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[ CAS No. 16870-28-3 ] {[proInfo.proName]}

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Chemical Structure| 16870-28-3
Chemical Structure| 16870-28-3
Structure of 16870-28-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 16870-28-3 ]

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Product Details of [ 16870-28-3 ]

CAS No. :16870-28-3 MDL No. :MFCD00061127
Formula : C7H5IO3 Boiling Point : -
Linear Structure Formula :- InChI Key :UQOZVZTUJNRMBV-UHFFFAOYSA-N
M.W : 264.02 Pubchem ID :72874
Synonyms :

Calculated chemistry of [ 16870-28-3 ]      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 ?2

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) : -5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.12
Log Po/w (XLOGP3) : 3.34
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 1.71
Consensus Log Po/w : 1.95

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.92
Solubility : 0.0318 mg/ml ; 0.000121 mol/l
Class : Soluble
Log S (Ali) : -4.23
Solubility : 0.0157 mg/ml ; 0.0000595 mol/l
Class : Moderately 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 [ 16870-28-3 ]

Signal Word:Danger Class:9
Precautionary Statements:P264-P270-P273-P280-P301+P312+P330-P302+P352+P312-P305+P351+P338+P310-P391-P405-P501 UN#:3077
Hazard Statements:H302-H311-H318-H400 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 16870-28-3 ]

* 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.

  • Downstream synthetic route of [ 16870-28-3 ]

[ 16870-28-3 ] Synthesis Path-Downstream   1~14

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  • [ 65-49-6 ]
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YieldReaction ConditionsOperation in experiment
85 - 90% Step A: 4-Aminosalicylic acid (4.0 g, 26 mmol) was suspended in H2SO4 (26 mL, 2.7M) at -50C. Sodium nitrite (1.8 g, 26.1 mmol) in H2O (6.5 mL) was cooled to ice bath temperature and was added dropwise to the aminosalicylic acid mixture over 5 minutes. The resulting suspension was stirred at -5 C for 15 minutes. A solution of KI (6.8 g, 41 mmol) in H2SO4 (13 mL, IM) was added dropwise to the diazonium salt, with considerable evolution of N2. The reaction mixture was heated at 7O0C for 20 minutes. The reaction mixture was then partitioned between H2O and EtOAc. The organic layer was dried and concentrated. Purification by silica gel chromatography (7/3, hexanes/acetone, 1% acetic acid) yielded 4-iodosalicylic acid (5.33g, 85-90% pure).
39.8% In a 0.5 L 3 necked flask, 4-aminosalicylic acid 45 (15.3 g, 100 mmol) was mixed with H2O (100 ml), Conc. H2SO4 (14 ml, 25.8 g, 263 mmol). The mixture was stirred and cooled to 3-5 C. and diazotated by gradual addition of cold solution of NaNO2 (6.9 g, 100 mmol) in 20 ml water with control with iodine:starch paper of excess NaNO2. Dark solution was obtained. The diazotated solution was added to cold solution of KI (26 g, 156.6 mmol) in 25 ml 1N H2SO4. After 1 min, strong and rapid evolution of nitrogen was observed without heating. Ether (10-20 ml) was added to destroy the foam. The beaker with reaction mixture was heated at 75-80 C. for 10 min. The precipitate was filtered and washed with water and dried in air to obtain 17 g of raw product, which was purified by column chromatography: 340 g SiO2, 2% MeOH in CHCl3. 10.5 g, Yield: 39.8%.
35%. With potassium iodide; sodium nitrite;copper(I) iodide; In sulfuric acid; water; (b) Preparation of 2-hydroxy-4-iodobenzoic acid: To 20% sulfuric acid solution (650 ml) were added 4-amino-2-hydroxybenzoic acid and 200 ml of 20% sulfuric acid solution. The solution was cooled to -10 C. and a solution of sodium nitrite (47 g, 0.34 mol) in water (100 ml) was added over 5 hours. The solution obtained was added dropwise to a suspension of potassium iodide (69.5 g, 0.42 mol) and copper(I) iodide (69.5 g, 0.36 mol) in 370 ml of 20% sulfuric acid. The mixture was stirred for 36 hours at room temperature and was then filtered. The filtrate was extracted with ethyl acetate, washed twice with saturated sodium sulfite solution and twice with water. The organic phase was concentrated on a rotary evaporator under vacuum at 40 C. The properties of the final product were as follows: White solid. Mass: 24.25 g. Yield: 35%. m.p.: 192 C. 1 H NMR (DMSO, 250 MHz): 7.17 (1H, Ar, d, J=8.25 Hz), 7.25 (1H, Ar, s), 7.42 (1H, Ar, d, J=8.25 Hz).
A suspension of 4-aminosalicylic acid (60.6 g) , water (240 mL), C-H2SO4 (90 mL) and acetic acid (240 mL) was cooled with an ice-bath. A solution of sodium nitrite (30.0 g) in water (60 mL) was added dropwise to the suspension over 30 min and the mixture was stirred at 00C for 1 hr. Then a solution of potassium iodide (200 g) in water (160 mL) was added dropwise over 30 min and the cooling-bath was removed. The mixture was stirred at room temperature for 20 hr, diluted with water and extracted with ethyl acetate (three times) . The extracts were combined, washed with 5% Na2S2Oa solution and brine, dried over MgSO4 and concentrated. The residue was suspended in acetonitrile and collected by filtration to give the title compound as a powder (35.0 g) .1H-NMR (300 MHz, DMSO-d6) delta: 7.30 (dd, J = 8.1, 1.8 Hz, IH), 7.38 (d, J = 1.8 Hz, IH), 7.51 (d, J = 8.1 Hz, IH).
A sample of 4-amino-2-hydroxysalicylic acid (10 g, 65.3 mmol) is charged to a 2 liter Erlenmeyer flask equipped with a large stir bar, cooled in an ice/water bath and treated with concentrated sulfuric acid (20 mL) and enough water to make a free flowing suspension (50 mL). After stirring for 20 minutes, the reaction is treated with a solution of sodium nitrite (4.55 g, 66.0 mmol) in water (20 mL) over the course of 10 minutes. After stirring an additional 3 minutes, the reaction is treated with a solution of potassium iodide (16.9 g, 101 mmol) in water (30 mL) over the course of 15 minutes. The cooling bath is removed and the reaction is carefully monitored and stirred as it generates a significant amount of nitrogen gas. After the reaction subsides, it is briefly heated to 70 C. after which it is allowed to cool to room temperature and sit overnight. The resulting solid is collected by filtration, washed with water and dried to give crude 2-hydroxy-4-iodo-benzoic acid that is used in the next reaction without further purification: ESMS m/z 265.0 (M+H+).
Example 1 Synthesis of 4-[2-(4-carboxy-3-hydroxy-phenyl)ethynyl]-2-hydroxy-benzoic acid (I) Synthesis of Compound 2 11.0 g (72.0 mmol) of 4-aminosalicylic acid (1) was taken in 110.0 ml 50% H2SO4 and cooled to -5 C. and stirred for 20 minutes. To this NaNO2 solution (5.5 g, 80 mmol of NaNO2 in 6.5 ml deionized water) was added drop wise maintaining temperature below 0 C. and stirred for 20 minutes. This diazonium salt solution was added drop wise to the freshly prepared CuI solution* at -5 C. After addition, temperature of the reaction mixture was raised to room temperature and then heated to 90 C. for 1 h. After completion of reaction, the reaction mixture was cooled to room temperature and filtered to obtain yellow solid which was washed with water and dried. This solid was dissolved in hot ethanol and filtered. The inorganic residue remained was washed with ethanol and the filtrate was evaporated to dryness under vacuum to obtain 16.0 g of crude Compound 2 as a brown solid. *(CuI solution: 17.95 g (72.0 mmol) CuSO4.5H2O, 5.5 g (86.0 mmol) Cu-powder and 55.0 g (332.0 mmol) KI were taken in 100.0 ml deionized water. To this 100.0 ml 20% H2SO4 was added with constant stirring. Reaction mixture was allowed to stirred at room temperature for 1 h and then it was cooled to -5 C. CuI gets precipitated out as off-white solid. The above solution of CuI is directly used for the preparation of Compound 2. Yield: 84.6% Analysis: 1H NMR (300 MHz, MeOD): delta 7.48 (d, 1H); 7.24 (d, 1H); 7.19 (dd, 1H). MS (m/z): 263 (M+-H)
Example 1 Synthesis of 4-[2-(4-carboxy-3-hydroxy-phenyl)ethynyl]-2-hydroxy-benzoic acid (I) Synthesis of Compound 2 11.0 g (72.0 mmol) of 4-aminosalicylic acid (1) was taken in 110.0 ml 50% H2SO4 and cooled to -5 C. and stirred for 20 minutes. To this NaNO2 solution (5.5 g, 80 mmol of NaNO2 in 6.5 ml deionized water) was added drop wise maintaining temperature below 0 C. and stirred for 20 minutes. This diazonium salt solution was added drop wise to the freshly prepared CuI solution* at -5 C. After addition, temperature of the reaction mixture was raised to room temperature and then heated to 90 C. for 1 h. After completion of reaction, the reaction mixture was cooled to room temperature and filtered to obtain yellow solid which was washed with water and dried. This solid was dissolved in hot ethanol and filtered. The inorganic residue remained was washed with ethanol and the filtrate was evaporated to dryness under vacuum to obtain 16.0 g of crude Compound 2 as a brown solid. *(CuI solution: 17.95 g (72.0 mmol) CuSO4.5H2O, 5.5 g (86.0 mmol) Cu-powder and 55.0 g (332.0 mmol) KI were taken in 100.0 ml deionized water. To this 100.0 ml 20% H2SO4 was added with constant stirring. Reaction mixture was allowed to stirred at room temperature for 1 h and then it was cooled to -5 C. CuI gets precipitated out as off-white solid. The above solution of CuI is directly used for the preparation of Compound 2. Yield: 84.6% Analysis: 1H NMR (300 MHz, MeOD): delta 7.48 (d, 1H); 7.24 (d, 1H); 7.19 (dd, 1H). MS (m/z): 263 (M+-H)

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  • C21H14I2O11 [ No CAS ]
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  • [ 105417-09-2 ]
  • 2-Hydroxy-4-trifluorovinyl-benzoic acid [ No CAS ]
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  • [ 77-78-1 ]
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YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; N,N-dimethyl-formamide; In toluene; at 20℃; for 1h;Inert atmosphere; Under nitrogen atmosphere, <strong>[16870-28-3]2-hydroxy-4-iodo-benzoic acid</strong> (975 mg, 3.69 mmol) is dissolved in toluene and oxalyl dichloride (3.693 mL of 2 M, 7.39 mmol) is added. The reaction is stirred for 2 minutes and dimethylformamide (13.5 mg, 15 mu, 0.185 mmol) is added. The reaction is stirred at room temperature for 1 hour. The solvent is removed under reduced pressure to afford the title compound. The latter is used as is for the next step
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  • [ 100-39-0 ]
  • [ 170282-08-3 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate; In acetone; for 24h;Inert atmosphere; Reflux; In a 50 mL dry, two necked round bottom flask, under N 2 atmosphere was added <strong>[16870-28-3]2-hydroxy-4-iodobenzoic acid</strong> 4 (5 mmol, 1.32 g), anhydrous acetone (25 mL), K 2 CO 3 (11 mmol, 1.52 g), and benzyl bromide (11 mmol, 1.30 mL) dropwise and the reaction was stirred overnight under reflux. The volatiles are evaporated and the residue was diluted with water (25 mL). The content was transferred to a separation funnel and extracted with EtOAc (3 x 25 mL). The organic combined was dried over MgSO 4 , filtered off and volatiles were evaporated. It was recovered a white solid with enough purity to further steps. Yield: 85% m.p.: 75-77C 1 H NMR: (300 MHz, CDCl 3 ): delta (ppm) 7.54 (d, J= 8.1 Hz, 1H), 7.50-7.30 (m, 12H), 5.31 (s, 2H), 5.10 (s, 2H). 13 C NMR: (75 MHz, CDCl 3 ): delta (ppm) 165.7, 158.4, 136.0, 136.0, 133.1, 130.0, 128.7, 128.6, 128.3, 128.2, 128.1, 127.3, 123.2, 120.4, 100.0, 71.0, 66.9. IR: max (neat, cm -1 ): 3064, 3030, 2944, 1726, 1601, 1568, 1492, 1456, 1432, 1380, 1274, 1259, 1223, 1160, 1091, 1000, 823, 756, 723, 693. HRMS: (ESI) m/z, calcd for [C 21 H 17 IO 3 + Na]: 467,0120; found: 467,0126.
In N-methyl-acetamide; mineral oil; Sodium hydride (4.7 g, 60% dispersion in mineral oil) is added portionwise over 15 minutes to a solution of <strong>[16870-28-3]4-iodosalicylic acid</strong> (15.4 g) in dry dimethylformamide (150 mL). After stirring for 40 minutes benzyl bromide (19.9 g) is added and the mixture heated at 60 C. for 1.5 hours. The reaction mixture is evaporated and the residue partitioned between chloroform and water. The organic phase is dried over magnesium sulphate, evaporated and the residue triturated with ether to give benzyl 2-benzyloxy-4-iodobenzoate (14.2 g) as a cream coloured solid.
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  • [ 16870-28-3 ]
  • [ 70744-47-7 ]
  • 3-hydroxy-4'-methoxy-biphenyl-4-carboxylic acid [ No CAS ]
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  • [ 16870-28-3 ]
  • [ 67-63-0 ]
  • 2-hydroxy-4-iodo-benzoic acid isopropyl ester [ No CAS ]
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