Di-tert-butyl dicarbonate
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Di-tert-butyl dicarbonate
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CAS No:
24424-99-5
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Formula:
C10H18O5
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Chemical Name:
Di-tert-butyl dicarbonate
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Synonyms:
Dicarbonic acid,1,3-bis(1,1-dimethylethyl) ester;Formic acid,oxydi-,di-tert-butyl ester;Dicarbonic acid,bis(1,1-dimethylethyl) ester;Pyrocarbonic acid di-tert-butyl ester;Di-tert-butyl pyrocarbonate;Di-tert-butyl dicarbonate;Bis(1,1-dimethylethyl) dicarbonate;Di-tert-butyl oxydiformate;BOC-anhydride;(Boc)2O;tert-Butyl dicarbonate;tert-Butoxycarbonyl anhydride;Bis(tert-butyl) dicarbonate;Bis(tert-butoxycarbonyl) ether;tert-Butoxycarbonyl tert-butyl carbonate;di-tert-butyl dicarbonate;tert-Butoxycarboxylic anhydride
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CAS No:
Description
White to off-white microcrystalline powder Di-tert-butyl dicarbonate (Boc2O) and di-tert-butyl tricarbonate ((BocO)2CO) have been used as amine carbonylating reagents to obtain linear or branched aliphatic isocyanates.
most of the known methods for transforming amines into isocyanates are not mild enough and furnish undefined products as a result of uncontrolled side reactions. However, 4-dimethylaminopyridine (DMAP)-catalyzed reaction with activated carbonates as C1 building blocks cons
Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis. This carbonate ester reacts with amines to give N-tert-butoxycarbonyl or so-called Boc derivatives. These derivatives do not behave as amines, which allows certain subsequent transformations to occur that would have otherwise affected the amine functional group. The Boc can later be removed from the amine using acids. Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis. It is unreactive to most bases and nucleophiles, allowing for an orthogonal Fluorenylmethyloxycarbonyl chloride (FMOC-Cl) protection.
OtherSolid
Tert-butoxycarbonyl anhydride is an acyclic carboxylic anhydride. It derives from a dicarbonic acid.
Di-tert-butyl dicarbonate Basic Attributes
218.25
218.25
1911173
246-240-1
Z10Q236C3G
DTXSID4051904
29209010
Characteristics
61.8
2.88
White Low Melting Crystalline Solid
0.949
23 °C(lit.)
64-67 °C @ Press: 1 Torr
99 °F
1.431
Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water.
2-8°C
LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg
Safety Information
I
6.1
UN 2929 6.1/PG 1
3
11-19-26-36/37/38-43-10-40
16-26-28-36/37-45-7/9-37/39-24-36/37/39-33
HT0230000
T+,T,F,Xi,F+
Flammable/Irritant/Very Toxic
P210-P260-P280-P304 + P340 + P310-P305 + P351 + P338 + P310-P370 + P378
H226-H315-H317-H318-H330-H335
UN 2929 6.1/PG 1
P210; P280; P304 + P340 + P310; P305 + P351 + P338 + P310; P370 + P378; P403 + P235
|Danger|H225 (29.34%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P272, P280, P284, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 168 companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Di-tert-butyl dicarbonate Use and Manufacturing
Potassium tert-butoxide is dissolved in anhydrous tetrahydrofuran, and dry carbon dioxide is passed through at -5 to -20°C to form a slurry, which is kept at a low temperature, and phosgene benzene solution is added dropwise to prepare di-tert-butyl tricarbonate. Dissolve it in carbon tetrachloride, add an appropriate amount of 1, 4-diazabicyclo[2, 2, 2]octane, stir at 25°C to release carbon dioxide completely, and convert it into di-tert-butyl dicarbonate.
Reagent for the preparation of Boc-amino acids and peptides in high yields.
Processing aids, not otherwise listed
100,000 - 500,000 lb
Pharmaceutical and medicine manufacturing|Dicarbonic acid, 1,3-bis(1,1-dimethylethyl) ester: ACTIVE
Computed Properties
Molecular Weight:218.25
XLogP3:2.7
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:218.11542367
Monoisotopic Mass:218.11542367
Topological Polar Surface Area:61.8
Heavy Atom Count:15
Complexity:218
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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