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CAS No. : | 636-46-4 | MDL No. : | MFCD00010391 |
Formula : | C8H6O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BCEQKAQCUWUNML-UHFFFAOYSA-N |
M.W : | 182.13 | Pubchem ID : | 12490 |
Synonyms : |
|
Chemical Name : | 4-Hydroxyisophthalic acid |
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 42.38 |
TPSA : | 94.83 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.34 cm/s |
Log Po/w (iLOGP) : | 0.69 |
Log Po/w (XLOGP3) : | 1.51 |
Log Po/w (WLOGP) : | 0.79 |
Log Po/w (MLOGP) : | 0.63 |
Log Po/w (SILICOS-IT) : | 0.15 |
Consensus Log Po/w : | 0.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.13 |
Solubility : | 1.35 mg/ml ; 0.00741 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.11 |
Solubility : | 0.142 mg/ml ; 0.000777 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -0.57 |
Solubility : | 49.0 mg/ml ; 0.269 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.34 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With thionyl chloride; for 1h;Cooling with ice; Reflux; | To a 50 ml three-necked flask, 30 ml of ethanol was added, and 1.82 g (0.01 mol)<strong>[636-46-4]4-hydroxy-1,3-benzenedicarboxylic acid</strong>,1.5 ml (0.02 mol, 2.38 g) of SOCl2 was added dropwise under an ice bath,After completion of the dropwise addition, the reaction was continued for 1 hour, and the temperature was refluxed. The reaction mixture was concentrated to dryness,Ethyl acetate was added thereto, and the organic layer was washed successively with saturated sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The filtrate was evaporated to dryness under reduced pressure, and the residue was dissolved by adding 10 ml of ethanol and left in a refrigerator overnight,A white snowflake-like solid precipitation, filtration,The filter cake was washed with distilled water and the sample was dried at low temperature to give 2.26 g of product in 95.0% yield |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With water; sodium carbonate;N,N,N,N,-tetramethylethylenediamine; copper(I) bromide; at 85℃; for 18h; | 4-bromoasophthalic acid (1 g, 4.1 mmol) was dissolved in distilled water (4 mL) and sodium bicarbonate (1.2 g, 11 mmol) was added. The resulting solution was stirred for 1 and a half our at 85 C. N1, N1, N2, N2-tetramethylethane-1,2-diamine (31 mg, 270 umol) and cooper bromide (18 mg, 126 umol) were dissolved in distilled water (0.5 mL). The resulting solution was stirred for 1 hour. The two resulting solutions were mixed and stirred for 18 hours at 85 C., cooled to room temperature, and acidified with 1N HCl aqueous solution. The resulting solid was filtered under reduced pressure, washed with water, and dried under reduced pressure to yield Compound XXXVI (720 mg (97%)).1H NMR (600 MHz, DMSO-d6) delta 8.34 (t, J=3.6 Hz, 1H), 8.04 (dt, J=1.2 Hz, 13.2 Hz, 1H), 7.05 (dd, J=3.6 Hz, 12.6 Hz, 1H) |
97% | With N,N,N,N,-tetramethylethylenediamine; sodium hydrogencarbonate; copper(I) bromide; In water; at 85℃; for 20.5h; | 4-bromoasophthalic acid (1 g, 4.1 mmol) was dissolved in distilled water (4 mL) and sodium bicarbonate (1.2 g, 11 mmol) was added. The resulting solution was stirred for 1 and a half our at 85C. N1, N1, N2, N2-tetramethylethane-1,2-diamine(31 mg, 270 umol) and cooper bromide (18 mg, 126 umol) were dissolved in distilled water (0.5 mL). The resulting solution was stirred for 1 hour. The two resulting solutions were mixed and stirred for 18 hours at 85C, cooled to room temperature, and acidified with 1N HCl aqueous solution. The resulting solid was filtered under reduced pressure, washed with water, and dried under reduced pressure to yield Compound XXXVI (720 mg (97%)). 1H NMR (600MHz, DMSO-d6) delta 8.34(t, J = 3.6Hz, 1H), 8.04(dt, J = 1.2Hz, 13.2Hz, 1H), 7.05(dd, J =3.6Hz, 12.6Hz, 1H) |
82% | The same procedure as described in Example 24 was performed but using 2.45 g (10.0 mmol) of 4-bromoisophthalic acid as the substrate and 2.70 g (25.5 mmol) of Na2CO3 instead of Ca(OH)2. A total of 1.49 g (8.2 mmol, 82% yield) of 4-hydroxyisophthalic acid was collected. The purity was determined by 1H NMR to be 88%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32.88 g | With water; sodium hydroxide; at 100℃; for 2h; | 100.00 g of the waste residue of wintergreen oil was dissolved in 300 ml of methanol, water bath stirring while hot filtration, the filtrate was allowed to settle to precipitate a solid. The filter cake was collected by filtration and dried to collect 30.56 g of crude 4-hydroxyisophthalic acid dimethyl ester, take 17.00gNaOH solid with water as the solvent preparation 30percent NaOH solution, the crude dimethyl 4-hydroxyisophthalate was dissolved in the aqueous NaOH solution and refluxed in a water bath at 100 ° C for 2 hours. After cooling to room temperature, the filtrate was collected by filtration, decolorized by the addition of 3.00 g of activated charcoal, and refluxed at 100 ° C for 1 hour in a water bath. The filter cake was collected by filtration and dried to obtain 32.88 g of 4-hydroxyisophthalic acid. The reaction mixture was filtered and washed with water. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; N,N-dimethyl-formamide;Heating / reflux; | Intermediate D: 4-hydroxy-N,N'-bis[(4-methoxyphenyl)methyl]-1,3- benzenedicarboxamide A mixture of <strong>[636-46-4]4-hydroxyisophthalic acid</strong> (2.0 g; 11 mmol) in thionyl chloride (20 ml) and DIMETHYLFORMAMIDE (2 drops) was heated at reflux under stirring overnight. The excess of thionyl chloride was removed by evaporation and the residue dissolved into dichloromethane (100 ml). After cooling, 4-methoxybenzylamine (6.8 g; 50 mmol) was added in one portion and the mixture obtained was stirred at room temperature for 1 hour. The insoluble solid was separated by filtration and purified by chromatography on silica gel (CH2CL2 95/methanol 5) to give 2.0 g of the entitled compound (yield: 43%) as a white solid pure in TLC (CH2CI2 90/methanol 10; Rf = 0.70). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With trifluoroacetic acid; trifluoroacetic anhydride; at 100℃; for 24h; | Example 19; 5- {r {4-( (4-butylphenyl)ethynyl]benzyl} (hexyl)amino ] carbonyl } -2-hydroxy- benzoic acid. N-methvl-D-glucamine (i.e. 1-deox(at)(methylamino(at) (at) glucitoi) salt; Step a); Formation of 2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carbbxylic acid; A suspension of 4-hydroxyisophtalic acid (Aldrich, 5.0 g, 27.5 mmol) in acetone (10 mL), TFA (30 mL) and TFAA (10 mL) was heated at 100C for 24 hrs. The reaction mixture was concentrated under reduced pressure. The residue was taken up with an aqueous solution of HCI (100 mL, IN) and extracted with EtOAc (3x200 mL): The combined organic layers were dried over MgS04 and the solvents were removed under reduced pressure. The crude compound was recrystallized in EtzO (50 mL) to give 4.67 g (77%) of the title compound as a beige powder. |
57% | With trifluoroacetic acid; trifluoroacetic anhydride; at 100℃; for 8h; | Compound XXXVI (720 mg, 3.95 mmol) was dissolved in trifluoroacetic acid (4.32 mL). Acetone (2 mL) and trifluoroacetic anhydride (TFAA) (1.45 mL) were added sequentially. The resulting solution was stirred for 8 hours at 100 C., cooled to room temperature, and concentrated under reduced pressure. The resultant was dissolved in ethyl acetate (100 mL) and washed with 1N HCl aqueous solution (50 mL). The organic layer was dehydrated with anhydrous sodium sulfate and concentrated under reduced pressure. The thus-obtained solid was filtered under reduced pressure to yield Compound XXXVII (500 mg (57%)).1H NMR (600 MHz, chloroform-d1) delta 8.76 (d, J=2.4 Hz, 1H), 8.30 (dd, J=9.0 Hz, 1.8 Hz, 1H), 7.08 (d, J=8.4 Hz, 1H), 1.78 (s, 6H) |
57% | With trifluoroacetic acid; trifluoroacetic anhydride; at 100℃; for 8h; | Compound XXXVI (720 mg, 3.95 mmol) was dissolved in trifluoroacetic acid (4.32 mL). Acetone (2 mL) and trifluoroacetic anhydride (TFAA) (1.45 mL) were added sequentially. The resulting solution was stirred for 8 hours at 100C, cooled to room temperature, and concentrated under reduced pressure. The resultant was dissolved in ethyl acetate (100 mL) and washed with 1N HCl aqueous solution (50 mL). The organic layer was dehydrated with anhydrous sodium sulfate and concentrated under reduced pressure. The thus-obtained solid was filtered under reduced pressure to yield Compound XXXVII (500 mg (57%)). 1H NMR (600MHz, chloroform-d1) delta 8.76(d, J= 2.4Hz, 1H), 8.30(dd, J =9.0Hz, 1.8Hz, 1H), 7.08(d, J = 8.4Hz, 1H), 1.78(s, 6H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; In ethanol; for 4h;Heating / reflux; | a) 4-Hydroxyisophthalic acid 1-ethyl ester To a solution of <strong>[636-46-4]4-hydroxyisophthalic acid</strong> (10.0 g) in ethanol (100 mL) was added conc. sulfuric acid (3.0 mL), and the mixture was heated for 4 hours under reflux. The reaction solution was allowed to stand for cooling to room temperature, and poured into ice-water. Sodium bicarbonate was added thereto while stirring until the pH reached 10 to 11. The resulting precipitated solid was filtered off. To the filtrate was added conc. hydrochloric acid until the pH reached 2 to 3, and the precipitated solid was fltered off. The filtered solid was recrystallized from methanol and water (2:1, v/v) to give the title compound (4.53 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; In methanol; | EXAMPLE 64 4-Ethoxy-N'1, N"3-bis-(3-methoxy-benzyl)-isophthalamide Into a flask was placed <strong>[636-46-4]4-hydroxy-isophthalic acid</strong> (25.46 g) and 200 mL of methanol. Concentrated sulfuric acid (20 mL) was slowly added. The mixture was refluxed for 48 hours; upon cooling a copious white precipitate formed, which was collected by filtration. The white solid obtained was washed with water, then dried under vacuum at 50° C. to yield 26.65 g of <strong>[636-46-4]4-hydroxy-isophthalic acid</strong> dimethyl ester. | |
In methanol; | i 4-Hydroxy-1,3-benzenedioic acid, dimethyl ester A mixture of <strong>[636-46-4]4-hydroxyisophthalic acid</strong> (25 g) and trimethylsily chloride (100 ml) in methanol (200 ml) was heated at reflux for 4 hours. The mixture was evaporated and partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic phase was dried (MgSO4) and evaporated. Yield 25.67 g. Used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In hexane; dichloromethane; N,N-dimethyl-formamide; | (a) benzyl 4-hydroxyisophthalate To a solution of 5.5 g (30 mmoles) of <strong>[636-46-4]4-hydroxyisophthalic acid</strong> in 200 ml of DMF, there are added, by small portions 1.8 g (60mmoles) of sodium hydride (80% in oil). The mixture is stirred until the cessation of gaseous emission. There are then added 7.2 ml (60 mmoles) of benzyl bromide and the mixture is stirred for 4 hours at ambient temperature. The reaction medium is poured into water and extracted with ethyl ether. The organic phase is decanted, washed with water, dried on magnesium sulfate and evaporated. The resulting residue is purified by chromatography on a silica column by eluding with a 30:70 mixture of dichloromethane and hexane. After evaporation of the solvents, 6.5 g (60% yield) of the expected ester having a melting point of 68-70 C. are recovered. |
60.7% | With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 1h;Cooling with ice; Reflux; | 1.82 g (0.01 mol) of <strong>[636-46-4]4-hydroxy-1,3-benzenedicarboxylic acid</strong> was dissolved in 70 ml of DMF,0.48 g (0.02 mol) of sodium hydride was stirred until no more gas was generated, and then 2.4 ml (0.02 mol) of benzyl bromide was added dropwise, After stirring at room temperature for 1 h, the reaction was heated and refluxed. The reaction solution was cooled and poured into water, The mixture was extracted with ether and washed with brine, dried over anhydrous sodium sulfate, and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by column chromatography(Ethyl acetate: petroleum ether = 5: 1) to give 2.20 g of a white solid in 60.7% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With thionyl chloride; triethylamine; In N,N-dimethyl-formamide; | EXAMPLE 11 Preparation of 2-hydroxy-5-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]-propylamido]benzoic acid To a solution of <strong>[636-46-4]4-hydroxyisophthalic acid</strong> (5 g, 0.0275 mol) in DMF (25 ml) at 200 C. was added thionyl chloride (2.2 ml, 0.03 mol), over 10 minutes, and the mixture was left to react for 1 hour. This yellow solution was poured over 1 hour into a mixture of triethylamine (6.1 g, 0.06 mol) and heptamethylaminopropyltrisiloxane (8.4 g, 0.03 mol). The mixture, which became heterogenous, was left stirring for 6 hours at 20 C. This reaction mixture was poured into water. The gummy paste obtained was triturated with water and then with dichloromethane. The precipitate obtained was recrystallized from an ethanol/water mixture to give 2.5 g (yield: 20%) of 2-hydroxy-5-?3-[1,3,3,3-tetramethyl-[1-[(trimethyl-silyl)oxy]disiloxanyl]propyl-amido]benzoic acid in the form of a white powder. m.p.: 222-224 C. UV (ethanol) lambdamax =308 nm, epsilonmax =100 Elemental analysis for C18 H33 NO6 Si3 theory: C 48.7 H 7.5 N 3.1 Si 19.0 found: C 48.9 H 7.4 N 2.9 Si 19.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | COMPARATIVE EXAMPLE 3 STR9 Comparative Example 1 was repeated except that 36.4 g (200 mmoles) of <strong>[636-46-4]4-hydroxyisophthalic acid</strong> was used instead of 27.6 g (200 mmoles) of p-hydroxybenzoic acid to obtain 26.9 g of 2-(2'-hydroxyphenyl)benzotriazol-3',5'-dicarboxylic acid. The yield was 45%. The wavelength of the maximal absorption of ultraviolet light on the product obtained, in ethanol, was 310 nm. The analysis results of the product are as follows. Mass spectrometery 299 (M+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dimethyl sulfoxide; | a. Ethyl p-nitrobenzoate (1.95g.) was heated in dimethylsulphoxide (15 ml.) with dry powdered potassium cyanide (2g.) at 110-120C. for 31/2 hours. The solution was poured into water and acidified. The filtered solid was shaken with 10% aqueous sodium carbonate containing some sodium hydroxide, filtered and acidified. The crystals obtained on standing were recrystallized from hot water to give ethyl 3-cyano-4-hydroxybenzoate, m.p. 192-193C., which was hydrolyzed with concentrated hydrochloric acid to yield 4-hydroxyisophthalic acid, m.p. 310C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | In N-methyl-acetamide; thionyl chloride; dichloromethane; | Intermediate D: 4-hydroxy-N,N'-bis[(4-methoxyphenyl)methyl]-1,3-benzenedicarboxamide A mixture of <strong>[636-46-4]4-hydroxyisophthalic acid</strong> (2.0 g; 11 mmol) in thionyl chloride (20 ml) and dimethylformamide (2 drops) was heated at reflux under stirring overnight. The excess of thionyl chloride was removed by evaporation and the residue dissolved into dichloromethane (100 ml). After cooling, 4-methoxybenzylamine (6.8 g; 50 mmol) was added in one portion and the mixture obtained was stirred at room temperature for 1 hour. The insoluble solid was separated by filtration and purified by chromatography on silica gel (CH2Cl2 95/methanol 5) to give 2.0 g of the entitled compound (yield: 43%) as a white solid pure in TLC (CH2Cl2 90/methanol 10; Rf=0.70). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetone; at 50℃; | To a suspension of 4-hydroxy-1 ,3-benzenedicarboxylic acid (5 g, 27.5 mmol) and K2C03 ( 3.66 g, 99 mmol) in acetone ( 80 mi) stirred at room temperature was added bromomethyl)benzene (16.90 g, 99 mmol) dropwise. The reaction mixture was stirred at 50 C overnight. The mixture was cooled to room temperature, and filtered. The filtrate was concentrated to afford the crude product, which was added to a silica gei column (100g) and was eluted with hexanes/ethyl acetate = 10:1 (2 L) to yield the title compound as a colourless oil. 6.6 g.MS (eiectrospray): m/z [M+Na]+ = 474.9 |
Tags: 636-46-4 synthesis path| 636-46-4 SDS| 636-46-4 COA| 636-46-4 purity| 636-46-4 application| 636-46-4 NMR| 636-46-4 COA| 636-46-4 structure
[ 71989-93-0 ]
2,4,6-Trihydroxybenzoic acid hydrate
Similarity: 0.93
[ 71989-93-0 ]
2,4,6-Trihydroxybenzoic acid hydrate
Similarity: 0.93
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H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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