Structure of 619-45-4
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Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong ; Han, Min Su ;
Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.
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CAS No. : | 619-45-4 |
Formula : | C8H9NO2 |
M.W : | 151.16 |
SMILES Code : | C1=C(C=CC(=C1)N)C(OC)=O |
MDL No. : | MFCD00007891 |
InChI Key : | LZXXNPOYQCLXRS-UHFFFAOYSA-N |
Pubchem ID : | 12082 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
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 | 42.13 |
TPSA ? Topological Polar Surface Area: Calculated from |
52.32 ?2 |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.62 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.35 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.06 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.32 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.97 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.26 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.9 |
Solubility | 1.91 mg/ml ; 0.0126 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.05 |
Solubility | 1.34 mg/ml ; 0.0089 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.1 |
Solubility | 1.21 mg/ml ; 0.008 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.26 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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 |
---|---|---|
41% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; | (a) methyl 4-(N-[2-(tert.-butyldimethylsilyloxy)ethyl]-amino)benzoate To a solution of 1-(tert.-butyldimethylsilyloxy)-2-iodoethane (45.10 gm, 160 mmol) in DMF (50 mL) was added methyl 4-aminobenzoate (4.54 gm, 30 mmol) and diisopropylethylamine (6 mL, 34 mmol). This solution was heated at 95° for approximately 21 hours. The solvent was removed by concentration, in vacuo, and the residue obtained was partitioned between CH2 Cl2 (150 mL) and water (150 mL). The layers were separated and the aqueous phase extracted with CH2 Cl2 (150 mL). The combined organic extracts were washed with 10percent Na2 S2 O3 (120 mL), dried over Na2 SO4 and concentrated, in vacuo, to give an orange oil which was purified by flash chromatography. Elution with hexane:EtOAc (9:1) provided the product as a colorless oil (3.85 gm, 41percent yield). The following analyses indicated that the product was methyl 4-(N-[2-(tert.-butyldimethylsilyloxy)ethyl]amino)benzoate: NMR(CDCL3) delta=7.86(2H, d, J=8.8 Hz), 6.57(2H, d, J=8.8 Hz), 4.48(1H, broad), 3.85(3H, s), 3.82(2H, t, J=5.2 Hz), 3.27(2H, q, J=5.2 Hz), 0.90(9H, s), 0.06(6H, s) |
41% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; | (a) methyl 4-(N-[2-(tert.-butyldimethylsilyloxy)ethyl]-amino) benzoate To a solution of 1-(tert.-butyldimethylsilyloxy)-2-iodoethane (45.10 gm, 160 mmol) in DMF (50 mL) was added methyl 4-aminobenzoate (4.54 gm, 30 mmol) and diisopropylethylamine (6 mL, 34 mmol). This solution was heated at 95° for approximately 21 hours. The solvent was removed by concentration, in vacuo, and the residue obtained was partitioned between CH2 Cl2 (150 mL) and water (150 mL). The layers were separated and the aqueous phase extracted with CH2 Cl2 (150 mL). The combined organic extracts were washed with 10percent Na2 S2 O3 (120 mL), dried over Na2 SO4 and concentrated, in vacuo, to give an orange oil which was purified by flash chromatography. Elution with hexane: EtOAc (9:1) provided the product as a colorless oil (3.85 gm, 41percent yield). The following analyses indicated that the product was methyl 4-(N-[2-(tert.-butyldimethylsilyloxy)ethyl]amino)benzoate: NMR(CDCL3) delta=7.86(2H, d, J=8.8 Hz), 6.57(2H, d, J=8.8 Hz), 4.48(1H, broad), 3.85(3H, s), 3.82(2H, t, J=5.2 Hz), 3.27(2H, q, J=5.2 Hz), 0.90(9H, s), 0.06(6H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; for 2h; | Step 1:A solution of DIPEA (1.2 mL, 7.0 mmol), Al5a (Aldrich, 530 mg, 3.5 mmol) and Ala (300 mg,2.3 mmol) in DMF (14 mL) is treated with HATU (1 .3 g, 3.5 mmol). The mixture is stirred for 2 hand then is diluted with water and EtOAc. The organic layer is separated and washed with water(2 x). The organic layer is passed through a phase separator and the filtrate evaporated todryness. The product is purified by Combif lash to give A15b. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With laccase of Xylaria polymorpha MTCC-1100; oxygen; In aq. acetate buffer; at 20℃; for 24h;pH 4.5;Enzymatic reaction; | General procedure: Equimolar solutions of p-hydroquinone I and an aromatic amine IIa-IId [17] were incubated with laccase (activity 1.96 IU/mL) in 20 mM sodium acetate buffer (pH 4.5) under atomsphere of oxygen at room temperature with constant stirring. Products were isolated after 24 h of the process as coloured solids and recrytallised from methanol. 20 μL of the methanol solutions of the recrystallized products were analyzed by Waters HPLC Model 600E using spherisorb C18 5 UV, 4.5 × 250 mm column, methanol eluent at the flow rate of 0.5 mL/min, and Waters UV detector model 2487 at 254 nm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With 3-Methylpyridine; methanesulfonyl chloride; In acetonitrile; at 0 - 20℃; for 17h; | Step 1: Synthesis of methyl 4-(l-methyl-3-phenyl-lH-pyrazole-5-amido)benzoate 41.1 [00491] Methanesulfonyl chloride (0.05 ml, 0.69 mmol) was added to a mixture of methyl 4- aminobenzoate (75mg, 0.49 mmol), l-methyl-3 -phenyl- lH-pyrazole-5-carboxylic acid (100 mg, 0.49 mmol) and 3-picoline (0.14 ml, 1.48 mmol) in MeCN (dry, 5ml) at 0C. After addition, the reaction mixture was allowed to reach rt and stirred for 17h. The reaction mixture was diluted with DCM (50ml) and water (50ml). The aqueous layer was further extracted with DCM (2 x 30ml) and the combined layers dried over Na2S04. Evaporation of the solvent afforded a material which was triturated from DMSO:MeCN (1 :2) to afford 134mg (77%) of methyl 4-(l- methyl-3 -phenyl- lH-pyrazole-5-amido)benzoate 41.1 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With sodium azide; methanesulfonic acid; trifluoroacetic acid; In hexane; at 40℃; for 4h;Sealed tube; | General procedure: A 20 ml vial equipped with a magnetic stirring bar was charged with secondary alcohols (0.3 mmol, 1 equiv.), NaN3 (0.75 mmol, 2.5 equiv.), n-hexane (1.0 ml, 0.3 M) and TFA (5.4 mmol, 18 equiv.) or a mixture of TFA (3.6 mmol,12 equiv.) and MeSO3H (1.8 mmol, 6 equiv.). The vial was sealed and stirred under air at 40 C for 4 h. On completion, the reaction mixture was quenched by 2 M NaOH (5 m), extracted by ethyl acetate (5 × 2 m) and the combined organic phase was washed with brine and dried over Na2SO4. Then the mixture was concentrated and purified by flash chromatography on a short silica gel column. |
78% | With sodium azide; methanesulfonic acid; trifluoroacetic acid; In hexane; at 40℃; for 10h; | Take a reaction tube, add 50 mg of sodium azide, 54 mg of <strong>[84851-56-9]1-(4-methoxycarbonylphenyl)ethanol</strong>, and 300 uL of trifluoroacetic acid.150 uL of methanesulfonic acid and 1.0 mL of n-hexane were stirred at 40 C for 10 hours.After the reaction was completed, 10 mL of a sodium hydroxide solution was added to quench the reaction, and the mixture was extracted three times with ethyl acetate.Column chromatography gave 32.3 mg of p-methoxycarbonylaniline in a yield of 78%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In methanol; for 3h;Reflux; | General procedure: Imines 2a-2h, 3a-3h, 4a-4h, 5a-5h, and 6a-6h were synthesized according to Krtk etal.(2020). Briefly, 1 mmol of amino compound (2, 4, 5, 6) was dissolved in 7 ml of MeOH and then appropriate aldehyde (1.1 mmol) was added in one portion. In the case of imines 3a-3h, 3,5-diaminobenzoic acid 3 (1 mmol) was dissolved in 10 ml of MeOH and 2.2 mmol of appropriate aldehyde was added. The reaction mixture was refluxed for 3 hours. After additional 12 hours of stirring at room temperature, the reaction mixture was stored at -20C for 1 h. The precipitate formed was filtered off and washed successively by MeOH and diethyl ether thoroughly. If necessary, the products were crystallized from tetrahydrofuran/MeOH to obtain pure Schiff bases. |
Tags: 619-45-4 synthesis path| 619-45-4 SDS| 619-45-4 COA| 619-45-4 purity| 619-45-4 application| 619-45-4 NMR| 619-45-4 COA| 619-45-4 structure
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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 |
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