1-bromo-2-methyl-1-oxopropan-2-yl acetate

• ChemBase ID: 145622
• Molecular Formular: C6H9BrO3
• Molecular Mass: 209.03786
• Monoisotopic Mass: 207.97350615
• SMILES: CC(=O)OC(C)(C)C(=O)Br
• Canonical SMILES: CC(=O)OC(C(=O)Br)(C)C
• InChI: InChI=1S/C6H9BrO3/c1-4(8)10-6(2,3)5(7)9/h1-3H3
• InChIKey: OOKAXSHFTDPZHP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-bromo-2-methyl-1-oxopropan-2-yl acetate
• IUPAC Traditional name: 1-bromo-2-methyl-1-oxopropan-2-yl acetate
• Synonyms: α-Acetoxyisobutyryl bromide; 2-Acetoxy-2-methylpropionyl bromide; 1-Bromocarbonyl-1-methylethyl acetate; 1-Bromocarbonyl-1-methylethyl acetate; 2-Acetoxyisobutyryl bromide; α-Acetoxy-isobutyryl bromide; α-乙酰氧基异丁酰溴; 2-乙酰氧基异丁酰溴; 乙酸 1-溴羰基-1-甲基乙酯; 2-乙酸基异丁酰溴; 2-乙酸基异丁酰溴; α-乙酰氧基异丁酰溴

Database IDs

• CAS Number: 40635-67-4
• MDL Number: MFCD00040923
• Beilstein Number: 2432585
• PubChem SID: 162239827; 24845092; 24862463
• PubChem CID: 2724715

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.0854442
• LogD (pH = 7.4): 1.0854442
• Log P: 1.0854442
• Molar Refractivity: 39.162 cm^3
• Polarizability: 15.666674 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 100-110°C/25mm; 40 °C/0.5 mmHg(lit.); 75-77 °C/12 mmHg(lit.)
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.420; 1.420 g/mL at 20 °C; 1.431 g/mL at 25 °C(lit.)
• Refractive Index: 1.4570; n20/D 1.457; n20/D 1.457(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 14-34-37
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H318-H335; H314-H335
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (AT); 96%
• Grade: purum
• Linear Formula: CH3COOC(CH3)2COBr

DETAILS

Sigma Aldrich - 364878

Application
Reagent for deoxygenation of vicinal diols, as well as in the preparation of 2′,3′-dideoxycytidine and other dideoxy and deoxynucleosides from the corresponding ribo series.1
Packaging
25, 100 g in glass bottle

Sigma Aldrich - 00853

Other Notes
Reagent for the preparation of bromo acetates from glycols; used for the synthesis of various nucleosides via the 2′,3′-bromo acetates 1,2,3; Synthesis of epoxides from glycols via a bromo acetate 4

REFERENCES

• Reagent for conversion of glycols to bromoacetates, useful in the formation of 3'-deoxynucleosides: J. Am. Chem. Soc., 95, 4016 (1973); Tetrahedron Lett., 26, 4295 (1985); 30, 6257 (1989).