Structure of 615-37-2
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CAS No. : | 615-37-2 |
Formula : | C7H7I |
M.W : | 218.04 |
SMILES Code : | CC1=CC=CC=C1I |
MDL No. : | MFCD00001042 |
InChI Key : | RINOYHWVBUKAQE-UHFFFAOYSA-N |
Pubchem ID : | 5128 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 44.12 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.16 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.94 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.6 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.53 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.32 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.91 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.6 |
Solubility | 0.0549 mg/ml ; 0.000252 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.6 |
Solubility | 0.545 mg/ml ; 0.0025 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.74 |
Solubility | 0.0396 mg/ml ; 0.000182 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
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) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.54 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) |
1.53 |
* 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 |
---|---|---|
99% | Stage #1: With potassium carbonate In toluene at 148℃; for 21 h; Heating / reflux Stage #2: With hydrogenchloride In water Stage #3: With sodium hydroxide In water |
(R)-N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride:; A 3 -necked 100 ml glass reactor was flushed for 15 min with N2 and subsequently charged with 15 g (90.8 mmol) of the above mentioned (3R)-methyl-3-hydroxy-3- phenylpropylamine (>99 percent ee, chiral HPLC), potassium phosphate (28.9 g, 136.2 mmol) and 1.73 g copper(I)iodide (9.8 mmol, 10 mol-percent). 60 ml of toluene was added to the mixture and the suspension was stirred for 5 min. 12.8 ml (100 mmol) of 2-iodotoluene was added and the reaction mixture was heated to reflux for 24 h. After cooling to room temperature, the suspension was filtered and the filter cake was washed with 60 ml of toluene. 75 ml of water was added to the filtrate and the mixture was stirred for 10 min at room temperature. The aqueous phase was brought to pH 1-2 with 30 percent HCl and the phases were separated. 60 ml of toluene was added to the aqueous phase and aqueous NaOH was added until pH 12-14 of the aqueous phase was reached. After stirring for EPO <DP n="16"/>10 min the phases were separated. The organic phase was evaporated under reduced pressure yielding 25 g of an oil.The oil was redissolved in 80 ml of toluene, warmed to 80 °C and 36 g of a 10 percent HCl- ethyl acetate solution was added dropwise to the solution. During cooling of the solution a white solid precipitated. After 5 h at room temperature, the suspension was filtered and the residue was dried in vacuum at about 50 °C to yield 22 g (75.4 mmol, 83 percent) of (R)- N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride.The (R)-N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride salt was placed in a 100 ml reaction vessel and 55 ml of isopropanol was added. Upon heating to reflux temperature all solids were dissolved. Slow cooling to room temperature gave 18.1 g (82 percent) of colorless (R)-N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride (>99 percent ee, HPLC). |
94% | Stage #1: With potassium carbonate In toluene at 148℃; for 21 h; Heating / reflux Stage #2: With hydrogenchloride In water Stage #3: With sodium hydroxide In water |
(R)-N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride:; A 3 -necked 100 ml glass reactor was flushed for 15 min with N2 and subsequently charged with 15 g (90.8 mmol) of the above mentioned (3R)-methyl-3-hydroxy-3- phenylpropylamine (>99 percent ee, chiral HPLC), potassium phosphate (28.9 g, 136.2 mmol) and 1.73 g copper(I)iodide (9.8 mmol, 10 mol-percent). 60 ml of toluene was added to the mixture and the suspension was stirred for 5 min. 12.8 ml (100 mmol) of 2-iodotoluene was added and the reaction mixture was heated to reflux for 24 h. After cooling to room temperature, the suspension was filtered and the filter cake was washed with 60 ml of toluene. 75 ml of water was added to the filtrate and the mixture was stirred for 10 min at room temperature. The aqueous phase was brought to pH 1-2 with 30 percent HCl and the phases were separated. 60 ml of toluene was added to the aqueous phase and aqueous NaOH was added until pH 12-14 of the aqueous phase was reached. After stirring for EPO <DP n="16"/>10 min the phases were separated. The organic phase was evaporated under reduced pressure yielding 25 g of an oil.The oil was redissolved in 80 ml of toluene, warmed to 80 °C and 36 g of a 10 percent HCl- ethyl acetate solution was added dropwise to the solution. During cooling of the solution a white solid precipitated. After 5 h at room temperature, the suspension was filtered and the residue was dried in vacuum at about 50 °C to yield 22 g (75.4 mmol, 83 percent) of (R)- N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride.The (R)-N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride salt was placed in a 100 ml reaction vessel and 55 ml of isopropanol was added. Upon heating to reflux temperature all solids were dissolved. Slow cooling to room temperature gave 18.1 g (82 percent) of colorless (R)-N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride (>99 percent ee, HPLC). |
82% | Stage #1: With potassium phosphate In toluene for 24 h; Heating / reflux Stage #2: With hydrogenchloride In water Stage #3: With sodium hydroxide In water |
(R)-N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride:; A 3 -necked 100 ml glass reactor was flushed for 15 min with N2 and subsequently charged with 15 g (90.8 mmol) of the above mentioned (3R)-methyl-3-hydroxy-3- phenylpropylamine (>99 percent ee, chiral HPLC), potassium phosphate (28.9 g, 136.2 mmol) and 1.73 g copper(I)iodide (9.8 mmol, 10 mol-percent). 60 ml of toluene was added to the mixture and the suspension was stirred for 5 min. 12.8 ml (100 mmol) of 2-iodotoluene was added and the reaction mixture was heated to reflux for 24 h. After cooling to room temperature, the suspension was filtered and the filter cake was washed with 60 ml of toluene. 75 ml of water was added to the filtrate and the mixture was stirred for 10 min at room temperature. The aqueous phase was brought to pH 1-2 with 30 percent HCl and the phases were separated. 60 ml of toluene was added to the aqueous phase and aqueous NaOH was added until pH 12-14 of the aqueous phase was reached. After stirring for EPO <DP n="16"/>10 min the phases were separated. The organic phase was evaporated under reduced pressure yielding 25 g of an oil.The oil was redissolved in 80 ml of toluene, warmed to 80 °C and 36 g of a 10 percent HCl- ethyl acetate solution was added dropwise to the solution. During cooling of the solution a white solid precipitated. After 5 h at room temperature, the suspension was filtered and the residue was dried in vacuum at about 50 °C to yield 22 g (75.4 mmol, 83 percent) of (R)- N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride.The (R)-N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride salt was placed in a 100 ml reaction vessel and 55 ml of isopropanol was added. Upon heating to reflux temperature all solids were dissolved. Slow cooling to room temperature gave 18.1 g (82 percent) of colorless (R)-N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride (>99 percent ee, HPLC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate; basolite C300; In water; N,N-dimethyl-formamide; at 130℃; for 4.25h;Green chemistry; | General procedure: A mixture of iodobenzene (2.0 mmol), potassium 5-methyl-1,3,4-oxadiazole-2-thiolate (1) (3.0 mmol), MOF-199 (8 mg, 10 % mol) were added to a flask containing 2 mL DMF/H2O (20:1), The reaction continued at 130 C under atmospheric conditions until completion. Thereaction progress was controlled by thin-layer chromatography. The reaction mixture was then filtered. The filtrate was evaporated under vacuum, CH2Cl2 (20 ml) was addedand the mixture was washed with H2O (2 x 15 ml). Theorganic layer was dried over anhydrous Na2SO4. The solvent was evaporated to give the crude diaryl disulfide, which was purified by plate chromatography (silica gel,n-hexane-ethyl acetate, 20:1). All spectra of the diaryl disulfides are mentioned in the electronic supplementary material. |
97% | With morpholinium morpholine-1-carbodithioate; copper(l) chloride; potassium hydroxide; In water; N,N-dimethyl-formamide; at 110℃; for 20h;Green chemistry; | General procedure: To a stirred mixture of aryl (alkyl) halide (2.0 mmol), morpholin-4-ium morpholine-4-carbodithioate(0.75 g, 3.0 mmol) in DMF/H2O (2:1) was added CuCl (0.3 g, 3.0 mmol) followed byKOH (2.0 g) and heated at 110C under atmospheric conditions until completion (20 h). Theprogress of the reaction was monitored by TLC. Upon completion of the reaction, the mixturewas cooled to room temperature and then filtered. The filtrate was evaporated under vacuum,CH2Cl2 (20 ml) was added and the mixture was washed with H2O (2 × 15 ml). The combinedorganic layer was dried over Na2SO4, and filtered to afford the crude diaryl (dialkyl) disulfide,which was purified by plate chromatography (silica gel, n-hexane: ethyl acetate, 20:1; in the caseof 3i and 3k was 4:1). |
95% | With indium(III) oxide; ammonia; water; sulfur; In ethanol; at 60℃;Green chemistry; | General procedure: A mixture of alkyl/aryl halide, 1 (1.2 mmol), ammonium hydroxide (1 mmol) and nanosulfur powder (3 mmol, 96 mg) was stirred in 5mL of solvent (ethanol/water (2:1)) at 60 C. Under this stirring condition indium oxide nanoparticles (3 mol-%) were added to it and the reaction was stirred for a period of 10 min to 1 h at 60 C. After completion of the reaction as indicated by thin layer chromatography (TLC), the reaction mixture was cooled to room temperature and a 2:1 mixture of ethyl acetate/water (15 mL) was added and indium oxide was removed by centrifuge. The combined organic extracts were dried with anhydrous sodium sulfate and concentrated to give desired product in high purity. |
92% | With [2,2]bipyridinyl; copper(l) iodide; sodium carbonate; sulfur; aluminium; In N,N-dimethyl-formamide; at 110℃; for 24h;Inert atmosphere; | To a mixture of sulfur (10.6 mg, 0.3 mmol), CuI (8.5 mg, 0.045 mmol), aluminum powder (53-150 μm) (16.2 mg, 0.6 mmol), Na2CO3 (15.9 mg, 0.15 mmol), bpy (7.0 mg, 0.045 mmol), and 2-iodotoluene 1a (65.4 mg, 0.3 mmol), DMF (0.5 mL) was added, and the mixture was stirred at 110 C for 24 h. After the reaction mixture was diluted with Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (hexane) gave di(2-methylphenyl) disulfide (34.0 mg, 92%). 1H NMR (270 MHz, CDCl3) δ 7.49-7.52 (m, 2H), 7.10-7.15 (m, 6H), 2.42 (s, 6H); 13C NMR (67 MHz, CDCl3) δ 137.4, 135.4, 130.3, 128.7, 127.3, 126.7, 20.0. Anal. Calcd for C14H14S2: C, 68.24; H, 5.73. Found: C, 68.19; H, 5.70. |
90% | With carbon disulfide; potassium cyanide; copper(l) iodide; In N,N-dimethyl-formamide; at 20 - 120℃; for 1.7h; | General procedure: KCN (1.1 mmol, 0.07 g) and CS2 (1.3 mmol, 0.07 mL) were added to a flask containing DMF (1 mL) at room temperature. After 15 min, iodobenzene (1.0 mmol, 0.11 mL) and CuI (20 mol%, 0.038 g) were added and the reaction mixture stirred at 120 C. Upon reaction completion (TLC, 1.25 h), the mixture was cooled to room temperature, diluted with H2O (1 mL) and extracted with n-hexane/ethyl acetate (1:1, 4 × 1 mL). The combined organic extracts were concentrated and the residue purified by silica gel column chromatography using n-hexane as eluent to give the pure diphenyldisulfane as a white crystalline powder in 92% (0.10 g) yield. |
89% | With potassium ethyl xanthogenate; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 8h; | General procedure: A mixture of the requisite alkyl (aryl) halide (2.0 mmol), potassiumO-ethylcarbonodithioate (0.48 g, 3.0 mmol) and MOF-199(8 mg) in DMF (15.0 mL) in a 25 mL round-bottom flask wasstirred at 120 C for 8 h. The reaction was monitored by TLCanalysis. Upon completion of the reaction, the mixture wascooled to room temperature and then filtered. The filtrate wasevaporated under vacuum, CH2Cl2 (20 mL) was added, and themixture was washed with H2O (2 × 15 mL). The combinedorganic layers were dried over Na2SO4, filtered, and solvent wasremoved in vacuo. The residue was purified by thick-layer chromatographyon silica gel (eluting with n-hexane-ethyl acetate,20:1; in the case of 4e and 4f, 4:1 and 2:1, respectively) to givethe corresponding products. |
75% | With 1H-imidazole; copper(l) iodide; sodium thiosulfate pentahydrate; potassium carbonate; In water; dimethyl sulfoxide; at 130℃; for 24h;Green chemistry; | General procedure: A mixture of iodobenzene (1.0 mmol, 0.115 mL),Na2S2O3•5H2O (3 mmol, 248.21 mg), using CuI (0.7 mmol,190.45 mg) catalyst in the presence of K2CO3(2mmol,138.21 mg) and in the presence imidazole (1.6 mmol, 68.08mg) in DMSO/H2O (2 mL) at 130C for 21 h under normal atmospheric conditions until completion. The reaction progresswas controlled by thin-layer chromatography. Also itcan be controlled by color change of litmus paper [38]. Thereaction mixture was then filtered. The filtrate was evaporatedunder vacuum, CH2Cl2 (20 mL) was added and themixture was washed with H2O (2 × 15 mL). The organiclayer was dried over anhydrous Na2SO4. The solvent wasevaporated to give the crude diaryl/alkyl disulfide, whichwas purified by plate chromatography (silica gel, n-hexane-ethyl acetate, 20:1) |
70% | With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate; nickel(II) chloride hexahydrate; ethylene glycol; potassium hydroxide; In water; N,N-dimethyl-formamide; at 130℃; for 8h; | General procedure: A mixture of iodobenzene (2.0 mmol), potassium 5-methyl-1,3,4-oxadiazole-2-thiolate (1, 0.462 g, 3.0 mmol), NiCl2·6H2O (10 mol%) and KOH (1.0 g, 18 mmol) were added to a flask containing DMF-H2O (2 mL, 20:1) and EG (0.11 mL, 2 mmol). The reaction mixture was heated at 130 C under atmospheric conditions until completion, monitored by TLC. The reaction mixture was then filtered, the filtrate was evaporated under reduced pressure, CH2Cl2 (20 mL) was added, and the mixture was washed with H2O (2 × 15 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and the solvent was evaporated to give the crude diaryl/alkyl disulfide, which was purified by preparative TLC (silica gel; n-hexane-EtOAc, 20:1). |
70% | With 1,10-Phenanthroline; potassium sulfide; iron oxide; potassium hydroxide; In N,N-dimethyl-formamide; at 120℃; for 15.5h;Inert atmosphere; Green chemistry; | General procedure: A mixture of aryl iodide (1.0 mmol), K2S(1.0 mmol), Fe3O4 nanoparticle (6 mg), 1,10-Phenanthroline (6 mg) and KOH(0.05 g) were added to a flask containing 2 mL DMF. Thereaction continued at 120 C under N2atmospheric conditionsuntil completion.The reaction progress was controlledby thin-layer chromatography. The reaction mixture wasthen filtered. The filtrate was evaporated under vacuum;afterward, CH2Cl2(20 mL) was added and the mixture waswashed with H2O(2 × 15 mL). The organic layer was driedover anhydrous Na2SO4.The solvent was evaporated to givethe crude diaryl disulfide, which was purified by plate chromatography(silica gel, n-hexane-ethyl acetate, 20:1). (Fordetails, please see Electronic Supplementary Information.) |
68% | With potassium sulfide; nickel(II) chloride hexahydrate; acetylacetone; potassium hydroxide; In water; N,N-dimethyl-formamide; at 110℃; for 24h; | General procedure: To a stirred mixture of aryl (primary alkyl) halide (2.0 mmol), 0.33 g potassium sulfide (3.0 mmol) and acac (20 mol%) in 2 cm3 DMF (containing a few drops water),NiCl2.6H2O (10 mol%) and then 1.0 g KOH (18.0 mmol) were added and the whole reaction mixture was heated at 110 C under atmospheric conditions until completion. The progress of the reaction was monitored by TLC. Upon completion of the reaction, the mixture was cooled to room temperature. Then, the pH of mixture was adjusted to 7 with 5 % HCl and filtered. The filtrate was evaporated under vacuum, 20 cm3 ethyl acetate was added and the mixture was washed with H2O (2 x 15 cm3). The combined organic layer was dried over Na2SO4 and filtered to afford the crude diaryldisulfide and dialkyldisulfide, which was purified by preparative chromatography (silica gel, n-hexane:ethyl acetate 20:1; in the case of Table 3, entries 12-15 was 4:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate; at 85℃; for 24h;Inert atmosphere; Green chemistry; | General procedure: To a mixture of the catalyst 3 (20mg containing 0.05mol% Pd for aryl iodides and 40mg containing 0.1mol% Pd for aryl bromides and chlorides), aryl halide (1mmol), alkyne (1.5mmol), and K2CO3 (1.5mmol, 207mg) was added PEG 200 (2mL) under argon atmosphere. The reaction mixture was stirred for the appropriate reaction time at 85 or 130C (see, Table 2). The progress of the reaction was monitored by using gas chromatography. After completion of the reaction, pure products were obtained by using column chromatography with hexane and ethyl acetate as eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium t-butanolate; In dimethyl sulfoxide; at 110℃; for 12h;Green chemistry; | General procedure: Aryl halide (1.0 mmol), secondary amines (1mmol),2 mmol tBuONa and 0.2 mol% ofPd/Nf-G catalyst were addedin a 1 mL DMSO and the reaction was carried at 110C for 12h. The progress ofthe reaction was monitored by Gas Chromatography (GC). After completion ofreaction, the reaction mixture was cooled to room temperature and it was extracted with ethyl acetate. The catalyst was easily recovered by simple filtration followed by washing with ethanol and drying and preserved for nextruns. The pure products were obtained by column chromatography using hexane:ethyl acetate as the eluent. The preserved catalyst reused in a subsequent runfor recyclability study. The conversion of reactant was determined by Gaschromatography (GC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium azide; copper diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 95℃; for 5h; | 1.0 mmol o-methyl iodobenzene,1.2 mmol sodium azide,0.15 mmol DBUAnd 0.1mmol of copper acetate were sequentially added to a reaction flask equipped with 3mL of dimethyl sulfoxide,The reaction mixture was stirred at 95 C for 5.0 h,TLC was followed until the reaction was complete,A few drops of aqueous ammonia were added to the reaction mixture,Then extracted with ethyl acetate (10 mL × 3),Then washed once with saturated saline,dry,Suction filtration,Remove the solvent,Purification by column chromatography gave the desired product,Yield 75%. |
75% | With sodium azide; copper(II) acetate monohydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 95℃; for 5h; | General procedure: CAUTION: Azides are potentially explosive and so appropriateprecautions against blast must be taken when preparing, handlingand heating them. Reactions must be carried out on a small scale. A mixture of the aryl iodide (1.0 mmol), sodium azide (1.2 mmol),DBU (0.15 mmol) and Cu(OAc)2·H2O (0.1 mmol) in DMSO (3.0 mL)in a 10 mL flask was heated to 95 C (the temperature in the reaction flask was monitored) for 1.5-5.0 h. After the reaction was completed asjudged by TLC, the cooled mixture was poured into water (30 mL)containing several drops of ammonia. The resulting aqueous phase was extracted with ethyl acetate (3 × 30 mL). The combined organic phases were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was loaded on asilica gel column and eluted with petroleum ether (boiling range 60-90 C)/ethyl acetate to afford the product. |
82%Chromat. | With sodium azide; bis(2,2,6,6-tetramethyl-3,5-heptanedionato)copper(II); In N,N-dimethyl-formamide; at 100℃; for 12h;Sealed tube; | General procedure: In a 10-mL sealed tube with a spin bar, halobenzene (1 mmol) was used, or in 25-ml round-bottom flask with a spin bar equipped with condenser, boronic acid (1 mmol), was used and DMF (4 ml), sodium azide (1.2 mmol), and Cu(TMHD)2 (0.20 mmol) were added and containers were sealed properly. The reaction mixturewas heated at the 100 C with stirring for desired time and cooled to room temperatureon completion of the reaction. Then the mixture poured into 15 ml of ice-coldwater and extracted with diethyl ether (310 ml). The residue obtained was purifiedby column chromatography (silica gel, 60:20 mesh; petroleum ether = ethyl acetate98:2%) to afford the desired azide products. The organic solution was analyzed by GC and confirmed by GCMS and NMR. The purity of compounds was determinedby GC-MS analysis. All products are known in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With copper(l) iodide; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; at 140℃; for 3h; | A flask was charged with 2-iodotoluene (0.964mL, 7.57 mmol), <strong>[5932-27-4]ethyl-1H-pyrazole-3-carboxylate</strong> (1.00 g,7.14 mmol), Cul (272 mg, 1.43 mmol), trans-N,N'-dimethylcyclohexane-1,2-diamine (0.451 mL, 2.86 mmol), and K2CO3 (3.15 g, 22.8 mmol). The reaction mixture was then heated to 140° C. for 3 h. The reaction was then partitioned between CH2C12 and saturated aqueous NH4C1 and separated.The organic layer was washed with water, dried over Na2SO4, filtered and concentrated. The crude was purified via flash chromatography on silica gel (90:10-70:30 hexanes:methyl tert-butyl ether) to give the product (238 mg, 1.03mmol, 14percent) as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; potassium carbonate; triphenylphosphine; In benzene; at 150℃; for 24h;Sealed tube; | General procedure: In a 30-mL sealed tube, <strong>[2622-63-1]1-methyl-2-phenylbenzimidazole</strong> (1, 0.25mmol), [RuCl2(p-cymene)]2 (0.0125 mmol), Ph3P (0.075 mmol),K2CO3 (0.50 mmol), and iodoarene (0.25 mmol) were combined inanhydrous benzene (2 mL) under air. The mixture was then stirredat 150 °C for 24 h. The mixture was cooled to r.t., diluted with EtOAc, and filtered through a small pad of Celite. The filtrate was concentrated in vacuo and purified by flash chromatography (silicagel, EtOAc?hexane) to give the analytically pure 2-(biphenyl-2-yl)benzimidazoles. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In toluene; at 130℃; for 18h;Inert atmosphere; | In a 300 mL three-necked flask vacuum dried and purged with nitrogen, 14 g (73 mmol) of <strong>[53848-17-2]2-bromo-6-methylaniline</strong>,17 g (80 mmol) of 2-iodotoluene,12 g (1.2 × 102 mmol) of sodium tert-butoxide,0.67 g (0.73 mmol) of tris (dibenzylideneacetone) dipalladium (0) and 0.81 g (1.5 mmol) of 1,1'-bis (diphenylphosphino) ferrocene were added. To the mixture was added 160 mL of dehydrated toluene, and the mixture was refluxed at 130 C. for 18 hours under a nitrogen atmosphere.After stirring, the temperature was returned to room temperature, ethyl acetate and water were added to the mixture, and the mixture was subjected to liquid separation operation, and the organic layer was washed with saturated brine. After washing, anhydrous magnesium sulfate was added to the mixture, dried and suction filtered to obtain a filtrate. The resulting filtrate was concentrated. The concentrated mixture was purified by silica gel column chromatography with 100% hexane. The obtained fraction was concentrated to obtain a yellow liquid (intermediate D-1; 2-bromo-6-methyl-N- (ortho-tolyl) aniline) in a yield of 15 g in a yield of 77%. |
Tags: 615-37-2 synthesis path| 615-37-2 SDS| 615-37-2 COA| 615-37-2 purity| 615-37-2 application| 615-37-2 NMR| 615-37-2 COA| 615-37-2 structure
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Code | Phrase |
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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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