Structure of 2-Naphthoic acid
CAS No.: 93-09-4
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Synonyms: Naphthalene-2-carboxylic acid
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CAS No. : | 93-09-4 |
Formula : | C11H8O2 |
M.W : | 172.18 |
SMILES Code : | O=C(O)C1=CC=C2C=CC=CC2=C1 |
Synonyms : |
Naphthalene-2-carboxylic acid
|
MDL No. : | MFCD00004101 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 50.91 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.64 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.28 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.54 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.64 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.35 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.49 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.48 |
Solubility | 0.0574 mg/ml ; 0.000333 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.74 |
Solubility | 0.0315 mg/ml ; 0.000183 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.44 |
Solubility | 0.0622 mg/ml ; 0.000361 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 |
-5.02 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 |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 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 |
---|---|---|
53.4% | With bromine; iodine; In acetic acid; for 0.5h;Heating / reflux; | To a boiling solution of 2-naphthoic acid (10.00 g, 58.14 mmol) in acetic acid (50 mL) is added dropwise bromine (3 mL) containing iodine (0.25 g). After the addition is complete, the solution is refluxed for 0.5 hr. A white precipitate forms during cooling and is isolated by filtration, washed with acetic acid and then water. The solid is triturated in methanol (100 mL) and 7.01 g (53.4percent yield) of the desired product is obtained as a white solid. m.p. 248-250° C. 1H NMR (300 MHz, CD3OD): delta 8.94 (d, J=1.8 Hz, 1H), 8.52-8.42 (m, 3H), 8.27 (dd, J=1.8, 7.5 Hz, 1H), 7.79 (t, J=8.4 Hz, 1H). |
46% | With bromine;iodine; In acetic acid; for 0.583333h;Heating / reflux; | Preparation 3 [0106] Preparation of 6-Iodo-1-methoxy-naphthalene. [CHEMMOL-00022] [0107] Preparation of 5-Bromo-2-naphthalenecarboxylic acid. [0108] 2-Naphthoic acid (50;0 g, 0.290 mol), glacial acetic acid (250 mL), bromine (15 mL, 0.291 mol) and iodine (1.3 g, 0.005 mol) were combined in a flask under N2 atmosphere. The mixture was heated at reflux for 35 minutes then cooled to room temperature. The thick yellow mixture was stirred at room temperature for 1 hour. The mixture was filtered and the pale orange solid was rinsed with 100 mL of the filtrate. The solid was dried in vacuo at 55° C. overnight to yield 55.5 g of pale orange solid. The solid was slurried in 275 mL of 1 N NaOH for 30 minutes. The solid was filtered off and rinsed 3 times with 50 mL portions of the filtrate. The solid was air dried in the hood over the weekend to yield 46.7 g of solid. The solid was added to 220 mL of water. Concentrated HCl (15 mL) was added to obtain pH of 1.3 and the mixture was stirred for 4 hours. The solid was filtered off and washed with 200 mL of water. The solid was dried in vacuo at 50° C. to give 37.6 g of intermediate title compound as white crystals (HPLC: 90percent with 9percent 2-naphthoic acid, 46percent yield). |
76 g (75%) | With I2; bromine; acetic acid; | A. 5-Bromo-2-Naphthoic Acid A 75 g (0.44 mole) portion of 2-naphthoic acid, 375 ml of acetic acid, 22.5 ml of Br2 (70 g, 0.44 mole) and 1.9 g (0.015 mole) of I2 were placed in a 1 l. 3-necked flask and refluxed with stirring for 0.6 hours. The reaction mixture was cooled to 25° and filtered. The cream solid was washed with small portions of the filtrate, air dried and dried to a constant weight at 60° to give 76 g (75percent) of a light tan-cream solid, m.p. 224°-233° dec. The crude product was slurried with 375 ml of 1 N NaOH for 0.5 hours and filtered. |
With bromine;iodine; In acetic acid; at 20 - 116℃; for 1.58333h;Heating / reflux; | 2-Naphthoic acid (50.0 g, 0.290 mol), glacial acetic acid (250 mL), bromine (15 mL, 0.291 mol) and iodine (1.3 g, 0.005 mol) were combined in a flask under N2 atmosphere. The mixture was heated at reflux for 35 minutes then cooled to room temperature. The thick yellow mixture was stirred at room temperature for 1 hour. The mixture was filtered and the pale orange solid was rinsed with ?100 mL of the filtrate. The solid was dried in vacuo at 55 C. overnight to yield 55.5 g of pale orange solid. The solid was slurried in 275 mL of 1 N NaOH for 30 minutes. The solid was filtered off and rinsed 3 times with 50 mL portions of the filtrate. The solid was air dried in the hood over the weekend to yield 46.7 g of solid. The solid was added to 220 mL of water. Concentrated HCl (15 mL) was added to obtain pH of 1.3 and the mixture was stirred for 4 hours. The solid was filtered off and washed with 200 mL of water. The solid was dried in vacuo at 50 C. to give 37.6 g of intermediate title compound as white crystals (HPLC: 90percent with 9percent 2-naphthoic acid, 46percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Unless otherwise specified, carboxylic acid (0.542 mmol), TCT (0.0400 g, 0.216 mmol) and K2CO3 (0.2247 g, 1.626 mmol) were mixed together and hand ground for one minute using porcelain mortar and pestle. After addition of ammonium thiocyanate (0.0495 g, 0.650 mmol), the mixture was ground manually for further five minute. During the grinding, THF (calculated to be less than 1 L/mg of solids) was added to aid homogeneous mixing. The crude material was then purified by short column chromatography (column diameter 1.5 cm, packed with 3-4 g silica gel ) using 40-50percent ethyl acetate/hexane as an eluent. | |
With ammonium hydroxide;N,N-dimethyl-formamide; In oxalyl dichloride; hexane; water; | (1) PREPARATION OF NAPHTHALENE-2-CARBOXYLIC ACID AMIDE To a solution of 2-naphthoic acid (25 g, 0.145 mol) in MC (200 ml), oxalyl chloride (38 ml, 0.4356 mol) and a catalytic amount of DMF were added and stirred at room temperature for 2 hrs. After the solvent was evaporated, the crude acyl chloride was diluted with MC (200 ml), to which a solution of ammonium hydroxide in water (160 ml) was dropwise added at an ice bath temperature. After stirring for 1 hr, the precipitated product was collected by suction filtration, triturated in hexane and dried to obtain the title compound, which was used next step without further purification. | |
With ammonia; at 195℃; for 0.5h; | General procedure: Into a 1L open reactor was added 500g of carboxylic acid raw material (chemically pure) and stirring was turned on (600 r/min) from the reactorThe bottom is continuously fed with ammonia gas (chemical purity, water content of 5.1percent by weight, flow rate of 100 g/min) to the carboxylic acid feed. After the reaction was allowed to proceed for TC hours at the reaction temperature TA, ammonia gas flow was stopped. The contents of the reactor were sampled and subjected to nuclear magnetic proton and elemental analysis to characterize the amide intermediate. Specific reaction conditions and characterization results are shown in Table A-1, Table A-2, Table A-3, Table A-4, Table A-5 and Table A-6. These characterization results show that the amide intermediates obtained have an extremely high purity (above 99percent).In this embodiment, the ammonia gas can be directly replaced with waste ammonia gas (from Yangzi Petrochemical Plant, containing approximately50wtpercent of ammonia gas, the rest were toluene, oxygen, nitrogen, steam, carbon monoxide, and carbon dioxide, and the flow rate of this waste ammonia was 130g/min). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cell-free extract of amidase gene cloned from Klebsiella oxytoca KCTC 1686 and functionally expressed in Escherichia coli BL21(DE3); In methanol;Enzymatic reaction; | General procedure: The substrate specificity of recombinant KamH was tested using various aliphatic and aromatic amides. Cell-free extract of E. coli BL21(DE3)/pET-Ami2 was mixed with various concentrations of substrate under standard reaction conditions; 10percent (v/v) methanol was added as cosolvent to solubilize the substrate. The enzyme activity toward the various amides was determined by monitoring the formation of either carboxylic acid or ammonia [36]. Several racemic amides were used to study the stereoselectivity of the recombinant enzyme, including 2-phenylacetamide, mandelamide, 2,2-dimethylcyclopropanecarboxamide, and 2-(4-chlorophenyl)-3-methylbutyramide. Enantiomeric excess values were obtained by HPLC analysis using an AY-RH column. The enantiomeric excess and enantiomeric ratio of the product were determined according to Chen et al. [37]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydrogensulfate; water; at 65℃; for 48h; | General procedure: A mixture of the amide (1, 1 mmol), alcohol (15 mL), and pulverized potassium bisulfate (1.1 g, 8 mmol) was refluxed for the specified time. The alcohol was removed in vacuo and the residue was triturated with hexanes (or other appropriate solvent such as DCM or ethyl acetate to dissolve the product). Removal of hexanes in vacuo provided the following pure products |
Tags: 93-09-4 synthesis path| 93-09-4 SDS| 93-09-4 COA| 93-09-4 purity| 93-09-4 application| 93-09-4 NMR| 93-09-4 COA| 93-09-4 structure
A1267947 [1346602-42-3]
2-Naphthalenecarboxylic Acid-13C6
Reason: Stable Isotope
A109729 [716-76-7]
[1,1'-Biphenyl]-3-carboxylic acid
Similarity: 0.97
A153483 [4371-28-2]
[1,1'-Biphenyl]-3,3',5,5'-tetracarboxylic acid
Similarity: 0.97
A109729 [716-76-7]
[1,1'-Biphenyl]-3-carboxylic acid
Similarity: 0.97
A153483 [4371-28-2]
[1,1'-Biphenyl]-3,3',5,5'-tetracarboxylic acid
Similarity: 0.97
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