Production Method 1

825-52-5

Reaction Conditions

1.1 Reagents: Nitromethane ,  4-(Dimethylamino)pyridine ,  Sodium hydroxide ,  Copper sulfate ,  Oxygen Solvents: Tetrahydrofuran ;  24 h, 1 atm, 120 °C

Reference

Copper(II)-dioxygen facilitated activation of nitromethane: nitrogen donors for the synthesis of substituted 2-hydroxyimino-2-phenylacetonitriles and phthalimides

Xiang, Shiqun; et al, Frontiers in Chemistry (Lausanne, 2020, 8,

Production Method 2

825-52-5

Reaction Conditions

1.1 Reagents: Potassium hydroxide ,  Nitric oxide Solvents: Methanol ;  250 kPa, rt → 60 °C; 24 h, 250 kPa, 60 °C

Reference

A New Synthetic Route to 3-Oxo-4-amino-1,2,3-oxadiazole from the Diazeniumdiolation of Benzyl Cyanide: Stable Sydnone Iminium N-Oxides

Bohle, D. Scott; et al, Journal of Organic Chemistry, 2009, 74(4), 1621-1626

Production Method 3

825-52-5

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ;  3 h, 2 - 3 atm, 35 - 38 °C
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Preparation of α-(hydroxyimino)benzeneacetonitrile

, China, , ,

Production Method 4

613-90-1

825-52-5

Reaction Conditions

1.1 Reagents: Hydroxyamine hydrochloride Solvents: Water ;  0.5 h, rt → reflux; 30 min, reflux

Reference

Synthesis of N-Aryl Oxindole Nitrones through a Metal-Free Selective N-Arylation Process

Wu, Si-Yi; et al, Journal of Organic Chemistry, 2017, 82(6), 3232-3238

Production Method 5

825-52-5

Reaction Conditions

1.1 Solvents: Diethyl ether ;  0 - 5 °C
2.1 Reagents: Trifluoroacetic acid ,  Trifluoroacetic anhydride ;  72 h, 25 °C

Reference

Oxodiazonium ion generation 5. 3-(N-Nitroamino)-4-phenylfuroxan: synthesis and reactivity

Zelenov, V. P.; et al, Russian Chemical Bulletin, 2012, 61(2), 351-354

Production Method 6

825-52-5

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  38 - 42 °C
2.1 Reagents: Sodium hydroxide Solvents: Water ;  3 h, 2 - 3 atm, 35 - 38 °C
2.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Preparation of α-(hydroxyimino)benzeneacetonitrile

, China, , ,

Production Method 7

932-90-1

825-52-5

Reaction Conditions

1.1 Reagents: tert-Butyl hypochlorite Solvents: Isopropanol ,  Dichloromethane
1.2 Reagents: Triethylamine Solvents: Water
1.3 Solvents: Dichloromethane
1.4 Reagents: Sulfuric acid Solvents: Water

Reference

A convenient synthesis of α-hydroxyiminoacetonitriles from aldoximes

Ma, Jun-An; et al, Synthetic Communications, 1999, 29(22), 3863-3868

Production Method 8

932-90-1

534-17-8

825-52-5

Reaction Conditions

1.1 Reagents: tert-Butyl hypochlorite Solvents: Isopropanol ,  Dichloromethane
1.2 Reagents: Triethylamine Solvents: Water
1.3 Solvents: Dichloromethane
1.4 Reagents: Sulfuric acid Solvents: Water

Reference

A convenient synthesis of α-hydroxyiminoacetonitriles from aldoximes

Ma, Jun-An; et al, Synthetic Communications, 2000, 30(9), 1563-1567

Production Method 9

4589-97-3

825-52-5

Reaction Conditions

1.1 Reagents: Sulfur monochloride Solvents: Dimethylformamide ;  -25 °C; -25 °C → 20 °C; 20 h, 20 °C; 4 h, 60 °C

Reference

Synthesis of 4-substituted 3-chloro-1,2,5-thiadiazoles from monosubstituted glyoximes

Kryshenko, F. I.; et al, Russian Chemical Bulletin, 2016, 65(11), 2678-2681

Production Method 10

1415839-40-5

825-52-5

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid ,  Trifluoroacetic anhydride ;  72 h, 25 °C

Reference

Oxodiazonium ion generation 5. 3-(N-Nitroamino)-4-phenylfuroxan: synthesis and reactivity

Zelenov, V. P.; et al, Russian Chemical Bulletin, 2012, 61(2), 351-354

Production Method 11

10349-06-1

825-52-5

Reaction Conditions

1.1 Reagents: Water Solvents: Water

Reference

Nitro derivatives of 3-phenyl-1,2,5-oxadiazole

De Munno, A.; et al, Atti della Societa Toscana di Scienze Naturali Residente in Pisa, 1975, 81, 334-42

Production Method 12

29945-54-8

825-52-5

Reaction Conditions

1.1 Reagents: Ammonium nitrate ,  Nitric acid Solvents: Water ;  -5 °C; 3 h, -8 - -2 °C
2.1 Solvents: Diethyl ether ;  0 - 5 °C
3.1 Reagents: Trifluoroacetic acid ,  Trifluoroacetic anhydride ;  72 h, 25 °C

Reference

Oxodiazonium ion generation 5. 3-(N-Nitroamino)-4-phenylfuroxan: synthesis and reactivity

Zelenov, V. P.; et al, Russian Chemical Bulletin, 2012, 61(2), 351-354

Production Method 13

4589-97-3

825-52-5

5728-14-3

Reaction Conditions

1.1 Reagents: Pyridine ,  Sulfur monochloride Solvents: Acetonitrile ;  4 h, 20 °C

Reference

Synthesis of 4-substituted 3-chloro-1,2,5-thiadiazoles from monosubstituted glyoximes

Kryshenko, F. I.; et al, Russian Chemical Bulletin, 2016, 65(11), 2678-2681

Production Method 14

1704-56-9

1940-57-4

825-52-5

107960-27-0

486-25-9

Reaction Conditions

1.1 Solvents: Benzene ,  Nitrogen

Reference

Reaction of the silver salts of arylnitroacetonitrile with 9-bromofluorene. Synthesis of 9-(α-cyanoarylidene)fluorenes

Lianis, Pygmalion S.; et al, Liebigs Annalen der Chemie, 1987, (6), 537-40

Production Method 15

825-52-5

1113056-44-2

Reaction Conditions

1.1 Reagents: Potassium methoxide ,  Nitric oxide ;  4 h, 250 kPa, rt; overnight, rt

Reference

A New Synthetic Route to 3-Oxo-4-amino-1,2,3-oxadiazole from the Diazeniumdiolation of Benzyl Cyanide: Stable Sydnone Iminium N-Oxides

Bohle, D. Scott; et al, Journal of Organic Chemistry, 2009, 74(4), 1621-1626

N-Hydroxybenzimidoyl cyanide Raw materials

• Benzaldoxime
• Benzeneacetaldehyde, a-(hydroxyimino)-, oxime
• Benzeneacetonitrile, α-nitro-, ion(1-), Ag(1+) (1:1)
• Cesium carbonate
• 9-Bromofluorene
• Benzoyl cyanide
• 1,2,5-Oxadiazole,3-phenyl-
• 1,2,5-Oxadiazol-3-amine, 4-phenyl-, 2-oxide
• 1,2,5-Oxadiazole, 3-(2-methoxy-2-oxidodiazenyl)-4-phenyl-, 2-oxide

N-Hydroxybenzimidoyl cyanide Preparation Products

• 9H-Fluorene-9-acetonitrile, α-nitro-α-phenyl- (107960-27-0)
• 1,2,3-Oxadiazol-5-amine, 4-phenyl-, 3-oxide (1113056-44-2)
• N-Hydroxybenzimidoyl cyanide (825-52-5)
• 3-Chloro-4-phenyl-1,2,5-thiadiazole (5728-14-3)
• 9-Fluorenone (486-25-9)

• 1. An inter-tangled network of redox-active and conducting polymers as a cathode for ultrafast rechargeable batteries
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzene and substituted derivatives
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives

Comprehensive Overview of N-Hydroxybenzimidoyl cyanide (CAS No. 825-52-5): Properties, Applications, and Innovations

N-Hydroxybenzimidoyl cyanide (CAS No. 825-52-5) is a specialized organic compound that has garnered significant attention in recent years due to its unique chemical structure and versatile applications. This compound, often referred to by its systematic name or CAS number, belongs to the class of cyanide derivatives and is characterized by the presence of a hydroxyl group attached to a benzimidoyl framework. Its molecular formula, C₈H₆N₂O, highlights its potential for diverse chemical reactions, making it a valuable intermediate in synthetic chemistry.

The growing interest in N-Hydroxybenzimidoyl cyanide is driven by its role in the development of pharmaceutical intermediates and agrochemicals. Researchers have explored its utility in constructing heterocyclic compounds, which are pivotal in drug discovery. For instance, its reactivity with nucleophiles enables the synthesis of imidazole derivatives, a class of compounds widely used in antifungal and antibacterial agents. This aligns with the current trend of optimizing green chemistry processes, where efficient and sustainable synthetic routes are prioritized.

One of the most frequently searched questions about CAS No. 825-52-5 revolves around its safety profile and handling precautions. While the compound is not classified as hazardous under standard regulations, proper laboratory practices, such as the use of personal protective equipment (PPE) and adequate ventilation, are recommended. This emphasis on safety resonates with the broader scientific community's focus on responsible chemical management and risk mitigation.

In the context of material science, N-Hydroxybenzimidoyl cyanide has shown promise as a precursor for functionalized polymers. Its ability to undergo polymerization or cross-linking reactions makes it a candidate for designing advanced materials with tailored properties. This application is particularly relevant to industries seeking high-performance coatings or adhesives, where thermal stability and chemical resistance are critical.

Another area of interest is the compound's potential in catalysis. Recent studies have investigated its role as a ligand in transition metal-catalyzed reactions, which are central to asymmetric synthesis. This aligns with the demand for chiral building blocks in the production of enantiomerically pure pharmaceuticals, a hot topic in medicinal chemistry.

From an environmental perspective, the biodegradability and eco-toxicity of N-Hydroxybenzimidoyl cyanide are subjects of ongoing research. As regulatory frameworks tighten around persistent organic pollutants, understanding the environmental fate of such compounds becomes paramount. This ties into the broader discourse on sustainable chemistry and the development of benign alternatives.

In summary, N-Hydroxybenzimidoyl cyanide (CAS No. 825-52-5) is a multifaceted compound with applications spanning pharmaceuticals, materials science, and catalysis. Its relevance to contemporary research themes, such as green chemistry and sustainable development, ensures its continued prominence in scientific literature. As innovation progresses, this compound is likely to play an even greater role in addressing global challenges in health and technology.

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