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CAS No. : | 2682-45-3 | MDL No. : | MFCD00004951 |
Formula : | C12H9NS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OUXMJRMYZCEVKO-UHFFFAOYSA-N |
M.W : | 199.27 | Pubchem ID : | 75892 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 13 |
Fraction Csp3 : | 0.08 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 62.09 |
TPSA : | 41.13 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.65 cm/s |
Log Po/w (iLOGP) : | 2.59 |
Log Po/w (XLOGP3) : | 4.03 |
Log Po/w (WLOGP) : | 3.76 |
Log Po/w (MLOGP) : | 2.83 |
Log Po/w (SILICOS-IT) : | 4.65 |
Consensus Log Po/w : | 3.57 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.3 |
Solubility : | 0.00995 mg/ml ; 0.0000499 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.6 |
Solubility : | 0.00504 mg/ml ; 0.0000253 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.04 |
Solubility : | 0.00183 mg/ml ; 0.00000918 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.11 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
70% | With sodium dodecyl-sulfate In water for 0.166667 - 0.25 h; | 1-aminonaphthalene-2-thiol was added to 20 ml of water, and 20 mg of sodium dodecylsulfate was added while agitating to obtain a uniform mixture.7.5mmol of acetic anhydride was added for 5 minutes. A precipitation product was obtained in 5-10 minutes. The precipitation product was <n="16"/>filtrated and rinsed with 1 ml of water twice followed by drying under vacuum.A non-precipitated reaction mixture was extracted with 25 ml of ethyl acetate twice. The separated organic layer was dried with anhydrous sodium sulfate, and a solvent was removed using a rotatary evaporator under a reduced pressure to obtain 2-methyl naphtothiazole at a yield of 70percent. |
70% | With sodium dodecyl-sulfate In water for 0.166667 - 0.25 h; | EXAMPLE 1Compound 1: Synthesis of (MNTZ)2Ir(acac)Synthesis of 2-methyl naphtothiazole (MNTZ): 5 mmol of 1-aminonaphthalene-2-thiol was added to 20 ml of water, and 20 mg of sodium dodecylsulfate was added while agitating to obtain a uniform mixture. 7.5 mmol of acetic anhydride was added for 5 minutes. A precipitation product was obtained in 5-10 minutes. The precipitation product was filtrated and rinsed with 1 ml of water twice followed by drying under vacuum. A non-precipitated reaction mixture was extracted with 25 ml of ethyl acetate twice. The separated organic layer was dried with anhydrous sodium sulfate, and a solvent was removed using a rotatary evaporator under a reduced pressure to obtain 2-methyl naphtothiazole at a yield of 70percent.Synthesis of (MNTZ)2l Ir(Cl)2Ir(MNTZ)2: 5 mmol of 2-methyl naphtothiazole and 10 mmol of IrCl3xH2O were dissolved in 100 mL of 2-ethoxyethanol and refluxed for 24 hours under a nitrogen atmosphere. The solution was cooled down into room temperature, and 5percent hydrochloric acid aqueous solution 200 mL was added to the solution for eduction, filtrated, rinsed with water and an ether solvent, and dried to thereby produce (MNTZ)2Ir(Cl)2Ir(MNTZ)2 at a yield of 93percent.Synthesis of (MNTZ)2Ir(acac): 5 mmol of (MNTZ)2Ir(Cl)2Ir(MNTZ)2 and 25 mmol of 2,4-pentadione, and 50 mmol of potassium carbonate were mixed in 100 mL of 1,2-dichloroethane and refluxed for 24 hours under a nitrogen atmosphere. After the reaction was complete, the solution was cooled down into about 50° C. and filtrated. The filtrate solution was purified by using column chromatography to thereby produce (MNTZ)2Ir(acac) at a yield of 91percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The following compounds of formula I are those which are preferred within the scope of the invention:...2-(2-dimethylaminoethenyl)-benzothiazole,2-propionylbenzothiazole,4-chloro-2-methylbenzothiazole,5,6-dimethoxy-2-methylbenzothiazole,2-methylnaphtho[1,2-d]thiazole,6-methoxy-2-methylbenzothiazole,5-trifluoromethylsulphonyl-2-methylbenzothiazole,6-benzoyl-(2H)-benzoxazolone and... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium dodecyl-sulfate; In water; for 0.166667 - 0.25h; | 1-aminonaphthalene-2-thiol was added to 20 ml of water, and 20 mg of sodium dodecylsulfate was added while agitating to obtain a uniform mixture.7.5mmol of acetic anhydride was added for 5 minutes. A precipitation product was obtained in 5-10 minutes. The precipitation product was <n="16"/>filtrated and rinsed with 1 ml of water twice followed by drying under vacuum.A non-precipitated reaction mixture was extracted with 25 ml of ethyl acetate twice. The separated organic layer was dried with anhydrous sodium sulfate, and a solvent was removed using a rotatary evaporator under a reduced pressure to obtain 2-methyl naphtothiazole at a yield of 70percent. |
70% | With sodium dodecyl-sulfate; In water; for 0.166667 - 0.25h; | EXAMPLE 1Compound 1: Synthesis of (MNTZ)2Ir(acac)Synthesis of 2-methyl naphtothiazole (MNTZ): 5 mmol of 1-aminonaphthalene-2-thiol was added to 20 ml of water, and 20 mg of sodium dodecylsulfate was added while agitating to obtain a uniform mixture. 7.5 mmol of acetic anhydride was added for 5 minutes. A precipitation product was obtained in 5-10 minutes. The precipitation product was filtrated and rinsed with 1 ml of water twice followed by drying under vacuum. A non-precipitated reaction mixture was extracted with 25 ml of ethyl acetate twice. The separated organic layer was dried with anhydrous sodium sulfate, and a solvent was removed using a rotatary evaporator under a reduced pressure to obtain 2-methyl naphtothiazole at a yield of 70percent.Synthesis of (MNTZ)2l Ir(Cl)2Ir(MNTZ)2: 5 mmol of 2-methyl naphtothiazole and 10 mmol of IrCl3xH2O were dissolved in 100 mL of 2-ethoxyethanol and refluxed for 24 hours under a nitrogen atmosphere. The solution was cooled down into room temperature, and 5percent hydrochloric acid aqueous solution 200 mL was added to the solution for eduction, filtrated, rinsed with water and an ether solvent, and dried to thereby produce (MNTZ)2Ir(Cl)2Ir(MNTZ)2 at a yield of 93percent.Synthesis of (MNTZ)2Ir(acac): 5 mmol of (MNTZ)2Ir(Cl)2Ir(MNTZ)2 and 25 mmol of 2,4-pentadione, and 50 mmol of potassium carbonate were mixed in 100 mL of 1,2-dichloroethane and refluxed for 24 hours under a nitrogen atmosphere. After the reaction was complete, the solution was cooled down into about 50° C. and filtrated. The filtrate solution was purified by using column chromatography to thereby produce (MNTZ)2Ir(acac) at a yield of 91percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In 2-ethoxy-ethanol; for 24h;Heating / reflux; | deltammol of 2-methyl naphtothiazole and IOmmol of IrCI3XH2O were dissolved in 10OmL of 2-ethoxyethanol and refluxed for 24 hours under a nitrogen atmosphere. The solution was cooled down into room temperature, and 5percent hydrochloric acid aqueous solution 20OmL was added to the solution for eduction, filtrated, rinsed with water and an ether solvent, and dried to thereby produce(MNTZ)2Ir(CI)2Ir(MNTZ)2 at a yield of 93percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.50 g (63%) | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; | Reference Example 15 To 3.98 g of <strong>[2682-45-3]2-methylnaphtho[1,2-d]thiazole</strong> dissolved in carbon tetrachloride (40 ml) was added 3.56 g of N-bromosuccinimide and 0.20 g of benzoyl peroxide, followed by 6 hours of heating under reflux. After cooling the reaction solution, insoluble matter was removed by filtration, and the solvent was evaporated. The residue was subjected to silica gel column chromatography eluted with hexane-chloroform (5:1) to obtain 3.50 g (63percent) of 2-bromomethylnaphtho[1,2-d]thiazole. Mass spectrometry value (m/z): 277, 279 (M+) Nuclear magnetic resonance spectrum (CDCl3, TMS internal standard) delta: 4.94 (2H, s), 7.5-7.7 (2H, m), 7.8-8.0 (3H, m), 8.77 (1H, dd) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With ammonium cerium(IV) nitrate; lithium bromide; In acetonitrile; at 20℃; for 1h; | For introduction of a methoxy substituent to ring structure A, 2-methylnaphth[l,2-d]thiazol (Ig, 5.02 mmol) and LiBr (0.479g, 5.52 mmol) were suspended in 10 mL water- free acetonitrile. CAN ((NH4)2Ce(NC>3)6, 3.026 g, 5.52 mmol) suspended in acetonitrile was added dropwise and stirred under a nitrogen atmosphere for 1 h at room temperature (according to Subhas Chandra Roy et al,. Tetrahedron Lett. 42, 6941 (2001)). Aqueous purification and column chromatography using dichloromethane yields a light yellow solid (30% yield, 0.436 g, 1.57 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In 2-ethoxy-ethanol; for 24h;Heating / reflux; | EXAMPLE 1Compound 1: Synthesis of (MNTZ)2Ir(acac)Synthesis of 2-methyl naphtothiazole (MNTZ): 5 mmol of 1-aminonaphthalene-2-thiol was added to 20 ml of water, and 20 mg of sodium dodecylsulfate was added while agitating to obtain a uniform mixture. 7.5 mmol of acetic anhydride was added for 5 minutes. A precipitation product was obtained in 5-10 minutes. The precipitation product was filtrated and rinsed with 1 ml of water twice followed by drying under vacuum. A non-precipitated reaction mixture was extracted with 25 ml of ethyl acetate twice. The separated organic layer was dried with anhydrous sodium sulfate, and a solvent was removed using a rotatary evaporator under a reduced pressure to obtain 2-methyl naphtothiazole at a yield of 70percent.Synthesis of (MNTZ)2l Ir(Cl)2Ir(MNTZ)2: 5 mmol of 2-methyl naphtothiazole and 10 mmol of IrCl3xH2O were dissolved in 100 mL of 2-ethoxyethanol and refluxed for 24 hours under a nitrogen atmosphere. The solution was cooled down into room temperature, and 5percent hydrochloric acid aqueous solution 200 mL was added to the solution for eduction, filtrated, rinsed with water and an ether solvent, and dried to thereby produce (MNTZ)2Ir(Cl)2Ir(MNTZ)2 at a yield of 93percent.Synthesis of (MNTZ)2Ir(acac): 5 mmol of (MNTZ)2Ir(Cl)2Ir(MNTZ)2 and 25 mmol of 2,4-pentadione, and 50 mmol of potassium carbonate were mixed in 100 mL of 1,2-dichloroethane and refluxed for 24 hours under a nitrogen atmosphere. After the reaction was complete, the solution was cooled down into about 50° C. and filtrated. The filtrate solution was purified by using column chromatography to thereby produce (MNTZ)2Ir(acac) at a yield of 91percent. |
61% | In 2-ethoxy-ethanol; water; at 130℃; for 68h; | In detail, iridium (III) chloride hydrate (4.0 g, 0.011 mol) and 2-methylnaphth[l,2-d]thiazole (5.6 g, 0.028 mol) were suspended in 2-ethoxyethanol (138 mL) and water (46 mL) and stirred under an inert gas atmosphere for 68 hours at 130 °C. The reaction solution is filtered off and washed with /z-hexane and diethylether. The product is a yellow, fine powdery solid (61percent yield). |
61 - 77% | In 2-ethoxy-ethanol; water; at 130℃; for 68h; | In detail, iridium (III) chloride hydrate (4.0 g, 0.011 mol) and 2-methylnaphth[l,2-d]thiazole (5.6 g, 0.028 mol) were suspended in 2-ethoxyethanol (138 mL) and water (46 mL) and stirred under an inert gas atmosphere for 68 hours at 130 0C. The reaction solution is filtered off and washed with n-hexane and diethylether. The product is a yellow, fine powdery solid (61percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With silver trifluoroacetate; at 120℃; for 75h; | Under an inert gas atmosphere, di-mu-chlorotetrakis(2-methylnaphth[l,2-d]thiazole)di- iridium(III) (500 mg, 0.4 mmol) was stirred for 75 hours at 120 °C with 2-methylnaphth[l,2- d]thiazole (319 mg, 1.6 mmol) and with the silver salt of trifluoro acetic acid (177 mg, 0.8 mmol). The solid is isolated and washed with ethanol. After purification by column chromatography using dichloromethane as the eluent and recrystallization from methanol, a white yellowish powder is obtained (18percent yield).The following characteristics were determined:1H NMR ([D6J-DMSO): delta = 7.88 (d, IH), 7.78 (d, IH), 7.35 (d, IH), 6.91 (m, IH), 6.34 (d, IH), 2.15 (s, 3H).13C NMR ([D6J-DMSO): delta = 168.5 (s), 157.5 (s), 143.3 (s), 138.4 (s), 131.4 (d), 130.3 (s), 127.1 (d), 126.1 (d), 124.8 (s), 117.9 (d), 117.8 (d), 16.6 (q).MS (EI): m/z (percent): 787 (100) [M]+.UV/Vis (CH2Cl2): lambda /nm (epsilon) = 341 (16 900), 278 (41 000), 230 (106 000).C36H30IrN3O3 (744.86) calculated: C 54.94 H 3.07 N 5.34 determined: C 54.61 H 3.17 N 5.31. |
6 - 18% | With silver trifluoroacetate; at 120℃; for 75h; | Under an inert gas atmosphere, di-mu-chlorotetrakis(2-methylnaphth[l,2-d]thiazole)di- iridium(III) (500 mg, 0.4 mmol) was stirred for 75 hours at 120 0C with 2-methylnaphth[l,2- d]thiazole (319 mg, 1.6 mmol) and with the silver salt of trifluoro acetic acid (177 mg, 0.8 mmol). The solid is isolated and washed with ethanol. After purification by column chromatography using dichloromethane as the eluent and recrystallization from methanol, a white yellowish powder is obtained (18percent yield).The following characteristics were determined: delta = 7.88 (d, IH), 7.78 (d, IH), 7.35 (d, IH), 6.91 (m, IH), 6.34 (d, IH), 2.15 (s, 3H).delta = 168.5 (s), 157.5 (s), 143.3 (s), 138.4 (s), 131.4 (d), 130.3 (s), 127.1 (d), 126.1 (d),124.8 (s), 117.9 (d), 117.8 (d), 16.6 (q). MS (EI): m/z (percent): 787 (100) [M]+.UV/Vis (CH2Cl2): lambda /nm (epsilon) = 341 (16 900), 278 (41 000), 230 (106 000).C36H30IrN3O3 (744.86) calculated: C 54.94 H 3.07 N 5.34 determined: C 54.61 H 3.17 N 5.31. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; for 15h;Reflux; | General procedure: Quinoline heterocycles were prepared according to the literature procedure [34]. Quaternary salts A were synthesized when a mixture of 0.016mmol quinoline heterocycles and 0.023mmol methyl iodide in ethanol was refluxed for 15h. After cooling, the product was filtered off and purified by recrystallization from EtOH. The dyes 1?13 were synthesized according to the literature [28,29]. The synthesis of dyes 14?20 followed the procedure [29] with slight modification. Various quaternary salts A (1mmol), aromatic aldehydes B (1mmol), 15mL anhydrous ethanol and a few drops of piperidine were mixed thoroughly together at ambient temperature in a dried round-bottom flask (50mL) equipped with a reflux condenser capped with an anhydrous CaCl2 drying tube. The mixture was subjected to microwave irradiation at appropriate time, power and temperature. After cooling, the crude products was filtered off and purified by two different methods depending on the dyes' solubility. For dyes 14?16, the crude products was recrystallized from EtOH?H2O to afford pure dyes. For dyes 17?20, having very poor solubility, the crude products was washed with diethyl ether and extracted with EtOH by Soxhlet extraction in 15h. The reaction details and yields of dyes 14?20 were listed in Table1. |
Tags: 2682-45-3 synthesis path| 2682-45-3 SDS| 2682-45-3 COA| 2682-45-3 purity| 2682-45-3 application| 2682-45-3 NMR| 2682-45-3 COA| 2682-45-3 structure
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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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