113388-41-3

Basic information

• Product Name: 3-Furancarboxaldehyde, 2-nitro- (9CI)
• Synonyms: 3-Furancarboxaldehyde, 2-nitro- (9CI)
• CAS NO: 113388-41-3
• Molecular Formula: C₅H₃NO₄
• Molecular Weight: 141.08162
• Product Categories: ALDEHYDE
• Mol File: 113388-41-3.mol

Chemical Properties

• Melting Point: 81-82 °C
• Boiling Point: 265.9±25.0 °C(Predicted)
• Appearance: /
• Density: 1.473±0.06 g/cm3(Predicted)
• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• CAS DataBase Reference: 3-Furancarboxaldehyde, 2-nitro- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Furancarboxaldehyde, 2-nitro- (9CI)(113388-41-3)
• EPA Substance Registry System: 3-Furancarboxaldehyde, 2-nitro- (9CI)(113388-41-3)

Safety Data

• Hazardous Substances Data: 113388-41-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Furancarboxaldehyde, 2-nitro(9CI) is used as a key intermediate in the synthesis of 2,4-Dichlorofuro[2,3-d]pyrimidine, a furopyrimidine derivative. This derivative is utilized in the preparation of phosphoinositide 3-kinase (PI3K) inhibitors, which play a crucial role in the development and progression of various cancers. By targeting PI3K, these inhibitors can potentially halt tumor growth and improve the effectiveness of cancer treatments.

Upstream product

• 122947-92-6 3-(dibromomethyl)-2-nitrofuran 
• 113388-39-9 3-Dichlormethyl-2-nitrofuran 

Relevant articles and documents

Five membered ring analogues of nifedipine - Part 1: 2-Nitro-3-furanecarbaldehyde and 2-nitro-3-thiophenecarbaldehyde in the Hantzsch pyridine synthesis

The heterocyclic aldehydes 4 in the Hantzsch pyridine synthesis afforded dependent on the choosen variation, either the 1,4-dihydropyridines (DHP) 5, the 1,2-DHP 6 or the 1,2,3,4-tetrahydropyrimidines (THPM) 7 as main products. 5-7 were dehydrogenated to the corresponding heteroaromatics 8-10 by cerium(IV). The lactames 11 and 12 were isolated by appropiate reduction of the nitro group from 8 and 9 by neighbour group participation of an ester function. The synthesis of 12 represents for the second time the evidence of an 2-aminofurane compound. 11 and 12 were converted with phosphorous oxychloride to form the annulated chloronaphthyridines 13 and 14 which were cyclized with sodium azide to yield the tetrazoles 15 and 16. The half wave potentials E1/2 of the DHP and THPM 5-7 were determined by anodic oxidation with the rotating platinum electrode using difference pulse voltammetry (DPV). These are comparable with those of the 2-nitrophenyl analogues.

Dihalomethylation of Nitroarenes via Vicarious Nucleophilic Substitution of Hydrogen with Trihalomethyl Carbanions

Trichloro- and tribromomethyl carbanions generated by deprotonation of haloforms with potassium tert-butoxide in a THF-DMF mixture at ca. -70 deg C react with a variety of carbocyclic and heterocyclic nitroarenes according to the vicarious nucleophilic substitution scheme.The reaction provides an efficient and convenient way for the direct introduction of dihalomethyl substituents ortho and para to the nitro group, which in turn can be hydrolyzed to produce nitroaryl aldehydes.

DIRECT FORMYLATION OF NITROARENES VIA VICARIOUS NUCLEOPHILIC SUBSTITUTION OF HYDROGEN

A new method of synthesis of nitroaromatic aldehydes via vicarious nucleophilic substitution of hydrogen with dichloromethyl group and its hydrolysis is described.