2-Acetoxyisobutyryl chloride

Base Information

• Chemical Name: 2-Acetoxyisobutyryl chloride
• CAS No.: 40635-66-3
• Molecular Formula: C6H9ClO3
• Molecular Weight: 164.589
• Hs Code.: 2918.90
• European Community (EC) Number: 255-016-2
• DSSTox Substance ID: DTXSID80193641
• Nikkaji Number: J89.371D
• Wikidata: Q72517678
• Mol file: 40635-66-3.mol

Synonyms:40635-66-3;2-Acetoxyisobutyryl chloride;1-Chloro-2-methyl-1-oxopropan-2-yl acetate;1-Chlorocarbonyl-1-methylethyl acetate;Propanoyl chloride, 2-(acetyloxy)-2-methyl-;2-Acetoxy-2-methylpropionyl chloride;2-Acetoxyisobutyroyl chloride;2-Chloro-1,1-dimethyl-2-oxoethyl acetate;(1-chloro-2-methyl-1-oxopropan-2-yl) acetate;EINECS 255-016-2;MFCD00000708;(2-Chloro-1,1-dimethyl-2-oxo-ethyl) acetate;2-Acetoxy-2-methylpropanoyl chloride;SCHEMBL18253;2-Acetoxylisobutyryl Chloride;acetoxyisobutyric acid chloride;DTXSID80193641;2-(chlorocarbonyl)propan-2-yl acetate;AKOS015903737;Lactoyl chloride, 2-methyl-, acetate;JC10158;BS-17223;1-Chloro-2-methyl-1-oxopropan-2-ylacetate;FT-0622107;1-Chlorocarbonyl-1-methylethyl acetate, 95%;EN300-175607;acetic acid 1-chlorocarbonyl-1-methylethyl ester;acetic acid 1-chlorocarbonyl-1-methyl-ethyl ester;Acetic acid 2-chloro-1,1-dimethyl-2-oxoethyl ester;W-106340;F2191-0265

Chemical Property of 2-Acetoxyisobutyryl chloride

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 0.973mmHg at 25°C
• Refractive Index: n20/D 1.428(lit.)
• Boiling Point: 178.775 °C at 760 mmHg
• Flash Point: 68.333 °C
• PSA: 43.37000
• Density: 1.179 g/cm³
• LogP: 1.09350
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 164.0240218
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

97% ^*data from raw suppliers

2-Acetoxyisobutyryl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC(C)(C)C(=O)Cl
• General Description: 1-Chlorocarbonyl-1-methylethyl acetate (also known as 2-acetoxyisobutyryl chloride) is a reactive acyl halide used in the modification of nucleosides, such as adenosine and uridine, facilitating the synthesis of chloro- and acyloxy-substituted derivatives. It reacts selectively with nucleoside hydroxyl groups, leading to intermediates like 3'-O-acetyl-2'-chloro-2'-deoxyuridine or 9-(2-O-acetyl-3-chloro-3-deoxy-β-D-xylofuranosyl)adenine, which can be further processed to form anhydro or deoxy nucleosides, including Cordycepin (3'-deoxyadenosine). Its reactivity is influenced by neighboring group participation, particularly in uridine derivatives, where the uracil carbonyl group promotes cis-stereochemistry in the resulting products.

Technology Process of 2-Acetoxyisobutyryl chloride

There total 4 articles about 2-Acetoxyisobutyryl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

O-acetyl-α-hydroxyisobutyric acid (15805-98-8) → 2-acetoxy-2-methylpropanoyl chloride (40635-66-3)

Guidance literature:

With thionyl chloride;

Reference yield:

2-methyllactic acid (594-61-6) + acetyl chloride (75-36-5) → 2-acetoxy-2-methylpropanoyl chloride (40635-66-3)

Guidance literature:

Multistep reaction; (i), (ii) (COCl)2;

Reference yield:

2-methyllactic acid (594-61-6) + acetic anhydride (108-24-7) → 2-acetoxy-2-methylpropanoyl chloride (40635-66-3)

Guidance literature:

Multistep reaction; (i) H₂SO₄, (ii) SOCl₂;

upstream raw materials:

O-acetyl-α-hydroxyisobutyric acid

2-methyllactic acid

acetic anhydride

acetyl chloride

Downstream raw materials:

1-(2,5-dimethylphenyl)-1-ethanone

α-acetoxy-isobutyric acid phenyl ester

2-Acetoxy-2-methyl-propionic acid 4-nitro-phenyl ester

2-chloro-1-phenylethyl acetate

Refernces

Reactions of 2-acyloxyisobutyryl halides with nucleosides. I. Reactions of model diols and of uridine.

10.1021/ja00793a031

The research investigates the reactions of 2-acyloxyisobutyryl halides with various nucleosides, particularly focusing on adenosine and uridine. Key chemicals involved include 2-acetoxyisobutyryl chloride and the corresponding acyl bromide. For adenosine, the reaction with 2-acetoxyisobutyryl chloride in acetonitrile at 80°C yielded 9-(2-O-acetyl-3-chloro-3-deoxy-β-D-xylofuranosyl)adenine (4a) as a major product, with the 5'-hydroxy group present as a 2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl ether. This compound can be further processed to remove the dioxolanone and acetyl groups, leading to the formation of 2',3'-anhydroadenosine. The study also explores the formation of 9-(3-O-acetyl-2-chloro-2-deoxy-β-D-arabinofuranosyl)adenine (5) and the subsequent hydrogenolysis of related brominated compounds to produce 3'-deoxyadenosine (Cordycepin) and 2',3'-dideoxyadenosine. For uridine, the reaction with 2-acetoxyisobutyryl chloride leads to the formation of 3'-O-acetyl-2'-chloro-2'-deoxyuridine derivatives, with the overall cis stereochemistry influenced by the participation of the uracil ring's C2 carbonyl group.