Di-tert-butyl dicarbonate

1.Introduction of Di-tert-butyl dicarbonate

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.

2.The properties of Di-tert-butyl dicarbonate

(1)EINECS: 246-240-1; (2)ACD/LogP: 2.88; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.88; (5)ACD/LogD (pH 7.4): 2.88; (6)ACD/BCF (pH 5.5): 90.45; (7)ACD/BCF (pH 7.4): 90.45; (8)ACD/KOC (pH 5.5): 874.99; (9)ACD/KOC (pH 7.4): 874.99; (10)#H bond acceptors: 5; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 6; (13)Index of Refraction: 1.431; (14)Molar Refractivity: 53.6 cm³; (15)Molar Volume: 207 cm³; (16)Surface Tension: 31.2 dyne/cm; (17)Density: 1.054 g/cm³; (18)Flash Point: 103.7 °C; (19)Melting Point: 22-24 °C; (20)Enthalpy of Vaporization: 47.26 kJ/mol; (21)Boiling Point: 235.8 °C at 760 mmHg; (22)Vapour Pressure: 0.049 mmHg at 25 °C.

3.Structure descriptors of Di-tert-butyl dicarbonate

(1)SMILES: O=C(OC(=O)OC(C)(C)C)OC(C)(C)C
(2)InChI: InChI=1/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3
(3)InChIKey: DYHSDKLCOJIUFX-UHFFFAOYAG
 

4.Preparation of Di-tert-butyl dicarbonate

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

5.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 %.

6.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).

7. The toxicity data is as follows: