tert-butyl acetate

• ChemBase ID: 103086
• Molecular Formular: C6H12O2
• Molecular Mass: 116.15828
• Monoisotopic Mass: 116.08372962
• SMILES: CC(=O)OC(C)(C)C
• Canonical SMILES: CC(=O)OC(C)(C)C
• InChI: InChI=1S/C6H12O2/c1-5(7)8-6(2,3)4/h1-4H3
• InChIKey: WMOVHXAZOJBABW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl acetate
• IUPAC Traditional name: tert-butyl acetate
• Synonyms: tert-BUTYL ACETATE; Acetic acid tert-butyl ester; t-BUTYLACETATE; acetic acid tert-butyl estert-butyl acetate; TBAc; tert-Butyl acetate; 乙酸叔丁酯

Database IDs

• CAS Number: 540-88-5
• EC Number: 208-760-7
• MDL Number: MFCD00008807
• Beilstein Number: 1699506
• Merck Index: 141537
• PubChem SID: 24892097; 162091214; 24869333
• PubChem CID: 10908
• Chemspider ID: 10446
• Wikipedia Title: Tert-Butyl_acetate

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.97650796
• LogD (pH = 7.4): 0.97650796
• Log P: 0.97650796
• Molar Refractivity: 31.2184 cm^3
• Polarizability: 12.552849 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.8 wt% at 22 °C in water
• Apperance: Colourless liquid with fruity odour
• Melting Point: -62°C
• Boiling Point: 94-96°C; 97-98 °C(lit.); 97–98 °C (370–371 K, 207–208 °F); 98 °C (208 °F); 98°C
• Flash Point: 16 °C; 4°C(39°F); 60.8 °F
• Density: 0.863; 0.866 g/cm^3, liquid; 0.866 g/mL at 20 °C(lit.); 0.867 at 20 °C (water = 1); 0.867 g/ml
• Refractive Index: 1.3865; n20/D 1.386(lit.); n20/D 1.387
• Vapor Density: 4.0 (air = 1)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: AF7400000
• European Hazard Symbols: Flammable (F); Nature polluting (N)
• UN Number: 1123; 3082; UN1123
• German water hazard class: 1
• Hazard Class: 3; 9
• Packing Group: 2; II; III
• Australian Hazchem: 2X
• Risk Statements: 11-66; R:11-58-66; R:58-11-66
• Safety Statements: 16-23-25-29-33; S:16-23-25-29-33-61
• EU Hazard Identification Number: 10
• Emergency Response Guidebook(ERG) Number: 171
• TSCA Listed: 是
• GHS Pictograms: GHS02
• GHS Signal Word: Danger
• Main Hazard: Flammable
• GHS Hazard statements: H225
• GHS Precautionary statements: P210; P210-P241-P280-P303+P361+P353-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1123 3/PG 2
• Supplemental Hazard Statements: Repeated exposure may cause skin dryness or cracking.

Product Information

• Purity: ≥99%; ≥99.0% (GC); 99%
• Grade: purum
• Linear Formula: CH3COOC(CH3)3

DETAILS

MP Biomedicals - 02150536

Reagent to convert N-protected amino acids into t-butyl esters that are resistant to ammonolysis, hydrolysis, and hydrogenolysis.

MP Biomedicals - 05211677

MP Biomedicals Rare Chemical collection

Sigma Aldrich - B88209

Packaging
5, 100, 500 mL in glass bottle

Sigma Aldrich - 45880

Other Notes
Reagent used for the synthesis of tert-butyl esters1,2

REFERENCES

• Amino acids can be protected as their t-butyl esters, without prior N-protection, in the presence of perchloric acid in 1,4-dioxane: Liebigs Ann. Chem., 646, 134 (1961); or tosic acid and excess sulfuric acid: Org. Prep. Proced. Int., 18, 13 (1986). See Appendix 6. Mild transesterification of, e.g. methyl esters to the t-butyl analogues in the presence of catalytic KO-t-Bu has been reported: J. Org. Chem., 62, 8240 (1997).
• For lithiation with LDA and addition to acetone in quantitative yield, see: J. Am. Chem. Soc., 95, 3050 (1973). Coupling of the lithio-derivative with esters gives high yields of t-butyl 3-oxoalkanoates: Synthesis, 45 (1985).