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
- MDL Number:
- MFCD00008805
- MOL File:
- 24424-99-5.mol
- MSDS File:
- SDS
| 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) |
| EWG's Food Scores | 1 |
| FDA UNII | Z10Q236C3G |
| 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(70)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 8.52261 | Di-tert-butyl dicarbonate Novabiochem? | 24424-99-5 | 25g | $32.8 | 2024-03-01 | Buy |
| Sigma-Aldrich | 8.52261 | Di-tert-butyl dicarbonate Novabiochem? | 24424-99-5 | 100g | $87.9 | 2024-03-01 | Buy |
| Sigma-Aldrich | 34660 | Di-tert-butyl dicarbonate ≥98.0% (GC) | 24424-99-5 | 25g | $57.6 | 2024-03-01 | Buy |
| Sigma-Aldrich | 205249 | Di-tert-butyl dicarbonate ReagentPlus , 99% | 24424-99-5 | 10g | $53.8 | 2024-03-01 | Buy |
| Sigma-Aldrich | 34660 | Di-tert-butyl dicarbonate ≥98.0% (GC) | 24424-99-5 | 100g | $147 | 2024-03-01 | Buy |
Di-tert-butyl dicarbonate Chemical Properties,Uses,Production
Chemical Properties
Di-tert-butyl dicarbonate (BOC Anhydride, DiBOC) is a colorless to white to yellow crystals, solidified mass or clear liquid. It melts around room temperature (m.p.=23°C). It does not decompose at this or even slightly higher temperatures. For example, it is typically purified by distillation under reduced pressure at temperatures up to around 65°C. At higher temperatures it will decompose to isobutene, t-butyl alcohol and carbon dioxide.
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.
Definition
ChEBI: Di-tert-butyl dicarbonate is an acyclic carboxylic anhydride. It is functionally related to a dicarbonic acid.
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%.
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
Flammability and Explosibility
Flammable
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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Preparation Products
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| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Shanghai Time Chemicals CO., Ltd. | +86-021-57951555 +8617317452075 | jack.li@time-chemicals.com | China | 1807 | 55 |
| SIMAGCHEM CORP | +86-13806087780 | sale@simagchem.com | China | 17367 | 58 |
| Neostar United (Changzhou) Industrial Co., Ltd. | +86-519-519-85557386 | marketing1@neostarunited.com | China | 8349 | 58 |
| Shandong Zhishang New Material Co., Ltd. | +8617653113209 | sales002@sdzschem.com | China | 3050 | 58 |
| Chemtour Biotech Co., Ltd | +8617327281506 | market@chemtour.com | China | 1472 | 58 |
| GenChem & GenPharm (Changzhou) Co., Ltd. | +86-86020003 +86-18861157602 | sales03@genchem.cn | China | 79 | 58 |
| Hunan aslsen technology co.,ltd | +8619313031929 | aslsd@aslsen.com | China | 128 | 58 |
| Hebei Mojin Biotechnology Co., Ltd | +8613288715578 | sales@hbmojin.com | China | 12456 | 58 |
| Anhui Yiao New Material Technology Co., Ltd | +86-199-55145978 +8619955145978 | sales8@anhuiyiao.com | China | 253 | 58 |
| Anhui Ruihan Technology Co., Ltd | +8617756083858 | daisy@anhuiruihan.com | China | 994 | 58 |
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View Lastest Price from Di-tert-butyl dicarbonate manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-04-23 | Di-tert-butyl dicarbonate
24424-99-5
|
US $10.00 / kg | 1kg | 99.9% | 200000kg | Ouhuang Engineering Materials (Hubei) Co., Ltd | |
 |
2024-04-22 | Di-tert-butyl dicarbonate
24424-99-5
|
US $0.00 / kg | 1kg | 99% | 20 tons | Hunan aslsen technology co.,ltd | |
 |
2024-01-22 | Di-tert-butyl dicarbonate
24424-99-5
|
US $8.00-0.80 / KG | 1KG | 99% | g-kg-tons, free sample is available | Henan Fengda Chemical Co., Ltd |
-
- Di-tert-butyl dicarbonate
24424-99-5
- US $10.00 / kg
- 99.9%
- Ouhuang Engineering Materials (Hubei) Co., Ltd
-
- Di-tert-butyl dicarbonate
24424-99-5
- US $0.00 / kg
- 99%
- Hunan aslsen technology co.,ltd
-
- Di-tert-butyl dicarbonate
24424-99-5
- US $8.00-0.80 / KG
- 99%
- Henan Fengda Chemical Co., Ltd