Benzaldehyde,4-(dimethylamino)-2-hydroxy- supplier

Name
4-(DIMETHYLAMINO)SALICYLALDEHYDE
EINECS
CAS No. 41602-56-6
Article Data33
CAS DataBase
Density 1.201 g/cm³
Solubility
Melting Point 78-78 °C
Formula C₉H₁₁NO₂
Boiling Point 301.111 °C at 760 mmHg
Molecular Weight 165.192
Flash Point 135.908 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Salicylaldehyde,4-(dimethylamino)- (6CI,7CI);2-Hydroxy-4-(dimethylamino)benzaldehyde;4-(Dimethylamino)-2-hydroxybenzaldehyde;4-(Dimethylamino)salicylaldehyde;4-(N,N-Dimethylamino)-2-hydroxybenzaldehyde;4-N,N-Dimethylaminosalicylaldehyde;p-(Dimethylamino)salicylaldehyde;
PSA 40.54000
LogP 1.27070

Synthetic route

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

: 99-07-0
3-Dimethylaminophenol

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

Conditions

Conditions	Yield
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%

: 58343-05-8
5-dimethylamino-2-(1,3-diphenyl-imidazolidin-2-yl)-phenol

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

Conditions

Conditions	Yield
With hydrogenchloride; water at 25℃; for 2h;	90%

: 122-51-0
orthoformic acid triethyl ester

: 99-07-0
3-Dimethylaminophenol

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

Conditions

Conditions	Yield
With aluminium trichloride In chloroform for 0.166667h; Ambient temperature;	65%

: 50-00-0
formaldehyd

: 99-07-0
3-Dimethylaminophenol

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

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

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

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

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

Conditions

Conditions	Yield
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;

...Expand

: 24589-97-7
2-Benzoyloxy-4-(N,N-dimethylamino)-benzaldehyd

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

Conditions

Conditions	Yield
(alkaline hydrolysis);

: 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

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

Conditions

Conditions	Yield
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

: 157279-47-5
3-(dimethylamino)phenyl benzoate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (formylation) 2: (alkaline hydrolysis) View Scheme

: 3724-43-4, 149409-22-3
Vilsmeier reagent

: 99-07-0
3-Dimethylaminophenol

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

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 60 - 70℃; for 1h;

: 99-07-0
3-Dimethylaminophenol

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorobenzene / 6 h / 100 °C / Inert atmosphere 2: hydrogenchloride; water / 2 h / 25 °C View Scheme

: 74-96-4
ethyl bromide

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

: 4-(dimethylamino)-2-ethoxybenzaldehyde

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetone at 40℃; for 16h;	100%

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

: 75-36-5
acetyl chloride

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	99%

: 1266669-75-3
C36H42Br2N6O4

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

: 5970-45-6
zinc(II) acetate dihydrate

: C54H58Br2N8O6Zn

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Inert atmosphere;	95%

...Expand

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

: 107-91-5
cyanoacetic acid amide

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

Conditions

Conditions	Yield
With piperidine In ethanol Heating;	93%

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

: 594-19-4
tert.-butyl lithium

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

Conditions

Conditions	Yield
In tetrahydrofuran; pentane at -78 - 20℃; Inert atmosphere;	92%

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

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

Conditions

Conditions	Yield
With pyridine; hydroxylamine hydrochloride In ethanol at 60℃; for 3h; Inert atmosphere;	92%

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

: 105-45-3
acetoacetic acid methyl ester

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

Conditions

Conditions	Yield
With piperidine In ethanol for 3h; Reflux;	92%

: 371-42-6
4-Fluorothiophenol

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

: 109-77-3
malononitrile

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

Conditions

Conditions	Yield
With triethylamine In ethanol for 4h; Temperature; Reflux;	90%

...Expand

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

: 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

Conditions	Yield
With acetic acid In ethanol for 5h; Reflux;	90%

: 137-43-9
Cyclopentyl bromide

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

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

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetone for 24h; Inert atmosphere; Reflux;	89.2%

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

: 126-81-8
dimedone

: 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

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; methanol at 20℃;	89%

...Expand

: 4946-22-9
N,N-dimethyl-4-aminothiophenol

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

: 109-77-3
malononitrile

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

Conditions

Conditions	Yield
With triethylamine In ethanol for 4h; Temperature; Reflux;	88%

...Expand

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

: 100-39-0
benzyl bromide

: 1268353-44-1
C16H17NO2

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 8h;	87.6%

: 24544-04-5
2,6-diisopropylbenzenamine

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

: C21H28N2O

Conditions

Conditions	Yield
With acetic acid In ethanol for 2h; Reflux;	87%

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

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

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

Conditions

Conditions	Yield
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%

: 752950-25-7
N,N′-bisoctadecyl-L-aminoglutamicdiamide

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

: C50H92N4O3

Conditions

Conditions	Yield
In ethanol at 80℃; for 8h;	85%

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

: 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

Conditions

Conditions	Yield
With perchloric acid In acetic acid for 0.5h; Heating;	83%

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

: 141-97-9
ethyl acetoacetate

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

Conditions

Conditions	Yield
With piperidine In ethanol for 6h; Heating / reflux;	81%

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

: 109-77-3
malononitrile

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

Conditions

Conditions	Yield
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%

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

: 108-45-2
m-phenylenediamine

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

Conditions

Conditions	Yield
In ethanol for 5h; Reflux;	79%

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

: 141-97-9
ethyl acetoacetate

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

Conditions

Conditions	Yield
With perchloric acid In acetic acid for 0.5h; Heating;	76%

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

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

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

Conditions

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

: 5055-39-0
indole-2-carbohydrazide

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

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

Conditions

Conditions	Yield
In ethanol Reflux;	76%

: 103-82-2
phenylacetic acid

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

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

Conditions

Conditions	Yield
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In acetonitrile for 2h; Heating;	75%

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

: C20H31NO5

: C29H39N2O5(1+)*ClO4(1-)

Conditions

Conditions	Yield
With sulfuric acid at 100℃; for 2h;	74%

: 15317-58-5
1H-indole-3-carboxylic acid hydrazide

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

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

Conditions

Conditions	Yield
In ethanol Reflux;	73%

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

: 21382-82-1
(carbethoxyethylidene)triphenylphosphorane

: 7-(dimethylamino)-3-methylcoumarin

Conditions

Conditions	Yield
at 180℃; for 2h;	72%

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

: 108-24-7
acetic anhydride

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

Conditions

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

Benzaldehyde,4-(dimethylamino)-2-hydroxy- Specification

The Benzaldehyde,4-(dimethylamino)-2-hydroxy-, with the CAS registry number 41602-56-6, is also known as 4-(Dimethylamino)salicylaldehyde. This chemical's molecular formula is C₉H₁₁NO₂ and molecular weight is 165.1891. Its systematic name is called 4-(dimethylamino)-2-hydroxybenzaldehyde.

Physical properties of Benzaldehyde,4-(dimethylamino)-2-hydroxy-: (1)ACD/LogP: 1.76; (2)ACD/LogD (pH 5.5): 2; (3)ACD/LogD (pH 7.4): 2; (4)ACD/BCF (pH 5.5): 12; (5)ACD/BCF (pH 7.4): 10; (6)ACD/KOC (pH 5.5): 212; (7)ACD/KOC (pH 7.4): 176; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.634; (12)Molar Refractivity: 49.201 cm³; (13)Molar Volume: 137.52 cm³; (14)Surface Tension: 52.045 dyne/cm; (15)Density: 1.201 g/cm³; (16)Flash Point: 135.908 °C; (17)Enthalpy of Vaporization: 56.287 kJ/mol; (18)Boiling Point: 301.111 °C at 760 mmHg; (19)Vapour Pressure: 0.001 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=Cc1ccc(cc1O)N(C)C
(2)InChI: InChI=1/C9H11NO2/c1-10(2)8-4-3-7(6-11)9(12)5-8/h3-6,12H,1-2H3
(3)InChIKey: KURCTZNCAHYQOV-UHFFFAOYAH

Product Name

4-(DIMETHYLAMINO)SALICYLALDEHYDE

Synthetic route

Benzaldehyde,4-(dimethylamino)-2-hydroxy- Specification

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