Description

4-Nitrobenzyl chloroformate (CAS No. 4457-32-3) is a highly reactive and versatile chemical reagent with the molecular formula C₈H₆ClNO₄. This compound, also known as (4-nitrophenyl)methyl carbonochloridate, is widely used in organic synthesis and peptide chemistry as a protecting group for amines and alcohols. Its nitrobenzyl moiety enhances its stability and reactivity, making it ideal for selective deprotection under mild conditions. The product is supplied as a high-purity crystalline solid, ensuring consistent performance in sensitive applications. Proper storage in a cool, dry, and well-ventilated area is recommended to maintain its integrity.

Properties

• CAS Number: 4457-32-3
• Complexity: 220
• IUPAC Name: (4-nitrophenyl)methyl carbonochloridate
• InChI: InChI=1S/C8H6ClNO4/c9-8(11)14-5-6-1-3-7(4-2-6)10(12)13/h1-4H,5H2
• InChI Key: MHSGOABISYIYKP-UHFFFAOYSA-N
• Exact Mass: 214.9985354
• Molecular Formula: C8H6ClNO4
• Molecular Weight: 215.59
• SMILES: C1=CC(=CC=C1COC(=O)Cl)[N+](=O)[O-]
• Topological: 72.1
• Monoisotopic Mass: 214.9985354
• Synonyms: 4-Nitrobenzyl chloroformate, 4457-32-3, Carbonochloridic acid, (4-nitrophenyl)methyl ester, p-Nitrobenzyl chloroformate, (4-nitrophenyl)methyl carbonochloridate, 4-Nitrobenzyloxycarbonyl chloride, DG2GS0JJV0, EINECS 224-708-6, DTXSID6063482, DTXCID4040341, 224-708-6, 4-Nitrobenzyl carbonochloridate, 4-Nitrobenzyl Chlorocarbonate, 4-Nitrocarbobenzoxychloride, (4-nitrophenyl)methyl chloroformate, Chloroformic Acid 4-Nitrobenzyl Ester, p-Nitrobenzyloxycarbonyl chloride, Chloroformic acid p-nitrobenzyl ester, Formic acid, chloro-, p-nitrobenzyl ester, Chloroformic Acid p-Nitrobenzyl Ester; 4-Nitrobenzyl Chloroformate; 4-Nitrobenzyloxycarbonyl Chloride; p-Nitrobenzyl Chloroformate; p-Nitrobenzyloxycarbonyl Chloride; p-Nitrocarbobenzoxy Chloride, MFCD00007375, 4nitrobenzyl chloroformate, UNII-DG2GS0JJV0, p-Nitrocarbobenzoxy chloride, p-nitrobenzyl chlorocarbonate, (4-nitrobenzyl)chloroformate, 4-Nitrobenzylcarbonochloridate, 4-(nitro)benzyl chloroformate, SCHEMBL158920, MHSGOABISYIYKP-UHFFFAOYSA-, p-nitrobenzyloxy-carbonyl chloride, 4-Nitrobenzyl chloridocarbonate #, 4-Nitrobenzyl chloroformate, 97%, BCP28673, Chloroformic acid 4-nitrobenyl ester, SBB063036, AKOS015888117, AKOS024437890, CS-W014887, AS-11619, BP-24064, NS00031439, ST51038068, EN300-66748, F15442, InChI=1/C8H6ClNO4/c9-8(11)14-5-6-1-3-7(4-2-6)10(12)13/h1-4H,5H2

Application

4-Nitrobenzyl chloroformate is commonly employed as a protecting group reagent in peptide synthesis, particularly for the temporary protection of amino acids. It is also utilized in the preparation of carbamate derivatives and other organic intermediates. Its selective deprotection under photolytic or reductive conditions makes it valuable in controlled-release applications. Researchers favor this compound for its compatibility with a wide range of functional groups and solvents.

Safety and Hazards

GHS Hazard Statements

• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Precautionary Statements

• P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501

Hazard Classes and Categories

• Skin Corr. 1B (100%)

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