3-Bromo-5,6-dihydro-4H-pyrrolo[1,2-B]pyrazole

Base Information

• Chemical Name: 3-Bromo-5,6-dihydro-4H-pyrrolo[1,2-B]pyrazole
• CAS No.: 174790-35-3
• Molecular Formula: C6H7BrN2
• Molecular Weight: 187.03700
• European Community (EC) Number: 868-556-4
• DSSTox Substance ID: DTXSID701252219
• Nikkaji Number: J3.223.332E
• Mol file: 174790-35-3.mol

Synonyms:3-BROMO-5,6-DIHYDRO-4H-PYRROLO[1,2-B]PYRAZOLE;174790-35-3;3-BROMO-4H,5H,6H-PYRROLO[1,2-B]PYRAZOLE;4H-PYRROLO[1,2-B]PYRAZOLE, 3-BROMO-5,6-DIHYDRO-;MFCD18250428;3-Bromo-5,6- dihydro-4H-pyrrolo[1,2-b]pyrazole;SCHEMBL14061688;ASLSBGAOXZIHHP-UHFFFAOYSA-N;DTXSID701252219;AMY21169;ZGA79035;AKOS023559743;AB72973;AS-67283;SY272038;CS-0054995;C73342;EN300-173162;A855942

Chemical Property of 3-Bromo-5,6-dihydro-4H-pyrrolo[1,2-B]pyrazole

Chemical Property:

• Appearance/Colour: No Data Available
• Melting Point: No Data Available
• Boiling Point: No Data Available
• PSA: 17.82000
• LogP: 1.59180
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 185.97926
• Heavy Atom Count: 9
• Complexity: 118

Purity/Quality:

97% ^*data from raw suppliers

3-Bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C=NN2C1)Br
• Uses: 3-Bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole is used in the preparation of withasomnine molecules, pyrazole alkaloids, for their application towards antiinflammatory compounds and analgesics.

Technology Process of 3-Bromo-5,6-dihydro-4H-pyrrolo[1,2-B]pyrazole

There total 7 articles about 3-Bromo-5,6-dihydro-4H-pyrrolo[1,2-B]pyrazole 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: 87.0%

5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole (107862-65-7) → 3-bromo-5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole (174790-35-3)

Guidance literature:

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.3987/COM-17-13772

Reference yield:

3-(3-chloropropyl)-1H-pyrazole (174790-34-2) → 3-bromo-5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole (174790-35-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 38 percent / potassium hydroxide / aq. propan-2-ol / 4 h / Heating

2: 75 percent / bromine, sodium acetate / aq. acetic acid / 0 °C

With potassium hydroxide; bromine; sodium acetate; In acetic acid; isopropyl alcohol;

DOI:10.1016/0040-4039(95)02313-5

Reference yield:

1-bromo-6-chlorohexan-3-one → 3-bromo-5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole (174790-35-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / diethyl ether / 3 h / 20 °C / Inert atmosphere

2.1: bromine; potassium bromide / isopropyl alcohol; water / 0 - 20 °C / Inert atmosphere

2.2: 12 h

3.1: potassium hydroxide / isopropyl alcohol; water / 4 h / Reflux

4.1: N-Bromosuccinimide / chloroform / 0.08 h / 20 °C / Inert atmosphere

With N-Bromosuccinimide; bromine; triethylamine; potassium bromide; potassium hydroxide; In diethyl ether; chloroform; water; isopropyl alcohol;

DOI:10.1016/j.tet.2013.06.009

upstream raw materials:

5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole

3-(3-chloropropyl)-1H-pyrazole

6-chlorohexa-1-en-3-one

1,2-dibromo-6-chlorohexan-3-one

Downstream raw materials:

3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde

3-(4-chlorophenyl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

withasomnine