3-Bromodihydro-3-methylfuran-2(3H)-one

Base Information

• Chemical Name: 3-Bromodihydro-3-methylfuran-2(3H)-one
• CAS No.: 33693-67-3
• Molecular Formula: C5H7 Br O2
• Molecular Weight: 179.013
• Hs Code.: 2932209090
• European Community (EC) Number: 251-639-9
• NSC Number: 238959
• DSSTox Substance ID: DTXSID501301395
• Nikkaji Number: J308.521J
• Mol file: 33693-67-3.mol

Synonyms:33693-67-3;alpha-Bromo-alpha-methyl-gamma-butyrolactone;3-bromo-3-methyloxolan-2-one;3-Bromodihydro-3-methylfuran-2(3H)-one;EINECS 251-639-9;3-bromo-3-methyldihydrofuran-2(3h)-one;NSC238959;SCHEMBL1788143;3-Bromo-3-methyl-2-butyrolactone;DTXSID501301395;MFCD00191853;AKOS015916376;3-Bromo-3-methyltetrahydrofuran-2-one;NSC 238959;NSC-238959;alpha -Bromo- alpha -methyl- gamma -butyrolactone;alpha-Bromo-alpha-methyl-gamma-butyrolactone, 96%;J-019297

Chemical Property of 3-Bromodihydro-3-methylfuran-2(3H)-one

Chemical Property:

• Vapor Pressure: 0.0293mmHg at 25°C
• Refractive Index: n20/D 1.494(lit.)
• Boiling Point: 245.1°Cat760mmHg
• Flash Point: 102°C
• PSA: 26.30000
• Density: 1.641g/cm³
• LogP: 1.08690
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 177.96294
• Heavy Atom Count: 8
• Complexity: 124

Purity/Quality:

99% ^*data from raw suppliers

α-Bromo-α-methyl-γ-butyrolactone ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CCOC1=O)Br

Technology Process of 3-Bromodihydro-3-methylfuran-2(3H)-one

There total 4 articles about 3-Bromodihydro-3-methylfuran-2(3H)-one 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: 81.0%

3-methyltetrahydro-2-furanone (1679-47-6) → α-bromo-α-methyl-γ-butyrolactone (33693-67-3,122040-92-0)

Guidance literature:

With phosphorus; bromine; at 80 ℃; for 3h;

DOI:10.1080/00397919108019801

Reference yield:

4,5-dihydro-3-hydroxy-3-methyl-2(3H)-furanone (1192-42-3) → α-bromo-α-methyl-γ-butyrolactone (33693-67-3,122040-92-0) + 3-methyl-5H-furan-2-one (22122-36-7)

Guidance literature:

With pyridine; phosphorus tribromide; In chloroform; at 0 ℃; for 6h; Yield given;

Reference yield:

3-(1-Ethoxy-ethoxy)-3-methyl-dihydro-furan-2-ylideneamine → α-bromo-α-methyl-γ-butyrolactone (33693-67-3,122040-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 20percent aq. H₂SO₄ / tetrahydrofuran; methanol / Ambient temperature

2: pyridine, phosphorus tribromide / CHCl₃ / 6 h / 0 °C

With pyridine; sulfuric acid; phosphorus tribromide; In tetrahydrofuran; methanol; chloroform;

upstream raw materials:

3-methyltetrahydro-2-furanone

4,5-dihydro-3-hydroxy-3-methyl-2(3H)-furanone

Downstream raw materials:

3-methyl-5H-furan-2-one

3-(4-bromo-phenylsulfanyl)-3-methyl-dihydro-furan-2-one

2-{6-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl}ethyl (3-nitrophenyl)carbamate

2-{6-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl}ethyl (3-aminophenyl)carbamate

Refernces

• 1、 Cruz-Almanza,Padilla Higareda. "A useful synthesis of 3-methyl-2(5H)-furanone". . p. 1097 - 1104. Retrieved 2007/10/02.