1199-59-3

Basic information

• Product Name: 4-DIMETHYLAMINO-O-TOLUALDEHYDE
• Synonyms: Benzaldehyde, 4-(dimethylamino)-2-methyl-;2-METHYL-4-DIMETHYLAMINOBENZALDEHYDE;4-DIMETHYLAMINO-O-TOLUALDEHYDE;4-DIMETHYLAMINO-2-METHYLBENZALDEHYDE;TIMTEC-BB SBB008015;4-(N,N-Dimethylamino)-2-methylbenzaldehyde
• CAS NO: 1199-59-3
• Molecular Formula: C₁₀H₁₃NO
• Molecular Weight: 163.22
• EINECS: 214-846-5
• Mol File: 1199-59-3.mol

Chemical Properties

• Melting Point: 64-66°C
• Boiling Point: 292.7 °C at 760 mmHg
• Flash Point: 113.1 °C
• Appearance: /
• Density: 1.05 g/cm³
• Vapor Pressure: 0.0018mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: 4-DIMETHYLAMINO-O-TOLUALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-DIMETHYLAMINO-O-TOLUALDEHYDE(1199-59-3)
• EPA Substance Registry System: 4-DIMETHYLAMINO-O-TOLUALDEHYDE(1199-59-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 1199-59-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 21, p. 56, 1978 DOI: 10.1021/jm00199a010

InChI:InChI=1/C10H13NO/c1-8-6-10(11(2)3)5-4-9(8)7-12/h4-7H,1-3H3

Upstream product

• 63082-45-1 4-fluoro-2-methylbenzaldehyde 
• 506-59-2 N,N-dimethylammonium chloride 
• 121-72-2 N,N-dimethyl-m-toluidine 
• 68-12-2 N,N-dimethyl-formamide 
• 98-47-5 3-Nitrobenzenesulfonic acid 
• 100-97-0 hexamethylenetetramine 

Downstream Products

• 22269-63-2 2-(2-chloro-phenyl)-4-(4-dimethylamino-2-methyl-benzylidene)-4H-oxazol-5-one 
• 22269-64-3 2-(4-chloro-phenyl)-4-(4-dimethylamino-2-methyl-benzylidene)-4H-oxazol-5-one 
• 22269-66-5 4-(4-dimethylamino-2-methyl-benzylidene)-2-(4-nitro-phenyl)-4H-oxazol-5-one 
• 22269-62-1 4-(4-dimethylamino-2-methyl-benzylidene)-2-(4-methoxy-phenyl)-4H-oxazol-5-one 
• 127034-54-2 (E)-3-(4-Dimethylamino-2-methyl-phenyl)-1-(2,3,4-trimethoxy-phenyl)-propenone 
• 1314664-72-6 C₁₅H₂₃NOSi 
• 55489-33-3 2-[2’-methyl,4’-(dimethylamino)phenyl]benzothiazole 
• 65399-14-6 4-(dimethylamino)-2-methylbenzoic acid 
• 1399697-88-1 C₂₁H₂₂N₄ 
• 22269-53-0 C₁₃H₁₅N₃O 
• 188247-01-0 ortho-methyl-para-dimethylamino-Hoechst 

Relevant articles and documents

BODIPY Fluorophores for Membrane Potential Imaging

Fluorophores based on the BODIPY scaffold are prized for their tunable excitation and emission profiles, mild syntheses, and biological compatibility. Improving the water-solubility of BODIPY dyes remains an outstanding challenge. The development of water-soluble BODIPY dyes usually involves direct modification of the BODIPY fluorophore core with ionizable groups or substitution at the boron center. While these strategies are effective for the generation of water-soluble fluorophores, they are challenging to implement when developing BODIPY-based indicators: direct modification of BODIPY core can disrupt the electronics of the dye, complicating the design of functional indicators; and substitution at the boron center often renders the resultant BODIPY incompatible with the chemical transformations required to generate fluorescent sensors. In this study, we show that BODIPYs bearing a sulfonated aromatic group at the meso position provide a general solution for water-soluble BODIPYs. We outline the route to a suite of 5 new sulfonated BODIPYs with 2,6-disubstitution patterns spanning a range of electron-donating and -withdrawing propensities. To highlight the utility of these new, sulfonated BODIPYs, we further functionalize them to access 13 new, BODIPY-based, voltage-sensitive fluorophores (VF). The most sensitive of these BODIPY VF dyes displays a 48% ΔF/F per 100 mV in mammalian cells. Two additional BODIPY VFs show good voltage sensitivity (≥24% ΔF/F) and excellent brightness in cells. These compounds can report on action potential dynamics in both mammalian neurons and human stem cell-derived cardiomyocytes. Accessing a range of substituents in the context of a water-soluble BODIPY fluorophore provides opportunities to tune the electronic properties of water-soluble BODIPY dyes for functional indicators.

Benzothiazole-Based Neutral Ratiometric Fluorescence Sensor for Amyloid Fibrils

Early detection of amyloid fibrils is very important for the timely diagnosis of several neurological diseases. Thioflavin-T (ThT) is a gold standard fluorescent probe for amyloid fibrils and has been used for the last few decades. However, due to its positive charge, ThT is incapable of crossing the blood–brain barrier and cannot be used for in vivo imaging of fibrils. In the present work, we synthesized a neutral ThT derivative, 2-[2’-Me,4’-(dimethylamino)phenyl]benzothiazole (2Me-DABT), which showed a strong affinity towards the amyloid fibrils. On association with the amyloid fibrils, 2Me-DABT not only showed a large increase in its emission intensity, but also, unlike ThT, a large blueshift in its emission spectrum was observed. Thus, unlike ThT, 2Me-DABT is a potential candidate for the ratiometric sensor of the amyloid fibrils. Detailed photophysical properties of 2Me-DABT in amyloid fibrils and different solvent media were studied to understand its sensory activity. Fluorescence resonance energy transfer (FRET) studies suggested that the sites of localization for ThT and 2Me-DABT in amyloid fibrils are not same and their average distance of separation in amyloid fibrils was determined. The experimental data was nicely supported by molecular docking studies, which confirmed the binding of 2Me-DABT in the inner core of the amyloid fibrils.

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Voltage-sensitive fluorophores enable the direct visualization of membrane potential changes in living systems. To pair the speed and sensitivity of chemically synthesized fluorescent indicators with cell-type specific genetic methods, we here develop Rhodamine-based Voltage Reporters (RhoVR) that can be covalently tethered to genetically encoded, self-labeling enzymes. These chemical-genetic hybrids feature a photoinduced electron transfer triggered RhoVR voltage-sensitive indicator coupled to a chloroalkane HaloTag ligand through a long, water-soluble polyethylene glycol linker (RhoVR-Halo). When applied to cells, RhoVR-Halo dyes selectively and covalently bind to surface-expressed HaloTag enzyme on genetically modified cells. RhoVR-Halo dyes maintain high voltage sensitivities - up to 34% ΔF/F per 100 mV - and fast response times typical of untargeted RhoVRs, while gaining the selectivity of genetically encodable voltage indicators. We show that RhoVR-Halos can record action potentials in single trials from cultured rat hippocampal neurons and can be used in concert with green-fluorescent Ca2+ indicators like GCaMP to provide simultaneous voltage and Ca2+ imaging. In a brain slice, RhoVR-Halos provide exquisite labeling of defined cells and can be imaged using epifluorescence, confocal, or two-photon microscopy. Using high-speed epifluorescence microscopy, RhoVR-Halos provide a read-out of action potentials from labeled cortical neurons in a rat brain slice, without the need for trial averaging. These results demonstrate the potential of hybrid chemical-genetic voltage indicators to combine the optical performance of small-molecule chromophores with the inherent selectivity of genetically encodable systems, permitting imaging modalities inaccessible to either technique individually.

SN1-type reactions in the presence of water: Indium(III)-promoted highly enantioselective organocatalytic propargylation of aldehydes

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Radioprotectors

A compound of the formula (Ib): wherein X is NCH3, Y is N, Z is N, R3 is N(CH3)2, and (a) R1 is CH3, R2, R4 and R5 to R11 are hydrogen or (b) R5 is CH3 and R1, R2, R4 and R6 to R11 are hydrogen, and salts and tautomers thereof.

Radioprotectors

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Radioprotectors

A compound of the formula: is disclosed. This compound is useful in methods of protecting a subject of of protecting biological materials from radiation damage.

N'-(2,6-Dichloro-4-(substituted-benzylamino)phenyl)-N,N-dimethyl-formamidines

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N'-[2,6-Dichloro-4-(substituted-benzylideneamino)phenyl]-N,N-dimethylformamidines

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