109467-00-7

Basic information

• Product Name: 2-Amino-5-methylbenzaldehyde
• Synonyms: 2-Amino-5-methylbenzaldehyde
• CAS NO: 109467-00-7
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16316
• Mol File: 109467-00-7.mol

Chemical Properties

• Boiling Point: 266.6±28.0 °C(Predicted)
• Appearance: /
• Density: 1.129±0.06 g/cm3(Predicted)
• PKA: 0.79±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-5-methylbenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-methylbenzaldehyde(109467-00-7)
• EPA Substance Registry System: 2-Amino-5-methylbenzaldehyde(109467-00-7)

Safety Data

• Hazardous Substances Data: 109467-00-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-methylbenzaldehyde is utilized as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicinal compounds. Its chemical structure allows for the creation of a diverse range of therapeutic agents.
Used in Dye Industry:
In the dye industry, 2-Amino-5-methylbenzaldehyde serves as a crucial component in the production of different types of dyes. Its ability to form various chemical bonds makes it suitable for creating a wide array of colorants used in textiles, printing, and other applications.
Used in Corrosion Inhibition:
2-Amino-5-methylbenzaldehyde is studied for its potential as a corrosion inhibitor, which can be applied in various industrial settings to protect metals from degradation. Its chemical properties may offer a means to reduce corrosion rates and extend the lifespan of metal components.
Used in Polymer and Resin Production:
As a precursor in the production of polymers and resins, 2-Amino-5-methylbenzaldehyde plays a significant role in the manufacturing of materials with specific properties required for various applications, including coatings, adhesives, and composites. Its integration into these materials can enhance their performance characteristics.

Upstream product

• 5858-28-6 5-methyl-2-nitrobenzaldehyde 
• 34897-84-2 2-amino-5-methylbenzyl alcohol 
• 2941-78-8 2-Amino-5-methylbenzoic acid 

Downstream Products

• 171917-56-9 Methyl 3-(benzyloxy)-6-methylquinoline-2-carboxylate 
• 916657-01-7 (6-methyl-2-phenyl-quinolin-3-yl)-acetic acid 
• 15104-17-3 2-phenyl-6-methyl-1,4-dihydro-4-oxoquinoline 
• 1353000-35-7 2-(4-methoxyphenyl)-6-methylquinazoline 
• 877-43-0 2,6-dimethylquinoline 
• 1395473-90-1 (S)-2-(4-methoxyphenyl)-6-methyl-1,2,3,4-tetrahydroquinoline 
• 1345511-07-0 2-(biphenyl-4-yl)-7-methyl-1,2,3,4-tetrahydroacridine 
• 1345511-05-8 2-(4-chlorophenyl)-7-methyl-1,2,3,4-tetrahydroacridine 
• 1345511-04-7 2-(4-methoxyphenyl)-7-methyl-1,2,3,4-tetrahydroacridine 
• 1345511-03-6 7-methyl-2-p-tolyl-1,2,3,4-tetrahydroacridine 
• 1345511-00-3 7-methyl-2-phenyl-1,2,3,4-tetrahydroacridine 

Relevant articles and documents

Chemoselective Oxidation of Benzyl, Amino, and Propargyl Alcohols to Aldehydes and Ketones under Mild Reaction Conditions

Catalytic oxidation reactions often suffer from drawbacks such as low yields and poor selectivity. Particularly, selective oxidation of alcohols becomes more difficult when a compound contains more than one oxidizable functional group. In order to deliver a methodology that addresses these issues, herein we report an efficient, aerobic, chemoselective and simplified approach to oxidize a broad range of benzyl and propargyl alcohols containing diverse functional groups to their corresponding aldehydes and ketones in excellent yields under mild reaction conditions. Optimal yields were obtained at room temperature using 1 mmol substrate, 10 mol% copper(I) iodide, 10 mol% 4-dimethylaminopyridine (DMAP), ands 1 mol% 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) in acetonitrile, under an oxygen balloon. The catalytic system can be applied even when sensitive and oxidizable groups such as alkynes, amines, and phenols are present; starting materials and products containing such groups were found to be stable under the developed conditions.

Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes

A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.

Mild, selective oxidation of aromatic alcohols using β-cyclodextrin- functionalized glass microparticles: Characterization, stability, and application

The surface of glass microparticle (GMP) was functionalized with β-cyclodextrin (→ GMP-β-CD) and was characterized by x-ray photoelectron spectroscopy (XPS). GMP-β-CD was used to catalyze oxidation of alcohols into aldehydes and katones with excellent yield (86-92%). The modified surface of GMP-β-CD showed no change or degradation after repeated use as confirmed from XPS analysis after 10 cycles. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright

Gold(I)-catalyzed unprecedented rearrangement reaction between 2-aminobenzaldehydes with propargyl amines: An expedient route to 3-aminoquinolines

Access to aminoquinolines: A gold(I)-catalyzed unprecedented rearrangement reaction between 2-aminobenzaldehydes with propargyl amine was studied. The study provided, for the first time, direct access to 3-aminoquinolines in one step starting from readily available starting materials (see scheme). Elegantly designed experiments were employed to unravel the mechanism of this unprecedented rearrangement, which are corroborated by DFT calculations.

Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.

TETRAHYDROQUINOLINES USED IN THE FORM OF MODULATORS OF MITOTIC MOTOR-PROTEINS EG5

The invention relates to compounds of formula (i), wherein W, R, R1, R2, R3, R4, R5, R6 and R7 have meanings given in claim 1 and can be used for treating tumors.

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Nineteen racemic ring A substituted analogues of the antitumor agent 20(S)-camptothecin were prepared by total synthesis and evaluated for in vitro cytotoxic activity against KB cell culture and in vivo antileukemic activity against L1210. These compounds bore a wide variety of substitutents at C11 designed to confer upon the ring system a broad range of combinations of electronic, steric, and lipophilic effects. A few C10-substituted derivatives as well as C10,C11-disubstituted analogues prepared as part of a concurrent study have also been included for general comparison. With the notable exception of the cyano derivative, the 11-substituted compounds displayed only modest in vitro and in vivo activities, and there was a remarkable insensitivity toward the nature of the substituent. In contrast, the 9- and 10-substituted compounds exhibited a considerably higher level of dose potency and activity both in vitro and in vitro.