Di-tert-butyl dicarbonate
BOC · (BOC)2O · DIBOC · BOC ANHYDRIDE · DI-T-BUTYL DICARBONATE · tert-Butoxycarbonyl Anhydride · tert-butyldicarbonate · DI-TERT-BUTYL PYROCARBONATE
Identifiers & Physical Properties
| CAS No. | 24424-99-5 |
|---|---|
| Molecular formula | C10H18O5 |
| Average molar mass | 218.25 g/mol |
| Monoisotopic mass | 218.11542368 g/mol |
| SMILES | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C |
| InChIKey | DYHSDKLCOJIUFX-UHFFFAOYSA-N |
| PubChem CID | 90495 |
| ChEBI | CHEBI:48500 |
| EC No. | 246-240-1 |
| DTXSID | DTXSID4051904 |
Chemical & Physical Properties
| XLogP | 2.7 |
|---|---|
| Topological polar surface area | 61.8 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 5 |
| Rotatable bonds | 6 |
| Heavy atoms | 15 |
| Formal charge | 0 |
| Complexity | 218 |
| Chemical classes | Other Classes -> Esters, Other |
| Physical Description | White solid with a mild odormp = 22-24 deg C[Alfa Aesar MSDS] |
| Melting point | 23 °C (lit.) |
| Boiling point | 56-57 °C/0.5 mmHg (lit.) |
| Density | 0.95 g/mL at 25 °C (lit.) |
| Vapor pressure | 3.85Pa at 25℃ |
| Refractive index | n20/D 1.409(lit.) |
| Flash point | 99 °F |
| Storage conditions | 2-8°C |
| Solubility | Chloroform (Sparingly), Methanol (Slightly)Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water. |
| Physical state | Low Melting Crystalline Solid |
| Color | White |
| Specific gravity | 0.950 |
| Sensitivity | Moisture Sensitive |
| BRN | 1911173 |
| Stability | Acid Sensitive |
| Major applications | peptide synthesis |
| InChI | 1S/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3 |
| InChIKey | DYHSDKLCOJIUFX-UHFFFAOYSA-N |
| SMILES | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C |
| LogP (partition coefficient) | 1.87 at 25℃ |
| CAS DataBase Reference | 24424-99-5(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | Z10Q236C3G |
| EPA Substance Registry System | Dicarbonic acid, bis(1,1-dimethylethyl) ester (24424-99-5) |
| UNSPSC Code | 12352302 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS05,GHS06 |
| Signal word | Danger |
| GHS hazard statements | H226-H315-H317-H318-H330-H335 |
| GHS precautionary statements | P210-P233-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | T+,T,F,Xi,F+ |
| Risk statements (R) | 11-19-26-36/37/38-43-10-40 |
| Safety statements (S) | 16-26-28-36/37-45-7/9-37/39-24-36/37/39-33 |
| UN transport number | UN 2929 6.1/PG 1 |
| Water hazard class (WGK) | 3 |
| RTECS number | HT0230000 |
| F | 4.4-10-21 |
| Autoignition temperature | 460 °C |
| Hazard Note | Flammable/Irritant/Very Toxic |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 1 InhalationEye Dam. 1Flam. Liq. 3Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Packing group | I |
| Customs code | 29209010 |
| Storage class | 3 - Flammable liquids |
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg |
| REACH registrations | Active |
| Limited quantities | 0.5 Kg (solid) |
| Excepted quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 0.5% (1 of 183) of reports.DangerH225 (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. |
|---|---|
| Regulatory information | Chemical: Dicarbonic acid, bis(1,1-dimethylethyl) esterStatus: Active Update: 05-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/5501Di(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 injuryMay cause skin sensitizationHighly 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 Categories | Flam. Liq. 2 (26.8%) |
| Protective Action Criteria (PAC) | 0.067 [mg/m3]0.73 [mg/m3]4.4 [mg/m3] |
| Toxicity Data | LC50 (rat) = 100 mg/m3/4hr |
| F | 4.4-10-21 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | HT0230000 |
| UN transport number | UN 2929 6.1/PG 1 |
| Customs code | 29209010 |
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg |
| Risk statements (R) | 11-19-26-36/37/38-43-10-40 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS05,GHS06 |
| Hazard symbols | T+,T,F,Xi,F+ |
| hazard_note | Flammable/Irritant/Very Toxic |
| Safety statements (S) | 16-26-28-36/37-45-7/9-37/39-24-36/37/39-33 |
| Hazard class | 6.1Acute Tox. 1 InhalationEye Dam. 1Flam. Liq. 3Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Storage class | 3 - Flammable liquids |
| Packing group | I |
| Target organs | Respiratory system |
| GHS hazard statements | H226-H315-H317-H318-H330-H335 |
| Limited quantities | 0.5 Kg (solid) |
| Excepted quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| Autoignition temperature | 460 °C |
| GHS precautionary statements | P210-P233-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 |
Applications & Uses
Uses
Di-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 Description
Di-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 & Synthesis
Preparation
The 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%.