Di-tert-butyl dicarbonate
- CAS No.
- 24424-99-5
- Chemical Name:
- Di-tert-butyl dicarbonate
- Synonyms
- BOC;(BOC)2O;DIBOC;BOC ANHYDRIDE;DI-T-BUTYL DICARBONATE;DBDC;DI-TERT-BUTYL PYROCARBONATE;tert-Butoxycarbonyl Anhydride;Di-tert-butyL;tert-butyldicarbonate
- CBNumber:
- CB4267614
- Molecular Formula:
- C10H18O5
- Molecular Weight:
- 218.25
- MOL File:
- 24424-99-5.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/6/22 7:31:40
| 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 |
n |
| Flash point | 99 °F |
| storage temp. | 2-8°C |
| solubility | Chloroform (Sparingly), Methanol (Slightly) |
| form | Low Melting Crystalline Solid |
| color | White |
| Specific Gravity | 0.950 |
| Water Solubility | Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water. |
| Sensitive | Moisture Sensitive |
| BRN | 1911173 |
| Stability | Acid Sensitive |
| InChIKey | DYHSDKLCOJIUFX-UHFFFAOYSA-N |
| LogP | 1.87 at 25℃ |
| CAS DataBase Reference | 24424-99-5(CAS DataBase Reference) |
| EPA Substance Registry System | Dicarbonic acid, bis(1,1-dimethylethyl) ester (24424-99-5) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS02,GHS05,GHS06 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H226-H315-H317-H318-H330-H335 | |||||||||
| Precautionary statements | P210-P233-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 | |||||||||
| Hazard Codes | T+,T,F,Xi,F+ | |||||||||
| Risk Statements | 11-19-26-36/37/38-43-10-40 | |||||||||
| Safety Statements | 16-26-28-36/37-45-7/9-37/39-24-36/37/39-33 | |||||||||
| RIDADR | UN 2929 6.1/PG 1 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | HT0230000 | |||||||||
| F | 4.4-10-21 | |||||||||
| Autoignition Temperature | 460 °C | |||||||||
| Hazard Note | Flammable/Irritant/Very Toxic | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 6.1 | |||||||||
| PackingGroup | I | |||||||||
| HS Code | 29209010 | |||||||||
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg | |||||||||
| NFPA 704 |
|
Di-tert-butyl dicarbonate price More Price(37)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | 8.52261 | Di-tert-butyl dicarbonate Novabiochem? | 24424-99-5 | 25G | ₹2020 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.18282 | Di-tert-butyl dicarbonate for synthesis | 24424-99-5 | 25ML | ₹4700 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.52261 | Di-tert-butyl dicarbonate Novabiochem? | 24424-99-5 | 100G | ₹5170 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.18282 | Di-tert-butyl dicarbonate for synthesis | 24424-99-5 | 100ML | ₹8210 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.18282 | Di-tert-butyl dicarbonate for synthesis | 24424-99-5 | 500ML | ₹56290 | 2022-06-14 | Buy |
Di-tert-butyl dicarbonate Chemical Properties,Uses,Production
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.
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%.
Definition
ChEBI: Di-tert-butyl dicarbonate is an acyclic carboxylic anhydride. It is functionally related to a dicarbonic acid.
Application
Di-tert-butyl dicarbonate has the following uses:
(1) As part of a series of bovine plasma amine oxidase inactivators. Aminomethylenes were prepared by the reaction of Boc propargylamine with formaldehyde, diisopropylamine and copper bromide.
(2) It can be used as a general purpose carboxylation reagent. Carbon nucleophiles generated by a non-nucleophilic base (LDA) were effectively trapped with di-tert-butyl dicarbonate (Boc-anhydride) to provide the corresponding tert-butyl aryl acetates, di-tert-butyl aryl malonates, unsymmetrical aryl malonates and tert-butyl benzoates in high yields.
(3) Alcohols as Boc derivatives were catalytically protected by Lewis acids. Reagents for the introduction of Boc protecting groups.
(4) Reagents for the preparation of Boc-protected amines. Tri-tert-butoxycarbonyl-protected hydrazines prepare Fmoc esters in chromogenic reagents for monitoring solid-phase aldehydes.
Reactions
The reaction of substituted anilines with Boc2O in the presence of a stoichiometric amount of 4-dimethylaminopyridine (DMAP) in an inert solvent (acetonitrile, dichloromethane, ethyl acetate, tetrahydrofuran, toluene) at room temperature leads to aryl isocyanates in almost quantitative yields within 10 min.
Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited. Their reactions with amines and alcohols
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.
Hazard
An irritant that may cause serious eye injury; May cause skin sensitization; Highly toxic by inhalation
Purification Methods
Melt the ester by heating at ~35o, and distil it in a vacuum. If IR and NMR ( 1810m 1765 cm-1 , in CCl4 1.50 singlet) suggest very max impure, then wash with an equal volume of H2O containing citric acid to make the aqueous layer slightly acidic, collect the organic layer and dry it over anhydrous MgSO4 and distil it in a vacuum. [Pope et al. Org Synth 57 45 1977, Keller et al. Org Synth 63 160 1985, Grehn et al. Angew Chem 97 519 1985.] FLAMMABLE.
Di-tert-butyl dicarbonate Preparation Products And Raw materials
Raw materials
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chevron_rightPreparation Products
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chevron_right| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| BTC pharm India | +918790379245 | AndhraPradesh, India | 1269 | 58 | Inquiry |
| R SCIENTIFIC | +919000280374 | Hyderabad, India | 143 | 58 | Inquiry |
| SAGAR LIFE SCIENCES PVT LTD | +91-8770359041 +91-8770359041 | Gujarat, India | 79 | 58 | Inquiry |
| Vardhaman P Golechha | 9704422000 | Telangana, India | 294 | 58 | Inquiry |
| ADVENT CHEMBIO PRIVATE LIMITED | +91-9821524116 +91-9821524116 | Mumbai, India | 353 | 58 | Inquiry |
| JIVICHEM SYNTHESIS PVT LTD | +91-7028392790 +91-7028392790 | Maharashtra, India | 337 | 58 | Inquiry |
| ANJI BIOSCIENCES | +91-9000100077 +91-9000100077 | Hyderabad, India | 430 | 58 | Inquiry |
| BTC pharm India | +918790379245 | Telangana, India | 145 | 58 | Inquiry |
| Arown Pharma | +91-914040277600 +91-8309108338 | Hyderabad, India | 46 | 58 | Inquiry |
| AMINO ORGANICS | +919866989891 | Hyderabad, India | 275 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| BTC pharm India | 58 |
| R SCIENTIFIC | 58 |
| SAGAR LIFE SCIENCES PVT LTD | 58 |
| Vardhaman P Golechha | 58 |
| ADVENT CHEMBIO PRIVATE LIMITED | 58 |
| JIVICHEM SYNTHESIS PVT LTD | 58 |
| ANJI BIOSCIENCES | 58 |
| BTC pharm India | 58 |
| Arown Pharma | 58 |
| AMINO ORGANICS | 58 |
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