5-Bromo-2,2-dimethylchroman

Base Information

• Chemical Name: 5-Bromo-2,2-dimethylchroman
• CAS No.: 263903-19-1
• Molecular Formula: C11H13BrO
• Molecular Weight: 241.12432
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID60697410
• Wikidata: Q82627304
• Mol file: 263903-19-1.mol

Synonyms:5-Bromo-2,2-dimethylchroman;263903-19-1;5-bromo-2,2-dimethyl-3,4-dihydrochromene;5-bromo-2,2-dimethylchromane;DTXSID60697410;5-Bromo-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran

Chemical Property of 5-Bromo-2,2-dimethylchroman

Chemical Property:

• PSA: 9.23000
• LogP: 3.55270
• Storage Temp.: 2-8°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 240.01498
• Heavy Atom Count: 13
• Complexity: 191

Purity/Quality:

97% ^*data from raw suppliers

5-bromo-2,2-dimethyl-3,4-dihydro-2H-chromene 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CCC2=C(O1)C=CC=C2Br)C

Technology Process of 5-Bromo-2,2-dimethylchroman

There total 8 articles about 5-Bromo-2,2-dimethylchroman 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: 92.0%

5-bromo-2,2-dimethyl-2H-chromene (310404-32-1) → 5-bromo-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran (263903-19-1)

Guidance literature:

With hydrogen; Rh/Al₂O₃; In ethanol; at 20 ℃; for 2h;

DOI:10.1021/ja0568852

Reference yield:

2-(2-methoxy-phenyl)-1-methyl-imidazolidine → 5-bromo-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran (263903-19-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tert-BuLi / diethyl ether; pentane / 7 h / -20 °C

1.2: (BrCl₂C)2 / diethyl ether / -78 - 20 °C

2.1: 94 percent / BBr₃ / CH₂Cl₂ / 0.5 h / 20 °C

3.1: t-BuLi / diethyl ether / -78 - 20 °C

3.2: TsOH / toluene / 20 - 50 °C

4.1: 92 percent / H₂ / Rh/Al₂O₃ / ethanol / 2 h / 20 °C

With hydrogen; tert.-butyl lithium; boron tribromide; Rh/Al₂O₃; In diethyl ether; ethanol; dichloromethane; pentane;

DOI:10.1021/ja0568852

Reference yield:

2,2-dimethyl-2H-chromen-5-yl trifluoromethanesulfonate (910822-52-5) → 5-bromo-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran (263903-19-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hexamethylditin; bis(diphenylphosphinyl)ferrocene; LiCl / Pd(PPh₃)4 / dioxane / 72 h / 110 °C

1.2: 75 percent / NBS / tetrahydrofuran / 1 h / 20 °C

2.1: 92 percent / H₂ / Rh/Al₂O₃ / ethanol / 2 h / 20 °C

With bis(diphenylphosphinyl)ferrocene; hydrogen; hexamethyldistannane; lithium chloride; Rh/Al₂O₃; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; ethanol;

DOI:10.1021/ja0568852

upstream raw materials:

5-bromo-2,2-dimethyl-2H-chromene

2,2-dimethyl-2H-chromen-5-yl trifluoromethanesulfonate

Δ³-2,2-dimethyl-5-hydroxy-benzopyran

2-bromo-6-hydroxybenzaldehyde