2-Acetoxyisobutyryl bromide

Base Information

• Chemical Name: 2-Acetoxyisobutyryl bromide
• CAS No.: 40635-67-4
• Molecular Formula: C6H9BrO3
• Molecular Weight: 209.04
• Hs Code.: 2918.90
• European Community (EC) Number: 629-266-1
• DSSTox Substance ID: DTXSID50369215
• Nikkaji Number: J319.662C
• Wikidata: Q72434372
• Mol file: 40635-67-4.mol

Synonyms:40635-67-4;2-Acetoxyisobutyryl bromide;2-Acetoxy-2-methylpropionyl bromide;1-Bromocarbonyl-1-methylethyl acetate;(1-bromo-2-methyl-1-oxopropan-2-yl) acetate;2-Acetoxyisobutyrylbromide;alpha-Acetoxyisobutyryl bromide;1-BROMO-2-METHYL-1-OXOPROPAN-2-YL ACETATE;Propanoyl bromide, 2-(acetyloxy)-2-methyl-;2-acetoxy-2-methylpropanyl bromide;A-ACETOXYISOBUTYRYL BROMIDE;MFCD00040923;SCHEMBL317990;2-Acetoxyisobutyric acid bromide;DTXSID50369215;OOKAXSHFTDPZHP-UHFFFAOYSA-N;AKOS015900486;JC10156;AS-77140;1-Bromocarbonyl-1-methylethyl acetate, 96%;FT-0622106;(2-bromo-1,1-dimethyl-2-oxo-ethyl) acetate;A825208;Q-200615

Chemical Property of 2-Acetoxyisobutyryl bromide

Chemical Property:

• Appearance/Colour: clear to light yellow liquid
• Vapor Pressure: 0.542mmHg at 25°C
• Refractive Index: n20/D 1.457
• Boiling Point: 190.4 °C at 760 mmHg
• Flash Point: 72.2 °C
• PSA: 43.37000
• Density: 1.478 g/cm³
• LogP: 1.24960
• 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: 207.97351
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

98%, ^*data from raw suppliers

2-AcetoxyisobutyrylBromide ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC(C)(C)C(=O)Br
• Uses: 1-Bromocarbonyl-1-methylethyl acetate (α-Acetoxyisobutyryl bromide) may be used:in the chemoenzymatic synthesis of (1R,2S)-1,2-epoxy-1,2-dihydroacridine (acridine 1,2-oxide)in the synthesis of protected 3′-deoxyadenosine and 3′-deoxyguanosine as 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.

Technology Process of 2-Acetoxyisobutyryl bromide

There total 2 articles about 2-Acetoxyisobutyryl bromide 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: 52.0%

2-acetoxy-2-methylpropanoyl chloride (40635-66-3) → acetoxyisobutyryl bromide (40635-67-4)

Guidance literature:

With lithium bromide; In ethyl acetate; at 80 ℃; for 2h;

DOI:10.1002/(SICI)1522-2675(19990407)82:4<597::AID-HLCA597>3.0.CO;2-V

Reference yield:

O-acetyl-α-hydroxyisobutyric acid (15805-98-8) → acetoxyisobutyryl bromide (40635-67-4)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 2 h / Heating

2: 52 percent / LiBr / ethyl acetate / 2 h / 80 °C

With thionyl chloride; lithium bromide; In ethyl acetate;

DOI:10.1002/(SICI)1522-2675(19990407)82:4<597::AID-HLCA597>3.0.CO;2-V

Reference yield: 90.0%

acetoxyisobutyryl bromide (40635-67-4) + cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohex-3-ene (174817-06-2) → (+)-(1S,2R)-1-acetoxy-2,3-dibromocyclohex-3-ene (176166-10-2)

Guidance literature:

DOI:10.1039/cc9960000045

upstream raw materials:

2-acetoxy-2-methylpropanoyl chloride

O-acetyl-α-hydroxyisobutyric acid

Downstream raw materials:

(+)-methyl (3R,4S,5R)-3-bromo-4-acetoxy-5-hydroxy-1-cyclohexene-1-carboxylate

<(+/-)-(1α,2β,4aα,11bα)>-1,2,4a,11b-Tetrahydro-1-acetoxy-2-bromo-7-(phenylmethoxy)-6H-<1,3>benzodioxolo<5,6-c><1>benzopyran-6-one

<(+/-)-(1α,4α,4aα,11bα)>-1,4,4a,11b-Tetrahydro-1-acetoxy-4-bromo-7-(phenylmethoxy)-6H-<1,3>benzodioxolo<5,6-c><1>benzopyran-6-one

(4S,5S,1'R,2'S)-5-<1-acetoxy-2-<<(benzyloxy)carbonyl>amino>-3-phenylpropyl>-4-benzyloxazolidin-2-one

Refernces

• 1、 Russell,Greenberg,Moffatt. "Reactions of 2-acyloxyisobutyryl halides with nucleosides. II. Reactions of adenosine.". . p. 4025 - 4030. Retrieved 2007/10/04.