1-chloro-2-methyl-1-oxopropan-2-yl acetate

• ChemBase ID: 146698
• Molecular Formular: C6H9ClO3
• Molecular Mass: 164.58686
• Monoisotopic Mass: 164.02402183
• SMILES: CC(=O)OC(C)(C)C(=O)Cl
• Canonical SMILES: CC(=O)OC(C(=O)Cl)(C)C
• InChI: InChI=1S/C6H9ClO3/c1-4(8)10-6(2,3)5(7)9/h1-3H3
• InChIKey: RBTCRFLJLUNCLL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-chloro-2-methyl-1-oxopropan-2-yl acetate
• IUPAC Traditional name: 1-chloro-2-methyl-1-oxopropan-2-yl acetate
• Synonyms: α-Acetoxyisobutyryl chloride; 2-Acetoxy-2-methylpropionyl chloride; 1-Chlorocarbonyl-1-methylethyl acetate; 1-Chloro-2-methyl-1-oxopropan-2-yl acetate; 1-Chlorocarbonyl-1-methylethyl acetate; 2-Acetoxyisobutyryl chloride; α-Acetoxyisobutyryl chloride; 2-乙酰氧基异丁酰氯; 2-乙酸基-2-甲基丙酰氯; 2-乙酰氧基异丁酰氯

Database IDs

• CAS Number: 40635-66-3
• EC Number: 255-016-2
• MDL Number: MFCD00000708
• Beilstein Number: 507772
• PubChem SID: 162240890; 24845093; 24859568
• PubChem CID: 123496

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.9353914
• LogD (pH = 7.4): 0.9353914
• Log P: 0.9353914
• Molar Refractivity: 36.5631 cm^3
• Polarizability: 14.627106 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 55-56 °C/6 mmHg(lit.); 55-56°C/6mm
• Flash Point: 154.4 °F; 68 °C; 68°C(154°F)
• Density: 1.136 g/mL at 25 °C(lit.); 1.150; 1.150 g/mL at 20 °C
• Refractive Index: 1.4290; n20/D 1.428(lit.); n20/D 1.429

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; 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; H314-H318-H335-H227
• GHS Precautionary statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A; 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: ≥98.0% (GC); 95%; 95+%; 97%; 98%
• Grade: purum
• Linear Formula: (CH3)2C(OCOCH3)COCl

DETAILS

Sigma Aldrich - 326178

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 00855

Other Notes
Reagent used for chloro-acetylations of diols; formation of chlorinated or 2,2′-anhydro nucleosides1,2,3; stereoselective bis(chloroacetylation) of arabitol4

REFERENCES

• Reagent for conversion of cis-1,2-diols, including nucleosides, via cyclic dioxolanone intermediates, into trans-chloroalkyl acetates. The reaction is selective for the 2'-OH of uridine derivatives and converts pyrimidine nucleosides to their anhydro forms: J. Am. Chem. Soc., 95, 4016 (1973). Application to synthesis of deoxy-sugars, by dechlorination with Bu₃SnH: J. Chem. Soc., Chem. Commun., 677 (1978).
• Reaction of the chloroalkyl acetate (from a cis-glycol) with azide ion provides a route to the cis-amino alcohol: Tetrahedron Lett., 37, 2529 (1996). Compare O-Acetylsalicyloyl chloride, L00919.