1006-26-4

Basic information

• Product Name: 3,4-Diethyl-1H-pyrrole-2-carbaldehyde
• Synonyms: 3,4-Diethyl-1H-pyrrole-2-carbaldehyde;2-Formyl-3,4-diethylpyrrole;3,4-Diethyl-2-formylpyrrole;3,4-Diethylpyrrole-2-carbaldehyde;3,4-Diethylpyrrole-2-carboxaldehyde;NSC 620163
• CAS NO: 1006-26-4
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.20562
• Mol File: 1006-26-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 42-45℃
• Boiling Point: 244℃
• Flash Point: 107℃
• Appearance: /
• Density: 1.042
• CAS DataBase Reference: 3,4-Diethyl-1H-pyrrole-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Diethyl-1H-pyrrole-2-carbaldehyde(1006-26-4)
• EPA Substance Registry System: 3,4-Diethyl-1H-pyrrole-2-carbaldehyde(1006-26-4)

Safety Data

• Hazardous Substances Data: 1006-26-4(Hazardous Substances Data)

Usage

General Description

3,4-Diethyl-1H-pyrrole-2-carbaldehyde is a chemical compound that belongs to the class of pyrrole derivatives. It is a yellow liquid with a characteristic odor and is commonly used as an intermediate in the synthesis of various pharmaceuticals and agricultural chemicals. 3,4-Diethyl-1H-pyrrole-2-carbaldehyde is also known for its use as a flavoring agent in the food and beverage industry. 3,4-Diethyl-1H-pyrrole-2-carbaldehyde is considered to be a versatile building block in organic synthesis due to its reactivity and ability to undergo various chemical reactions. It is important to handle this compound with caution due to its potential hazards and toxicity.

Upstream product

• 64276-60-4 3-acetyl-4-ethylpyrrole 
• 763-93-9 hex-3-en-2-one 
• 16200-52-5 3,4-diethyl-1H-pyrrole 
• 127-09-3 sodium acetate 
• 97336-41-9 ethyl 3,4-diethyl-1H-pyrrole-2-carboxylate 
• 3750-83-2 4-acetoxy-3-nitrohexane 
• 5342-71-2 4-Nitrohexan-3-ol 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 144586-89-0 5-ethynyl-3,4-diethyl-2-formylpyrrole 
• 35050-46-5 octaethylbiliverdin 
• 2683-82-1 2,3,7,8,12,13,17,18-octaethyl-porphyrin 

Relevant articles and documents

Dipyrrolylnaphthyridine-based Schiff-base cryptands and their selective gas adsorption properties

Presented here is the synthesis of three new Schiff-base cryptands, 4-6. Dynamic covalent imine bond formation via the condensation of a dialdehyde (7 or 8) with two different tris-amines allowed for the preparation of 4-6 in 84%, 80% and 83% yield, respectively. These systems were characterized by NMR spectroscopy, mass spectra, and, in the case of 5, single crystal X-ray diffraction analysis. These cages act as selective CO2 gas adsorbing materials in the solid state.

Octaethyl-21H,24H-bilin-1,19-dione (Octaethylbilatriene-abc)

A synthesis of the octaethylbilindione (1) from 3,4-diethylpyrrole is described which is suitable for the preparation of this valuable model compound in quantity.

Regioselective substituent effects upon the synthesis of dipyrrins from 2-formyl pyrroles

The synthesis of symmetric α-free meso-H-dipyrrin hydrobromides from 5-H-2-formyl pyrroles was investigated. The self-condensation produces regioisomeric dipyrrins through adoption of two mechanistic pathways. The key difference between the two pathways lies in which position of the pyrrole directs nucleophilic attack. Through a systematic study involving various substituted and (or) isotopically labelled 5-H-2-formyl pyrroles, we herein provide evidence to suggest that not only do two mechanistic pathways exist, but the steric bulk of the substituent adjacent to the 5-unsubstituted position influences which pathway dominates.

Expanded scope of synthetic bacteriochlorins via improved acid catalysis conditions and diverse dihydrodipyrrin-acetals

(Chemical Equation Presented) Bacteriochlorins are attractive candidates for a wide variety of photochemical studies owing to their strong absorption in the near-infrared spectral region. The prior acid-catalysis conditions [BF 3 · O(Et)2 in CH3CN at room temperature] for self-condensation of a dihydrodipyrrin-acetal (bearing a geminal dimethyl group in the pyrroline ring) typically afforded a mixture of three macrocycles: the expected 5-methoxybacteriochlorin (MeOBC-type), a 5-unsubstituted bacteriochlorin (HBC-type), and a free base B,D-tetradehydrocorrin (TDC-type). Here, a broad survey of >20 acids identified four promising acid catalysis conditions of which TMSOTf/2,6-di-tert-butylpyridine in CH2Cl 2 at room temperature was most attractive owing to formation of the 5-methoxybacteriochlorin as the sole macrocycle regardless of the pyrrolic substituents in the dihydrodipyrrin-acetal (electron-withdrawing, electron-donating, or no substituent). Eleven new dihydrodipyrrin-acetals were prepared following standard routes. Application of the new acid catalysis conditions has afforded diverse bacteriochlorins (e.g., bearing alkyl/ester, aryl/ester, diester, and no substituents) in a few days from commercially available starting materials. Consideration of the synthetic steps and yields for formation of the dihydrodipyrrin-acetal and bacteriochlorin underpins evaluation of synthetic plans for early installation of bacteriochlorin substituents via the dihydrodipyrrin-acetal versus late installation via derivatization of β-bromobacteriochlorins. Treatment of the 5-methoxybacteriochlorins with NBS gave regioselective 15-bromination when no pyrrolic substituents were present or when each pyrrole contained two substituents; on the other hand, the presence of a β-ethoxycarbonyl group caused loss of regioselectivity. The 15 new bacteriochlorins prepared herein exhibit a long-wavelength absorption band in the range 707-759 nm, providing tunable access to the near-infrared region. Taken together, this study expands the scope of available bacteriochlorins for fundamental studies and diverse applications. 2010 American Chemical Society.