No renderable structure data available
C1=CC=C(C=C1)C=NNChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | benzylidenehydrazine |
|---|---|
| IUPAC Name | — |
| CAS Number | 5281-18-5 |
| Database ID | 95742 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
benzylidenehydrazine (CAS 5281-18-5) 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 95742
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-c10e101df37a4474bd4a1bfb73b75ee7Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-474fd2ae36bd406fbd0818c9ccf82dbdConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1 L flask equipped with a mechanical stirrer, thermometer, and addition funnel was charged with 250 mL of methanol and cooled to 0° C. Barium oxide (9.8 g, 64 mmol) was added portion-wise with exotherm. The reaction was cooled to 0° C., and hydrazine monohydrate (64.1 g, 1.28 mol) was slowly added. The reaction mixture was stirred for 10 minutes, after which time benzaldehyde (135.8 g, 1.28 mol) was added drop-wise over a 30 minute period. The reaction was then stirred for 1 hour, while maintaining a temperature below 8 (C. 1H NMR indicated the absence of ketone and a complete reaction. Ether (200 mL) was added, and the BaO was filtered through a bed of silica gel. The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature. A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3) δ (ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration, and the filtrate was distilled to provide ca. 12 g of distillate benzylidene-hydrazine. The material was stored under refrigeration. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.74 (s, 1H), 7.53 (m, 2H), 7.35 (m, 3H), 5.5 (br, 2H). A 1 L flask equipped with a mechanical stirrer thermometer, and addition funnel The reaction was cooled to 0° C. The reaction was then stirred for 1 hour while maintaining a temperature below 8 (C a complete reaction the BaO was filtered through a bed of silica gel The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3) δ (ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration the filtrate was distilled
Source ID: ord-afcdc90991a942b0ba52dee8c77f2278Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c10e101df37a4474bd4a1bfb73b75ee7Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c10e101df37a4474bd4a1bfb73b75ee7Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1 L flask equipped with a mechanical stirrer, thermometer, and addition funnel was charged with 250 mL of methanol and cooled to 0° C. Barium oxide (9.8 g, 64 mmol) was added portion-wise with exotherm. The reaction was cooled to 0° C., and hydrazine monohydrate (64.1 g, 1.28 mol) was slowly added. The reaction mixture was stirred for 10 minutes, after which time benzaldehyde (135.8 g, 1.28 mol) was added drop-wise over a 30 minute period. The reaction was then stirred for 1 hour, while maintaining a temperature below 8° C. 1H NMR indicated the absence of ketone and a complete reaction. Ether (200 mL) was added, and the BaO was filtered through a bed of silica gel. The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature. A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3)δ(ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration, and the filtrate was distilled to provide ca. 12 g of distillate benzylidene-hydrazine. The material was stored under refrigeration. 1H-NMR (300 MHz, CDCl3)δ(ppm): 7.74 (s, 1H), 7.53 (m, 2H), 7.35 (m, 3H), 5.5 (br, 2H). A 1 L flask equipped with a mechanical stirrer thermometer, and addition funnel The reaction was cooled to 0° C. The reaction was then stirred for 1 hour while maintaining a temperature below 8° C a complete reaction the BaO was filtered through a bed of silica gel The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3)δ(ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration the filtrate was distilled
Source ID: ord-d3f913c977f74a5eb769d9490399ffb5Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1 L flask equipped with a mechanical stirrer, thermometer, and addition funnel was charged with 250 mL of methanol and cooled to 0° C. Barium oxide (9.8 g, 64 mmol) was added portion-wise with exotherm. The reaction was cooled to 0° C., and hydrazine monohydrate (64.1 g, 1.28 mol) was slowly added. The reaction mixture was stirred for 10 minutes, after which time benzaldehyde (135.8 g, 1.28 mol) was added drop-wise over a 30 minute period. The reaction was then stirred for 1 hour, while maintaining a temperature below 8° C. 1H NMR indicated the absence of ketone and a complete reaction. Ether (200 mL) was added, and the BaO was filtered through a bed of silica gel. The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature. A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3)δ(ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration, and the filtrate was distilled to provide ca. 12 g of distillate benzylidene-hydrazine. The material was stored under refrigeration. 1H-NMR (300 MHz, CDCl3)δ(ppm): 7.74 (s, 1H), 7.53 (m, 2H), 7.35 (m, 3H), 5.5 (br, 2H). A 1 L flask equipped with a mechanical stirrer thermometer, and addition funnel The reaction was cooled to 0° C. The reaction was then stirred for 1 hour while maintaining a temperature below 8° C a complete reaction the BaO was filtered through a bed of silica gel The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3)δ(ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration the filtrate was distilled
Source ID: ord-d3f913c977f74a5eb769d9490399ffb5Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1 L flask equipped with a mechanical stirrer, thermometer, and addition funnel was charged with 250 mL of methanol and cooled to 0° C. Barium oxide (9.8 g, 64 mmol) was added portion-wise with exotherm. The reaction was cooled to 0° C., and hydrazine monohydrate (64.1 g, 1.28 mol) was slowly added. The reaction mixture was stirred for 10 minutes, after which time benzaldehyde (135.8 g, 1.28 mol) was added drop-wise over a 30 minute period. The reaction was then stirred for 1 hour, while maintaining a temperature below 8 (C. 1H NMR indicated the absence of ketone and a complete reaction. Ether (200 mL) was added, and the BaO was filtered through a bed of silica gel. The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature. A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3) δ (ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration, and the filtrate was distilled to provide ca. 12 g of distillate benzylidene-hydrazine. The material was stored under refrigeration. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.74 (s, 1H), 7.53 (m, 2H), 7.35 (m, 3H), 5.5 (br, 2H). A 1 L flask equipped with a mechanical stirrer thermometer, and addition funnel The reaction was cooled to 0° C. The reaction was then stirred for 1 hour while maintaining a temperature below 8 (C a complete reaction the BaO was filtered through a bed of silica gel The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3) δ (ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration the filtrate was distilled
Source ID: ord-afcdc90991a942b0ba52dee8c77f2278Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1 L flask equipped with a mechanical stirrer, thermometer, and addition funnel was charged with 250 mL of methanol and cooled to 0° C. Barium oxide (9.8 g, 64 mmol) was added portion-wise with exotherm. The reaction was cooled to 0° C., and hydrazine monohydrate (64.1 g, 1.28 mol) was slowly added. The reaction mixture was stirred for 10 minutes, after which time benzaldehyde (135.8 g, 1.28 mol) was added drop-wise over a 30 minute period. The reaction was then stirred for 1 hour, while maintaining a temperature below 8 (C. 1H NMR indicated the absence of ketone and a complete reaction. Ether (200 mL) was added, and the BaO was filtered through a bed of silica gel. The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature. A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3) δ (ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration, and the filtrate was distilled to provide ca. 12 g of distillate benzylidene-hydrazine. The material was stored under refrigeration. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.74 (s, 1H), 7.53 (m, 2H), 7.35 (m, 3H), 5.5 (br, 2H). A 1 L flask equipped with a mechanical stirrer thermometer, and addition funnel The reaction was cooled to 0° C. The reaction was then stirred for 1 hour while maintaining a temperature below 8 (C a complete reaction the BaO was filtered through a bed of silica gel The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3) δ (ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration the filtrate was distilled
Source ID: ord-afcdc90991a942b0ba52dee8c77f2278Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-474fd2ae36bd406fbd0818c9ccf82dbdConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To benzaldehyde hydrazone (5.95 g, 0.05 moles) in 1,2-dichloroethane (50 ml) containing 1,1,3,3-tetramethylguanidine (26.4 ml) and iodine (2 ml, 1% w/v solution) was added peracetic acid solution (11.4 ml, 1.27 × 0.05 moles) over 12 minutes at 0°. The red solution, which was gently evolving nitrogen, was stirred for 20 minutes at 0° to -5° before being washed with water (5 × 250 ml) and made up to 250 ml in a volumetric flask. An aliquot (50 ml) treated with excess acetic acid yielded 199 ml gas at NTP which corresponded to a yield of diazoalkane of 88.9%. before being washed with water (5 × 250 ml) made up to 250 ml in a volumetric flask An aliquot (50 ml) treated with excess acetic acid
Source ID: ord-76870d5574c74ff6bf704d4e8a40f82bConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1 L flask equipped with a mechanical stirrer, thermometer, and addition funnel was charged with 250 mL of methanol and cooled to 0° C. Barium oxide (9.8 g, 64 mmol) was added portion-wise with exotherm. The reaction was cooled to 0° C., and hydrazine monohydrate (64.1 g, 1.28 mol) was slowly added. The reaction mixture was stirred for 10 minutes, after which time benzaldehyde (135.8 g, 1.28 mol) was added drop-wise over a 30 minute period. The reaction was then stirred for 1 hour, while maintaining a temperature below 8° C. 1H NMR indicated the absence of ketone and a complete reaction. Ether (200 mL) was added, and the BaO was filtered through a bed of silica gel. The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature. A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3) δ (ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration, and the filtrate was distilled to provide ca. 12 g of distillate benzylidene-hydrazine. The material was stored under refrigeration. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.74 (s, 1H), 7.53 (m, 2H), 7.35 (m, 3H), 5.5 (br, 2H). A 1 L flask equipped with a mechanical stirrer thermometer, and addition funnel The reaction was cooled to 0° C. The reaction was then stirred for 1 hour while maintaining a temperature below 8° C a complete reaction the BaO was filtered through a bed of silica gel The resultant clear filtrate was liberated of methanol on a rotary evaporator at or below room temperature A large mass of bright yellow solid azine (1H-NMR (300 MHz, CDCl3) δ (ppm): 8.67 (s, 2H), 7.85 (m, 4H), 7.47 (m, 6H)), was removed by filtration the filtrate was distilled
Source ID: ord-b5f20025d5464496b589f18df3dfcff8PubChem References
These sources are listed in the compound's public database record.
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