| Identification | Back Directory | [Name]
tert-Butyl phenyl carbonate | [CAS]
6627-89-0 | [Synonyms]
Einecs 229-601-8
BUTTPARK 52\11-34
t-Butyl phenyl carbonate
ert-Butyl phenyl carbonate
tart-Butylphenyl carbonate
TERT-BUTYL PHENYL CARBONATE
(2-tert-butylphenyl) carbonate
(tert-Butoxycarbonyloxy)benzene
tert-Butyl phenyl carbonate 98%
tert-Butyl Phenyl Carbonate >
Carbonic acid tert-butylphenyl ester
2-Methyl-2-propanyl phenyl carbonate
Carbonicacidtert-butylesterphenylester
tert-Butyl phenyl carbonate≥ 98%(HPLC)
Carbonic acid O-phenyl O-tert-butyl ester
Carbonic acid O-tert-butyl O-phenyl ester
Carbonic acid, 1,1-dimethylethyl phenyl ester
tert-Butyl phenyl carbonate Carbonic acid tert-butyl phenyl ester | [EINECS(EC#)]
229-601-8 | [Molecular Formula]
C11H14O3 | [MDL Number]
MFCD00008804 | [MOL File]
6627-89-0.mol | [Molecular Weight]
194.23 |
| Chemical Properties | Back Directory | [Boiling point ]
83 °C0.6 mm Hg(lit.)
| [density ]
1.05 g/mL at 20 °C(lit.)
| [refractive index ]
n20/D 1.480
| [Fp ]
214 °F
| [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Slightly) | [form ]
Liquid or Low Melting Solid | [color ]
Colorless | [Water Solubility ]
Slightly soluble in water. | [BRN ]
2361602 | [InChI]
1S/C11H14O3/c1-11(2,3)14-10(12)13-9-7-5-4-6-8-9/h4-8H,1-3H3 | [InChIKey]
UXWVQHXKKOGTSY-UHFFFAOYSA-N | [SMILES]
CC(C)(C)OC(=O)Oc1ccccc1 | [NIST Chemistry Reference]
Carbonic acid 1,1-dimethylethyl ester(6627-89-0) |
| Hazard Information | Back Directory | [Chemical Properties]
Clear light yellow liquid | [Uses]
tert-Butyl phenyl carbonate is used in determination of octanol-water partition coefficients by microemulsion electrokinetic chromatography. It is also used in the synthesis of 2-nitroindoles and as a reagent for mono-Boc protection of α,ω-diamines. | [Synthesis]
GENERAL METHOD: Di-tert-butyl dicarbonate (Boc2O, 1.0 mmol) was added to a round-bottomed flask containing phenol (1.0 mmol) and magnesium bromide ethyl ether compound (MgBr2-OEt2, 0.1 mmol). After gas escape was observed, the reaction mixture was magnetically stirred at room temperature (heated to about 60 °C if necessary). The progress of the reaction was monitored by thin-layer chromatography (TLC) and left until the phenol was completely consumed (reaction time was usually 3-16 h). Upon completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate (EtOAc, 3 x 20 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using a gradient elution of 5-30% ethyl acetate/hexane to afford the target product tert-butyl phenyl carbonate. | [Purification Methods]
If IR is free from OH, then purify it by redistillation; otherwise dissolve it in Et2O, wash it with 5% HCl, then H2O, dry it (MgSO4), evaporate and distil it through a Claisen head under vacuum. Care should be taken as distillation of large quantities can lead to decomposition with liberation of CO2 and isobutylene; use the necessary precautions. [Carpino J Am Chem Soc 79 98 1957, Beilstein 6 IV 629.] | [References]
[1] Green Chemistry, 2011, vol. 13, # 2, p. 436 - 443
[2] Canadian Journal of Chemistry, 1985, vol. 63, p. 153 - 162
[3] Canadian Journal of Chemistry, 1985, vol. 63, p. 153 - 162
[4] Organic Letters, 2005, vol. 7, # 3, p. 427 - 430
[5] Synlett, 2006, # 13, p. 2104 - 2108 |
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