Products
Di-tert-butyl dicarbonate
Synonyms:bis(tert-butoxycarbonyl)oxide;Boc(2)O cpd;Boc2O cpd;di-tert-butyl dicarbonate;di-tert-butyl pyrocarbonate;di-tert-butyldicarbonate
Chemical Property of Di-Tert-Butyl Dicarbonate
● Appearance/Colour:white to off-white microcrystalline powder
● Vapor Pressure:0.7mmHg at 25°C
● Melting Point:22-24 °C
● Refractive Index:1.4090
● Boiling Point:235.8 °C at 760 mmHg
● Flash Point:103.7 °C
● PSA：61.83000
● Density:1.054 g/cm3
● LogP:2.87320
● Storage Temp.:2-8°C
● Sensitive.:Moisture Sensitive
● Water Solubility.:Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylform
● XLogP3:2.7
● Hydrogen Bond Donor Count:0
● Hydrogen Bond Acceptor Count:5
● Rotatable Bond Count:6
● Exact Mass:218.11542367
● Heavy Atom Count:15
● Complexity:218
Safty Information
● Pictogram(s):
T, T+, 
F, F+, 
Xi
● Hazard Codes:T+,T,F,Xi,F+
● Statements:11-19-26-36/37/38-43-10-40
● Safety Statements:16-26-28-36/37-45-7/9-37/39-24-36/37/39-33
Useful
Chemical Classes:Other Classes -> Esters, Other
Canonical SMILES:CC(C)(C)OC(=O)OC(=O)OC(C)(C)C
Uses:Di-tert-butyl dicarbonate (Boc2O) is a widely used reagent for introducing protecting groups in peptide synthesis. It plays an important role in the preparation of 6-acetyl-1,2,3,4-tetrahydropyridine by reacting with 2-piperidone. It serves as a protecting group used in solid phase peptide synthesis.
Detailed Introduction
Di-tert-butyl dicarbonate is a reagent used in organic synthesis. It is also known as t-BOC anhydride or Boc anhydride. It is commonly used to protect amine functional groups during chemical reactions. Di-tert-butyl dicarbonate reacts with amines to form carbamate derivatives, providing temporary protection for the amine group. Once the desired reaction is complete, the carbamate group can be easily removed by treatment with acid, yielding the original amine functionality. This is a useful strategy for selectively modifying certain functional groups in organic molecules.
Application
In addition to protecting amine groups, di-tert-butyl dicarbonate has various other applications in organic synthesis:
Protection of hydroxyl groups: Di-tert-butyl dicarbonate can react with alcohols to form carbonates, protecting the hydroxyl group. The carbonate group can then be removed using appropriate conditions, allowing for selective modification of other functional groups.
Carbonylation reactions: Di-tert-butyl dicarbonate can be used as a source of carbon monoxide in carbonylation reactions. It reacts with nucleophiles such as amines, alcohols, and thiols to form carbonylated products.
Preparation of acid chlorides: Reacting di-tert-butyl dicarbonate with thionyl chloride or oxalyl chloride yields the corresponding acid chlorides. Acid chlorides are versatile reagents used in a variety of synthetic transformations.
Solid-phase peptide synthesis: Di-tert-butyl dicarbonate is commonly used in the protection and deprotection steps in solid-phase peptide synthesis. It is used to protect amino acids during chain extension and to remove protecting groups to expose amino groups for subsequent coupling reactions.
Polymerization reactions: Di-tert-butyl dicarbonate can act as a chain transfer agent in polymerization reactions. It can react with growing polymer chains, terminating their growth or generating new reactive sites.
These are just a few examples of the many applications of di-tert-butyl dicarbonate in organic synthesis. Its versatility and ease of use make it a valuable reagent in various chemical transformations.
