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4-(DIMETHYLAMINO)SALICYLALDEHYDE, also known as DASAL, is a yellow solid chemical compound derived from salicylaldehyde and dimethylamine. It is widely recognized for its fluorescent properties and is commonly used in the pharmaceutical and research industries.
Used in Pharmaceutical and Research Industries:
4-(DIMETHYLAMINO)SALICYLALDEHYDE is used as a fluorescent dye for detecting and quantifying biological molecules such as proteins and amino acids, due to its unique fluorescent properties.
Used in Sensor and Probe Development:
4-(DIMETHYLAMINO)SALICYLALDEHYDE is used as a component in the development of sensors and probes for detecting metals and other analytes in environmental and biological samples, leveraging its ability to fluoresce in response to specific interactions.
Used in Biochemical and Analytical Applications:
4-(DIMETHYLAMINO)SALICYLALDEHYDE is used as a valuable tool in various biochemical and analytical applications, owing to its fluorescent characteristics that facilitate the study and measurement of biological processes and substances.
Used in Therapeutic and Medicinal Research:
4-(DIMETHYLAMINO)SALICYLALDEHYDE is used as a subject of investigation for its potential anti-cancer and anti-inflammatory effects, indicating its possible use in the development of new therapeutic agents.

41602-56-6

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41602-56-6 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 41602-56-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,1,6,0 and 2 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 41602-56:
(7*4)+(6*1)+(5*6)+(4*0)+(3*2)+(2*5)+(1*6)=86
86 % 10 = 6
So 41602-56-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H11NO2/c1-10(2)8-4-3-7(6-11)9(12)5-8/h3-6,12H,1-2H3

41602-56-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(Dimethylamino)-2-hydroxybenzaldehyde

1.2 Other means of identification

Product number -
Other names 4-(dimethylamino)-2-hydroxybenzaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:41602-56-6 SDS

41602-56-6Synthetic route

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.0833333h;
Stage #2: 3-Dimethylaminophenol at 20 - 70℃; for 2h;
100%
With methanesulfonyl chloride at 20 - 100℃; for 1h;90.9%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 20℃; Inert atmosphere;
Stage #2: 3-Dimethylaminophenol at 20 - 90℃; Vilsmeier-Haack reaction; Inert atmosphere;
Stage #3: With water
70%
5-dimethylamino-2-(1,3-diphenyl-imidazolidin-2-yl)-phenol
58343-05-8

5-dimethylamino-2-(1,3-diphenyl-imidazolidin-2-yl)-phenol

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

Conditions
ConditionsYield
With hydrogenchloride; water at 25℃; for 2h;90%
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

Conditions
ConditionsYield
With aluminium trichloride In chloroform for 0.166667h; Ambient temperature;65%
formaldehyd
50-00-0

formaldehyd

3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

3-<<(diethylamino)carbonyl>oxy>-N,N-dimethylaniline
63907-38-0

3-<<(diethylamino)carbonyl>oxy>-N,N-dimethylaniline

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

B

5-(dimethylamino)-2-formylphenyl diethylcarbamate
96649-22-8

5-(dimethylamino)-2-formylphenyl diethylcarbamate

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium 1.) cyclohexane, THF, -78 deg C, 1 h, 2.) a) -78 deg C, 4 h, b) from -78 deg C to RT, 2 h, c) RT, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;
2-Benzoyloxy-4-(N,N-dimethylamino)-benzaldehyd
24589-97-7

2-Benzoyloxy-4-(N,N-dimethylamino)-benzaldehyd

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

Conditions
ConditionsYield
(alkaline hydrolysis);
3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

<3.6-bis-diethylamino-9-oxy-xanthyl>-benzene-pentacarboxylic acid

<3.6-bis-diethylamino-9-oxy-xanthyl>-benzene-pentacarboxylic acid

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) sodium hydride / 1.) diethyl ether, DMF, 15 min, 2.) RT, 1.5 h
2: 1.) sec-BuLi, TMEDA / 1.) cyclohexane, THF, -78 deg C, 1 h, 2.) a) -78 deg C, 4 h, b) from -78 deg C to RT, 2 h, c) RT, 0.5 h
View Scheme
3-(dimethylamino)phenyl benzoate
157279-47-5

3-(dimethylamino)phenyl benzoate

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (formylation)
2: (alkaline hydrolysis)
View Scheme
Vilsmeier reagent
3724-43-4, 149409-22-3

Vilsmeier reagent

3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 60 - 70℃; for 1h;
3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chlorobenzene / 6 h / 100 °C / Inert atmosphere
2: hydrogenchloride; water / 2 h / 25 °C
View Scheme
ethyl bromide
74-96-4

ethyl bromide

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

4-(dimethylamino)-2-ethoxybenzaldehyde

4-(dimethylamino)-2-ethoxybenzaldehyde

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In acetone at 40℃; for 16h;100%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

acetyl chloride
75-36-5

acetyl chloride

5-(dimethylamino)-2-formylphenyl acetate
174269-30-8

5-(dimethylamino)-2-formylphenyl acetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;99%
C36H42Br2N6O4
1266669-75-3

C36H42Br2N6O4

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

C54H58Br2N8O6Zn

C54H58Br2N8O6Zn

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 4h; Inert atmosphere;95%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

7-Dimethylamino-2-imino-2H-chromene-3-carboxylic acid amide
79604-92-5

7-Dimethylamino-2-imino-2H-chromene-3-carboxylic acid amide

Conditions
ConditionsYield
With piperidine In ethanol Heating;93%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

tert.-butyl lithium
594-19-4

tert.-butyl lithium

5-(dimethylamino)-2-(1-hydroxy-2,2-dimethylpropyl)phenol
1322596-77-9

5-(dimethylamino)-2-(1-hydroxy-2,2-dimethylpropyl)phenol

Conditions
ConditionsYield
In tetrahydrofuran; pentane at -78 - 20℃; Inert atmosphere;92%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

(E)-4-(dimethylamino)-2-hydroxybenzaldehyde oxime

(E)-4-(dimethylamino)-2-hydroxybenzaldehyde oxime

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol at 60℃; for 3h; Inert atmosphere;92%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

3-acetyl-7-(dimethylamino)-2H-1-benzopyran-2-one
74696-95-0

3-acetyl-7-(dimethylamino)-2H-1-benzopyran-2-one

Conditions
ConditionsYield
With piperidine In ethanol for 3h; Reflux;92%
4-Fluorothiophenol
371-42-6

4-Fluorothiophenol

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

malononitrile
109-77-3

malononitrile

2,4-diamino-8-(dimethylamino)-5-((4-fluorophenyl)thio)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

2,4-diamino-8-(dimethylamino)-5-((4-fluorophenyl)thio)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol for 4h; Temperature; Reflux;90%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carbohydrazide

3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carbohydrazide

(E)-N'-(4-(dimethylamino)-2-hydroxybenzylidene)-3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carbohydrazide

(E)-N'-(4-(dimethylamino)-2-hydroxybenzylidene)-3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carbohydrazide

Conditions
ConditionsYield
With acetic acid In ethanol for 5h; Reflux;90%
Cyclopentyl bromide
137-43-9

Cyclopentyl bromide

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

2-(cyclopentoxy)-4-(dimethylamino)benzaldehyde

2-(cyclopentoxy)-4-(dimethylamino)benzaldehyde

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In acetone for 24h; Inert atmosphere; Reflux;89.2%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

dimedone
126-81-8

dimedone

malononitrile
109-77-3

malononitrile

2-amino-4-(4-(dimethylamino)-2-hydroxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

2-amino-4-(4-(dimethylamino)-2-hydroxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; methanol at 20℃;89%
N,N-dimethyl-4-aminothiophenol
4946-22-9

N,N-dimethyl-4-aminothiophenol

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

malononitrile
109-77-3

malononitrile

2,4-diamino-8-(dimethylamino)-5-((4-(dimethylamino)phenyl)thio)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

2,4-diamino-8-(dimethylamino)-5-((4-(dimethylamino)phenyl)thio)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol for 4h; Temperature; Reflux;88%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

benzyl bromide
100-39-0

benzyl bromide

C16H17NO2
1268353-44-1

C16H17NO2

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 8h;87.6%
2,6-diisopropylbenzenamine
24544-04-5

2,6-diisopropylbenzenamine

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

C21H28N2O

C21H28N2O

Conditions
ConditionsYield
With acetic acid In ethanol for 2h; Reflux;87%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

7-(N,N-dimethylamino)-2-oxo-2H-chromene

7-(N,N-dimethylamino)-2-oxo-2H-chromene

Conditions
ConditionsYield
at 170 - 180℃; for 1h;86%
at 180℃; for 1h; Inert atmosphere;77%
at 180℃; for 1h; Inert atmosphere;62%
at 180℃; for 1h; Inert atmosphere;62%
N,N′-bisoctadecyl-L-aminoglutamicdiamide
752950-25-7

N,N′-bisoctadecyl-L-aminoglutamicdiamide

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

C50H92N4O3

C50H92N4O3

Conditions
ConditionsYield
In ethanol at 80℃; for 8h;85%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

3-acetyl-7-(dimethylamino)-2H-1-benzopyran-2-one
74696-95-0

3-acetyl-7-(dimethylamino)-2H-1-benzopyran-2-one

7,7'-Bis-dimethylamino-2'-oxo-2'H-[2,3']bichromenyl-1-ylium; perchlorate

7,7'-Bis-dimethylamino-2'-oxo-2'H-[2,3']bichromenyl-1-ylium; perchlorate

Conditions
ConditionsYield
With perchloric acid In acetic acid for 0.5h; Heating;83%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

ethyl acetoacetate
141-97-9

ethyl acetoacetate

3-acetyl-7-(dimethylamino)-2H-1-benzopyran-2-one
74696-95-0

3-acetyl-7-(dimethylamino)-2H-1-benzopyran-2-one

Conditions
ConditionsYield
With piperidine In ethanol for 6h; Heating / reflux;81%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

malononitrile
109-77-3

malononitrile

3-cyano-7-dimethylaminocoumarin
53050-52-5

3-cyano-7-dimethylaminocoumarin

Conditions
ConditionsYield
Stage #1: 4-dimethylamino-2-hydroxy-benzaldehyde; malononitrile With sodium hydroxide In water at 20℃; for 1.5h;
Stage #2: With hydrogenchloride In water for 1h; Reflux;
81%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

m-phenylenediamine
108-45-2

m-phenylenediamine

6,6'-((1,3-phenylenebis(azanylylidene))bis(methanylylidene))bis(3-(dimethylamino)phenol)

6,6'-((1,3-phenylenebis(azanylylidene))bis(methanylylidene))bis(3-(dimethylamino)phenol)

Conditions
ConditionsYield
In ethanol for 5h; Reflux;79%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

ethyl acetoacetate
141-97-9

ethyl acetoacetate

7,7'-Bis-dimethylamino-2'-oxo-2'H-[2,3']bichromenyl-1-ylium; perchlorate

7,7'-Bis-dimethylamino-2'-oxo-2'H-[2,3']bichromenyl-1-ylium; perchlorate

Conditions
ConditionsYield
With perchloric acid In acetic acid for 0.5h; Heating;76%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

1-ethynylcyclobutan-1-ol
98135-75-2

1-ethynylcyclobutan-1-ol

2-(2-(4-(dimethylamino)-2-hydroxyphenyl)-2-oxoethyl)cyclopentanone

2-(2-(4-(dimethylamino)-2-hydroxyphenyl)-2-oxoethyl)cyclopentanone

Conditions
ConditionsYield
With [Rh(OH)(cod)]2; triphenylphosphine In 1,2-dichloro-ethane at 70℃; for 12h; Sealed tube;76%
indole-2-carbohydrazide
5055-39-0

indole-2-carbohydrazide

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

N'-{[4-(dimethylamino)-2-hydroxyphenyl]methylidene}-1H-indole-2-carbohydrazide

N'-{[4-(dimethylamino)-2-hydroxyphenyl]methylidene}-1H-indole-2-carbohydrazide

Conditions
ConditionsYield
In ethanol Reflux;76%
phenylacetic acid
103-82-2

phenylacetic acid

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

3-phenyl-7-(N,N-dimethylamino)coumarin

3-phenyl-7-(N,N-dimethylamino)coumarin

Conditions
ConditionsYield
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In acetonitrile for 2h; Heating;75%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

C20H31NO5

C20H31NO5

C29H39N2O5(1+)*ClO4(1-)

C29H39N2O5(1+)*ClO4(1-)

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 2h;74%
1H-indole-3-carboxylic acid hydrazide
15317-58-5

1H-indole-3-carboxylic acid hydrazide

4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

N'-{[4-(dimethylamino)-2-hydroxyphenyl]methylidene}-1H-indole-3-carbohydrazide

N'-{[4-(dimethylamino)-2-hydroxyphenyl]methylidene}-1H-indole-3-carbohydrazide

Conditions
ConditionsYield
In ethanol Reflux;73%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

(carbethoxyethylidene)triphenylphosphorane
21382-82-1

(carbethoxyethylidene)triphenylphosphorane

7-(dimethylamino)-3-methylcoumarin

7-(dimethylamino)-3-methylcoumarin

Conditions
ConditionsYield
at 180℃; for 2h;72%
4-dimethylamino-2-hydroxy-benzaldehyde
41602-56-6

4-dimethylamino-2-hydroxy-benzaldehyde

acetic anhydride
108-24-7

acetic anhydride

5-(dimethylamino)-2-formylphenyl acetate
174269-30-8

5-(dimethylamino)-2-formylphenyl acetate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 1h;71%

41602-56-6Relevant academic research and scientific papers

Turn on ESPT: Novel salicylaldehyde based sensor for biological important fluoride sensing

Liu, Kai,Zhao, Xiaojun,Liu, Qingxiang,Huo, Jianzhong,Fu, Huifang,Wang, Ying

, p. 75 - 79 (2014)

A novel and simple salicylaldehyde based anion fluorescent sensor 1 has been designed, which can selectively sense fluoride by 'turn on' excited-state intermolecular proton transfer (ESPT). The binding constant and the stoichiometry were obtained by non-linear least-square analysis of the titration curves.

Temperature insensitive fluorescence intensity in a coumarin monomer-aggregate coupled system

Liu, Xiaogang,Mao, Deqi,Cole, Jacqueline M.,Xu, Zhaochao

, p. 9329 - 9332 (2014)

The emission intensities of a fluorescent monomer-aggregate coupled system, based on 7-(dimethylamino)-coumarin-3-carbaldehyde, exhibit ultra-low temperature dependence with a low temperature coefficient of only 0.05% per °C, by judicious selection of the excitation wavelength. This finding has significant implications to temperature-sensitive fluorescent applications.

Anagostic interactions in chiral separation. Polymorphism in a [Co(II)(L)] complex: Crystallographic and theoretical studies

Awwadi, Firas F.,Hodali, Hamdallah A.

, p. 373 - 381 (2018)

Syntheses and crystal structures of two polymorphs of the complex [Co(II)(L)], where H2L = 2,2’-[cis-1,2-diaminocyclohexanediylbis (nitrilo-methylidyne)]bis (5-dimethyl-amino]phenol, have been studied. The two polymorphs concomitantly crystallized by vapour diffusion of solvent. The first polymorph (I) crystallized as a racemate in the centrosymmetric tetragonal I41/a space group. The second polymorph (II) crystallized in the chiral orthorhombic space group P212121. The chiral conformers of symmetrical cis-1,2-disubstituted cyclohexane molecules cannot be resolved in the liquid or gas phases, due to the rapid ring inversion. In the present study, the two chiral conformers are present in crystals of polymorph I, whereas, only one chiral conformer is present in crystals of polymorph II. Crystal structure analysis indicated that the formation of two different polymorphs of [Co(II)(L)] complex can be rationalized based on C–H?Co anagostic interactions. Density Functional Theory (DFT) calculations indicated that C–H?Co interactions are due to HOMO-LUMO interactions.

Synthesis and study of novel coumarin derivatives potentially utilizable as memory media

Flasik, Radoslav,Stankovicova, Henrieta,Gaplovsky, Anton,Donovalova, Jana

, p. 4838 - 4848 (2009)

Novel coumarin derivatives, 2-oxo-2H-chromenecarbaldehyde hydrazones were prepared by reaction of substituted 2-oxo-2H-chromenecarbaldehydes with N-aminoimides in ethanol in the presence of 4-toluenesulfonic acid as catalyst. The photochromic and thermochromic properties of the prepared compounds were investigated.

Imidazolyl–benzocoumarins as ratiometric fluorescence probes for biologically extreme acidity

Kim, Hyerim,Sarkar, Sourav,Nandy, Madhurima,Ahn, Kyo Han

, (2021)

A rational approach to develop a fluorescent probe for sensing biologically “extreme” acidity (pH a = 1.3 among ratiometric probes known so far, which is ascribed due to a unique sensing mechanism. The probe has high quantum yields, high chemical stability and good aqueous solubility. The probe was successfully applied to ratiometric fluorescence imaging of intrabacterial acidity from pH 4.0–1.0, offering a practical means for studying biological systems under the extreme pH conditions.

Synthesis of N,N-Dialkylamino-nor-Dihydroxanthene-Hemicyanine Fused Near-Infrared Fluorophores and Their First Water-Soluble and/or Bioconjugatable Analogues

Ong, Michelle Jui Hsien,Debieu, Sylvain,Moreau, Mathieu,Romieu, Anthony,Richard, Jean-Alexandre

, p. 936 - 946 (2017)

The effective synthesis of extended conjugated N,N-dialkylamino-nor-dihydroxanthene-based fluorophores is described from diversely functionalized salicylic aldehydes. The access to these original fluorescent derivatives proceeded in two steps through a one-pot construction of the unusual nor-dihydroxanthene (nor-DHX) scaffold followed by a diversification step providing a wide variety of nor-DHX-hemicyanine fused dyes emitting in the range of 730–790 nm. The versatility of our approach has enabled a further extension to the late-stage introduction of negatively/positively charged polar groups onto their terminal nitrogen heterocyclic subunit, thereby giving access to the first water-soluble and/or bioconjugatable members of this emerging class of NIR fluorophores. Our water-solubilizing method is easily implementable, and the nor-DHX-hemicyanine skeleton maintains satisfying fluorescence quantum yields (5–20 %) under physiological conditions. Finally, the bioconjugation ability of fluorescent derivatives bearing a free carboxylic acid was demonstrated through the covalent labeling of a model protein, namely, bovine serum albumin.

Fluoride-driven 'turn on' ESPT in the binding with a novel benzimidazole-based sensor

Liu, Kai,Zhao, Xiaojun,Liu, Qingxiang,Huo, Jianzhong,Zhu, Bolin,Diao, Shihua

, p. 563 - 567 (2015)

A novel fluorescence sensor (BIP) bearing NH and OH subunits displayed a highly selective and sensitive recognition property for fluoride over other anions. Fluoride-driven ESPT, poorly used in anion recognition and sensing, was suggested to be responsible for the fluorescence enhancement with a blue shift of 35 nm in the emission spectrum.

A Color-Shifting Near-Infrared Fluorescent Aptamer–Fluorophore Module for Live-Cell RNA Imaging

J?schke, Andres,Sunbul, Murat,Wang, Lu,Zhang, Jingye

supporting information, p. 21441 - 21448 (2021/08/23)

Fluorescent light-up RNA aptamers (FLAPs) have become promising tools for visualizing RNAs in living cells. Specific binding of FLAPs to their non-fluorescent cognate ligands results in a dramatic fluorescence increase, thereby allowing RNA imaging. Here, we present a color-shifting aptamer-fluorophore system, where the free dye is cyan fluorescent and the aptamer-dye complex is near-infrared (NIR) fluorescent. Unlike other reported FLAPs, this system enables ratiometric RNA imaging. To design the color-shifting system, we synthesized a series of environmentally sensitive benzopyrylium-coumarin hybrid fluorophores which exist in equilibrium between a cyan fluorescent spirocyclic form and a NIR fluorescent zwitterionic form. As an RNA tag, we evolved a 38-nucleotide aptamer that selectively binds the zwitterionic forms with nanomolar affinity. We used this system as a light-up RNA marker to image mRNAs in the NIR region and demonstrated its utility in ratiometric analysis of target RNAs expressed at different levels in single cells.

ACYL SULFONAMIDES FOR TREATING CANCER

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Page/Page column 305, (2020/11/03)

The present invention provides acyl sulfonamide compounds of general formula (I): in which X, R1, R2, R3, R4, R5, R6, Ra and Rb are as described and defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of hyperproliferative disorders, as a sole agent or in combination with other active ingredients as well as methods of treating and/or prophylaxing diseases, particularly cancer, more particularly cancer in which KAT6A and/or KAT6B is focally amplified, said method comprising administering an effective amount of at least one compound of formula (I) to a subject in need thereof.

A lysosome-targeting and polarity-specific fluorescent probe for cancer diagnosis

Fan, Li,Wang, Xiaodong,Ge, Jinyin,Li, Feng,Wang, Xiao,Wang, Juanjuan,Shuang, Shaomin,Dong, Chuan

supporting information, p. 4703 - 4706 (2019/05/02)

A lysosome-targeting and polarity-specific fluorescent probe CPM has been rationally designed for cancer diagnosis and imaging. We have successfully shown that lysosome polarity may serve as an ubiquitious marker for cancer detection. The potential of CPM for cancer diagnosis has also been demonstrated at the levels of live cells, organs, whole animal, and clinical patient tissue samples.

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