1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole

Basic Information

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CAS Number

86832-06-6

Molecular Formula

C14H10N4O4

Molecular Weight

298.25 g/mol

Basic Physical Properties

Boiling Point

518.4±0.0 °C at 760 mmHg

Density

1.5±0.0 g/cm3

Flash Point

267.3±0.0 °C

Vapor Pressure

0.0±0.0 mmHg at 25°C

SMILES

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[O-][N+](=O)C1=CC=C(COC(=O)N2N=NC3=C2C=CC=C3)C=C1

InChI

1S/C14H10N4O4/c19-14(17-13-4-2-1-3-12(13)15-16-17)22-9-10-5-7-11(8-6-10)18(20)21/h1-8H,9H2

InChIKey

MKIHFLQNZUDOQW-UHFFFAOYSA-N

Complexity

420

Safety Information

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Hazard Statement

Synonyms & References

English

4-Nitrobenzyl 1H-benzo[d][1,2,3]triazole-1-carboxylate
1-(4-Nitrobenzyloxycarbonyl)benzotriazole
1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole
Nitrobenzyloxycarbonyl)benzotriazole
AMY37893
D83755
(4-nitrophenyl)methyl benzotriazole-1-carboxylate
(4-nitrophenyl)methyl 1H-1,2,3-benzotriazole-1-carboxylate

MDL Number

MFCD30536243

FAQ

What are the physical and chemical properties of 1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole (CAS: 86832-06-6)?

1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole is a white to off-white crystalline solid with a molecular weight of approximately 395.14 g/mol. It is relatively soluble in organic solvents such as dichloromethane and acetone, but poorly soluble in water. This compound exhibits moderate reactivity, particularly towards nucleophiles, and is commonly used in peptide coupling reactions. It is stable under normal storage conditions but should be protected from moisture and light.

How is 1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole (CAS: 86832-06-6) typically synthesized?

1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole is typically synthesized through the condensation of p-nitrobenzyl chloroformate with 1H-benzotriazole. This reaction proceeds in the presence of a base such as triethylamine, with excellent yield and selectivity. The process is carried out in anhydrous organic solvents like dichloromethane at ambient temperature.

What industries use 1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole (CAS: 86832-06-6)?

1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole is primarily used in the pharmaceutical and chemical industries for the synthesis of peptides and other bioactive molecules. It is also utilized in the semiconductor industry for the fabrication of organic thin-film transistors and sensors, where its reactivity and stability make it a valuable reagent.

What precautions should be taken when handling 1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole (CAS: 86832-06-6)?

When handling 1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole, it is essential to use appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. This compound should be stored in a cool, dry place away from moisture and light. In case of spills, they should be cleaned up using appropriate methods, and any contaminated materials should be disposed of properly as per local regulations. Refer to the Safety Data Sheet (SDS) for detailed handling instructions and emergency procedures.