Di-tert-butyl dicarbonate

Base Information

• Chemical Name: Di-tert-butyl dicarbonate
• CAS No.: 24424-99-5
• Deprecated CAS: 2254521-82-7
• Molecular Formula: C10H18O5
• Molecular Weight: 218.25
• Hs Code.: 29209010
• European Community (EC) Number: 246-240-1
• UNII: Z10Q236C3G
• DSSTox Substance ID: DTXSID4051904
• Nikkaji Number: J88.260G
• Wikipedia: Di-tert-butyl_dicarbonate
• Wikidata: Q175718
• Metabolomics Workbench ID: 87201
• Mol file: 24424-99-5.mol

Synonyms:bis(tert-butoxycarbonyl)oxide;Boc(2)O cpd;Boc2O cpd;di-tert-butyl dicarbonate;di-tert-butyl pyrocarbonate;di-tert-butyldicarbonate

Chemical Property of Di-tert-butyl dicarbonate

Chemical Property:

• Appearance/Colour: white to off-white microcrystalline powder
• Vapor Pressure: 0.7mmHg at 25°C
• Melting Point: 22-24 °C
• Refractive Index: 1.4090
• Boiling Point: 235.8 °C at 760 mmHg
• Flash Point: 103.7 °C
• PSA: 61.83000
• Density: 1.054 g/cm³
• LogP: 2.87320
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylform
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 218.11542367
• Heavy Atom Count: 15
• Complexity: 218

Purity/Quality:

98% ^*data from raw suppliers

Di-tert-butyl dicarbonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, T+, F, F+, Xi
• Hazard Codes: T+,T,F,Xi,F+
• 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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CC(C)(C)OC(=O)OC(=O)OC(C)(C)C
• Description: Di-tert-butyl dicarbonate (Boc-anhydride) is a widely used reagent in organic chemistry. It is an extremely efficient reagent to introduce the tert-butoxycarbonyl (BOC) protecting group for the amine functionality. It is also an efficient tert-butoxycarbonylating agent for alcohols and thiols. Di-tert-butyl dicarbonate is utilized for various synthetic transformations due to its versatility and ease of introduction and cleavage as a protecting group.
• Used in Organic Synthesis: Di-tert-butyl dicarbonate is used as a protecting group reagent to introduce the tert-butoxycarbonyl (BOC) group onto amine functionalities, allowing for selective modification of molecules during organic synthesis. ^[3]
• Used in Pharmaceutical Industry: Di-tert-butyl dicarbonate is employed in the pharmaceutical industry for the synthesis of various drug intermediates and active pharmaceutical ingredients. It serves as a versatile reagent for introducing protective groups and functionalizing molecules in drug synthesis processes.
• Used in Chemical Research: Di-tert-butyl dicarbonate finds application in chemical research as a reagent for the modification of amines, alcohols, and thiols. Its use in various synthetic transformations enables the study of new reaction pathways and the synthesis of novel compounds. ^{[1] [2]}
• Used in Environmental Remediation: Di-tert-butyl dicarbonate is utilized in environmental remediation processes, particularly in the reduction of pollutants such as hexavalent chromium in contaminated soil. Its reductive properties make it effective in converting toxic compounds into less harmful forms.
• Used in Food Science: Di-tert-butyl dicarbonate is employed in food science for the synthesis of flavor compounds and food additives. Its role in introducing specific functional groups allows for the customization of flavors and enhancement of food products.
• References: [1] Di-tert-butyl dicarbonate: a versatile carboxylating reagent; (DOI 10.1016/j.tet.2008.10.089); [2] A new efficient synthesis of isothiocyanates from amines using di-tert-butyl dicarbonate; (DOI 10.1016/j.tetlet.2008.03.045); [3] Alcohols and Di-tert-butyl Dicarbonate:? How the Nature of the Lewis Acid Catalyst May Address the Reaction to the Synthesis of tert-Butyl Ethers; (DOI 10.1021/jo061402d); [4] Di-tert-butyl Dicarbonate and 4-(Dimethylamino)pyridine Revisited. Their Reactions with Amines and Alcohols1; (DOI 10.1021/jo000257f)

Technology Process of Di-tert-butyl dicarbonate

There total 32 articles about Di-tert-butyl dicarbonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3-benzyl-9-tert-butyloxycarbonyl-3,9-diazabicyclo[3.3.1]nonane → di-tert-butyl dicarbonate (24424-99-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; under 2280.15 Torr;

DOI:10.1002/ejoc.201001073

Reference yield: 90.0%

potassium tert-butylate (865-47-4) + N-octylpyridinium chloride (4086-73-1) + methanesulfonyl chloride (124-63-0) → di-tert-butyl dicarbonate (24424-99-5)

Guidance literature:

With pyridine; sulfuric acid; sodium hydrogencarbonate; In hexane; water;

Reference yield: 89.0%

potassium tert-butylate (865-47-4) + methanesulfonyl chloride (124-63-0) → di-tert-butyl dicarbonate (24424-99-5)

Guidance literature:

With pyridine; sulfuric acid; sodium hydrogencarbonate; In hexane; water;

upstream raw materials:

di-tert-butyl tricarbonate

(2S,12bS)-2-Methyl-1,3,4,6,7,12b-hexahydro-2H-indolo[2,3-a]quinolizine-12-carboxylic acid tert-butyl ester

carbon dioxide

potassium tert-butylate

Downstream raw materials:

t-Boc-L-valine

(2R,3S)-2-tert-butoxycarbonylamino-3-hydroxybutyric acid

Boc-Thr-OH

N-tert-butoxycarbonyl-L-leucine

Refernces

• 1、 -. "Method for synthesizing di-tert-butyl dicarbonate ester by adopting phase transfer catalytic method". Paragraph 0018-0041. . Retrieved 2018/12/02.
• 2、 -. "Production technology of tert-butyl pyrocarbonate". Paragraph 0002; 0003. . Retrieved 2017/07/12.