Pyrrolizidine

Base Information

• Chemical Name: Pyrrolizidine
• CAS No.: 643-20-9
• Molecular Formula: C7H13 N
• Molecular Weight: 111.187
• Hs Code.: 2933990090
• European Community (EC) Number: 613-574-8
• NSC Number: 90874
• UNII: U81KWZ2JKN
• DSSTox Substance ID: DTXSID00214524
• Nikkaji Number: J110.405E
• Wikipedia: Pyrrolizidine
• Wikidata: Q1078442
• Metabolomics Workbench ID: 63589
• Mol file: 643-20-9.mol

Synonyms:PYRROLIZIDINE;643-20-9;Hexahydropyrrolizine;Hexahydro-1H-pyrrolizine;hexahydro-pyrrolizine;1H-Pyrrolizine, hexahydro-;1-Azabicyclo(3.3.0)octane;2,3,5,6,7,8-hexahydro-1H-pyrrolizine;1-Azabicyclo[3.3.0]octane;UNII-U81KWZ2JKN;U81KWZ2JKN;HSDB 4300;MFCD22200264;NSC 90874;NSC-90874;NSC-145060;Hexahydro-1H-pyrrolizine #;PYRROLIZIDINE [HSDB];SCHEMBL35282;CHEBI:64950;DTXSID00214524;NSC90874;1,2,3,4,5,6,7,8-octahydro-pyrrolizine;Q1078442

Chemical Property of Pyrrolizidine

Chemical Property:

• Vapor Pressure: 4.78mmHg at 25°C
• Refractive Index: 1.4731 (estimate)
• Boiling Point: 145.8°C at 760 mmHg
• Flash Point: 34.2°C
• PSA: 3.24000
• Density: 0.97g/cm³
• LogP: 1.18250
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 111.104799419
• Heavy Atom Count: 8
• Complexity: 80.4

Purity/Quality:

99%, ^*data from raw suppliers

Hexahydro-pyrrolizine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C1CC2CCCN2C1

Technology Process of Pyrrolizidine

There total 38 articles about Pyrrolizidine 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: 95.0%

1-Benzyloxycarbonyl-5-oxoperhydroazocine (80662-83-5) → pyrrolizidine (643-20-9)

Guidance literature:

With perchloric acid; hydrogen; palladium on activated charcoal; In methanol; for 6h; under 760.2 Torr; Ambient temperature;

DOI:10.1021/jo00347a024

Reference yield: 77.0%

1,2,5,6,7,8-hexahydro-3H-pyrrolizin-3-one (32548-24-6) → pyrrolizidine (643-20-9)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1055/s-2007-990946

Reference yield: 55.0%

2-(3-Oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester (209409-40-5) → pyrrolizidine (643-20-9)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; for 0.5h; Heating;

DOI:10.1002/jhet.5570350219

upstream raw materials:

tetrahydro-pyrrolizin-3,5-dione

1,4,7-tribromo-heptane

4-hydroxyimino-heptanedioic acid diethyl ester

dimethyl 4-nitro-1,7-heptanedioate

Downstream raw materials:

pyrrolizidinium picrate

1-(2-Hydroxyethyl)pyrrolizidinium bromide α-phenylcyclopentaneacetate

Refernces

• 1、 Kray,Reinecke. "-". . p. 225. Retrieved 1967.
• 2、 -. "ELECTROLYTE, ELECTROLYTIC SOLUTION, AND ELECTROCHEMICAL DEVICE USING THE SAME". . . Retrieved 2010/04/30.
• 3、 Zimmer, Reinhold,Collas, Markus,Czerwonka, Regina,Hain, Ute,Reissig, Hans-Ulrich. "A new access to pyrrolizidine derivatives: Ring contraction of methyl (E)-[1,2-oxazin-3-yl]propenoates". . p. 237 - 244. Retrieved 2008/12/21.