205249
Aldrich

Di-tert-butyl dicarbonate

ReagentPlus^®, 99%

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Synonym

Boc anhydride

Di-tert-butyl pyrocarbonate

Molecular Formula

[(CH₃)₃COCO]₂O

Molecular Weight

218.25

CAS Number

24424-99-5

Beilstein Registry Number

1911173

MDL number

MFCD00008805

PubChem Substance ID

24852315

EG/EC Number

246-240-1

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Descriptions

Application

Reagent for the introduction of the Boc protecting group.

Protection of alcohols as Boc derivatives via Lewis acid catalysis.⁴

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

Tris-Boc protected hydrazine allows preparation of Fmoc ester in a chromophoric reagent to monitor solid-phase aldehydes.³

Reagent for the preparation of t-Boc protected amines.²

Packaging

1 kg in amber poly

10, 50, 100 g in poly btl

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 Biotechnology LP and Sigma-Aldrich Co.

Properties

grade

ReagentPlus^®

assay

99%

refractive index

n20/D 1.409(lit.)

56-57 °C/0.5 mmHg(lit.)

23 °C(lit.)

density

0.95 g/mL at 25 °C(lit.)

References

Cited Reference

1. J. Am. Chem. Soc. 126, 8038-8045, (2004) abstract

2. Synth. Commun. 23, 1443, (1993)

3. J. Org. Chem. 69, 4586-4594, (2004) abstract

4. Synlett, 2104, (2006)

Reference

D.L. Flynn, N-BOC-ylation of amides. J. Org. Chem. 48, 2424, (1983)

D.S. Tarbell, Reagent for the clean and rapid introduction of the acid labile BOC-protecting group in amino acids, peptides and proteins. Proc. Natl. Acad. Sci. USA 69, 730, (1972)

D.S. Kemp, R.I. Carey J. Org. Chem. 54, 3640, (1989)

E. Ponnusamy, N-BOC-ylation of sensitive compounds under non-aqueous conditions. Synthesis, 48, (1986)

F. Houlihan, Protection of -OH and -SH functions. Can. J. Chem. 63, 153, (1985)

L. Grehn Angew. Chem. 97, 519, (1985)

O. Keller Org. Synth. 63, 160, (1985)

Tarbell, D.S., et al. Proc. Natl. Acad. Sci. USA 69, 730, (1972)

Fieser

Fieser 4,128 / Fieser 7,91 / Fieser 8,145 / Fieser 10,122 / Fieser 13,94 / Fieser 15,113

reference

Aldrich MSDS 1, 594:D / Corp MSDS 1 (1), 1099:B / FT-IR 1 (1), 611:C / FT-IR 2 (1), 977:B / FT-NMR 1 (1), 930:A / IR-Spectra (3), 365:D / NMR-Reference 2 (1), 517:B / RegBook 1 (1), 695:G / Sigma FT-IR 1 (2), 445:A / Sigma FT-IR 1 (2), 445:B / Structure Index 1, 105:C:6 / Vapor Phase 3, 634:D

Safety

Hazard Codes

T+

Risk Statements

10-26-36/37/38

Safety Statements

16-26-28-36/37-45-7/9

RIDADR

UN 2929 6.1/PG 1

WGK Germany

RTECS

HT0230000