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Chemical Structure| 58123-77-6
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Product Details of [ 58123-77-6 ]

CAS No. :58123-77-6 MDL No. :MFCD02068386
Formula : C7H5IO3 Boiling Point : -
Linear Structure Formula :- InChI Key :UABBBWVTEWIIMN-UHFFFAOYSA-N
M.W : 264.02 Pubchem ID :736854
Synonyms :

Calculated chemistry of [ 58123-77-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.14
TPSA : 57.53 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) : -6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 1.71
Consensus Log Po/w : 1.67

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.91
Solubility : 0.324 mg/ml ; 0.00123 mol/l
Class : Soluble
Log S (Ali) : -2.56
Solubility : 0.719 mg/ml ; 0.00272 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.15
Solubility : 1.88 mg/ml ; 0.00711 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.72

Safety of [ 58123-77-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 58123-77-6 ]

* 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 [ 58123-77-6 ]
  • Downstream synthetic route of [ 58123-77-6 ]

[ 58123-77-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 99-06-9 ]
  • [ 58123-77-6 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide; sodium hypochlorite; sodium iodide In methanol; water at 0 - 20℃; 21.0 g (0.52 mol, 1.05 eq.) of sodium hydroxide and then 78.7 g (0.52 mol, 1.05 eq.) of sodium iodide are added to a solution of 69.1 g (0.5 mol, 1 eq.) of 3-hydroxybenzoic acid in 700 ml of methanol. The reaction mixture is cooled to 0°C and then aqueous sodium hypochlorite solution (0.52 mol, 1.05 eq.) is added dropwise. The reaction medium is stirred at 0-5°C for 2 hours and then at ambient temperature overnight. The methanol is evaporated and then the reaction medium is acidified with a concentrated hydrochloric acid solution. The precipitated product is filtered off, washed with water and dried. 121 g of 3-hydroxy-4-iodobenzoic acid are obtained in the form of an off-white solid. Yield = 92percent
92%
Stage #1: With sodium hydroxide; potassium hypochlorite; sodium iodide In methanol; water at 0 - 20℃;
Stage #2: With hydrogenchloride In water
21.0 g (0.52 mol, 1.05 eq) of sodium hydroxide and then 78.7 g (0.52 mol, 1.05 eq) of sodium iodide are added to a solution of 69.1 g (0.5 mol, 1 eq) of 3-hydroxybenzoic acid in 700 ml of methanol. The reaction mixture is cooled to 0°C and potassium hypochlorite solution (0.52 mol, 1.05 eq) is then added dropwise. The reaction medium is stirred at 0-5°C for 2 hours and then at room temperature overnight. The methanol is evaporated off and the reaction medium is then acidified with concentrated hydrochloric acid solution. The precipitated product is filtered off, washed with water and dried. 121 g of 3-hydroxy-4-iodobenzoic acid are obtained in the form of an off-white solid. Yield = 92percent
56%
Stage #1: With sodium hypochlorite solution; sodium iodide; sodium hydroxide In methanol; water at 0 - 5℃;
Stage #2: With hydrogenchloride In water
21 g (520 mmol) of sodium hydroxide and then 79 g (520 mmol) of sodium iodide are added to a solution of 69 g (500 mmol) of 3-hydroxybenzoic acid in 700 ml of methanol. The reaction mixture is cooled to 0° C. and then Javel water (520 mmol) is added dropwise. The reaction mixture is stirred at 0-5° C. for 2 hours and then at room temperature for 15 h. After evaporating the methanol, the reaction mixture is acidified with a concentrated solution of hydrochloric acid. The precipitate is filtered, washed with water and dried. 41.9 g of 3-hydroxy-4-iodobenzoic acid is obtained in the form of a white solid with melting point of 218° C. The aqueous phase is extracted with ethyl acetate, the organic phase obtained is dried over magnesium sulfate, filtered, and evaporated. The residue obtained is taken up in heptane and the precipitate obtained is filtered.Analysis showed that 61.3 g (56percent) of 3-hydroxy-4-iodobenzoic acid is obtained.
54%
Stage #1: With iodine; ammonium hydroxide; potassium iodide In water at 20℃; for 1 h;
Stage #2: With hydrogenchloride In water
3-Hydroxybenzoic acid (13.8 g, 100 mmol) is dissolved in concentrated NH4OH (200 mL) using an overhead stirrer and is treated slowly drop-wise with a solution of iodine (23.4 g, 92 mmol) and KI (18.26 g, 110 mmol) in water (100 mL). The solution is stirred for 1 h at RT and then treated rapidly drop-wise with concentrated HCl (180 mL). The solid is collected via filtration, rinsed with water and dried overnight by pulling air through the solid to afford 13.1 g (54percent) of 3-hydroxy-4-iodobenzoic acid as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ7.13, 7.43, 7.80, 10.71, 12.98 ppm.
51% at 45℃; for 70 h; Large scale To a solution of 3-hydroxybenzoic acid (18; 1.90 kg, 13.8 mol) in acetic acid (9.0 L) was added iodine monochloride (3.32 kg, 20.6 mol). The resultant dark mixture was stirred and heated at 45 °C for 70 h. The mixture was then concentrated under vacuum to a thick slurry, and aqueous Na2S2O3 (1.5percent, 10 L). The mixture was stirred for 1 h, filtered, and rinsed with water (3 × 2.5 L). The resultant solid was treated with Na2S2O3 twice more, filtered, and rinsed. The solid was dried to give 1.85 kg (51percent) of product as a tan solid: HPLC analysis showed a purity of 95percent with a retention time of 3.7 min.
54% With hydrogenchloride; Ki; iodine In ammonium hydroxide; water EXAMPLE 13
N-[(1S,2R,4R)-7-Azabicyclo[2.2.1]hept-2-yl]-1-benzofuran-6-carboxamide hydrochloride
3-Hydroxybenzoic acid (13.8 g, 100 mmol) is dissolved in concentrated NH4OH (200 mL) using an overhead stirrer and is treated slowly dropwise with a solution of iodine (23.4 g, 92 mmol) and KI (18.26 g, 110 mmol) in water (100 mL).
The solution is stirred for 1 h at RT and then treated rapidly dropwise with concentrated HCl (180 mL).
The white solid is collected via filtration, rinsed with water and dried overnight by pulling air through the solid to afford 13.05 g (54percent) of 3-hydroxy-4-iodobenzoic acid as a tan solid.
280 g With sodium hypochlorite; sodium iodide; sodium hydroxide In methanol; water at -10 - -5℃; for 2 h; (a) Add 2L of methanol, 200g of m-hydroxybenzoic acid, 61g of NaOH and 226g of NaI to a 5L three-necked bottle.1.43L NaClO aqueous solution (mass content 9percent, drop rate 2L / h) and control temperature is -10 ° C ~ -5 ° C, reaction 2h; concentrated at 50 ° C under reduced pressure to remove methanol, followed by 1N (ie equivalent concentration) Hydrochloric acid adjusts the pH to about 1, at which time a large amount of white solid precipitates, is filtered, and dried to obtain 280 g of compound II; the nuclear magnetic spectrum of compound II is resolved as:

Reference: [1] Patent: WO2006/18325, 2006, A1, . Location in patent: Page/Page column 25-26
[2] Patent: WO2006/18326, 2006, A1, . Location in patent: Page/Page column 78
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 9, p. 1103 - 1114
[4] Beilstein Journal of Organic Chemistry, 2009, vol. 5,
[5] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 15, p. 2077 - 2086
[6] Dalton Transactions, 2015, vol. 44, # 19, p. 9281 - 9288
[7] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 83, p. 10328 - 10330,3
[8] Patent: US2010/144884, 2010, A1, . Location in patent: Page/Page column 9
[9] Chemical Communications, 2017, vol. 53, # 53, p. 7222 - 7225
[10] Patent: US2003/232853, 2003, A1, . Location in patent: Page 38
[11] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3366 - 3372
[12] Journal of Medicinal Chemistry, 2003, vol. 46, # 10, p. 1845 - 1857
[13] Justus Liebigs Annalen der Chemie, 1874, vol. 174, p. 100
[14] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 701
[15] Journal of the American Chemical Society, 1948, vol. 70, p. 2314,2317
[16] Synthesis, 2002, # 17, p. 2503 - 2512
[17] Synlett, 2007, # 9, p. 1383 - 1386
[18] Patent: US2003/105089, 2003, A1,
[19] Patent: US2002/198195, 2002, A1,
[20] Patent: US2009/12129, 2009, A1, . Location in patent: Page/Page column 21
[21] Patent: EP1217000, 2002, A1, . Location in patent: Page 60
[22] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2289 - 2310
[23] Patent: US2015/284405, 2015, A1, . Location in patent: Paragraph 0398
[24] Patent: WO2016/112088, 2016, A1, . Location in patent: Paragraph 0646
[25] Patent: CN108467375, 2018, A, . Location in patent: Paragraph 0011; 0013; 0014; 0015
  • 2
  • [ 99-06-9 ]
  • [ 58123-77-6 ]
YieldReaction ConditionsOperation in experiment
30% With Iodine monochloride In water; acetic acid Step 3
Synthesis of 3-hydroxy-4-iodobenzoic acid
30.0 g (217 mmol) of 3-hydroxybenzoic acid was dissolved in 200 ml of acetic acid. 53.0 g (326 mmol) of iodine monochloride was added to the obtained solution at room temperature.
After stirring at 45° C. for 15 hours, the solvent was evaporated under reduced pressure.
The residue was washed with 500 ml of 1percent aqueous sodium thiosulfate solution twice and with 500 ml of water twice and then dried to solid at 80° C. under reduced pressure to obtain the title compound.
Yield: 17.2 g (65.2 mmol) (yield: 30percent)
MS (FAB, m/z) 265 (MH+)
H-NMR (DMSO-d6) δ7.13 (1H, dd), 7.43 (1H, d), 7.80 (1H, d)
Reference: [1] Patent: US2002/193348, 2002, A1,
[2] Patent: US2003/109547, 2003, A1,
[3] Patent: US2001/56123, 2001, A1,
[4] Patent: US2001/56123, 2001, A1,
[5] Patent: EP976722, 2000, A1,
[6] Patent: EP976722, 2000, A1,
[7] Patent: EP1065200, 2001, A1,
  • 3
  • [ 99-06-9 ]
  • [ 58123-77-6 ]
Reference: [1] Patent: US6316009, 2001, B1,
[2] Patent: US6150413, 2000, A,
  • 4
  • [ 1310-73-2 ]
  • [ 99-06-9 ]
  • [ 58123-77-6 ]
Reference: [1] Patent: US2010/158843, 2010, A1,
  • 5
  • [ 2374-03-0 ]
  • [ 58123-77-6 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 701
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1924, vol. 178, p. 1286
  • 6
  • [ 100-83-4 ]
  • [ 58123-77-6 ]
Reference: [1] Chemische Berichte, 1923, vol. 56, p. 847
  • 7
  • [ 67-56-1 ]
  • [ 58123-77-6 ]
  • [ 157942-12-6 ]
YieldReaction ConditionsOperation in experiment
76% at 70℃; for 48 h; Overall, 61.31 g of 3-hydroxy-4-iodobenzoic acid are obtained in the form of a white solid. 47 g (150 mmol) of this 3-hydroxy-4-iodobenzoic acid are placed in 300 mL of methanol and 6.13 g (35.6 mmol) of para-toluenesulfonic acid are added. The reaction mixture is heated at 70° C. for 48 hours.- The reaction is stopped by addition of 11 of water. The precipitated product is filtered off and rinsed with water to neutral pH. 37.4 g (76percent) of methyl 3-hydroxy-4-iodobenzoate are obtained in the form of a beige-colored powder.
70% at 20℃; for 20 h; Heating / reflux 3-Hydroxy-4-iodobenzoic acid (12.55 g, 47.5 mmol) is dissolved in MeOH (200 mL), treated slowly drop-wise with thionyl chloride (32.3 mL, 443 mmol) at RT, then heated to reflux for 20 h. The mixture is concentrated to dryness and partitioned between CH2Cl2 (100 mL) and saturated NaHCO3 (50 mL). Not all of the residue dissolves, so the mixture is filtered and the solid is washed with a small amount of CH2Cl2 in MeOH. The original filtrate and the organic washes are combined, concentrated to dryness, dissolved in 10percent MeOH/CH2Cl2 (200 mL), diluted with water (50 mL) and the layers separated. The organics are washed with saturated NaHCO3 (2.x.50 mL), then water (50 mL), dried (Na2SO4) and concentrated to a tan solid. This solid is triturated with CH2Cl2 (50 mL) and filtered. The two solids are combined to afford 9.4 g (70percent) of methyl 3-hydroxy-4-iodobenzoate as a beige solid. HRMS (FAB) calcd for C8H7IO3+H: 278.9520, found 278.9521 (M+H)+.
70% for 144 h; Heating / reflux 59 ml (1.10 mol, 2.4 eq.) of sulphuric acid are added to a solution of 121 g (0.458 mol, 1 eq.) of 3-hydroxy-4-iodobenzoic acid in 700 ml of methanol. The reaction mixture is heated at reflux for 6 days. The methanol is evaporated and then the reaction medium is poured into water and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulphate. The solvent is concentrated and the solid obtained is filtered off and dried. 88.56 g of methyl 3-hydroxy-4-iodobenzoate are obtained in the form of white crystals. Yield = 70percent
70% for 144 h; Heating / reflux 59 ml (1.10 mol, 2.4 eq) of sulphuric acid are added to a solution of 121 g (0.458 mol, 1 eq) of methyl 3-hydroxy-4-iodobenzoic acid in 700 ml of methanol. Thereaction mixture is refluxed for 6 days. The methanol is evaporated off and the reaction medium is then poured into water and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvent is concentrated and the solid obtained is filtered off and dried. 88.56 g of methyl 3-hydroxy-4-iodobenzoate are obtained in the form of white crystals. Yield = 70percent

Reference: [1] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 83, p. 10328 - 10330,3
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 9, p. 1103 - 1114
[3] Patent: US2009/12129, 2009, A1, . Location in patent: Page/Page column 21
[4] Patent: US2003/232853, 2003, A1, . Location in patent: Page 38
[5] Patent: WO2006/18325, 2006, A1, . Location in patent: Page/Page column 26
[6] Patent: WO2006/18326, 2006, A1, . Location in patent: Page/Page column 78; 79
[7] Journal of Medicinal Chemistry, 2005, vol. 48, # 9, p. 3290 - 3312
[8] Patent: EP2017263, 2009, A1, . Location in patent: Page/Page column 173
[9] Patent: EP1217000, 2002, A1, . Location in patent: Page 60
[10] Journal of Medicinal Chemistry, 2009, vol. 52, # 18, p. 5685 - 5702
[11] Patent: US2010/286430, 2010, A1, . Location in patent: Page/Page column title page; 1
[12] Synthesis (Germany), 2012, vol. 44, # 23, p. 3598 - 3602
[13] Chemical Communications, 2017, vol. 53, # 53, p. 7222 - 7225
  • 8
  • [ 58123-77-6 ]
  • [ 104-15-4 ]
  • [ 157942-12-6 ]
YieldReaction ConditionsOperation in experiment
76% at 70℃; for 48 h; 6.1 g (35.6 mmol) of paratoluene sulfonic acid is added to a solution of 47 g (150 mmol) of 3-hydroxy-4-iodobenzoic acid in 300 ml of methanol. The reaction mixture is heated at 70° C. for 48 hours. After adding 1000 ml of water, the precipitate is filtered, and rinsed with water to neutral pH. 37.4 g (76percent) of methyl 3-hydroxy-4-iodobenzoate is obtained in the form of a beige powder.
Reference: [1] Patent: US2010/144884, 2010, A1, . Location in patent: Page/Page column 9
[2] Patent: US2010/158843, 2010, A1,
  • 9
  • [ 58123-77-6 ]
  • [ 157942-12-6 ]
YieldReaction ConditionsOperation in experiment
70% With thionyl chloride In methanol; dichloromethane 3-Hydroxy-4-iodobenzoic acid (12.55 g, 47.5 mmol) is dissolved in MeOH (200 mL), treated slowly dropwise with thionyl chloride (32.3 mL, 442.9 mmol) at rt, then heated to reflux for 20 h.
The mixture is concentrated to dryness and partitioned between CH2Cl2 (100 mL) and saturated NaHCO3 (50 mL).
Not all of the residue is solubilized, so the mixture is filtered and the solid is washed with a small amount of CH2Cl2 and MeOH.
The original filtrate and the organic washes are combined, concentrated to dryness, dissolved in 10percent MeOH/CH2Cl2 (200 mL), diluted with water (50 mL) and the layers separated.
The organics are washed with saturated NaHCO3 (2*50 mL), then water (50 mL), dried over anhydrous Na2SO4 and concentrated to a tan solid.
This solid is triturated with CH2Cl2 (50 mL) and filtered.
The two solids are combined to afford 9.4 g (70percent) of methyl 3-hydroxy-4-iodobenzoate as a beige solid. HRMS (FAB) calcd for C8H7IO3+H1: 278.9520, found 278.9521.
70% With thionyl chloride In methanol; dichloromethane 3-Hydroxy-4-iodobenzoic acid (12.55 g, 47.5 mmol) is dissolved in CH3OH (200 mL), treated slowly dropwise with thionyl chloride (32.3 mL, 442.9 mmol) at RT, then heated to reflux for 20 h.
The mixture is concentrated to dryness and partitioned between CH2Cl2 (100 mL) and saturated NaHCO3 (50 mL).
Not all of the residue is solubilized, so the mixture is filtered and the solid is washed with a small amount of CH2Cl2 and CH3OH.
The original filtrate and the organic washes are combined, concentrated to dryness, dissolved in 10percent CH3OH/CH2Cl2 (200 mL), diluted with water (50 mL) and the layers separated.
The organics are washed with saturated NaHCO3 (2*50 mL), then water (50 mL), dried over Na2SO4 and concentrated to a tan solid.
This solid is triturated with CH2Cl2 (50 mL) and filtered.
The two solids are combined to afford 9.4 g (70percent) of methyl 3-hydroxy-4-iodobenzoate as a beige solid. HRMS (FAB) calcd for C8H7IO3+H: 278.9520, found 278.9521 (M+H)+.
Reference: [1] Patent: US2003/73707, 2003, A1,
[2] Patent: US2003/105089, 2003, A1,
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  • [ 18107-18-1 ]
  • [ 157942-12-6 ]
Reference: [1] Patent: WO2014/176142, 2014, A1, . Location in patent: Page/Page column 53-54
  • 11
  • [ 58123-77-6 ]
  • [ 162401-62-9 ]
Reference: [1] Synthesis (Germany), 2012, vol. 44, # 23, p. 3598 - 3602
[2] Synthesis (Germany), 2012, vol. 44, # 23, p. 3598 - 3602
  • 12
  • [ 58123-77-6 ]
  • [ 773869-57-1 ]
YieldReaction ConditionsOperation in experiment
88% With borane-THF In tetrahydrofuran at 60℃; for 2 h; Reference Example 14
5-(hydroxymethyl)-2-iodophenol
To a solution of 3-hydroxy-4-iodobenzoic acid (20.9 g, 79.3 mmol) in anhydrous THF (160 mL) was added 1 M borane THF solution (240 mL, 240 mmol) by small portions, and the mixture was stirred at 60°C for 2 hr.
Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate.
The extract was washed with saturated brine, and dried over anhydrous sodium sulfate.
The solvent was evaporated under reduced pressure, and the residue was washed with diisopropyl ether and hexane to give the title compound (17.4 g, yield 88percent) as a white solid.
1H NMR (CDCl3) δ 1.69 (br, 1H), 4.64 (s, 2H), 5.33 (s, 1H), 6.70 (dd, J = 7.8, 1.5 Hz, 1H), 7.01 (d, J = 1.5 Hz, 1H), 7.63 (d, J = 7.8 Hz, 1H) .
Reference: [1] Patent: EP2351743, 2011, A1, . Location in patent: Page/Page column 117
  • 13
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  • [ 1243391-44-7 ]
Reference: [1] Synthesis (Germany), 2012, vol. 44, # 23, p. 3598 - 3602
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