55745-70-5

Basic information

• Product Name: 2,3-Dihydrobenzo[b]furan-5-carbaldehyde
• Synonyms: 2,3-DIBENZO[B]FURAN-5-CARBOXALDEHYDE;2,3-DIHYDRO-1-BENZOFURAN-5-CARBALDEHYDE;2,3-DIHYDROBENZOFURAN-5-CARBALDEHYDE;2,3-DIHYDROBENZOFURAN-5-CARBOXALDEHYDE;2,3-DIHYDROBENZO[B]FURAN-5-CARBALDEHYDE;2,3-DIHYDROBENZO[B]FURAN-5-CARBOXALDEHYDE;AKOS MSC-0772;BUTTPARK 27\04-60
• CAS NO: 55745-70-5
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.16
• EINECS: 259-788-1
• Product Categories: ALDEHYDE;Fluorobenzene;Carbonyl Compounds;Heterocycles;Heterocycle intermediates;Aromatics Compounds;Furans;Aromatics;Pharmaceutical intermediate;Benzofurans;Building Blocks;Heterocyclic Building Blocks
• Mol File: 55745-70-5.mol

Chemical Properties

• Melting Point: 191～193℃
• Boiling Point: 88-89 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.177 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00452mmHg at 25°C
• Refractive Index: n20/D 1.6000(lit.)
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 2,3-Dihydrobenzo[b]furan-5-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dihydrobenzo[b]furan-5-carbaldehyde(55745-70-5)
• EPA Substance Registry System: 2,3-Dihydrobenzo[b]furan-5-carbaldehyde(55745-70-5)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 55745-70-5(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow liquid

Uses

Hair dye composition.

InChI:InChI=1/C9H8O2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-2,5-6H,3-4H2

Upstream product

• 496-16-2 2.3-dihydrobenzofuran 
• 74-90-8 hydrogen cyanide 
• 542-88-1 bis(2-chloromethyl)ether 
• 4885-02-3 Dichloromethyl methyl ether 
• 68-12-2 N,N-dimethyl-formamide 
• 66826-78-6 5-bromo-2,3-dihydrobenzo[b]furan 
• 615-58-7 2,4-dibromophenol 
• 109-72-8 n-butyllithium 
• 76429-73-7 2,3-dihydrobenzofuran-5-carboxylic acid 
• 808750-22-3 3-bromo-4-methoxy-5-methyl benzaldehyde 
• 15174-69-3 4-hydroxy-3-methyl-benzaldehyde 
• 103529-11-9 3-bromo-4-hydroxy-5-methylbenzaldehyde 

Downstream Products

• 103262-35-7 (2,3-dihydrobenzo[b]furan-5-yl)methanol 
• 196597-65-6 ethyl (E)-3-(2,3-dihydrobenzofuran-5-yl)-2-propenoate 
• 203505-84-4 3-(2,3-dihydro-1-benzofuran-5-yl)-2-propenoic acid 
• 835885-26-2 1-(2,6-bis-benzyloxy-4-methyl-phenyl)-3-(2,3-dihydro-benzofuran-5-yl)-propenone 
• 943761-68-0 C₂₈H₂₆N₂O₃ 
• 943761-69-1 C₂₇H₂₃N₃O 
• 374926-58-6 1-(R)-1-(2,3-dihydrobenzofuran-5-yl)-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline 
• 701936-18-7 3-(2,3-dihydro-benzofuran-5-yl)-1-(2,6-dihydroxy-4-methyl-phenyl)-propan-1-one 
• 374927-33-0 2-[5-(3-benzyl-2-methyl-3H-imidazol-4-yl)pyrimidin-2-yl]-1-(2,3-dihydrobenzofuran-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline 
• 1028315-50-5 5-(2,3-dihydro-benzofuran-5-yl)-1-(4-methanesulfonyl-phenyl)-1H-imidazole 

Relevant articles and documents

Redox-Neutral Coupling between Two C(sp3)?H Bonds Enabled by 1,4-Palladium Shift for the Synthesis of Fused Heterocycles

The intramolecular coupling of two C(sp3)?H bonds to forge a C(sp3)?C(sp3) bond is enabled by 1,4-Pd shift from a trisubstituted aryl bromide. Contrary to most C(sp3)?C(sp3) cross-dehydrogenative couplings, this reaction operates under redox-neutral conditions, with the C?Br bond acting as an internal oxidant. Furthermore, it allows the coupling between two moderately acidic primary or secondary C?H bonds, which are adjacent to an oxygen or nitrogen atom on one side, and benzylic or adjacent to a carbonyl group on the other side. A variety of valuable fused heterocycles were obtained from easily accessible ortho-bromophenol and aniline precursors. The second C?H bond cleavage was successfully replaced with carbonyl insertion to generate other types of C(sp3)-C(sp3) bonds.

Pharmaceutical preparation containing copolyvidone

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Dihydrofuran and yinyin alkane - imidazole salt compound and its preparation method

The invention discloses a series of dihydrofuran indenoane-imidazole salts compounds and a preparation method thereof. The preparation method comprises the following steps of: carrying out Vilsmeier reaction and Perskin reaction on 2,3-dihydrobenzofuran taken as a raw material; reducing palladium/carbon in an acetic acid to 5-propionic acid dihydrobenzofuran and forming acyl chloride with thionyl chloride; carrying out intramolecular Friedel-Crafts reaction and reducing in an alcohol solution by using sodium borohydride to obtain dihydrofuran indenoanol; forming a chloride in a toluene solution with the thionyl chloride; and reflowing and reacting with imidazole or 2-methyl imidazole or 2-ethyl imidazole or benzimidazole in acetonitrile or a toluene solvent to synthesize 1-(dihydrofuran indenoane) imidazole, and reacting with a halide on the above basis to synthesize the compound. According to the dihydrofuran indenoane-imidazole salts compounds and the preparation method thereof, pharmacophores with obvious tumor resisting activity in natural products are used as precursors to carry out designing and synthesizing on anti-tumor medicine molecule, and when an imidazole structure unit in a synthesized compound is the benzimidazole, particularly a naphthoyl methyl imidazole salts compound, the compound has very good in-vitro anticancer physiological activity.

Method for recovering and utilizing byproduct of chlorination of phosphorus pentachloride

The invention relates to a technology for comprehensively utilizing the byproduct of chlorination of phosphorus pentachloride, and mainly relates to a post treatment, which scientifically utilizes the excess phosphorus pentachloride reagent. The byproduct is converted into an organic synthesis reagent with a wide application range. The wastes are converted into a valuable resource. The discharge of waste water, waste gas, and waste solid is reduced. The obtained reagent is an excellent active reagent, which is widely used in the chemical industry, pharmacy industry, and material industry. The production cost is reduced, and the environment is protected.

Selective reduction of carboxylic acids to aldehydes with hydrosilane: Via photoredox catalysis

The direct reduction of carboxylic acids to aldehydes with hydrosilane was achieved through visible light photoredox catalysis. The combination of both single electron transfer and hydrogen atom transfer steps offers a novel and convenient approach to selective reduction of carboxylic acids to aldehydes. The method also features mild conditions, high yields, broad substrate scope, and good functional group tolerance, such as alkyne, ester, ketone, amide and amine groups.

Nucleophilicity Parameters of Stabilized Iodonium Ylides for Characterizing Their Synthetic Potential

Kinetics and mechanisms of the reactions of the β-dicarbonyl-substituted iodonium ylides 1(a-d) with several π-conjugated carbenium and iminium ions have been investigated. All reactions proceed with rate-determining attack of the electrophile at the nucleophilic carbon center of the ylides to give iodonium ions, which rapidly expel iodobenzene and undergo different subsequent reactions. The second-order rate constants k2 for the reactions of the iodonium ylides with benzhydrylium ions correlate linearly with the electrophilicity parameters E of the benzhydrylium ions and thus follow the linear free energy relationship log k(20 °C) = sN(N + E) (eq 1), where electrophiles are characterized by one parameter (E), while nucleophiles are characterized by two parameters: the nucleophilicity N and the susceptibility sN. The nucleophilicity parameters 4 + at the carbanionic center of Meldrum's acid or dimedone, respectively, reduces the nucleophilicity by approximately 10 orders of magnitude. The iodonium ylides 1(a-d) thus have nucleophilicities similar to those of pyrroles, indoles, and silylated enol ethers and, therefore, should be suitable substrates in iminium-activated reactions. Good agreement of the measured rate constant for the cyclopropanation of the imidazolidinone-derived iminium ion 10a with the iodonium ylide 1a with the rate constant calculated by eq 1 suggests a stepwise mechanism in which the initial nucleophilic attack of the iodonium ylide at the iminium ion is rate-determining. The reaction of cinnamaldehyde with iodonium ylide 1a catalyzed by (5S)-5-benzyl-2,2,3-trimethyl-imidazolidin-4-one (11a, MacMillan's first-generation catalyst) gives the corresponding cyclopropane with an enantiomeric ratio of 70/30 and, thus, provides proof of principle that iodonium ylides are suitable substrates for iminium-activated cyclopropanations.

Novel tricyclic indeno[5,6-b]furan-imidazole hybrid compounds: Design, synthesis and antitumor activity

A series of novel hybrid compounds between tricyclic indeno[5,6-b]furan and imidazole has been prepared and evaluated in vitro against a panel of human tumor cell lines. The results suggest that the existence of benzimidazole ring and substitution of the imidazolyl-3-position with a naphthylacyl group were vital for modulating cytotoxic activity. In particular, hybrid compound 26 was found to be the most potent compound against 5 strains human tumor cell lines and more active than cisplatin (DDP), while compound 18 was more selective towards breast carcinoma (MCF-7) and colon carcinoma (SW480) with IC50 value 3.4-fold and 4.3-fold more sensitive to DDP.

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