579-72-6

Basic information

• Product Name: 2-(Dimethylamino)benzaldehyde
• Synonyms: 2-(Dimethylamino)benzaldehyde;N,N-Dimethyl-2-formylaniline, N,N-Dimethylanthranilaldehyde;2-(Dimethylamino)benzaldehyde97%
• CAS NO: 579-72-6
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.18974
• Mol File: 579-72-6.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 244.7°C at 760 mmHg
• Flash Point: 89.8°C
• Appearance: /
• Density: 1.072g/cm³
• Vapor Pressure: 0.03mmHg at 25°C
• Refractive Index: 1.595
• PKA: 3.80±0.18(Predicted)
• CAS DataBase Reference: 2-(Dimethylamino)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Dimethylamino)benzaldehyde(579-72-6)
• EPA Substance Registry System: 2-(Dimethylamino)benzaldehyde(579-72-6)

Safety Data

• Hazardous Substances Data: 579-72-6(Hazardous Substances Data)

Usage

General Description

2-(Dimethylamino)benzaldehyde is a chemical compound with the molecular formula C9H11NO. It is a pale yellow liquid that is commonly used as an intermediate in the synthesis of various pharmaceuticals and organic compounds. It is primarily utilized in the production of dyestuffs and in the formulation of perfumes and fragrances. The presence of a dimethylamino group and an aldehyde group in its structure makes 2-(Dimethylamino)benzaldehyde a versatile building block for the synthesis of complex organic molecules. It is also known for its use as a reagent in the preparation of imines and other nitrogen-containing compounds. Additionally, it exhibits mild to moderate toxicity and should be handled with caution.

InChI:InChI=1/C9H11NO/c1-10(2)9-6-4-3-5-8(9)7-11/h3-7H,1-2H3

Upstream product

• 117426-12-7 C₉H₁₂BrN 
• 124-40-3 dimethyl amine 
• 121-69-7 N,N-dimethyl-aniline 
• 68-12-2 N,N-dimethyl-formamide 
• 100-58-3 phenylmagnesium bromide 
• 506-59-2 N,N-dimethylammonium chloride 
• 446-52-6 2-Fluorobenzaldehyde 
• 135-02-4 ortho-anisaldehyde 
• 6136-58-9 2-(2-methoxyphenylmethyleneimino)phenol 
• 1952-36-9 2-(2-methoxy-benzylidenamino)-ethanol 
• 95-55-6 2-amino-phenol 
• 4707-56-6 (2-(dimethylamino)phenyl)methanol 
• 10072-05-6 methyl 2-(dimethylamino)benzoate 
• 615-36-1 2-bromoaniline 

Downstream Products

• 1292323-48-8 (E)-methyl 3-(2-(dimethylamino)phenyl)acrylate 
• 1292323-49-9 (E)-3-(2-(dimethylamino)phenyl)prop-2-en-1-ol 
• 1292323-50-2 (E)-3-(2-(dimethylamino)phenyl)acrylaldehyde 
• 1292323-51-3 (E)-tert-butyl 2-(3-(2-(dimethylamino)phenyl)allylamino)ethylcarbamate 
• 1292323-89-7 tert-butyl 2-(7-acetyl-9-(2-(dimethylamino)phenyl)-3-oxo-1H-pyrrolo[3,4-β]indolizin-2(3H)-yl)ethylcarbamate 
• 5339-18-4 N,N-dimethylaminostyrene 
• 1373497-84-7 (E)-1-methoxy-2-(3,3,3-trifluoroprop-1-en-1-yl)benzene 
• 32832-95-4 2-benzylbenzaldehyde 
• 1203-68-5 2-Phenylbenzaldehyde 
• 216443-17-3 3’-methyl-[1,1’]-biphenyl-2-carbaldehyde 
• 16191-28-9 2-(4-methylphenyl)benzaldehyde 

Relevant articles and documents

Rhodium(III)-Catalyzed Aldehyde C?H Activation and Functionalization with Dioxazolones: An Entry to Imide Synthesis

A rhodium(III)-based catalytic system has been used to develop a C?H bond activation of benzaldehyde derivatives and subsequent functionalization with dioxazolones in order to afford imides. The importance of the nature of the directing group to perform selectively the aldehydic C?H bond activation has been highlighted. The scope investigation showed that this transformation could be applied to various dioxazolones and many benzaldehyde derivatives as well as an acrolein derivative. Derivatization reactions of the imide products demonstrated the synthetic utility of this rhodium-catalyzed aldehydic C?H amidation.

Substituent Effect Induces Emission Modulation of Stilbene Photoswitches by Spatial Tuning of the N/B Electronic Constraints

We present a family of stilbene derivatives (1-4) ortho-functionalized with an electron donor and acceptor. Their emission was tuned by donor substitutions, dictating charge transfer dependent on the N···B spatial separation. The steric reduction of subst

Reductive Cross-Coupling between Unactivated C(aryl)-N and C(aryl)-O Bonds by Chromium Catalysis Using a Bipyridyl Ligand

Reductive cross-coupling between two chemically inert bonds remains a great challenge in synthetic chemistry. We report here the reductive cross-coupling between unactivated C(aryl)-N and C(aryl)-O bonds that was achieved by chromium catalysis. The simple and inexpensive CrCl2 salt, combined with important bipyridyl ligand and magnesium reductant, shows high reactivity in the successive cleavage of C(aryl)-N bonds of aniline derivatives and C(aryl)-O bonds of aryl esters, allowing the cross-coupling of these two unactivated and different bonds to occur in a reductive fashion to form a C(aryl)-C(aryl) bond. Mechanistic studies by deuterium-labeling experiments indicate that the C(aryl)-N bonds in anilines are preferentially cleaved by reactive Cr species, in which the ligation of bipyridyl with Cr by adopting a coordination model in 1:1 ratio can be considered.