3,4-Bis(bromomethyl)-1-hydroxy-2,2,5,5-tetramethylpyrrole

Base Information

• Chemical Name: 3,4-Bis(bromomethyl)-1-hydroxy-2,2,5,5-tetramethylpyrrole
• CAS No.: 229621-20-9
• Molecular Formula: C10H16 Br2 N O
• Molecular Weight: 326.051
• DSSTox Substance ID: DTXSID30618935
• Wikidata: Q82521707
• Mol file: 229621-20-9.mol

Synonyms:J-014921

Chemical Property of 3,4-Bis(bromomethyl)-1-hydroxy-2,2,5,5-tetramethylpyrrole

Chemical Property:

• Melting Point: 80-810C
• PSA: 3.24000
• LogP: 3.22900
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 326.96564
• Heavy Atom Count: 14
• Complexity: 245

Purity/Quality:

99% ^*data from raw suppliers

3,4-Bis(bromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxyRadical ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=C(C(N1O)(C)C)CBr)CBr)C

Technology Process of 3,4-Bis(bromomethyl)-1-hydroxy-2,2,5,5-tetramethylpyrrole

There total 6 articles about 3,4-Bis(bromomethyl)-1-hydroxy-2,2,5,5-tetramethylpyrrole 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:

trans-3-methoxycarbonyl-2,2,5,5-tetramethyl-4-nitromethylpyrrolidin-1-oxyl (119580-75-5) → 3,4-Bis(dibromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxyl radical (229621-20-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) KOH, 2.) KMnO₄, MgSO₄ / 1.) MeOH, 0 deg C, 15 min, 2.) MeOH, H₂O, 0 deg C, 2 h

2: 80 percent / NaBH₄ / ethanol / 0.5 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

4: NaI / tetrahydrofuran / 48 h / Heating

5: 82 percent / NaOH, H₂O / ethanol / 0.5 h / 78 °C

6: 1.) HCl, 2.) Br₂ / 1.) EtOH, 78 deg C, 30 min, 2.) CHCl₃, 61 deg C, 30 min

With hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; potassium permanganate; water; bromine; magnesium sulfate; triethylamine; sodium iodide; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1055/s-1999-3502

Reference yield:

trans-4-Formyl-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidin-1-yloxyl radical (229621-04-9) → 3,4-Bis(dibromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxyl radical (229621-20-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / NaBH₄ / ethanol / 0.5 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

3: NaI / tetrahydrofuran / 48 h / Heating

4: 82 percent / NaOH, H₂O / ethanol / 0.5 h / 78 °C

5: 1.) HCl, 2.) Br₂ / 1.) EtOH, 78 deg C, 30 min, 2.) CHCl₃, 61 deg C, 30 min

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; water; bromine; triethylamine; sodium iodide; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1055/s-1999-3502

Reference yield:

trans-3,4-Bis(hydroxymethyl)-2,2,5,5-tetramethylpyrrolidin-1-yloxyl radical (229621-07-2) → 3,4-Bis(dibromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxyl radical (229621-20-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

2: NaI / tetrahydrofuran / 48 h / Heating

3: 82 percent / NaOH, H₂O / ethanol / 0.5 h / 78 °C

4: 1.) HCl, 2.) Br₂ / 1.) EtOH, 78 deg C, 30 min, 2.) CHCl₃, 61 deg C, 30 min

With hydrogenchloride; sodium hydroxide; water; bromine; triethylamine; sodium iodide; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1055/s-1999-3502

upstream raw materials:

3,4-Bis(methylene)-2,2,5,5-tetramethylpyrrolidin-1-yloxyl radical

trans-3-methoxycarbonyl-2,2,5,5-tetramethyl-4-nitromethylpyrrolidin-1-oxyl

trans-4-Formyl-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidin-1-yloxyl radical

trans-3,4-Bis(hydroxymethyl)-2,2,5,5-tetramethylpyrrolidin-1-yloxyl radical

Downstream raw materials:

2,5-Dihydro-3,4-bis(methanesulfonylthiomethyl)-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxyl radical

1,3-Dihydro-1,1,3,3-tetramethyl-5-toluenesulfonyl-2H,5H-pyrrolo[3,4-c]pyrrol-2-yloxyl radical

C₁₉H₃₁N₂O₅

C₂₇H₃₂BrN₂O₃

Refernces