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CAS No. : | 2351-36-2 | MDL No. : | MFCD00228481 |
Formula : | C12H6Cl2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NZZGQZMNFCTNAM-UHFFFAOYSA-N |
M.W : | 253.08 | Pubchem ID : | 3485596 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405 | UN#: | 3261 |
Hazard Statements: | H314-H290 | Packing Group: | Ⅲ |
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 |
---|---|---|
89% | With N,N-dimethyl acetamide; Phthaloyl dichloride; In 1,4-dioxane; at 70℃; for 3h; | N, followed by stirring N- dimethylacetamide 4.3 g (49 mmol) and phthalic acid chloride 10.4 (51.5 mmol) at 30 C.. Reaction solution became impossible stirring immediately change to brown solidified. Overall the addition of 1,4-dioxane 50mL became homogeneous. It became a homogeneous solution and stirred 70 C.. 3 hours in suspension in addition 2,6-naphthalene dicarboxylic acid 4.3g (20 mmol). The solid was collected by filtration precipitated by cooling to room temperature, and dried after washing with 1,4-dioxane and hexane 2,6-naphthalene dicarboxylic acid chloride 4.5g was obtained. The yield was 89%. |
85% | With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; water; at 75℃; for 12h;Cooling with ice; Inert atmosphere; | A solution of 10.810 g (0.050 mmol) of 2,6-naphthalene dicarboxylic acid was added to a 250 ml three-necked flask, was added 100ml of water in addition to dichloromethane and 17.846 g (0.150 mol) of thionyl chloride was slowly added dropwise under ice-cooling, 3 to 4 drops of N, N-dimethylformamide was added dropwise as a catalyst, magnetically stirring with argon gas heated to 75 C the reaction was refluxed for 12h. The solvent was evaporated under reduced pressure and excess sodium dichlorosulfoxide to give a pale yellow solid in 85% yield. The intermediate structure is as follows: |
84% | With Vilsmeier reagent; In 1,4-dioxane; at 60℃; for 1h; | A mixture of naphthalene-2,6-dicarboxylic acid 0.93 g (4.3 mmol) and VR7 1.11 g (8.7 mmol) in 1,4-dioxane (5 mL) was stirred at 60 C for 1 h. The appearance in the flask changed from slurry to clear solution, and it was cooled to room temperature and filtered to give napthalene-2,6-dicarbonyl dichloride 0.91 g (84% yield) having mp 188-190 C (lit. 17 mp 189-190 C). GC-MS: m/z = 253(M+). IR (KBr): 1751 cm-1. |
With thionyl chloride; | 2) Synthesis of <strong>[1141-38-4]2,6-Naphthalenedicarboxylic acid</strong> dichloride STR39 <strong>[1141-38-4]2,6-Naphthalenedicarboxylic acid</strong> (0.5 g) was added to 10 ml of thionyl chloride, and N,N-dimethylformamide in a very small amount was added to the mixture. The resulting mixture was refluxed for 4 hours. The unaltered thionyl chloride was removed by evaporation to give the desired compound (0.48 g). | |
With thionyl chloride; In toluene; | The naphthalene-2,6-dicarboxylic acid chloride used as the starting material was prepared as follows: A mixture of 1 g of naphthalene-2,6-dicarboxylic acid and 100 ml of toluene was treated with 2 ml of thionyl chloride under a nitrogen atmosphere and subsequently heated under slight reflux overnight. The reaction mixture was concentrated, then treated with 50 ml of absolute toluene and again concentrated. This procedure was repeated twice. Subsequently, the solid residue was sublimed in a bulb tube. This gave 0.8 g of naphthalene-2,6-dicarboxylic acid chloride. | |
With thionyl chloride; | 1) 2,6-naphthalene dicarboxylic acid chloride STR29 2,6-naphthalene dicarboxylic acid (0.5 g) was added to 15 ml of thionyl chloride, and N,N-dimethylformamide in a very small amount was added to the mixture. The resulting mixture was refluxed for 4 hours. Unaltered thionyl chloride was removed by evaporation to give 0.45 g of the desired compound. | |
With thionyl chloride; for 4h;Reflux; | Example VII-IIIPreparation of Compound 204General Procedure VII-KNaphthalene-2,6-dicarboxylic acid (VII-IIIA) (2.2 g, 10.2 mmol) was dissolved in 20 mL of SOCl2 and the mixture was refluxed for 4 hrs. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was dissolved in 400 mL of acetone and was added into the solution of NaN3 (2.585 g, 39.73 mmol) in 50 mL of water at 0 C. The reaction was stirred at r.t. overnight. The precipitate formed was filtered, washed with water and dried to give compound VII-IIIB (2.48 g, yield 94%). 1H NMR (DMSO-d6, 400 MHz) delta 8.76 (s, 2H), 8.35 (d, J=8.8 Hz, 2H), 8.07 (d, J=8.4 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With triethylamine; lithium chloride; In DMF (N,N-dimethyl-formamide); at 0 - 65℃; for 5h; | 83.75 g (0.26 mole) of 4-amino-2,2,6,6-tetramethylpiperidine are dissolved in 350 ml of N,N-dimethyl formamide, in a 750 ml round bottomed 3 necked reaction flask with stirrer, thermometer, funnel and reflux-condenser. 30.71 g (0.304 mole) and 8.5 g (0.2 mole) of lithium chloride are added under constant stirring at room temperature. The solution is cooled to 0 C. and during 1 hour 65.8 g (0.26 mole) of naphthalene-2,6-dicarbonyl-dichloride are added in small portions under vigourous stirring. A faintly yellow suspension results. The reaction mass is kept at 0-5 C. for 1 hour. Within a further hour, the temperature is raised to room temperature and then the whole is kept at 65 C for further 2 hours. The reaction product is then diluted with 200 ml of isopropanol/water (1/4). The reaction mixture is then poured on 600 ml of water, under stirring. Then, the solid residue is filtered off and subsequently washed with several portions of isopropanol/water (1/1). Afterwards, the solid is dried in a vacuum drier at 80 C. for 15 hours. The desired product is obtained as a colourless powder. Yield: 76, 1 g (=76% of theory). Melting-point: higher than 300 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-(Dimethylamino)pyridine; triethylamine; In dichloromethane; | (1) Synthesis of 6-(1,1,1-trifluoro-2-octyl oxycarbonyl)naphthalene-2-carboxylic acid chloride STR20 To a solution of optically active 1,1,1-trifluoro-2-octyl alcohol (1.8 g) and triethylamine (1.0 g) in methylene chloride was gradually added <strong>[2351-36-2]2,6-naphthalenedicarbonyl dichloride</strong> (2.5 g). Furthermore, dimethylaminopyridine (0.3 g) was added and the mixture was stirred at room temperature for 24 hours. The solvent was distilled off to obtain a mixed chloride (about 2.0 g) containing the titled compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-(Dimethylamino)pyridine; triethylamine; In dichloromethane; | (1) Synthesis of 2-n-decyloxycarbonylnaphthalene-6-carboxylic acid chloride STR89 After a solution of n-decyl alcohol (0.5 g), naphthalene-2,6-dicarboxylic acid dichloride (0.6 g), and triethylamine (0.27 g) and a very small amount of dimethylaminopyridine in methylene chloride (50 ml) was stirred at room temperature overnight, the solution was distilled to remove the solvent, until the titled compound (about 0.5 g) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-(Dimethylamino)pyridine; triethylamine; In dichloromethane; | (1) Synthesis of 6-(1,1,1-trifluoro-2-octyloxycarbonyl)naphthalene-2-carboxychloride STR92 A solution of naphthalene 2,6-dicarboxylic acid dichloride (0.6 g), optically active 1,1,1-trifluoro-2-octyl alcohol (0.44 g), triethylamine (0.27 g) and a very small amount of dimethylaminopyridine in methylene chloride (50 ml) was stirred at room temperature overnight. After the solution was distilled to remove the solvent, the titled compound (about 0.8 g) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In 1,1-dichloroethane; | (1) 6-(1-Trifluoromethylheptyloxycarbonyl)-naphathalene-2-carboxylic acid chloride STR10 2,6-Naphthalene-dicarboxylic acid dichloride 0.84 g, optically active 1-trifluoro-2-octanol 0.55 g, triethyl amine 0.33 g and <strong>[823-39-2]dimethyl aminopyridine</strong> 0.02 g are dissolved in 50 ml dichloroethane to be stirred at the room temperature for a whole day. The reaction mixture liquid is filtered. The filtrate is used for the following reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-(Dimethylamino)pyridine; triethylamine; In 1,1-dichloroethane; | (1) 6-(1-Trifluoromethylheptyloxy-carbonyl)-naphthalene-2-carboxylic acid chloride STR22 2,6-Naphthalene-dicarboxylic acid dichloride 1.5 g, optically active 1-trifluoro-2-octanol 1.0 g, triethylamine 0.6 g and dimethylaminopyridine 0.04 g were dissolved in 100 ml dichloroethane to be stirred at the room temperature for a whole day. The reaction solution was filtered so as to use the filtrate in the following reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; | (1) 6-(1-Trifluoromethylheptyloxycarbonyl)-2-carboxynaphthalene STR25 2,6-Naphthalene-dicarboxylic acid chloride 14 g was dissolved in methylene chloride. The solution was gradually added under ice cooling with optically active 1-trifluoro-2-octanol 10 g and pyridine 0.85 g. After further reaction at the room temperature for a whole day, the reaction liquid was taken into water and extracted with methylene chloride. The extract was washed with ammonium chloride, water, 1N aqueous sodium hydrogenecarbonate solution and water in this order, and after neutrallization dried with anhydrous magnesium sulfurate. After distilling off the solvent, the crude product was subjected to silica gel column chromatography to obtain the captioned product in the amount of 2.5 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In trichlorophosphate; | First, 80 g of 2,6-naphthalene dicarboxylic acid is dispersed in 400 g of phosphoryl chloride. The dispersion kept thoroughly stirred and 8 g of dimethyl formamide (DMF) gradually added thereto are refluxed together on a hot water bath for 2.5 hours. After the ensuing reaction has been completed, the reaction mixture is distilled to expel phosphoryl chloride by evaporation. The residue of this distillation is recrystallized from benzene to obtain as needle crystals 61 g (yield: 65%) of 2,6-dichloroformylnaphthalene (melting point: 186 C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | 5.00 g of 6-(2H-tetrazol-5-yl)-2,2'-bipyridine was dissolved in 100 ml of pyridine, and dehydrated by azeotropy. 2.99 g of <strong>[2351-36-2]2,6-naphthalenedicarbonyl dichloride</strong> was added. Temperature was elevated to 110C, and stirring was conducted for 1 hour under reflux. After cooling to room temperature, the reaction solution was poured into water, and a sodium hydroxide aqueous solution was added. A precipitated solid was taken out by suction filtration, and washed with water. The solid was dried at 70C under reduced pressure to obtain 5.41 g (yield 84%) of a pale grayish brown BpyOXD(2, 6NP). The product was identified with NMR analysis. The result of NMR analysis (CDCl3) was as follows. 8.837 ppm (2H), 8.642-8.754 ppm (6H), 8.360-8.452 ppm (4H), 8.205-8.237 ppm (2H), 7.923-8.094 ppm (4H), 7.386-7.430 (2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium azide; In water; acetone; at 0 - 20℃; | Example VII-IIIPreparation of Compound 204General Procedure VII-KNaphthalene-2,6-dicarboxylic acid (VII-IIIA) (2.2 g, 10.2 mmol) was dissolved in 20 mL of SOCl2 and the mixture was refluxed for 4 hrs. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was dissolved in 400 mL of acetone and was added into the solution of NaN3 (2.585 g, 39.73 mmol) in 50 mL of water at 0 C. The reaction was stirred at r.t. overnight. The precipitate formed was filtered, washed with water and dried to give compound VII-IIIB (2.48 g, yield 94%). 1H NMR (DMSO-d6, 400 MHz) δ 8.76 (s, 2H), 8.35 (d, J=8.8 Hz, 2H), 8.07 (d, J=8.4 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25.6% | First Step A mixture of 2,2,6,6-tetramethyl-4-piperidinol (13.70 g, 87.12 mmol) and NaH (60%, 2.09 g, 87.09 mmol) was heated under reflux in THF for 2 hours. The resulting reaction mixture was cooled to -10 C. or lower, and then a THF solution of naphthalene-2,6-dichloride dicarboxylic acid (10 g, 39.51 mmol) was slowly added dropwise thereto while the mixture was maintained at the temperature. The resulting reaction mixture was stirred at room temperature for 1 hour, and then quenched with water. The resulting mixture was subjected to extraction with MTBE. Silica gel was added to organic layers combined, and then filtered off. A solvent was distilled off from the resulting solution to give bis(2,2,6,6-tetramethylpiperidine-4-yl)naphthalene-2,6-dicarboxylate (No. 8) (5 g, yield: 25.6%). 1H-NMR (delta ppm; CDCl3): 8.60 (s, 2H), 8.11 (dd, 2H), 8.00 (d, 2H), 5.52 (tt, 2H), 2.12 (dd, 4H), 1.55 (br, 2H), 1.37 (t, 4H), 1.32 (s, 12H), 1.22 (s, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With triethylamine; In toluene; at 80℃; for 40h; | EXAMPLE 10 Naphthalene dicarboxylic acid-(2,6)-di-((1R,2R)-2-(N-(4-trans-n-pentyl-cyclohexyl-carbonyl)-methylamino)--phenyl-1-propyl ester) compound X) The monoacylated amino alcohol produced according to Example 7A is dissolved in toluene and reacted in the presence of triethylamine with naphthalene-2-6-dicarboxylic acid chloride for 40 hours under agitation at 80 C. The column chromatographic purification of the crude product produced after the usual workup (silica gel, elution with toluene/ethyl acetate 3:1) gives the vitreously solidified end product with a yield of 30%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In dichloromethane; N,N-dimethyl-formamide; at 50℃; for 1h; | 2.53 g (10 mmol) of <strong>[2351-36-2]naphthalene-2,6-dicarbonyl dichloride</strong> was heated to dissolve in 30 mL of dichloromethane and 2 mL of DMF. Therein, a solution of 2.80 g (40 mmol) of 1,2,4-triazole in 8 mL of DMF was added dropwise. After stirring for 1 hour at 50 C., 100 mL of water was added and the crystals were collected by filtration, washed with 100 mL of water + 10 mL of acetone anymore It was washed once with 100 mL of water. After vacuum drying at 105 C. for 2 hours, 2.7 g (yield 85%) of crude naphthalene-2,6-dicarbonyl ditriazole was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In toluene; at 30℃; for 0.583333h;Sonication; | A solution of 1.12 g of p-fluoroaniline in a 100 mL round bottom flask was charged with 50 mL of toluene. The round bottom flask was placed in an ultrasonic reactor. The radiation power was set at 150 W and the reaction temperature was 30 C. The reactor was opened and the reaction mixture was added dropwise 10 mL of a toluene solution containing 1.26 g of 2,6-naphthalene dicarboxylic acid chloride. After 35 min reaction, the mixture was filtered and washed with 5 mL of 10 wt% sodium hydroxide solution to give 3 times a white solid. The yield was 76%, mp: 187.15-188.3 C.IRv: 3102 (Ν-Η) (Aromatic ring CH) η NMR (DMSO,400MHz): 10.22 (s, 2H, NH (1H) ), 8.29 (s, lH, Ar-H), 8.11 (d, 4H, Ar-H), 7.79 (d, 2 Hz, Αγ-Η), 7.29 (s, 1 Η, Αγ-Η) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.6% | With triethylamine; In N,N-dimethyl acetamide; at 100℃; for 24h;Cooling with ice; Inert atmosphere; | 18.376 g (0.12 mol) of 4-nitrobenzyl alcohol was added to a 500 ml three-necked flask, 200 ml of N, N-dimethylacetamide and 40 ml of triethylamine and and Reaction (1) <strong>[2351-36-2]naphthalene-2,6-dicarbonyl dichloride</strong> was added slowly under ice bath, magnetic stirring and argon gas, heated to 100C reaction 24h. The reaction solution was poured into a solution of 1000 ml of methanol and water of 1: 1, and a large amount of precipitate was precipitated.The resulting solid was recrystallized from N, N-dimethylformamideand the white solid was collected and dried in a vacuum oven at 50 C for 10 h to give 19.851 g of a white solid in81.6%yield,The intermediate structure is as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With pyridine; triphenyl phosphite; In 1-methyl-pyrrolidin-2-one; at 20 - 100℃; for 14h;Inert atmosphere; | A solution of 10.814 g (0.1 mol) of p-phenylenediamine in 150 ml of N-methylpyrrolidone and pyridine in a 4: 1 solution was slowly added to 5.061 g (0.02 mol) of <strong>[2351-36-2]naphthalene-2,6-dicarbonyl dichloride</strong>, Under an argon atmosphere, 12.420 g (0.04 mol) of triphenyl phosphite was added, and stirred at room temperature for 2 h, and then heated to 100 C for 12 h, After cooling, the reaction solution was poured into methanol, the precipitate was filtered off, washed thoroughly with methanol, recrystallized from N, N-dimethylformamide and water, and dried in a vacuum oven at 50 C for 10 h to obtain an off-white product N2,N6 -bi s (4-aminophenyl) naphthalene-2,6-dicarboxamide 6.739 g in a yield of 85%. The intermediate structure is as follows: |
Tags: 2351-36-2 synthesis path| 2351-36-2 SDS| 2351-36-2 COA| 2351-36-2 purity| 2351-36-2 application| 2351-36-2 NMR| 2351-36-2 COA| 2351-36-2 structure
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Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
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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