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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
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Structure of 2687-25-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 2687-25-4 |
Formula : | C7H10N2 |
M.W : | 122.17 |
SMILES Code : | NC1=CC=CC(C)=C1N |
MDL No. : | MFCD00011589 |
InChI Key : | AXNUJYHFQHQZBE-UHFFFAOYSA-N |
Pubchem ID : | 17593 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H301-H312-H315-H319-H341 |
Precautionary Statements: | P501-P270-P202-P201-P264-P280-P308+P313-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P302+P352+P312-P405 |
Class: | 6.1 |
UN#: | 2811 |
Packing Group: | Ⅲ |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 40.22 |
TPSA ? Topological Polar Surface Area: Calculated from |
52.04 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.24 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.92 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.18 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.15 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.87 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.07 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.67 |
Solubility | 2.61 mg/ml ; 0.0214 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.6 |
Solubility | 3.08 mg/ml ; 0.0252 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.02 |
Solubility | 1.17 mg/ml ; 0.00955 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) |
Yes |
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) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.39 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 |
---|---|---|
92% | With hydrogenchloride; thionyl chloride; In pyridine; | 4-Methyl-2,1,3-benzothiadiazole Thionyl chloride (166 g, 1.4 mol) was added to a solution of 2,3-diaminotoluene (71 g, 0.58 mol) in pyridine (430 mL) dropwise at a temperature below 45 C. Concentrated HCl (300 mL) was then added dropwise while care was taken to ensure that the reaction temperature did not exceed 65 C. After cooling to room temperature, the reaction mixture was subjected to a steam distillation. The light-yellow oil suspension in the water layer was extracted with diethyl ether. The combined extracts were washed with brine and dried over Na2SO4. After removal of the solvent by rotary evaporation, 4-methyl-2,1,3-benzothiadiazole was obtained as a light-yellow liquid in 92% (80.6 g) of yield. Rf=0.62 (hexane/ethyl acetate=3:1); 1H NMR (200 MHz, CDCl3) δ2.74 (s, 3H), 7.34 (m, 1H), 7.48 (d,J1=8.7 Hz, J2=6.7 Hz, 1H), 7.83 (m, 1H). |
89% | Combine 3-methyl-1,2-phenylenediamine (30.53g, 249.87mmol, 1.0 equivalent), triethylamine (138.92mL, 999.47mmol, 4.0 equivalent) and dichloromethane (300mL) Add a dry three-necked flask equipped with magnetic stirring and place in an ice bath.The mixture was stirred for more than 1 hour, and then thionyl chloride (36.25 mL, 499.74 mmol, 2.0 equivalents) and dichloromethane (100 mL) were slowly added dropwise. The mixture was stirred at this temperature for 1 hour and then the mixture was placed in an oil bath. After stirring for 20 hours at 40C, the reaction was monitored by thin layer chromatography until the reaction was completed.The reaction was stopped and the resulting mixture was cooled to room temperature and quenched by adding water.The mixture was extracted three times with ethyl acetate.The combined organic phase was washed with water, dried over anhydrous sodium sulfate and filtered.The filtrate was concentrated under reduced pressure, and the sample was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 10:1-4:1) to obtain 33.40 g of a colorless liquid with a yield of 89%. | |
77% | With thionyl chloride; triethylamine; In dichloromethane; at 45℃; for 7h;Cooling with ice; | Take compound XD-1 (2.26g) and dissolve it in DCM (60mL),Add triethylamine (Et3N, 10.3mL),Stir at room temperature until the solid is completely dissolved,Slowly drip thionyl chloride (SOCl2, 2.7mL) under ice bath,Heat in an oil bath at 45C for 7 hours and stop heating.The solvent was evaporated under reduced pressure, water (70mL) was added,Adjust the pH to 1 with 1N hydrochloric acid, and extract with ethyl acetate (30mL x 3),Dry with anhydrous sodium sulfate.The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 10:1).Compound XD-2 (2.1 g) was obtained as a yellow oil. |
63% | With pyridine; thionyl chloride; at 30℃;Cooling with ice; Inert atmosphere; | To the 500 mL two-necked flask to which the dropping funnel was attached, 12 g (98 mmol) of the above compound (1-e) and 100 mL of pyridine were added, and the mixture was stirred under ice cooling under an argon atmosphere.Thionyl chloride 16.4 mL (240 mmol) was slowly added dropwise so that the liquid temperature did not exceed 30 C. Next, 48 mL of concentrated HCl was slowly added dropwise so that the liquid temperature did not exceed 60 C, and the mixture was stirred at room temperature. Water was added to the reaction liquid, and the mixture was extracted with ether to give the compound (1-f) (yield: 9.3 g, yield: 63%) as a brown oily liquid. |
44% | With pyridine; thionyl chloride; at 60℃; for 9h;Reflux; | To a stirredsolution of 3-Methylbenzene-1,2-diamine (15; 5 g , 41 mmol) in 20 mL of pyridine,thionyl chloride was added very slowly (8.2 mL, 110 mmol,2.7 eq.), while the temperature was kept at 60C. After that, theresulting slurry was heated to reflux for 9 h. The dark reaction mixturewas allowed to cool to room temperature and hydrolyzed with water verycarefully. After adding 1 L of water the mixture was steam distilled. Thedistillation was stopped, after 800 mL of steam; the aqueous phase wassaturated with NaCl and extracted four times with diethyl ether. Thecombined organic layers were dried over Na2SO4 andevaporated to dryness to afford the oily product (2.7 g, 13 mmol,44%). 1H-NMR (300 MHz, Acetone): δ = 7.81 (d, J = 8.8Hz, 1H), 7.59 - 7.49 (m, 1H), 7.41 (d, J = 6.7 Hz, 1H), 2.67 (s,3H) ppm. 13C-NMR (75 MHz, Acetone): δ = 156.15, 155.74,132.29, 130.63, 128.90, 119.58, 17.80 ppm. MS (EI): m/z = 150 [M+].EA calc. for C7H6N2S: C, 55.97; H, 4.03; N,18.65; found: C, 56.20; H, 4.13; N, 18.41. |
With thionyl chloride; In pyridine; water; | A. 4-Methyl-benzo[1,2,5]thiadiazole (839A) To a solution of 2,3-diaminotoluene (5.0 g, 40.9 mmol) in pyridine (40 mL) at 0 C. was added thionyl chloride (7.0 mL, 98.2 mmol) dropwise. The reaction mixture was stirred at 0 C. for 30 mins, then water (200 mL) was added. The solution was extracted with dicholomethane (2*250 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give compound 839A (5.57 g) as a dark brown liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With 10 wtpercent sulfated polyborate; In neat (no solvent); at 100℃; for 0.05h;Green chemistry; | General procedure: To a mixture of substituted o-phenylenediamines derivative(2.0 mmol) and 1,2-diketone / alpha-hydroxy ketone (2.0 mmol),was added sulfated polyborate (10 wt%). The reaction mixture was stirred at 100 C in an oil bath. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature and quenched by water. The resultant product was filtered/extracted with EtOAc to get the product. Crude products were either recrystallized from ethanol or purified by column chromatography using silica as the stationary phase and EtOAc: pet. ether as mobile phase. The products obtained were known compounds and were identified by melting point and 1H and 13C NMR spectroscopy. The spectral data were compared with the literature values. |
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