Introduction of Di-tert-butyl dicarbonate

Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis.This carbonate ester reacts with amines to give N-tert-butoxycarbonyl or so-called t-BOC derivatives. These derivatives do not behave as amines, which allows certain subsequent transformations to occur that would have otherwise affected the amine functional group. The t-BOC can later be removed from the amine using acids. Thus, t-BOC serves as a protective group, for instance in solid phase peptide synthesis. It is unreactive to most bases and nucleophiles, allowing for an orthogonal Fmoc protection.

The IUPAC name of Boc anhydride is tert-butyl (2-methylpropan-2-yl)oxycarbonyl carbonate. With the CAS registry number 24424-99-5, it is also named as Di-tert-butyl dicarbonate. The product's categories are Amino Acid Derivatives; Starting Raw Materials & Intermediates; Organics; N-Protecting Reagents; Biochemistry; Peptide Synthesis; Protection & Derivatization Reagents (for Synthesis); Protective Reagents (Peptide Synthesis); Reagents for Oligosaccharide Synthesis; Synthetic Organic Chemistry; Boc-Amino Acid Series. Besides, it is white to off-white microcrystalline powder, which should be stored in closed containers in a cool, dry place at 2-8 °C.

1. Chemical Properties


Name:Di-tert butyl dicarbonate

EINECS:246-240-1

Molecular Formula:C10H18O5

CAS Registry Number:24424-99-5

Synonyms:Di-tert-butyl pyrocarbonate; di(tert-butyl) carbonate; di-t-Butyl-dicarbonate Dicarbonic acid, bis(1,1-dimethylethyl)ester; (t.-Boc)2O; DIBOC; Dibutyldicarbonate; BOC anhydride; BOC-20; Di-t-butyl pyrocarbonate; Di-tert butyl dicarbonate; Di-tert-butyl dicarbonate; Di-t-Butyl DICARBONATE; (BOC)2O; Di-tert-butyldicarbonate; Dicarbonic acid, C,C'-bis(1,1-dimethylethyl) ester; Dicarbonic acid, bis(1,1-dimethylethyl) ester

InChI:InChI=1S/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3

HS Code:29209010

Appearance:white solid and/or colorless liquid

Molecular Weight:218.24692

Density:0.949

Boiling Point:56-57°C(0.5 torr)

Melting Point:22-24°C

Flash Point:37°C

Storage Temperature:2-8°C

Refractive index:1.4075-1.4095

Solubility:insoluble

Stability:Stable under normal temperatures and pressures.

Vapour Pressure: 0.049 mmHg at 25 °C

Enthalpy of Vaporization: 47.26 kJ/mol

Surface Tension: 31.2 dyne/cm

2. Preparation of Di-tert-butyl dicarbonate

Di-tert-butyl dicarbonate can be prepared from tert-Butanol, Carbon dioxide, Phosgene, using DABCO as a base.

3. Uses of Di-tert-butyl dicarbonate

The Di-tert-butyl dicarbonate is an intermediate and amino-protecting agent widely used in organic synthesis. It is also used in the Synthesis of 6-acetyl-1,2,3,4-tetrahydropyridine. Simlilarly, it can react with 3-Amino-benzoic acid to get 3-tert-Butoxycarbonylamino-benzoic acid.(This reaction needs Et3N, H2O and Dioxane at temperature of 20 °C for 24 hours. The yield is 100 %.)

4. Safety information of Di-tert-butyl dicarbonate


The Di-tert-butyl dicarbonate is highly flammable that may form explosive peroxides. Please keep away from sources of ignition. It is also very toxic by inhalation, so you should keep container tightly closed in a well-ventilated place. Moreover, it is irritating to eyes, respiratory system and skin. And it may cause sensitization by skin contact. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. Additionally, you should wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin. After contact with skin, please wash immediately with plenty of soap-suds. And please take precautionary measures against static discharges. What's more, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible).