di-tert-butyl dicarbonate

• ChemBase ID: 85817
• Molecular Formular: C10H18O5
• Molecular Mass: 218.24692
• Monoisotopic Mass: 218.11542368
• SMILES: O(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C
• Canonical SMILES: O=C(OC(C)(C)C)OC(=O)OC(C)(C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: di-tert-butyl dicarbonate
• IUPAC Traditional name: di-tert-butyl dicarbonate
• Synonyms: Di-tert-butyl pyrocarbonate; Di-tert-butyl dicarbonate; di-tert-butyl pyrocarbonate; Boc₂O; Di-tert-butyl dicarbonate; Di-tert-butyl dicarbonate solution; C,C'-bis(1,1-Dimethylethyl) Ester Dicarbonic Acid; Bis(1,1-dimethylethyl) Ester Dicarbonic Acid; Oxydi-formic Acid Di-tert-butyl Ester; BOC-anhydride; Bis(1,1-dimethylethyl) Dicarbonate; Bis(tert-butyl) Dicarbonate; Di-tert-butyl Dicarbonate; Di-tert-butyl Oxydiformate; Pyrocarbonic Acid Di-tert-butyl Ester; tert-Butoxycarbonyl Anhydride; tert-Butyl Dicarbonate; tert-Butyl Dicarbonate; Bis(tert-butyl) pyrocarbonate; BOC anhydride; Bis(tert-butyl) dicarbonate 97+%; Di-t-butyl pyrocarbonate; DI-t-BUTYL DICARBONATE; 二叔丁基二碳酸酯; 焦碳酸二叔丁酯; 二碳酸二叔丁酯; 二碳酸二叔丁酯 溶液

Database IDs

• CAS Number: 24424-99-5
• EC Number: 246-240-1
• MDL Number: MFCD00008805
• Beilstein Number: 1911173
• PubChem SID: 24862282; 24852315; 162072933; 24867291; 24861420
• PubChem CID: 90495
• CHEBI ID: 48500
• Chemspider ID: 81704
• Wikipedia Title: Di-tert-butyl_dicarbonate

CALCULATED PROPERTIES

• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.033982
• LogD (pH = 7.4): 3.033982
• Log P: 3.033982
• Molar Refractivity: 52.9404 cm^3
• Polarizability: 21.461906 Å^3

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; insol in water; most organic solvents
• Apperance: colourless solid; Pale Yellow Solid
• Melting Point: 21-24°C; 22–24 °C; 22-26 °C; 23 °C(lit.); 23°C
• Boiling Point: 56-57 °C/0.5 mmHg(lit.); 56-57°C; 56-57°C/0.5mm; 56–57 °C (0.5 mmHg); 56-57°C/0.5mm; 65-67 °C
• Flash Point: -1 °C; 1.4 °F; 107 °C; -15 °C; -17 °C; 224.6 °F; 30.2 °F; 37 °C; 37°C; 37°C(99°F); 5 °F; 98.6 °F
• Density: 0.913 g/mL at 25 °C; 0.934 g/mL at 25 °C; 0.95; 0.95 g/mL at 25 °C(lit.); 0.95 g·cm^−3; 0.950; 0.950 g/ml; 0.951 g/mL at 25 °C; 1.162 g/mL at 25 °C
• Refractive Index: 1.4090; n20/D 1.389; n20/D 1.408; n20/D 1.409(lit.)

Safety Information

• Storage Condition: 0°C; Refrigerator
• Storage Warning: Moisture Sensitive; Very Toxic/Flammable/Irritant/Corrosive/Moisture Sensitive/Air Sensitive/Keep Cold/Store under Argon
• RTECS: HT0230000
• European Hazard Symbols: Flammable (F); Highly toxic (T+); Irritant (Xi)
• UN Number: 1992; 1993; 2810; 2929; UN2930
• German water hazard class: 3
• Hazard Class: 3; 6.1
• Packing Group: 1; 2; I; III
• Australian Hazchem: 3Y
• Risk Statements: 10-26-36/37/38-43; 11-19-26-36/37/38-43; 11-26-36/37/38-43; 11-26-37/38-41-43; 26-36/37/38-40-43; R:10-36/37/38
• Safety Statements: 16-26-28-36/37-45; 26-28-36/37-45; 7/9-16-26-28-36/37-45; 9-26-28-36/37/39-45-60; S:16-20-25-26-37/39
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 128
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• Main Hazard: toxic on inhalation T+
• GHS Hazard statements: H225-H315-H319-H330-H335; H225-H315-H319-H330-H335-H336; H226-H315-H317-H319-H330-H335; H315-H319-H330-H335-H351; H330-H315-H317-H335-H318-H228
• GHS Precautionary statements: P210-P260-P284-P305 + P351 + P338-P310; P260-P280-P284-P305 + P351 + P338-P310; P260-P281-P284-P305 + P351 + P338-P310; P280-P305+P351+P338-P302+P352-P304+P340-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1992 3/PG 2; UN 2810 6.1/PG 1; UN 2929 6.1/PG 1
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: 2-8°C

Product Information

• Purity: ~97-98%; ≥98.0% (GC); ≥99%; 97%; 97+%; 99%
• Concentration: 1.0 M in THF; 2 M in ethyl acetate; 2 M in methylene chloride; 2 M in THF
• Grade: purum; reagent grade; ReagentPlus®
• Linear Formula: [(CH3)3COCO]2O; O[CO2C(CH3)3]2

DETAILS

MP Biomedicals - 02150859

Purity: ~97-98%
Reagent for synthesis of t-Boc amino acids.

Apollo Scientific Ltd - OR28895

Reagent for the preparation of t-Boc protected amines

Sigma Aldrich - 703737

Packaging
100 mL in glass bottle

Sigma Aldrich - 361941

Application
Protection of alcohols as Boc derivatives via Lewis acid catalysis.
Reagent for the introduction of the Boc protecting group.
Packaging
5, 25 g in poly bottle
Warning
Hydrolyzes to t-butanol and CO2; causes internal pressure in bottle if exposed to moisture.
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 34660

Application
Reagent for the introduction of the Boc protecting group.
Other Notes
Reagent for the clean and rapid introduction of the acid labile BOC-protecting group in amino acids, peptides and proteins; 1 N-BOC-ylation of amides; 2,3 N-BOC-ylation of sensitive compounds under non-aqueous conditions.4
Warning
Hydrolyzes to t-butanol and CO2; causes internal pressure in bottle if exposed to moisture.

Sigma Aldrich - 50431

Application
Reagent for the introduction of the Boc protecting group.
Warning
Hydrolyzes to t-butanol and CO2; causes internal pressure in bottle if exposed to moisture.

Sigma Aldrich - 199133

Application
Reagent for the introduction of the Boc protecting group.
Packaging
100 g in poly bottle
Warning
Hydrolyzes to t-butanol and CO2; causes internal pressure in bottle if exposed to moisture.

Sigma Aldrich - 205249

Application
Aminomethyl allene was prepared by reaction of Boc propargyl amine with formaldehyde, diisopropylamine and copper bromide as part of a series of Bovine Plasma Amine Oxidase inactivators.1
Protection of alcohols as Boc derivatives via Lewis acid catalysis.
Reagent for the introduction of the Boc protecting group.
Reagent for the preparation of Boc protected amines.
Tris-Boc protected hydrazine allows preparation of Fmoc ester in a chromophoric reagent to monitor solid-phase aldehydes.
Packaging
1 kg in amber poly
10, 50, 100 g in poly bottle
15 kg in poly drum
Warning
Hydrolyzes to t-butanol and CO2; causes internal pressure in bottle if exposed to moisture.
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 703753

Packaging
100 mL in Sure/Seal™

Sigma Aldrich - 436267

Packaging
100, 800 mL in Sure/Seal™

Sigma Aldrich - 703745

Packaging
100 mL in Sure/Seal™

Toronto Research Chemicals - B691045

Reagent commonly used in organic chemistry for the introduction of the BOC protecting group.

REFERENCES

• Carboxylic acids have also been converted to Boc-protected amines, via a one-pot Curtius rearrangement, using the reagent in the presence of sodium azide, with catalytic amounts of TBAB and zinc triflate: Org. Lett., 7, 4107 (2005).
• Reagent for amino group protection as the tert-butyl carbamate (tert-butoxycarbonyl, Boc derivatives), in high yield under mild conditions, widely used in peptide chemistry; see Appendix 6. For practical details, literature references and tabulated results, see: Org. Synth. Coll., 7, 70 (1990). For further examples see: Synthesis, 223 (1987): Org. Synth.Coll., 9, 124, 300 (1998). Benzyl carbamates (Cbz, Z) may be transformed into Boc in a one pot procedure catalyzed by Pd/C: Tetrahedron Lett., 33, 3167 (1992).
• Rapid and efficient formation of Boc derivatives of amines, catayzed by Copper(II) tetrafluoroborate hexahydrate, 26127 has been described: Tetrahdron Lett., 47, 1087 (2006).
• For Boc protection of phenols, alcohols, thiols etc. under phase-transfer conditions, see: Can. J. Chem., 63, 153 (1985).
• Amides can be protected in the presence of a catalytic quantity of DMAP (4-(Dimethylamino)pyridine, A13016): J. Org. Chem., 48, 2424 (1983); Acta Chem. Scand. B, 40, 745 (1986); the amide link of the product undergoes facile alkaline hydrolysis or methanolysis. The nitrogen function of indoles and pyrroles can also be protected under similar conditions: J. Chem. Soc., Chem. Commun., 1699 (1984); Org. Synth.Coll., 9, 121 (1998). 1-Boc indoles may be synthesized from N-Boc 2-alkylanilines: Synthesis, 871 (1991).
• The Boc group is readily cleaved with acid, most often Trifluoroacetic acid, L06374.
• In the presence of 1 equivalent of DMAP in acetonitrile, arylamines are converted to isocyanates, generally in high yield; the dicarbonate here behaves as a convenient phosgene replacement: Angew. Chem. Int. Ed., 34, 2497 (1995). The same reagent system has also been applied to nitroalkanes for the ambient temperature generation of nitrile oxides which were trapped in situ with dipolarophiles: Synthesis, 309 (1997). Carboxylic acids can be esterified in the presence of a catalytic amount of DMAP: Synlett, 263 (2004).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 1995 (2001).