Di-tert-butyl dicarbonate 99%min supplier in China CAS NO.24424-99-5

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1. 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.

2. Properties of Di-tert-butyl dicarbonate

ACD/LogP: 2.631 ACD/LogD (pH 5.5): 2.63 ACD/LogD (pH 7.4): 2.63
ACD/BCF (pH 5.5): 58.78 ACD/BCF (pH 7.4): 58.78
ACD/KOC (pH 5.5): 642.73 ACD/KOC (pH 7.4): 642.73
#H bond acceptors: 5 #Freely Rotating Bonds: 6 Polar Surface Area: 61.83  2
Index of Refraction: 1.431 Molar Refractivity: 53.604 cm3
Molar Volume: 207.026 cm3 Polarizability: 21.25 10-24cm3
Surface Tension: 31.2080001831055 dyne/cm Density: 1.054 g/cm3
Flash Point: 103.65 °C Enthalpy of Vaporization: 47.261 kJ/mol
Boiling Point: 235.829 °C at 760 mmHg Vapour Pressure: 0.0489999987185001 mmHg at 25°C
 

3. Structure descriptors of Di-tert-butyl dicarbonate

IUPAC Name: tert-butyl (2-methylpropan-2-yl)oxycarbonyl carbonate

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

InChIKey: DYHSDKLCOJIUFX-UHFFFAOYSA-N

Canonical SMILES : CC(C)(C)OC(=O)OC(=O)OC(C)(C)C

4. Preparation of Di-tert-butyl dicarbonate

Di-tert-butyl dicarbonate is inexpensive, so it is usually purchased. Classically, this compound is prepared from tert-butanol, carbon dioxide, phosgene, using DABCO as a base:

This route is currently employed commercially by manufacturers in China and India. European and Japanese companies use the reaction of sodium tert-butylate with carbon dioxide, catalysed by p-toluenesulfonic acid or methanesulfonic acid. This process involves a distillation of the crude material yielding a very pure grade.

Boc anhydride is also available as a 70% solution in toluene or THF. Since boc anhydride is a low-melting solid, having the reagent in a solution simplifies storage and handling.

5. Other uses

The synthesis of 6-acetyl-1,2,3,4-tetrahydropyridine, an important bread aroma compound from 2-piperidone was accomplished using t-boc anhydride. (See Maillard reaction). The first step in this reaction sequence is the formation of the carbamate from the reaction of the secondary amine with boc anhydride in acetonitrile with DMAP as a catalyst.