4-Bromo-1H-pyrrole-2-carboxamide

Base Information

• Chemical Name: 4-Bromo-1H-pyrrole-2-carboxamide
• CAS No.: 196106-96-4
• Molecular Formula: C₅H₅BrN₂O
• Molecular Weight: 189.011
• Hs Code.: 2933990090
• European Community (EC) Number: 899-663-4
• DSSTox Substance ID: DTXSID00571806
• Nikkaji Number: J892.570D
• Wikidata: Q82459983
• Mol file: 196106-96-4.mol

Synonyms:4-BROMO-1H-PYRROLE-2-CARBOXAMIDE;196106-96-4;1H-Pyrrole-2-carboxamide, 4-bromo-;SCHEMBL15228733;DTXSID00571806;ZDOSNCDGCSOFIE-UHFFFAOYSA-N;WHA10696;MFCD11504939;AKOS009076870;DS-3452;SB62058;CS-0044147;C73743;J-012681

Chemical Property of 4-Bromo-1H-pyrrole-2-carboxamide

Chemical Property:

• PSA: 58.88000
• LogP: 1.57640
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 187.95853
• Heavy Atom Count: 9
• Complexity: 128

Purity/Quality:

97% ^*data from raw suppliers

4-Bromo-1H-pyrrole-2-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC=C1Br)C(=O)N

Technology Process of 4-Bromo-1H-pyrrole-2-carboxamide

There total 3 articles about 4-Bromo-1H-pyrrole-2-carboxamide 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: 98.0%

1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanone (72652-32-5) → 4-bromo-1H-pyrrole-2-carboxamide (196106-96-4)

Guidance literature:

With ammonia; In water; acetonitrile; at 20 ℃; for 24h;

DOI:10.1021/ol2029993

Reference yield: 9.0%

pyrrole-2-carboxamide (4551-72-8) → 5-bromo-1H-pyrrole-2-carboxamide (17543-94-1) + 4,5-dibromopyrrole-2-carbonamide (34649-20-2) + 4-bromo-1H-pyrrole-2-carboxamide (196106-96-4)

Guidance literature:

With 4-morpholineethanesulfonic acid; V_BrPO(AnI) bromoperoxidase; dihydrogen peroxide; sodium bromide; In water; tert-butyl alcohol; at 20 ℃; pH=6.2; Overall yield = 51 %;

DOI:10.1039/c3dt51582f

Reference yield:

1H-pyrrole-2-carbonitrile (4513-94-4) → 5-bromo-1H-pyrrole-2-carboxamide (17543-94-1) + 4,5-dibromopyrrole-2-carbonamide (34649-20-2) + 4-bromo-1H-pyrrole-2-carboxamide (196106-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: dihydrogen peroxide; potassium carbonate / dimethyl sulfoxide / 1.5 h / 0 - 20 °C

2: Ascophyllum nodosum vanadate(V)-dependent bromoperoxidase I; dihydrogen peroxide; sodium bromide / water; tert-butyl alcohol / 72 h / 23 °C / pH 6.2 / aq. buffer; Enzymatic reaction

With Ascophyllum nodosum vanadate(V)-dependent bromoperoxidase I; dihydrogen peroxide; potassium carbonate; sodium bromide; In water; dimethyl sulfoxide; tert-butyl alcohol;

DOI:10.1016/j.tet.2011.04.010

upstream raw materials:

1H-pyrrole-2-carbonitrile

pyrrole-2-carboxamide

1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanone

Refernces

• 1、 Troegel, Benjamin,Lindel, Thomas. "Microwave-assisted fluorination of 2-acylpyrroles: Synthesis of fluorohymenidin". supporting information; experimental part. p. 468 - 471. Retrieved 2012/03/26.