151051-65-9

Basic information

• Product Name: Cyclopenta[b]pyrrole, 1,4,5,6-tetrahydro-3-methyl- (9CI)
• Synonyms: Cyclopenta[b]pyrrole, 1,4,5,6-tetrahydro-3-methyl- (9CI)
• CAS NO: 151051-65-9
• Molecular Formula: C8H11N
• Molecular Weight: 121.17964
• Product Categories: PYRROLIDINE
• Mol File: 151051-65-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 28-29 °C
• Boiling Point: 236.2±9.0 °C(Predicted)
• Appearance: /
• Density: 1.071±0.06 g/cm3(Predicted)
• PKA: 18.24±0.20(Predicted)
• CAS DataBase Reference: Cyclopenta[b]pyrrole, 1,4,5,6-tetrahydro-3-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopenta[b]pyrrole, 1,4,5,6-tetrahydro-3-methyl- (9CI)(151051-65-9)
• EPA Substance Registry System: Cyclopenta[b]pyrrole, 1,4,5,6-tetrahydro-3-methyl- (9CI)(151051-65-9)

Safety Data

• Hazardous Substances Data: 151051-65-9(Hazardous Substances Data)

Upstream product

• 859936-43-9 3-methyl-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-2-carboxylic acid 
• 120-92-3 cyclopentanone 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 172907-59-4 1-(Dimethylamino)-1,4,5,6-tetrahydro-3-methylcyclopentapyrrole 
• 109839-16-9 Ethyl 3-methylcyclopentapyrrole-2-carboxylate 

Downstream Products

• 151051-66-0 3-Methylcyclopentapyrrole-2-carboxaldehyde 

Relevant articles and documents

New efficient, flexible and regioselective synthesis of 2,4-Di- and 2,3,4-trialkylated and arylated 1H-pyrroles

Starting from easily available 2-acetoxy aldehyde dimethylhydrazones rac-2, we prepared various alkyl- and aryl-substituted 1H-pyrroles 6 in good overall yield. The titanium-mediated a2-umpolung reaction of rac-2 with different acyclic and cyclic silyl enol ethers 3 leads directly or via 4-oxo hydrazones rac,anti-4 to 1-(dimethylamino)-1H-pyrroles 5. A novel method for the reductive removal of the dimethylamino group affording 1H-pyrroles 6 is presented. VCH Verlagsgesellschaft mbH, 1996.

Porphyrins with Exocyclic Rings. Part 3. A Reassessment on the Utility of Cyclopentapyrroles in the Synthesis of Porphyrin Molecular Fossils. Preparation of Three Type II Porphyrins Related to Deoxophylloerythroetioporphyrin (DPEP)

The utility of cyclopentapyrroles in porphyrin synthesis has been reinvestigated.A 6-oxocyclopentapyrrole 18 was prepared by cyclization of the propanoyl chloride sidechain of an α-unsubstituted pyrrole 17d in the presence of tin(IV) chloride.Subsequent reduction with sodium borohydride afforded the corresponding 6-hydroxy compound 10 and further acid catalyzed condensation with α-unsubstituted pyrroles 11a and 11b gave the novel 6-pyrrolylcyclopentapyrroles 22a and 22b in excellent yields.Attempts to prepare deoxophylloerythroetioporphyrin (DPEP; 2), a widespread sedimentary porphyrin molecular fossil, from these dipyrrolic intermediates using the tripyrrene-a,c-biladiene route were unsuccessful.However, the synthesis of three related meso,β-ethanoporphyrins using the MacDonald condensation was successfully carried out in moderate to good yields.Retention of an sp3 hybridized carbon bridge at the cyclopentene ring fusion site of the intermediary open chain tetrapyrroles appears to be crucial during macrocycle formation, as this diminishes the steric repulsion between the peripheral substituents and the carbocyclic ring.