No renderable structure data available
C1=CC=C(C(=C1)CC#N)CC#NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | o-Phenylenediacetonitrile |
|---|---|
| IUPAC Name | — |
| CAS Number | 613-73-0 |
| Database ID | 69180 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
o-Phenylenediacetonitrile (CAS 613-73-0) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 69180
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d7afae2754f6415480f376a3913efcedConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,2-Phenylenediacetonitrile (7.5 g, 48 mmol) dissolved in ethanol (150 ml) was added to Raney Ni (2 g) which had been previously washed with ethanol (3×20 ml). The mixture was then hydrogenated at 50° C. at 50 psi pressure with shaking for 24 h. The reaction mixture was then cooled to room temperature and filtered through a pad of kieselguhr and washed through with ethanol (100 ml). The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g), eluting with 2-10% methanol in CH2Cl2 to give the title compound as a brown oil (2.45 g, 35%). had been previously washed with ethanol (3×20 ml) was then hydrogenated at 50° C. at 50 psi pressure filtered through a pad of kieselguhr washed through with ethanol (100 ml) The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g) eluting with 2-10% methanol in CH2Cl2
Source ID: ord-b7d6ac030fc4475b99e314f89e6f35a4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24(t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16(q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H). heated to reflux for 6 hours the result solution was extracted with ethyl acetate (3×50 ml) dried with Na2SO4 Concentration of the ethyl acetate afforded a yellow liquid
Source ID: ord-230d734293e64b519f2325f6ea35b38eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The naphtholactam compounds of the formula (II) used as starting products are obtainable by reacting o-xylylenedicyanide with glyoxal in the presence of a base (NaOH, KOH) and of a solvent at temperatures below 50° C. (e.g. 0° to 40° C.) to give 1,4-dicyanonaphthalene, and subsequently either
Source ID: ord-6009ed9f7ab64d34978729b15188251fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,2-Phenylenediacetonitrile (7.5 g, 48 mmol) dissolved in ethanol (150 ml) was added to Raney Ni (2 g) which had been previously washed with ethanol (3×20 ml). The mixture was then hydrogenated at 50° C. at 50 psi pressure with shaking for 24 h. The reaction mixture was then cooled to room temperature and filtered through a pad of kieselguhr and washed through with ethanol (100 ml). The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g), eluting with 2-10% methanol in CH2Cl2 to give the title compound as a brown oil (2.45 g, 35%). had been previously washed with ethanol (3×20 ml) was then hydrogenated at 50° C. at 50 psi pressure filtered through a pad of kieselguhr washed through with ethanol (100 ml) The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g) eluting with 2-10% methanol in CH2Cl2
Source ID: ord-b7d6ac030fc4475b99e314f89e6f35a4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,2-Phenylenediacetonitrile (7.5 g, 48 mmol) dissolved in ethanol (150 ml) was added to Raney Ni (2 g) which had been previously washed with ethanol (3×20 ml). The mixture was then hydrogenated at 50° C. at 50 psi pressure with shaking for 24 h. The reaction mixture was then cooled to room temperature and filtered through a pad of kieselguhr and washed through with ethanol (100 ml). The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g), eluting with 2-10% methanol in CH2Cl2 to give the title compound as a brown oil (2.45 g, 35%). had been previously washed with ethanol (3×20 ml) was then hydrogenated at 50° C. at 50 psi pressure filtered through a pad of kieselguhr washed through with ethanol (100 ml) The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g) eluting with 2-10% methanol in CH2Cl2
Source ID: ord-b496c791c22a479b833bb2b691e70546Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d7afae2754f6415480f376a3913efcedConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,2-Phenylenediacetonitrile (7.5 g, 48 mmol) dissolved in ethanol (150 ml) was added to Raney Ni (2 g) which had been previously washed with ethanol (3×20 ml). The mixture was then hydrogenated at 50° C. at 50 psi pressure with shaking for 24 h. The reaction mixture was then cooled to room temperature and filtered through a pad of kieselguhr and washed through with ethanol (100 ml). The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g), eluting with 2-10% methanol in CH2Cl2 to give the title compound as a brown oil (2.45 g, 35%). had been previously washed with ethanol (3×20 ml) was then hydrogenated at 50° C. at 50 psi pressure filtered through a pad of kieselguhr washed through with ethanol (100 ml) The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g) eluting with 2-10% methanol in CH2Cl2
Source ID: ord-b496c791c22a479b833bb2b691e70546Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24 (t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16 (q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H). heated to reflux for 6 hours the result solution was extracted with ethyl acetate (3×50 ml) dried with Na2SO4 Concentration of the ethyl acetate afforded a yellow liquid
Source ID: ord-2ad4833eb84d445684fb294b3c8dfffaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24 (t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16 (q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H). heated to reflux for 6 hours the result solution was extracted with ethyl acetate (3×50 ml) dried with Na2SO4 Concentration of the ethyl acetate afforded a yellow liquid
Source ID: ord-2ad4833eb84d445684fb294b3c8dfffaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24 (t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16 (q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H). heated to reflux for 6 hours the result solution was extracted with ethyl acetate (3×50 ml) dried with Na2SO4 Concentration of the ethyl acetate afforded a yellow liquid
Source ID: ord-4854408af0154949b40e32439816a8e7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24(t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16(q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H). heated to reflux for 6 hours the result solution was extracted with ethyl acetate (3×50 ml) dried with Na2SO4 Concentration of the ethyl acetate afforded a yellow liquid
Source ID: ord-230d734293e64b519f2325f6ea35b38ePubChem References
These sources are listed in the compound's public database record.
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