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CAS No. : | 4110-35-4 | MDL No. : | MFCD00007228 |
Formula : | C7H3N3O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SSDNULNTQAUNFQ-UHFFFAOYSA-N |
M.W : | 193.12 | Pubchem ID : | 20062 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.8 |
TPSA : | 115.43 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.85 cm/s |
Log Po/w (iLOGP) : | 0.54 |
Log Po/w (XLOGP3) : | 2.29 |
Log Po/w (WLOGP) : | 1.37 |
Log Po/w (MLOGP) : | -0.71 |
Log Po/w (SILICOS-IT) : | -2.44 |
Consensus Log Po/w : | 0.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.67 |
Solubility : | 0.417 mg/ml ; 0.00216 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.35 |
Solubility : | 0.0086 mg/ml ; 0.0000445 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -1.25 |
Solubility : | 10.9 mg/ml ; 0.0564 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.28 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362+P364-P403+P233-P405-P501 | UN#: | 3439 |
Hazard Statements: | H301-H315-H319-H335-H373-H312+H332 | 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 |
---|---|---|
95% | With sodium azide; acetic acid; urea; In water; N,N-dimethyl-formamide; at 60 - 110℃; for 9h; | General procedure: The procedure for the synthesis of the tetrazole 2a is representative. A mixture of sodium azide (0.39 g 0.0060 mol), urea (0.36 g, 0.0060 mol) and water (2.5 mL) was taken in a round-bottom flask and stirred at 60 C for 1 h. Charged benzonitrile 1a (0.5 g 0.0048 mol), acetic acid(0.5 mL) and DMF (2.5mL) at 60 C and heat to 110C stirred for 8 h. After completion of the reaction (as indicated by TLC), the reaction mixture was cooled to room temperature and diluted the reaction mass with water (2.5 mL)and ethyl acetate (5.0 mL) at 25-35 C. Add 5N aqueous hydrochloric acid (2.5 mL) at 25-35 C. Stirred for 20- 30 min, the resultant organic layer was separated and the aqueous layer was extracted with ethyl acetate (2.5 mL). The combined organic layer was washed with 40 % aq.NaCl solution (2.5 mL) and dried over anhydrous Na2SO4 and concentrated to give a crude product, which was isolated using chilled water after 3-4 h maintenance, and eventually filtered off to give 0.67 g (95%) of an off-white solid. |
93% | With sodium azide; In N,N-dimethyl-formamide; at 110℃; for 5h; | General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol), Cu complex catalyst (0.4 mol%) and DMF (3 mL) was taken in a round-bottomed flask and stirred at 110 C temperature. After completion of the reaction the catalyst was separated from the reaction mixture with an external magnet and reaction mixture was treated with ethyl acetate (2 × 20 mL) and 1 N HCl (20 mL). The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (2 × 15 mL). The combined organic layers were washed with water, concentrated, and the crude material was chromatographed on silica gel (Hexane-EtoAc, 1:1) to afford the pure product. |
87% | With sodium azide; triethylamine hydrochloride; In N,N-dimethyl-formamide; for 6h;Heating; | The <strong>[4110-35-4]3,5-dinitrobenzonitrile</strong> (10 g, 0.052 mol), sodium azide(3.97 g, 0.061 mol) and triethylammonium chloride (8.4 g,0.061 mol) were mixed with DMF (50 mL). The reaction mixturewas heated at 100 C for 6 h. Upon completion, the reaction mixturewas filtered, DMF was evaporated, and the residue was dissolved inwater (100 mL). The solutionwas acidified with HCl to pH 1, and theprecipitated product was filtered, washed with water and dried.Yield: 87% as a yellowish solid, mp: 176-177 C (lit. [27]. 178-179 C). 1H NMR (300 MHz, DMSO-d6) delta 9.13 (dd, J =2.1, 0.5 Hz, 2H),8.96 (td, J = 2.1, 0.5 Hz, 1H). 13C NMR (75 MHz, DMSO) delta 154.92,148.92, 128.05, 126.97, 120.40. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Example 19 - Preparation of 3-Amino-5-[(7-chloroquinolin-4-yl)amino] benzonitrile hydrochloride (compound 73); Step A: 3,5-Diaminobenzonitrile; To <strong>[4110-35-4]3,5-dinitrobenzonitrile</strong> (5.0 g, 25.89 mmol) in 20 mL of HCI 1 M, was added SnCI2 (34.4 g, 7 eq). The reaction mixture was stirred at room temperature for 2h and then cooled to O'C. The mixture was made alkaline with a 50% aqueous solution of NaOH and the precipitate was removed by filtration. The filtrate was extracted with ethyl acetate and the combined organic layers were evaporated. The residue and the precipitate were purified by flash chromatography on silica gel (DCM/MeOH//95/5) to yield expected compound as an orange solid (1 .95 g, 57% yield), m/z (ESI) 134.0 [M+H]+. | |
With hydrogen;palladium(II) hydroxide/carbon; In ethanol; | Example 1.1.62: 5-(aminomethyl)-Nl, N l,N3,N3-tetramethylbenzene- 1,3 -diamine; 20% Pd(OH)2 (0.13 g) was added to a stirred suspension of <strong>[4110-35-4]3,5-dinitrobenzonitrile</strong> (0.50 g, 2.59 mmol, 1 eq, Aldrich) in 10 ml EtOH. A H2 balloon was added. After stirring over the weekend the mixture was filtered through Celite. The filter cake was rinsed with EtOH (x3). The organics were removed in vacuo. The residue was stirred in CHCl3 and the resulting mixture was filtered (x3). The CHCl3 fractions were combined, and the solvent was removed in vacuo to yield crude 3,5-diaminobenzonitrile. | |
With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; for 2h; | A solution of <strong>[4110-35-4]3,5-dinitrobenzonitrile</strong> (194 mg), Pd/C (10% by weight, 40 mg) in EtOAc (8.0 mL) was hydrogenated with a H2 balloon for 2.0 h at rt. After filtration and evaporation of solvent, 28A was obtained as sufficient pure for next step. 1H NMR (400 MHz, CDCl3) delta ppm 6.13 (s, 1 H), 6.32 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; | Example A32 A solution of 3,5-dinitro-benzonitrile (5 g, 25.9 mol), <strong>[74115-12-1]5-chloro-pyridin-3-ol</strong> (3.35 g, 25.9 mol) and K2CO3 (7.2 g, 52 mol) in DMF (150 mL) was heated at 100 C. overnight. The mixture was concentrated in vacuo and the residue was poured into water. The aqueous layer was extracted with ethyl acetate (3*150 mL) and the combined organics were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by silica gel chromatography to afford 3-(5-chloro-pyridin-3-yloxy)-5-nitro-benzonitrile (3.1 g, 44% yield). 1H NMR (400 MHz, DMSO-d6) delta 8.56 (s, 1H), 8.51 (s, 1H), 8.47 (s, 1H), 8.22 (s, 1H), 8.19 (s, 1H), 7.87 (s, 1H). |
44% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; | A solution of 3,5-dinitro-benzonitrile (5 g, 25.9 mol), 5- chloro-pyridin-3-ol (3.35 g, 25.9 mol) and K2C03 (7.2 g, 52 mol) in DMF (150 mL) was heated at 100 C overnight. The mixture was concentrated in vacuo and the residue was poured into water. The aqueous layer was extracted with ethyl acetate (3 x 150 mL) and the combined organics were washed with brine, dried (Na2SC>4), concentrated in vacuo and purified by silica gel chromatography to afford 3-(5-chloro-pyridin-3-yloxy)-5-nitro- benzonitrile (3.1 g, 44 % yield). 1H NMR (400 MHz, DMSO-i/6) delta 8.56 (s, 1 H), 8.51 (s, 1 H), 8.47 (s, 1 H), 8.22 (s, 1 H), 8.19 (s, 1 H), 7.87 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; | Example A33 <strong>[4110-35-4]3,5-dinitro-benzonitrile</strong> (3 g, 16 mmol), 6-methylpyridin-3-ol (1.7 g, 16 mmol), and K2CO3 (4.3 g, 31 mmol) were dissolved in DMF and heated to 110 C. overnight. The reaction mixture was poured into water and the mixture was extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by silica gel chromatography to provide 3-(6-methylpyridin-3-yloxy)-5-nitrobenzonitrile (3 g, 76% yield). 1H NMR (400 MHz, DMSO) delta 8.50 (s, 1H), 8.38 (s, 1H), 8.08 (s, 1H), 8.01 (s, 1H), 7.59-7.56 (d, J=10 Hz, 1H), 7.38-7.36 (d, J=8.4 Hz, 1H), 1.98 (s, 3H); MS (ESI) m/z; 256.3 [M+H]+. |
76% | With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; | <strong>[4110-35-4]3,5-dinitro-benzonitrile</strong> (3 g, 16 mmol), 6-methylpyridin-3-ol (1.7 g, 16 mmol), and K2CO3 (4.3 g, 31 mmol) were dissolved in DMF and heated to 1 10 C overnight. The reaction mixture was poured into water and the mixture was extracted with EtOAc. The combined organics were washed with brine, dried (Na2S04), concentrated in vacuo and purified by silica gel chromatography to provide 3-(6- methylpyridin-3-yloxy)-5-nitrobenzonitrile (3 g, 76% yield ). FontWeight="Bold" FontSize="10" H NMR (400 MHz, DMSO) delta 8.50 (s, 1 H), 8.38 (s, 1 H), 8.08 (s, 1 H), 8.01 (s, 1 H), 7.59-7.56 (d, J = 10 Hz, 1 H), 7.38-7.36 (d, J = 8.4 Hz, 1 H), 1.98 (s, 3 H); MS (ESI) m/z: 256.3 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 95℃; for 12h; | Intermediate 55 2- [4- (3-cyano-5-methylphenoxy)-2-methylphenoxy]-2-methylpropionic acid ethyl ester; Step A 2- [4- (3-cyano-5-nitrophenoxy)-2-methylphenoxy]-2-methylpropionic acid ethyl ester A mixture of <strong>[4110-35-4]3,5-dinitrobenzonitrile</strong> (3.65 g, 18. 90 mmol), compound (a) (WO 2003072102) (3 g, 12.60 mmol) and K2CO3 (2.1 g, 15.194 mmol) in DMF (40 mL, HPLC grade) is stirred at 95 C. After 12 h, the mixture is poured into brine, and extracted with EtOAc. The organic layer is dried, filtered and concentrated, and the crude obtained is flash chromatographed on Si02 (10 % EtOAc/hexanes) affording 5.54 g of the arylether (94%, white solid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34.5 g (96%) | With hydrogenchloride; In ethanol; | (1) Ethyl 3,5-dinitrobenzimidate hydrochloride was synthesised in the same manner as in Reference Example 2. That is, <strong>[4110-35-4]3,5-dinitrobenzonitrile</strong> (25.2 g, 0.130 mol) was treated with hydrogen chloride in ethanol (250 mL) to give 34.5 g (96%) of the target compound as pale-brown crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hydrogenchloride; sodium hydroxide; | a. 3,5-Diaminobenzonitrile To a solution of 210 grams of stannous chloride dihydrate in 590 ml. of concentrated hydrochloric acid is added portionwise 25 grams of <strong>[4110-35-4]3,5-dinitrobenzonitrile</strong>. The mixture is stirred for 3 hours at room temperature, then cooled to 0 in an ice-salt bath and a cold 50% sodium hydroxide solution added to the mixture until the mixture is strongly basic. During the addition the temperature is kept below 5. The mixture is extracted with methylene chloride and the solvent removed. There is obtained 2.25 grams of material melting at 185-8. Recrystallization from ethanol raises the melting point to 188-9. Analysis Calcd. for: C7 H7 N3 C, 63.14; H, 5.30; N, 31.56. Found: C, 62.87; H, 5.19; N, 31.72. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; | <strong>[4110-35-4]3,5-Dinitrobenzonitrile</strong> (1.50 g, 7.77 mmol) was added to a slurry of pyridin-3-ol (739 mg, 7.77 mmol) and potassium carbonate (10.7 g, 77.7 mmol) in DMF (15 mL), the mixture was warmed to 60 C. and stirred overnight. After cooling to RT the reaction was diluted with ethyl acetate (50 mL) and water (100 mL). The organic phase was separated, washed with saturated sodium bicarbonate (50 mL) and brine (50 mL), dried (Na2SO4), concentrated in vacuo and purified by chromatography (Si-40 column, ethyl acetate/hexanes) to give a light yellow solid identified as 3-nitro-5-(pyridin-3-yloxy)benzonitrile (1.31 g, 69% yield). MS (ESI) m/z: 242.0 (M+H+). |
69% | With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; | <strong>[4110-35-4]3,5-Dinitrobenzonitrile</strong>(1.50 g, 7.77 mmol) was added to a slurry of pyridin-3-ol (739 mg, 7.77 mmol) and potassium carbonate (10.7 g, 77.7 mmol) in DMF (15 mL), the mixture was warmed to 60 C and stirred overnight. After cooling to RT the reaction was diluted with ethyl acetate (50 mL) and water (100 mL). The organic phase was separated, washed with saturated sodium bicarbonate (50 mL) and brine (50 mL), dried ( a2S04), concentrated in vacuo and purified by chromatography (Si-40 column, ethyl acetate/hexanes) to give a light yellow solid identified as 3-nitro-5- (pyridin-3-yloxy)benzonitrile (1.31 g , 69% yield). MS (ESI) m/z: 242.0 (M+H+). |
32% | With potassium carbonate; In N,N-dimethyl-formamide; at 60 - 95℃; | 1A. Formula 103 where R1 is Pyridin-3-yl and Y is CN [0094] A solution of 1 equivalent (eq., 25.42 g, 131.6 mmol)) of 1,3 dinitro-5-cyanobenzene in 1.75 M DMF (75 mL),1 eq. 3-hydroxypyridine (12.52g, 131.6 mmol) and 2 eq. potassium carbonate (36.38 g, 263 mmol) was heated to 60Covernight. The reaction mixture was warmed to 95C for an additional 48 hours. The reaction mixture was diluted withEtOAc, washed with H2O, sat. NaHCO3, and brine, dried over Na2SO4 and concentrated in vacuo. Purification bychromatography over silica with 25% EtOAC/Hexane as the eluant afforded 10.04g of the desired compound of Formula103, 3-(pyridin-3-yloxy)-5-cyano-1-nitrobenzene, as a solid (32% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 110℃; | Example 137Alternative Preparation of 3-(4,5-dihydro-4-methyl-5-oxotetrazol-1-yl)-5-nitrobenzonitrileA mixture of <strong>[4110-35-4]3,5-dinitrobenzonitrile</strong> (386 mg, 2.0 mmol), 1-methyl-1H-tetrazol-5(4H)-one (400 mg, 4.0 mmol) and K2CO3 (552 mg, 4.0 mmol) in NMP (6 mL) was heated to 110 C. and stirred overnight. After allowing to cool, the mixture was poured in to H2O (75 mL) and EtOAc (40 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine (1×20 mL), dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using EtOAc/hexane (3:7 to 4:6) as eluent to give the product (182 mg, 37%) as a solid.Data identical to previously synthesized material. (Example 136)Note: 1-methyl-1H-tetrazol-5(4H)-one was prepared according to procedure detailed in EP643049 (1995); Preparation of 1-substituted-5(4H)-tetrazolinones by desulfurization of tetrazolinethiones, which is hereby incorporated by reference. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | at 155 - 160℃; for 10h; | General procedure: (Caution HMPA is not a friendly solvent). A solution of 0.5 g of a starting substrate in 15 ml of HMPA was kept at 155-160 C until the reactant was consumed (TLC; eluent, CHCl3). The reaction mass was cooled and poured into 150 ml of ice water. The precipitate was filtered off, washed with water and dried. The crude product was dissolved in chloroform, and the solution was filtered through a silica gel bed. The filtrate was evaporated, and the residue was crystallized from methanol. |
Tags: 4110-35-4 synthesis path| 4110-35-4 SDS| 4110-35-4 COA| 4110-35-4 purity| 4110-35-4 application| 4110-35-4 NMR| 4110-35-4 COA| 4110-35-4 structure
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P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
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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