Introduction of Di-tert-butyl dicarbonate.pdf

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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

1. Chemical Properties

Name:Di-tert butyl dicarbonate
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
HS Code:29209010
Appearance:white solid and/or colorless liquid
Molecular Weight:218.24692
Boiling Point:56-57℃ (0.5 torr)
Melting Point:22-24°C
Flash Point:37°C
Storage Temperature:2-8°C
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Refractive index:1.4075-1.4095
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).

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