Di-tert-butyl dicarbonate
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Basic information
- CAS
24424-99-5- Standard SMILES
CC(C)(C)OC(=O)OC(=O)OC(C)(C)C- InChIKey
DYHSDKLCOJIUFX-UHFFFAOYSA-N- Molecular formula
- C10H18O5
- Average molar mass
- 218.25 g/mol
- Monoisotopic mass
- 218.11542368
Overview
Tert-butoxycarbonyl anhydride is an acyclic carboxylic anhydride. It is functionally related to a dicarbonic acid.
Names & identifiers
- Preferred name
- Di-tert-butyl dicarbonate
- IUPAC
- tert-butyl (2-methylpropan-2-yl)oxycarbonyl carbonate
- English name
- Di-tert-butyl dicarbonate
- Molecular formula
- C10H18O5
- Molecular weight
- 218.25
Names & synonyms
Di-tert-butyl dicarbonate24424-99-5di-tert-Butyl pyrocarbonateBis(tert-butoxycarbonyl)oxideBOC-anhydrideBoc2ODi-tert-butyldicarbonateDicarbonic acid, bis(1,1-dimethylethyl) esterDi(tert-butyl) carbonateZ10Q236C3GDTXSID4051904Boc2O cpd
Show more names
BOC(BOC)2Otert-butyldicarbonateDBDCDi-tert-butyL
Boc(2)O cpdRefChem:132516DTXCID9030466246-240-1BOC anhydridedi-t-Butyl dicarbonatetert-Butoxycarbonyl anhydrideDiboc
Database identifiers
- CAS
24424-99-5- PubChem CID
- 90495
- DTXSID
DTXSID4051904- ChEBI
CHEBI:48500- UNII
- Z10Q236C3G
- EC Number
- 246-240-1
- Nikkaji
- J88.260G
Properties
Computed structural propertiesFilling in
- XLogP
- 2.7
- Topological polar surface area
- 61.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 218
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Esters, Other
Physical DescriptionWhite solid with a mild odor; mp = 22-24 deg C; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 23 °C · 23 °C (lit.)
- Boiling point
- 56 · 56-57 °C/0.5 mmHg (lit.)
- Density
- 0.95 g/mL · 0.95 g/mL at 25 °C (lit.)
- vapor pressure
- 3.85 Pa · 3.85Pa at 25℃
- refractive index
- 20 · n20/D 1.409(lit.)
- Flash point
- 99 °F · 99 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Sparingly), Methanol (Slightly)
- form
- Low Melting Crystalline Solid
- color
- White
- Specific Gravity
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.5% (1 of 183) of reports.
Danger
H225 (26.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P320, P321, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 183 reports by companies from 35 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Dicarbonic acid, bis(1,1-dimethylethyl) ester
Status: Active Update: 05-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/5501
Di(t-butyl) carbonate: HSNO Approval: HSR004455 Approved with controls
Hazards Summary
Causes dyspnea and weight loss in inhalation lethal-concentration studies of rats; [RTECS] An irritant that may cause serious eye injury; May cause skin sensitization; Highly toxic by inhalation; [Alfa Aesar MSDS] No results in PubMed: 24424-99-5 AND (sensitizer OR sensitization OR allergic OR contact dermatitis)
Hazard Classes and CategoriesFlam. Liq. 2 (26.8%)
Safety & protection
Protective Action Criteria (PAC)
0.067 [mg/m3]
0.73 [mg/m3]
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationDicarbonic acid, 1,3-bis(1,1-dimethylethyl) ester: ACTIVE
Applications
UsesDi-tert-butyl dicarbonate (Boc2O) is a widely used reagent for introducing protecting groups in peptide synthesis. It plays an important role in the preparation of 6-acetyl-1,2,3,4-tetrahydropyridine by reacting with 2-piperidone. It serves as a protecting group used in solid phase peptide synthesis.
General DescriptionDi-tert-butyl dicarbonate (Boc2O) is a reagent mainly used for the introduction of the Boc protecting group to amine functionalities. It is also used as a dehydrating agent in some organic reactions, particularly with carboxylic acids, certain hydroxyl groups, or with primary nitroalkanes.
Preparation methods
PreparationThe preparation of Di-tert-butyl dicarbonate is as follows:To a monoester sodium salt solution were added 2g of N, N-dimethylformamide, 1g of pyridine, 1g of triethylamine,Cooling to -5~0°C, 60g diphosgene was slowly added dropwise within 1.5h dropwise addition was complete, warmed to room temperature (25°C), incubated for 2h, the reaction was allowed to stand after filtration, washing organic solution. Dried with anhydrous magnesium sulfate, the solvent was distilled off at atmospheric pressure to give crude product 65~70g. After cooling and crystallization, 57-60g of di-tert-butyl dicarbonate were obtained in a yield of 60-63%.
Upstream & downstream products
Upstream raw materials
Related reactions
1,487 records
Compound notes
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