120-21-8

Basic information

• Product Name: 4-Diethylaminobenzaldehyde
• Synonyms: (diethylamino)benzaldehyde;4-(diethylamino)-benzaldehyd;Benzaldehyde, p-(diethylamino)-;benzaldehyde,-(diethylamino)-;Benzaldehyde,4-(diethylamino)-;N,N-Diethylaminobenzaldehyde;DEAB;LABOTEST-BB LT00924385
• CAS NO: 120-21-8
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.24
• EINECS: 204-377-4
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);electronic;Aldehydes;C10 to C21;Carbonyl Compounds;Pyridines
• Mol File: 120-21-8.mol
• Article Data: 28

Chemical Properties

• Melting Point: 37-41 °C(lit.)
• Boiling Point: 174 °C7 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Brown to green to black/Coarse Crystals, Chunks or Crystalline Solid
• Density: 1.03 g/cm3
• Vapor Pressure: 0.000176mmHg at 25°C
• Refractive Index: 1.5302 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 2.5g/l
• PKA: 3.36±0.32(Predicted)
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 511102
• CAS DataBase Reference: 4-Diethylaminobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Diethylaminobenzaldehyde(120-21-8)
• EPA Substance Registry System: 4-Diethylaminobenzaldehyde(120-21-8)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-50/53-21/22
• Safety Statements: 26-36-61-60-36/37
• WGK Germany: 2
• RTECS: CU5612850
• TSCA: Yes
• Hazardous Substances Data: 120-21-8(Hazardous Substances Data)

Usage

Description

4-Diethylaminobenzaldehyde is a member of the class of benzaldehydes, characterized by a diethylamino substituent at the 4th position. It is known for its dark brown to green coarse crystalline appearance.

Uses

Used in Pharmaceutical Industry:
4-Diethylaminobenzaldehyde is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. One of its applications is in the preparation of 5-(4-diethylamino-benzylidene)-selenazolidine-2,4-dione, which is achieved using aqueous methylamine as a reagent. 4-Diethylaminobenzaldehyde may have potential applications in the development of new drugs or drug candidates.
Used in Chemical Synthesis:
In the field of organic chemistry, 4-Diethylaminobenzaldehyde serves as a valuable building block for the synthesis of a wide range of organic compounds, including dyes, pigments, and other specialty chemicals. Its unique structure with the diethylamino substituent at the 4th position allows for various chemical reactions and modifications, making it a versatile compound in the synthesis of complex molecules.
Used in Research and Development:
4-Diethylaminobenzaldehyde is also utilized in research and development laboratories for studying its chemical properties, reactivity, and potential applications in various fields. Researchers may explore its use in the development of new materials, catalysts, or as a component in advanced chemical processes.

InChI:InChI=1/C11H15NO/c1-3-12(4-2)11-7-5-10(9-13)6-8-11/h5-9H,3-4H2,1-2H3

Synthetic route

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + N,N-diethylaniline (91-66-7) → 4-Diethylaminobenzaldehyde (120-21-8)

Conditions	Yield
With trichlorophosphate at 0 - 80℃; for 14h;	92.1%
With trichlorophosphate at 80℃; for 24h;	53%
With trichlorophosphate Vilsmeier reaction;
With trichlorophosphate at 0 - 20℃;

4-fluorobenzaldehyde (459-57-4) + diethylamine (109-89-7) → 4-Diethylaminobenzaldehyde (120-21-8)

Conditions	Yield
With Aliquat 336; potassium carbonate In dimethyl sulfoxide at 95℃; for 72h;	92%
In dimethyl sulfoxide
With Aliquat 336; potassium carbonate In dimethyl sulfoxide

(4-(diethylamino)phenyl)methanol (74974-49-5) → 4-Diethylaminobenzaldehyde (120-21-8)

Conditions	Yield
With periodic acid In water at 27℃; for 8h;	91%

bis-(4-diethylamino-phenyl)-mercury (56542-00-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4-Diethylaminobenzaldehyde (120-21-8)

Conditions	Yield
With trichlorophosphate In water at 70℃; for 1h;	85%

C11H16BrN (1054451-35-2) → 4-Diethylaminobenzaldehyde (120-21-8)

Conditions	Yield
With potassium hydrogencarbonate; dimethyl sulfoxide for 0.0666667h; Microwave irradiation;	84%

N,N-diethylaniline (91-66-7) + trimethyl orthoformate (149-73-5) → 4-Diethylaminobenzaldehyde (120-21-8)

Conditions	Yield
With titanium tetrachloride In dichloromethane at 0 - 25℃; for 5.5h;	75%

2,2,2-trichloro-1-(4-diethylamino-phenyl)-ethanol + alcoholic potash → chloroform (67-66-3) + 4-Diethylaminobenzaldehyde (120-21-8)

N,N-diethylaniline (91-66-7) → 4-Diethylaminobenzaldehyde (120-21-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated hydrochloric acid 2: glacial acetic acid; formaldehyde View Scheme
Multi-step reaction with 2 steps 1: ZnCl2 / 40 °C 2: alcoholic potash View Scheme

aniline (62-53-3) → 4-Diethylaminobenzaldehyde (120-21-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; sodium stearate; tetrabutylammomium bromide / water; ethanol / 100 °C 2: trichlorophosphate / 0 - 80 °C View Scheme

N,N-dimethyl-aniline (121-69-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4-Diethylaminobenzaldehyde (120-21-8)

Conditions	Yield
Stage #1: N,N-dimethyl-aniline; N,N-dimethyl-formamide With trichlorophosphate at 0 - 80℃; Vilsmeier-Haack Formylation; Stage #2: With sodium carbonate Vilsmeier-Haack Formylation;

(trifluoromethyl)trimethylsilane (81290-20-2) + 4-Diethylaminobenzaldehyde (120-21-8) → diethyl-[4-(2,2,2-trifluoro-1-trimethylsilanyloxy-ethyl)-phenyl]-amine

Conditions	Yield
With cesium fluoride In 1,2-dimethoxyethane for 3h;	100%

n-butyllithium (109-72-8, 29786-93-4) + 4-Diethylaminobenzaldehyde (120-21-8) → 1-(4-diethylaminophenyl)-1-pentanol

Conditions	Yield
In tetrahydrofuran; hexane at -78 - 20℃;	100%

propylamine (107-10-8) + 4-Diethylaminobenzaldehyde (120-21-8) → p-Diaethylamino-N-n-propylimino-methylbenzol

Conditions	Yield
at 20℃; for 12h;	100%

4-Diethylaminobenzaldehyde (120-21-8) + isopropylamine (75-31-0) → p-Diaethylamino-N-isopropylimino-methylbenzol

Conditions	Yield
at 20℃; for 12h;	100%

4-Diethylaminobenzaldehyde (120-21-8) + methylamine (74-89-5) → Diethyl-{4-[(E)-methyliminomethyl]-phenyl}-amine (72617-24-4)

Conditions	Yield
at 20℃; for 12h;	100%

4,4'-dimethyl-2,2'-bipyridines (1134-35-6) + 4-Diethylaminobenzaldehyde (120-21-8) → 4-{2-[4-(diethylamino)phenyl]-2-hydroxyethyl}-4'-methyl-2,2'-bipyridine (478550-41-3)

Conditions	Yield
Stage #1: 4,4'-dimethyl-2,2'-bipyridines With lithium diisopropyl amide In tetrahydrofuran; hexane at -20℃; for 2h; Stage #2: 4-Diethylaminobenzaldehyde In tetrahydrofuran at -20℃; for 2h;	99%

Upstream product

• 100-97-0 hexamethylenetetramine 
• 91-66-7 N,N-diethylaniline 
• 149796-22-5 5-(4-diethylamino-phenyl)-5-hydroxy-barbituric acid 
• 82529-61-1 N-<4-(diethylamino)benzylidene>-4-(dimethylamino)aniline 
• 50-00-0 formaldehyd 
• 64-19-7 acetic acid 
• 93-61-8 N-methyl-N-phenylformamide 
• 56542-00-8 bis-(4-diethylamino-phenyl)-mercury 
• 68-12-2 N,N-dimethyl-formamide 
• 459-57-4 4-fluorobenzaldehyde 
• 109-89-7 diethylamine 
• 149-73-5 trimethyl orthoformate 
• 1054451-35-2 C₁₁H₁₆BrN 
• 74974-49-5 (4-(diethylamino)phenyl)methanol 

Downstream Products

• 1519-09-1 N,N-diethyl-4-(trans-2-[2]pyridyl-vinyl)-aniline 
• 5447-23-4 3-((Ξ)-4-diethylamino-benzylidene)-dihydro-furan-2-one 
• 18096-82-7 trans-4-pyridine 
• 94906-15-7 N,N-diethyl-4-[2-(1-oxy-pyridin-4-yl)-vinyl]-aniline 
• 76869-46-0 (E)-N,N-diethyl-4-(2-(quinolin-2-yl)vinyl)benzenamine 
• 75194-88-6 5-(4-diethylamino-benzylidene)-2-thioxo-thiazolidin-4-one 
• 5397-61-5 N,N-diethyl-4-(2-quinolin-4-yl-vinyl)-aniline 
• 102660-42-4 N,N-diethyl-4-(trans-2-[1]isoquinolyl-vinyl)-aniline 
• 114695-27-1 N,N-diethyl-4-[trans!-2-(3-methyl-[4]quinolyl)-vinyl]-aniline 
• 112949-45-8 N,N-diethyl-4-[trans-2-(1-oxy-[2]quinolyl)-vinyl]-aniline 
• 32657-71-9 nicotinic acid-(4-diethylamino-benzylidenehydrazide) 
• 93726-13-7 isonicotinic acid-(4-diethylamino-benzylidenehydrazide) 
• 40176-21-4 5-[4-(dimethylamino)benzylidene]-2,4,6(1H,3H,5H)-pyrimidinetrione 
• 60045-59-2 5-{[4'(N,N-diethylamino)phenyl]methylidene}-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 

Relevant articles and documents

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Self-assembly of a series of thiocyanate complexes with high two-photon absorbing active in near-IR range and bioimaging applications

Abstract A series of novel complexes bearing high fluorescence quantum yields and showing the peak two-photon absorption (2 PA) cross-sections in the near-infrared region, Zn(SCN)2L2(1), [Cd(SCN)2L2]n(2), Co(SCN)2L4(3), Ni(SCN)2L4(4), [CdHgL2(SCN)4]n(5) and [MnHg(SCN)4L2]n(6), containing functional chromophore (L = (E)-(4-diethyl anilinostyryl)pyridine), were synthesized in high yields. Crystal structures of all the complexes were confirmed. Hetero-metal complexes (5, 6: L:M = 1:1) present much higher two-photon absorption (2 PA) cross-sections (σ) in comparison with those of the homo-metal complexes (L:M = 4:1 in 3 and 4, L:M = 2:1 in 1 and 2) and the free ligand (L) which may due to the fact that the hetero-metal complexes have more bridged anions (SCN-), conjugated subunits -[Hg(SCN)2M]- and -[Hg2(SCN)4M2]-. In addition, the results revealed that 2 PA response was much enhanced for the Zn(SCN)2L2 and two-photon fluorescence cell imaging experiment proved its potential application.

NOVEL CATHODE BUFFER LAYER MATERIAL AND ORGANIC PHOTOELECTRIC DEVICE INCLUDING SAME

The present invention relates to a novel cathode buffer layer material and an organic photoelectric device including the same. When the novel compound of the present invention is applied to a cathode buffer layer of an organic photoelectric device, for example, an organic solar cell or an organic photodiode, there is an effect in which the surface characteristics of an electron transport layer are improved through the high dipole moment of the novel compound to thereby facilitate electron extraction from a photoactive layer to a cathode electrode and to reduce series resistance and leakage current, and accordingly, the performance of an organic optoelectronic device (organic solar cell, organic photodiode, etc.) to be manufactured can be remarkably improved, which is industrially advantageous.

Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl) methane

Difluoro(phenylsulfanyl)methane (PhSCF 2 H) was found to undergo a reaction with aromatic compounds mediated by SnCl 4, through a thionium intermediate characterized by NMR and TD-DFT analyses, leading to the formation of a mixture of S, S ′-diphenyl dithioacetal and aromatic aldehyde which, after oxidative hydrolysis, provides the aromatic aldehyde in good to excellent yields. The salient feature of the present work is the reaction of activated aromatic compounds containing a deactivating ester functional group, leading to the formylated products in good yields.