6-Bromo-2,2-dimethyl-2H-chromene-5,8-dione

Base Information

• Chemical Name: 6-Bromo-2,2-dimethyl-2H-chromene-5,8-dione
• CAS No.: 557757-34-3
• Molecular Formula: C11H9BrO3
• Molecular Weight: 269.095
• DSSTox Substance ID: DTXSID60464482
• Nikkaji Number: J1.889.402E
• Wikidata: Q82289809
• Mol file: 557757-34-3.mol

Synonyms:6-Bromo-2,2-dimethyl-2H-chromene-5,8-dione;557757-34-3;6-BROMO-2,2-DIMETHYLCHROMENE-5,8-DIONE;DTXSID60464482;AB23808;CS-0531349

Chemical Property of 6-Bromo-2,2-dimethyl-2H-chromene-5,8-dione

Chemical Property:

• Vapor Pressure: 3.38E-05mmHg at 25°C
• Boiling Point: 354.3oC at 760 mmHg
• Flash Point: 168.1oC
• PSA: 43.37000
• Density: 1.61g/cm3
• LogP: 2.03610
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 267.97351
• Heavy Atom Count: 15
• Complexity: 453

Purity/Quality:

98%min ^*data from raw suppliers

6-BROMO-2,2-DIMETHYL-2H-CHROMENE-5,8-DIONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C=CC2=C(O1)C(=O)C=C(C2=O)Br)C

Technology Process of 6-Bromo-2,2-dimethyl-2H-chromene-5,8-dione

There total 1 articles about 6-Bromo-2,2-dimethyl-2H-chromene-5,8-dione 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:

4-bromo-2,5-dimethoxybenzaldehyde (31558-41-5) → 6-bromo-2,2-dimethyl-2H-chromene-5,8-dione (557757-34-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: m-CPBA / CH₂Cl₂ / 4 h / 25 °C

1.2: 99 percent / aq. NaOH / methanol / 1 h / 25 °C

2.1: 84 percent / DBU; CuCl₂ / acetonitrile / 6 h / 0 °C

3.1: cerium ammonium nitrate / acetonitrile; H₂O / 0.5 h / 25 °C

4.1: PhCH₃ / 0.5 h / 40 °C

With ammonium cerium(IV) nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; toluene; copper dichloride; In dichloromethane; water; acetonitrile; 1.1: Baeyer-Villiger oxidation / 4.1: Claisen cyclization;

DOI:10.1016/S0040-4039(03)00629-4

Reference yield:

6-bromo-2,2-dimethyl-2H-chromene-5,8-dione (557757-34-3) → 6-[2,5-bis-(tert-butyl-dimethyl-silanyloxy)-benzoyl]-2,2-dimethyl-2H-chromene-5,8-dione (557757-38-7)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄; AcOH / tetrahydrofuran / 0.5 h / 25 °C

2: DIPEA / CH₂Cl₂ / 2 h / 0 °C

3: 52 percent / n-BuLi / diethyl ether / 1 h / -78 - 0 °C

4: 66 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

5: 70 percent / ZnBr₂ / CH₂Cl₂ / 4 h / 25 °C

6: 31 percent / IBX / CHCl₃; dimethylformamide / 4 h / 25 °C

With sodium tetrahydroborate; n-butyllithium; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; zinc dibromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(03)00629-4

Reference yield:

6-bromo-2,2-dimethyl-2H-chromene-5,8-dione (557757-34-3) → [2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)-methanone (557757-37-6)

Guidance literature:

Multi-step reaction with 5 steps

1: NaBH₄; AcOH / tetrahydrofuran / 0.5 h / 25 °C

2: DIPEA / CH₂Cl₂ / 2 h / 0 °C

3: 52 percent / n-BuLi / diethyl ether / 1 h / -78 - 0 °C

4: 66 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

5: 70 percent / ZnBr₂ / CH₂Cl₂ / 4 h / 25 °C

With sodium tetrahydroborate; n-butyllithium; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; zinc dibromide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(03)00629-4

upstream raw materials:

4-bromo-2,5-dimethoxybenzaldehyde

Downstream raw materials:

6-(2,5-dihydroxy-benzoyl)-2,2-dimethyl-2H-chromene-5,8-dione

6-[2,5-bis-(tert-butyl-dimethyl-silanyloxy)-benzoyl]-2,2-dimethyl-2H-chromene-5,8-dione

[2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)-methanone

[2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-[5,8-bis-(2-methoxy-ethoxymethoxy)-2,2-dimethyl-2H-chromen-6-yl]-methanol

Refernces