
  • 31
  • [ 54073-94-8 ]
  • 4-carboxymethoxy-3,5-diiodo-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / anschliessend Erwaermen mit Chloressigsaeure-aethylester 2: ethanolic KOH-solution
  • 32
  • [ 50586-80-6 ]
  • [ 54073-94-8 ]
  • [ 1186436-44-1 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;
  • 33
  • [ 54073-94-8 ]
  • C25H26N2O3(2+)*2I(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate; C16H36N; tris-(o-tolyl)phosphine; palladium diacetate / N,N-dimethyl-formamide / 100 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere 3.1: acetonitrile / 1 h / 80 °C / Inert atmosphere 4.1: dihydrogen peroxide / Irradiation
  • 34
  • [ 54073-94-8 ]
  • [ 1415748-04-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; C16H36N; tris-(o-tolyl)phosphine; palladium diacetate / N,N-dimethyl-formamide / 100 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere
  • 35
  • [ 54073-94-8 ]
  • [ 1415748-09-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; C16H36N; tris-(o-tolyl)phosphine; palladium diacetate / N,N-dimethyl-formamide / 100 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere
  • 36
  • [ 54073-94-8 ]
  • C32H33BN2O5(2+)*I(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate; C16H36N; tris-(o-tolyl)phosphine; palladium diacetate / N,N-dimethyl-formamide / 100 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere 3.1: acetonitrile / 1 h / 80 °C / Inert atmosphere
  • 37
  • [ 100-43-6 ]
  • [ 54073-94-8 ]
  • [ 1415748-03-6 ]
YieldReaction ConditionsOperation in experiment
100% With palladium diacetate; potassium carbonate; C16H36N; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; Inert atmosphere;
  • 38
  • [ 54073-94-8 ]
  • [ 74-88-4 ]
  • [ 101871-75-4 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 4-hydroxy-3,5-diiodo-benzoic acid ethyl ester With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; Schlenk technique; Inert atmosphere; Synthesis of ethyl 3,5-diiodo-4-methoxybenzoate (2i) A dry and argon-flushed 25 mL Schlenk-flask equipped with a magnetic stirring bar and a septum was charged with ethyl 4-hydroxy-3,5-diiodobenzoate (834 mg, 2.00 mmol) and DMF (5 mL) and was cooled down to 0 °C. K 2 CO 3 (304 mg, 2.20 mmol) was added at 0 °C and the reaction solution was stirred for 30 min. Methyl iodide (0.15 mL, 2.40 mmol) was then added at 0 °C and the reaction was allowed to warm to room temperature overnight. The mixture was quenched with a sat. aq. NH 4 Cl solution (10 mL), diluted with water (10 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic extracts were dried over Na 2 SO 4 , filtered and concentrated in vacuo. The crude product was purified via column chromatography (isohexane:ethyl acetate = 90:10, R f = 0.65) to give the product 2i (858 mg, 1.98 mmol, 98% yield) as a white solid. M.p. (°C): 97-99. 1 H-NMR (400 MHz, CDCl 3 , ppm) = 8.42 (s, 2H), 4.36 (q, J = 7.1 Hz, 2H), 3.90 (s, 3H), 1.39 (t, J = 7.1 Hz, 3H). 13 C-NMR (101 MHz, CDCl 3 , ppm) = 163.5, 162.6, 141.3, 129.8, 90.2, 61.8, 60.9, 14.4. IR (ATR, cm -1 ) = 2978, 1711, 1271, 1259, 995. MS (EI, 70 eV, %) m/z = 433 (11), 432 (100), 404 (88), 389 (11), 387 (77), 344 (10), 305 (13), 290 (10), 287 (9), 262 (19), 245 (31), 231 (9), 229 (9), 218 (9), 217 (11), 189 (16), 178 (9). HRMS (EI, 70 eV) m/z: calc. C 10 H 10 I 2 O 3 : 431.8719; found: 431.8713.
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