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CAS No. : | 637-31-0 | MDL No. : | MFCD00059291 |
Formula : | C16H21N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZPGZNKGKCSYBGK-UHFFFAOYSA-N |
M.W : | 255.36 | Pubchem ID : | 69473 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 84.4 |
TPSA : | 18.51 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.22 cm/s |
Log Po/w (iLOGP) : | 2.79 |
Log Po/w (XLOGP3) : | 3.71 |
Log Po/w (WLOGP) : | 3.56 |
Log Po/w (MLOGP) : | 3.11 |
Log Po/w (SILICOS-IT) : | 1.96 |
Consensus Log Po/w : | 3.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.96 |
Solubility : | 0.0277 mg/ml ; 0.000109 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.79 |
Solubility : | 0.0414 mg/ml ; 0.000162 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.19 |
Solubility : | 0.00164 mg/ml ; 0.00000643 mol/l |
Class : | Moderately soluble |
PAINS : | 1.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.1 |
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: |
* 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 |
---|---|---|
The following compounds are exemplary of N-(R, R-phenyl)-N-(R1, R2 -phenyl)amines useful in the practice of this invention. Diphenylamine, ... 3,3'-Diethyl-5,5'-dinonyldiphenylamine, 3-Chloro-N-phenylaniline, 4-Dimethylamino-N-phenylaniline, Methyl-2-anilinobenzoate, 4,4'-Bis(dimethylamino)diphenylamine, 4-Acetamido-N-phenylaniline, 4,4'-Diacetamidodiphenylamine, 4,4'-Bis(diethylamino)diphenylamine, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 56 Following a procedure similar to that described in Example 1A but employing 3.1 g of 2-(1-ethyl-2-methyl-3-indolylcarbonyl)benzoic acid and 3.0 g of <strong>[637-31-0]4,4'-bis(dimethylamino)diphenylamine</strong> there was obtained 1.8 g of 3-(1-ethyl-2-methyl-3-indolyl)-3-[N-(4-dimethylaminophenyl)-N-(4-dimethylamino)phenylamino]phthalide, m.p. 76-85 C. A toluene solution of the product contacted with acidic clay or phenolic resin developed a grape-colored image. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 26 Following a procedure similar to that described in Example 4 but employing 5.2 g. of 2-[4-(dimethylamino)benzoyl]benzoic acid and 7.0 g. of 4,4'-bis-(dimethylamino)diphenylamine there was obtained 10.7 g. of 3-[4-(dimethylamino)phenyl]-3-[N-(4-dimethylaminophenyl)-N-(4-dimethylamino)phenylamino]phthalide, m.p. 67-143 C. A toluene solution of the product contacted with acidic clay or phenolic resin developed a brown-colored image. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A. Following a procedure similar to that described in Example 4 but employing 3.1 g. of 2-[4-(diethylamino)-2-methylbenzoyl]benzoic acid and 3.0 g. of <strong>[637-31-0]4,4'-bis(dimethylamino)diphenylamine</strong> there was obtained 2.95 g. of 3-[4-(diethylamino)-2-methylphenyl]-3-[N-(4-dimethylaminophenyl)-N-(4-dimethylaminophenyl)amino]phthalide, m.p. 67-83.5 C. A toluene solution of the product contacted with acidic clay or phenolic resin developed a black-colored image. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 44 Following a procedure similar to that described in Example 4 but employing 6.2 g. of 5-dimethylamino-2-[4-(dimethylamino)benzoyl]benzoic acid and 5.0 g. of 4,4'-bis-(dimethylamino)diphenylamine there was obtained 6.6 g. of 6-dimethylamino-3-[4-(dimethylamino)phenyl]-3-[N-(4-dimethylaminophenyl)-N-(4-dimethylamino)phenylamino]phthalide, m.p. 86-92 C. A toluene solution of the product contacted with acidic clay or phenolic resin developed a brown-colored image which changed to green on clay after fluorescent light exposure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; acetic anhydride; In acetone; toluene; | EXAMPLE 3 A mixture containing 2.0 g. of an isomer mixture comprising 3-[4-(diethylamino)-2-methylbenzoyl]-2-pyridinecarboxylic acid and 2-[4-(diethylamino)-2-methylbenzoyl]-3-pyridinecarboxylic acid, 0.81 g. of <strong>[637-31-0]4,4'-bis(dimethylamino)diphenylamine</strong>, 6 ml. of acetic anhydride and 0.5 ml. of pyridine was stirred 1 hour at room temperature and then poured into 200 ml. of 5% aqueous ammonium hydroxide and 100 ml. of toluene. The toluene layer was separated, washed with water and saturated aqueous sodium chloride and evaporated to dryness under vacuum. The residue was slurried in a minimum amount of acetone to give 0.5 g. of an isomer mixture comprising 7-[4-(diethylamino)-2-methylphenyl]-7-{bis[4-(dimethylamino)phenyl]amino}furo[3,4-b]pyridine-5(7H)-one and 5-[4-(diethylamino)-2-methylphenyl]5-{bis[4-(dimethylamino)phenyl]amino}furo[3,4-b]pyridine-7(5H)-one, as a light green solid, m.p. 184-186 C. A chloroform solution of the product contacted with acidic clay or phenolic resin developed a black image. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; acetic anhydride; | EXAMPLE 18 Following a procedure similar to that described in Example 3 but employing 1.63 g. of 3-[4-(diethylamino)-2-methylbenzoyl]-2-pyrazinecarboxylic acid, 1.3 g. of 4,4'-bis-(dimethylamino)diphenylamine, 0.5 ml. of pyridine and 6 ml. of acetic anhydride there was obtained 0.9 g. of 7-[4-(diethylamino)-2-methylphenyl]-7-{bis[4-(dimethylamino)phenyl]amino}furo[3,4-c]pyrazine-5(7H)-one as a light orange solid, m.p. 193.5-195 C. (dec.) A toluene solution of the product contacted with acidic clay or phenolic resin developed a black image. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; acetic anhydride; | EXAMPLE 20 Following a procedure similar to that described in Example 3 but employing 0.43 g. of 3-[4-(diethylamino)benzoyl]-2-pyrazinecarboxylic acid, 0.34 g. of 4,4'-bis-(dimethylamino)-diphenylamine, 0.5 ml. of pyridine and 6 ml. of acetic anhydride there was obtained 0.59 g. of 7-[4-(diethylamino)phenyl]-7-bis[4-(dimethylamino)phenyl]amino furo[3,4-b]pyrazine-5(7H)-one, m.p. 61-74 C. A toluene solution of the product contacted with acidic clay or phenolic resin developed a red-brown image. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 80℃; for 16.0h; | Step a):A mixture of 0.50 g (0.89 mmol) of N-(2,6-diisopropylphenyl)-9-bromoperylene-3,4-dicarboximide, 0.34 g (1.30 mmol) of Bindschedler's Green, 40 mg (0.045 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.45 ml (0.45 mmol) of tris(tert-butyl)phosphine, 120 mg (1.3 mmol) of sodium tert-butoxide and 30 ml of dry toluene was heated to 80 C. under argon and stirred at this temperature for 16 h.After the solvent had been distilled off, the crude product was subjected to column chromatography on silica gel with a methylene chloride/ethanol mixture (50:1) as the eluent.0.35 g of peryleneamine derivative was obtained in the form of a green solid, which corresponds to a yield of 53%.Analytical Data:UV-Vis (CH2Cl2): lambdamax=667 nm;MS (FD): m/z (rel. int.)=734.2 (100%) [M+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 80℃; for 13.0h; | Step a):A mixture of 0.400 g (0.27 mmol) of N-(2,6-diisopropylphenyl)-1,6,9,14-tetra[(4-tert-octyl)phenoxy]-11-bromoterrylene-3,4-dicarboximide, 0.141 g (0.54 mmol) of 1,4-benzenediamine, N'-(4-(dimethylamino)phenyl)-N,N-dimethyl, 0.013 g (0.014 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.273 g (0.135 mmol) of tris(tert-butyl)phosphine (10% solution/toluene), 0.026 g (0.27 mmol) of sodium tert-butoxide and 20 ml of dry toluene was heated to 80 C. under nitrogen and stirred at this temperature for 13 h.After the solvent had been distilled off, the crude product was subjected to column chromatography on silica gel with dichloromethane as the eluent.0.280 g of a blue-green solid was obtained, which corresponds to a yield of 62%.Analytical Data:MS (FD): m/z (rel. int.)=1675.0 (100%) [M+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 5%-palladium/activated carbon; hydrogen; In N,N-dimethyl acetamide; at 80 - 120℃; under 750.075 - 3000.3 Torr; for 8.0h;Autoclave; | 60.0 g of 4,4'-dinitrodiphenylamine (4),4.0 g of 5% palladium on carbon, 36.5 g of paraformaldehyde and 600 ml of DMACInto the autoclave,Hydrogen pressure after the replacement of hydrogen control 0.1-0.4MPa ; Then slowly raise the temperature to 80-120 C for about 8 hours. After the reaction, the material was cooled to room temperature and filtered to remove the palladium-carbon catalyst. The filtrate was removed under high vacuum at 5-10mmHg and the residue was 4,4'-dimethylaminodiphenylamine (3), which was directly used in the next step . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; sulfur; In 1-methyl-pyrrolidin-2-one; at 180 - 200℃; for 3.0h; | The crude product of 4,4'-dimethylaminodiphenylamine (3) obtained in Step 2,600 ml of N-methylpyrrolidone (NMP),15 g of sulfur and 0.5 g of iodine were charged into a closed kettle and the temperature was raised to 180-200 C for about 3 hours. After the completion of the reaction, the insoluble solid was removed by filtration to room temperature, and the filtrate was directly used for the next step of the oxidation reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.393 g | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene Reflux; | 3 1,3,5-Tris (3,5-dibromophenyl) benzene (0.3 g), bis (4-dimethylaminophenyl) amine (0.884 g), tris (dibenzylideneacetone) dipalladium (0.141 g) , Tri-tert-butylphosphine (0.0622 g) is dissolved in toluene (30 mL). Sodium tert-butoxide (0.665 g) is added to this mixture and the mixture is heated to reflux. After cooling to room temperature, add water and ethyl acetate to separate the liquids. The organic layer was filtered to give 0.393 g of product. When analyzed by 1H-NMR, it was found that this product was represented by the following formula. This product is referred to as "Compound 5". The 1H-NMR of Compound 5 is shown below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34.2% | In dichloromethane at 20℃; for 16h; | 1.S5; 2-6 S51. Take a 1L clean three-necked flask, add 15-20g triphosgene and about 200ml of dichloromethane liquid to it successively, stir until dissolved, cool to -18°C under nitrogen protection, slowly add solution d dropwise, solution d is changed from 15 -35g of glycine ethyl ester hydrochloride VII shown in formula VII, 55-65g of triethylamine and 600ml of dichloromethane are prepared. This dropwise addition process takes about 0.5h. After the dropwise addition, the three-necked flask is placed in a low temperature bath. , control the temperature in the three-necked flask to be 0-5 , keep the reaction for 0.5h, take samples to check whether the reaction of the raw materials is complete, after the reaction is complete, add solution e dropwise. (Dimethylamino)phenyl]amine V and 200ml of dichloromethane liquid. The dropwise addition process takes about 0.25h. At this time, the three-necked flask is taken out from the low temperature bath, slowly raised to room temperature, and the reaction is carried out at room temperature for 16h , Sampling to detect whether the reaction of the raw materials is over;S52. filter the reaction solution obtained in step S51 to obtain corresponding filtrate;S53. The filtrate obtained in step S52 is concentrated under reduced pressure, and then the pH value is adjusted to 1 with 5% dilute hydrochloric acid;S54. Extract the concentrated liquid obtained in step S53 with 20ml of ethyl acetate, this step is repeated three times, the obtained aqueous phase is neutralized with 5% sodium hydroxide solution and the pH value is 6; then use 20ml of dichloromethane to carry out Extraction, this step is repeated three times, the purpose is to purify;S55. the organic phase obtained in the drying step S54;S56. The organic phase in step S55 is concentrated under reduced pressure to obtain the green oily matter shown in 15-20g formula IX |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32.5% | With ammonium hydroxide; sodium dihydrosulfite; sodium hydroxide In lithium hydroxide monohydrate at 50℃; for 4.5h; Inert atmosphere; | 1.S3; 2-6 General procedure: S31. Take a dry 20L four-necked flask, add 840ml of water to the bottle, slowly add 75g of sodium hydroxide, stir evenly until it dissolves, then add 420ml of ammonia water, and under nitrogen protection, the amount of substances added is within 0.75-0.83mol Add sodium dithionite (commonly known as hydrosulfite), stir the solid to dissolve, add solution c dropwise, solution c is an aqueous solution of the intermediate compound shown in formula IV with a substance amount of 0.52mol, and the reaction solution is colorless during the dropping process. The transparent solution turned into a yellow turbid liquid, and the four-necked flask was heated to 50°C for 1 hour, followed by a 3-4h (about 3.5h) insulation reaction, and cooling after the reaction was completed;S32. filter the reaction solution obtained in step S31;S33. drying the resultant in step S32 to obtain a blue-gray solid;S34. the solid obtained in step S33 is recrystallized with 5L petroleum ether, filtered while hot, and the filtrate is spin-dried to obtain the pale yellow solid shown in 30-70g formula V |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24 % | With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 100℃; | Compound 51 (2.3 g, 3.6 mmol, 1.0 eq), Compound 52 (Tokyo Chemical Industry, 4.6 g, 18.1 mmol, 5.0 eq), Palladium(II)acetate (Tokyo Chemical Industry, 0.03 g, 0.1 mmol, 0.04 eq), tri-tert-butylphosphine (Fujifilm Wako Pure Chemical, 0.06 g, 0.3 mmol, 0.08 equivalent),Sodium tert-butoxide (Tokyo Kasei Kogyo, 2.2 g, 22.9 mmol, 6.4 equivalents) and 25 g of toluene were charged and heated to 100°C to carry out the reaction. After completion of the reaction, the mixture was cooled to room temperature, 18 g of water was added, and the aqueous layer was removed after stirring for 1 hour. The organic layer was washed twice with 18 g of water. After the organic layer was concentrated under reduced pressure at 60° C., it was purified by column chromatography to obtain hole-transporting material 2 (1.2 g, yield 24%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30 % | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos In 1,4-dioxane at 100℃; | 1.3; 2.3; 3.3 (3) Synthesis of rhodamine fluorescence quencher Rho-Q3 N,N-bis(4-dimethylaminophenyl)amine (256mg, 1mmol), tris(dibenzylideneacetone)dipalladium (30mg, 0.033mmol), 2-dicyclohexylphosphine-2',4 ',6'-triisopropylbiphenyl (50mg, 0.1mmol), cesium carbonate (300mg, 0.94mmol), fluorescein diflate (200mg, 0.33mmol) were dissolved in dry dioxane ( 10 mL); under the protection of nitrogen, the reaction solution was heated to 100 ° C, stirred for 16 h; the solvent was removed under reduced pressure, and the silica gel column was separated, and the dichloromethane and methanol with a volume ratio of 4:1 were used as eluents, and the solvent was removed to obtain blue Colored solid 80 mg, yield 30%. |
Tags: 637-31-0 synthesis path| 637-31-0 SDS| 637-31-0 COA| 637-31-0 purity| 637-31-0 application| 637-31-0 NMR| 637-31-0 COA| 637-31-0 structure
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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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