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[ CAS No. 13506-76-8 ] {[proInfo.proName]}

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Chemical Structure| 13506-76-8
Chemical Structure| 13506-76-8
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Product Details of [ 13506-76-8 ]

CAS No. :13506-76-8 MDL No. :MFCD00007267
Formula : C8H7NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :CCXSGQZMYLXTOI-UHFFFAOYSA-N
M.W : 181.15 Pubchem ID :16097
Synonyms :

Calculated chemistry of [ 13506-76-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.19
TPSA : 83.12 ?2

Pharmacokinetics

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) : -6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.75
Log Po/w (XLOGP3) : 0.75
Log Po/w (WLOGP) : 1.6
Log Po/w (MLOGP) : 0.84
Log Po/w (SILICOS-IT) : -0.47
Consensus Log Po/w : 0.69

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.65
Solubility : 4.1 mg/ml ; 0.0226 mol/l
Class : Very soluble
Log S (Ali) : -2.07
Solubility : 1.52 mg/ml ; 0.00841 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.54
Solubility : 5.24 mg/ml ; 0.0289 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 13506-76-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13506-76-8 ]

* 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 [ 13506-76-8 ]

[ 13506-76-8 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 13506-76-8 ]
  • [ 66232-57-3 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 2h; EXAMPLES; Example 1; 7-Methyl-1,2,3,4,4a,5-hexahydropyrazino[1,2-a]quinazolin-6-one; Part A. 2-Methyl-6-nitrobenzamide; To a solution of <strong>[13506-76-8]2-methyl-6-nitrobenzoic acid</strong> (10.0 g, 55.2 mmol) and oxalyl chloride (5.78 mL, 66.3 mmol) in dichloromethane (100 mL) was added DMF (5 drops). The reaction mixture stirred at RT for 2 hours and then concentrated to about 25 mL. The mixture was slowly poured into a cold solution (0 C.) of 7 N ammonia in methanol (500 mL). The reaction mixture was stirred at RT for 30 min, concentrated and the residue was dissolved in ethyl acetate (150 mL). The ethyl acetate solution was washed with with saturated sodium bicarbonate (2×200 mL), dried over sodium sulfate and concentrated to give the title compound (9.5 g, 67%) as a light brown solid.
With phosphorus pentachloride; In chloroform; cyclohexane; EXAMPLE 2 A mixture of 25 g of <strong>[13506-76-8]2-methyl-6-nitrobenzoic acid</strong> and 28.7 g of phosphorus pentachloride in 300 ml of cyclohexane was heated at reflux for 1 hour. The solution was concentrated and the residue was twice treated with chloroform and concentrated again to remove readily volatile materials and leave, as a residue, 2-methyl-6-nitrobenzoyl chloride as an oil.
With thionyl chloride;N,N-dimethyl-formamide; for 5.5h;Heating / reflux; To a solution of 2-methyl-6-nitrophenylbenzoic acid (3.02 g, 16.67 mmol) in thionyl chloride (0.56 M) was added DMF (cat.) and the mixture was heated to reflux for 5.5 h. The mixture was then cooled to room temperature and concentrated. The residue was then taken up in THF (30 mL) and added slowly over 20 min to a slurry of EPO <DP n="32"/>NaBH4 in THF (30 ml_) which pre-cooled to 0 C. The mixture was stirred at rt for 2 h and then quenched by addition of H2O followed by 4M HCI. The mixture was extracted with EtOAc. The combined organic phase was washed with sat. NaHCO3 and brine, dried over MgSO4 and concentrated to afford 2.52 g (90%) of the benzyl alcohol, an orange solid. 1H NMR (400 MHz, CDCI3) δ 2.55 (s, 3 H), 4.70 (s, 2 H), 7.35 (t, J=7.8 Hz, 1 H), 7.48 (d, J=7.6 Hz, 1 H), 7.70 (d, J=8.3 Hz, 1 H).
With thionyl chloride; In dichloromethane; at 80℃; for 3.5h; A mixture of <strong>[13506-76-8]2-methyl-6-nitrobenzoic acid</strong> (3.62g, 20.0 mmol) and thionyl chloride (15mL) was stirred at 80C for 3.5 hours. An excess of the thionyl chloride was distilled off under reduced pressure and the obtained residue was dissolved with methylene chloride (5mL). The solution was added dropwise to a methanol (10mL) solution of triethylamine (3.0mL) at 0C and stirred at 20-25C for 3 hours. The solvent was distilled off under reduced pressure. A saturated aqueous sodium bicarbonate solution was added to the obtained residue and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give methyl 2-methyl-6-nitrobenzoate (3.82g, 98%). 1H-NMR (CDCl3) δ :2.42(3H,s), 3.97(3H,s), 7.50(1H,t,J=7.9Hz), 7.55(1H,d, J=6.4Hz), 7.99(2H,d,J=8.0Hz)
With thionyl chloride; In toluene; for 2h;Reflux; A mixture of 2- methyl-6-nitrobenzoic acid (4.0 g, 22.0 mmol), toluene (20 mL) and thionyl chloride (SOC12)(10 g, 84 mmol) was heated at reflux for 2 h. The reaction was then concentrated at 45 C under reduced pressure, and THF (30 mL) was added to the resulting acid chloride. With cooling in an ice/water bath, N,N-diisopropylethylamine (10 mL) and o- toluidine (2.4 g, 22.4 mmol) were added. The reaction mixture was stirred at room temperature overnight. The mixture was then concentrated under reduced pressure, and the residue was dissolved in EtOAc (50 mL). This solution was washed with IN HCl (2 x 20mL) and an aqueous saturated NaHCO3 solution (2 x 20 mL) and concentrated in vacuo to afford 2-methyl-6-nitro-N-(o-tolyl)benzamide as an off-white solid (5.94 g, yield : 100%).

  • 2
  • [ 83-41-0 ]
  • [ 1975-50-4 ]
  • [ 13506-76-8 ]
  • [ 603-11-2 ]
YieldReaction ConditionsOperation in experiment
With oxygen; nitric acid; at 130 - 140℃; under 16501.7 - 18751.9 Torr; for 7h; (1) 3-Nitro-o-xylene (200 g) and 30% nitric acid (1000 g) are added to the oxidation reactor, the temperature is raised to 130-140 C, the oxygen pressure is 2.2-2.5 MPa, and the reaction is kept for 7 hours while stirring; (2) Cool down to 20-30C and filter to obtain 193 g of crude product (HPLC: 3-nitrophthalic acid 6.63%, 2-methyl-6-nitrobenzoic acid 15.92%, 3-nitro-2-methylbenzoic acid 60.74%, 3-nitro-o-xylene 8.66%); (3) The crude product was washed three times with 200 g of water to obtain 142 g of filter cake (HPLC spectrum shown in Figure 1: 3-nitrophthalic acid 0.52%, 2-methyl-6-nitrobenzoic acid 12.3%, 3-nitro-2-methylbenzoic acid 72.03%, 3-nitro-o-xylene 7.1%).
  • 3
  • [ 13506-76-8 ]
  • [ 4389-50-8 ]
YieldReaction ConditionsOperation in experiment
100% palladium; REFERENCE EXAMPLE 17 2-Amino-6-methylbenzoic acid To a methanolic solution (150 ml) of <strong>[13506-76-8]6-methyl-2-nitrobenzoic acid</strong> (14.25 g) was added palladium-on-carbon (1.40 g) and the hydrogenation reaction was conducted at atmospheric temperature and pressure (hydrogen consumption 5.3 1). The catalyst was filtered off and the filtrate was concentrated under reduced pressure to provide the title compound as light-yellow solid (15.12 g; yield 100%). 1 H-NMR (CDCl3) δ: 2.47(3H,s), 6.50(2H,t,J=8.1Hz), 7.00-7.07(4H,m). IR (KBr): 2927, 2645, 1645, 1599, 1545, 1470, 1394, 1334, 1288, 1236, 813, 775, 580, 419 cm-1.
1.2 g With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 2h; Pd/C (150 mg) was added to a solution of <strong>[13506-76-8]2-methyl-6-nitrobenzoic acid</strong> (1.5 g, 8.29 mmol) inCHOH (35 ml). The mixture was stirred at room temperature under H2 atmosphere for 2h.Then the mixture was filtered and concentrated to afford 1.2 g of the title compound as yellow solid. LCMS (ESI): calc’d for C8H9N02 [M+H]: 152, found: 152.
With 2 % platinum on carbon; hydrogen; In methanol; at 70 - 80℃; under 7500.75 - 9750.98 Torr;Autoclave; 2-Methyl-6-nitrobenzoic acid (500 g), platinum carbon (platinum content: 2%, 50 g), methanol (2000 g), put them into the autoclave, replace with nitrogen, and let the hydrogen pressure be 1.0-1.3 MPa, increase the temperature to 70-80C, control the temperature and control the reaction pressure until the reaction is complete (raw material
  • 5
  • [ 13506-76-8 ]
  • [ 74-88-4 ]
  • methyl 2-methyl-6-nitrobenzoate [ No CAS ]
  • 6
  • [ 38870-89-2 ]
  • [ 13506-76-8 ]
  • [ 19500-95-9 ]
  • [ 434935-69-0 ]
  • C11H11NO6 [ No CAS ]
  • 8
  • [ 13506-76-8 ]
  • [ 75-31-0 ]
  • [ 915375-64-3 ]
  • 9
  • [ 13506-76-8 ]
  • [ 74-88-4 ]
  • [ 61940-22-5 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 5h; Step 1: Methyl-(2-methyl-6-nitro)benzoate Into a suspension of 100 g (552 mmol) of <strong>[13506-76-8]2-methyl-6-nitrobenzoic acid</strong>, 114.4 g (828 mmol) of potassium carbonate in 500 mL of dimethylforamide was added dropwise 86 g (606 mmol) of iodomethane with stirring at ambient temperature. After addition, the suspension was stirred for additional 5 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate. Any solid was removed by filtration and the filtrate was concentrated to a 105.6 g of colorless oil as product in 98% yield. 1H NMR (CDCl3) (300 MHz) δ 2.7 (s, 3H), 3.95 (s, 3H), 8.01 (d, 3JHCCH=8.6 Hz, 1H), 7.62 (dd, 3JHCCH=8.6 Hz, 3JHCCH=7.6 Hz, 1H), 7.8 (d, 3JHCCH=7.6 Hz, 1H)
98% With potassium carbonate; In acetone; for 15h;Reflux; To the solution of <strong>[13506-76-8]2-methyl-6-nitrobenzoic acid</strong> (15 g, 82.8 mmol) dissolved in acetone (350 ml), iodomethane (25.8 ml, 414.0 mmol) and potassium carbonate (57.2 g, 414.0 mmol) were added, and the reaction mixture was refluxed for 15 hours and was stirred. The reaction mixture was cooled to a room temperature and was filtered. The filtrates were concentrated, and the residues were diluted, and then were extracted with EtOAc (250 ml*2times). The combined organic layer was dried on MgSO4, and the solvent was removed under vacuum to obtain yellow oil. The combined organic layer was concentrated under reduced pressure to obtain methyl 2-methyl-6-nitro benzoate (compound <16-1>) (15.9 g, 81.5 mmol, 98%) as a white solid.
94% With potassium carbonate;Reflux; To a solution of <strong>[13506-76-8]2-methyl-6-nitrobenzoic acid</strong> (5.0 g, 27.6 mmol) in acetone (60 mL) was added K2CO3 (5.7 g, 41.4 mmol) and MeI (4.3 g, 30.4 mmol), the resulting reaction mixture was heated to reflux overnight. Then it was quenched with water, extracted with EtOAc, and the combined organic phase was concentrated in vacuo to give a residue, which was purified by column chromatography (PE/EtOAc = 50/1 to 10/1) to give methyl 2-methyl-6-nitrobenzoate (5.1 g, yield 94%) as a light oil.1H NMR (300 MHz, DMSO-d6): d 8.03 (d, J = 8.1 Hz, 1H), 7.76 (d, J = 7.6 Hz, 1H), 7.65 (dd, J = 8.1, 7.6 Hz, 1H), 3.87 (s, 3H) ppm.
With potassium carbonate; In acetone; for 15h;Heating / reflux; To a solution of the 2-methyl-6-nitro-benzoic acid (5.6 g, 30.9 mmol, 1.0 eq, Aldrich) and acetone (100 mL) was added crushed K2CO3 (21.4 g, 154.6 mmol, 5 eq) and MeI (9.6 mL, 154.6 mmol, 5.0 eq.). The reaction was heated to reflux for 15 h then cooled to RT, filtered and concentrated in vacuo. The filtrate was dissolved in EtOAc, washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to give the desired compound as a reddish-brown oil which upon standing at RT crystallized as tan needles.
With potassium carbonate; In acetone; for 15h;Heating / reflux; To a solution of 2-methyl-6-nitro-benzoic acid (5.6 g, 30.9 mmol, 1.0 eq, Aldrich) and acetone (100 mL) was added crushed K2CO3 (21.4 g, 154.6 mmol, 5 eq) and MeI (9.6 mL, 154.6 mmol, 5.0 eq). The reaction was heated to reflux for 15 h then cooled to RT, filtered and concentrated in vacuo. The filtrate was dissolved in EtOAc, washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to give the desired compound as a reddish-brown oil which upon standing at RT crystallized to tan needles
With potassium carbonate; In butanone; for 18h;Reflux; Example 1. Preparation of N-(3-oxo-2-(3-(trifluoromethyl)phenyl)isoindolin-4- yl)pyrazine-2-carboxamide (Compound 100):Step 1) Synthesis of methyl 2-methyl-6-nitrobenzoate (2):2-Methyl-6-nitrobenzoic acid (1; 10 g, 0.0552 mol) was taken up in 200 mL of methyl ethyl ketone along with methyl iodide (17.2 mL, 0.276 mol) and anhydrous potassium carbonate (38.1 g, 0.276 mol). The reaction mixture was stirred under reflux for 18 h. It was then cooled to room temperature and filtered. The filtrate was diluted with EtOAc (300 mL), washed with water (2 x 50 mL), brine, dried (Na2SO4) and concentrated under reduced pressure to afford methyl 2- methyl-6-nitrobenzoate 2 (10.80 g).
With potassium carbonate; In butanone; for 18h;Reflux; Example 1. Preparation of N-(l-oxo-2-(3-(trifluoromethyl)phenyl)-l,2,3,4- tetrahydroisoquinolin-8-yl)pyrazine-2-carboxamide (Compound 101): Step 1) Synthesis of methyl 2-methyl-6-nitrobenzoate (2): 2-Methyl-6-nitrobenzoic acid (1; 10 g, 55.2 mol) was taken up in 200 mL of methyl ethyl ketone along with methyl iodide (17.2 mL, 276.0 mmol) and anhydrous potassium carbonate (38.1 g, 276.0 mmol). The reaction mixture was stirred under reflux for 18 h. It was then cooled to room temperature and filtered. The filtrate was diluted with EtOAc (300 mL), washed with water (2 x 50 mL), brine, dried (Na2SO4) and concentrated under reduced pressure to afford 10.80 g of methyl 2- methyl-6-nitrobenzoate 2. MS (ESI) calcd for C9H9NO4: 195.05; found: 196 [M + H].
10.80 g With potassium carbonate; In butanone; for 18h;Reflux; Step 1) Synthesis of methyl 2-methyl-6-nitrobenzoate (2) 2-Methyl-6-nitrobenzoic acid (1; 10 g, 55.2 mol) was taken up in 200 mL of methyl ethyl ketone along with methyl iodide (17.2 mL, 276.0 mmol) and anhydrous potassium carbonate (38.1 g, 276.0 mmol). The reaction mixture was stirred under reflux for 18 h. It was then cooled to room temperature and filtered. The filtrate was diluted with EtOAc (300 mL), washed with water (2*50 mL), brine, dried (Na2SO4) and concentrated under reduced pressure to afford 10.80 g of methyl 2-methyl-6-nitrobenzoate 2. MS (ESI) calcd for C9H9NO4: 195.05. found: 196 [M+H].

  • 10
  • [ 13506-76-8 ]
  • [ 169045-00-5 ]
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