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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.

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  • 120-21-8 Structure
  • Basic information

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

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

    1. Hazard Codes: Xi,N,Xn
    2. Statements: 36/37/38-50/53-21/22
    3. Safety Statements: 26-36-61-60-36/37
    4. WGK Germany: 2
    5. RTECS: CU5612850
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 120-21-8(Hazardous Substances Data)

120-21-8 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 120-21-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 0 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 120-21:
(5*1)+(4*2)+(3*0)+(2*2)+(1*1)=18
18 % 10 = 8
So 120-21-8 is a valid CAS Registry Number.
InChI:InChI=1/C11H15NO/c1-3-12(4-2)11-7-5-10(9-13)6-8-11/h5-9H,3-4H2,1-2H3

120-21-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A11825)  4-Diethylaminobenzaldehyde, 97%   

  • 120-21-8

  • 100g

  • 424.0CNY

  • Detail
  • Alfa Aesar

  • (A11825)  4-Diethylaminobenzaldehyde, 97%   

  • 120-21-8

  • 500g

  • 1186.0CNY

  • Detail

120-21-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(diethylamino)benzaldehyde

1.2 Other means of identification

Product number -
Other names Benzaldehyde, 4-(diethylamino)-

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:120-21-8 SDS

120-21-8Synthetic route

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

N,N-dimethyl-formamide

N,N-diethylaniline
91-66-7

N,N-diethylaniline

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

Conditions
ConditionsYield
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

4-fluorobenzaldehyde

diethylamine
109-89-7

diethylamine

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

Conditions
ConditionsYield
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-(diethylamino)phenyl)methanol

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

Conditions
ConditionsYield
With periodic acid In water at 27℃; for 8h;91%
bis-(4-diethylamino-phenyl)-mercury
56542-00-8

bis-(4-diethylamino-phenyl)-mercury

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

N,N-dimethyl-formamide

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

Conditions
ConditionsYield
With trichlorophosphate In water at 70℃; for 1h;85%
C11H16BrN
1054451-35-2

C11H16BrN

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

Conditions
ConditionsYield
With potassium hydrogencarbonate; dimethyl sulfoxide for 0.0666667h; Microwave irradiation;84%
N,N-diethylaniline
91-66-7

N,N-diethylaniline

trimethyl orthoformate
149-73-5

trimethyl orthoformate

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 0 - 25℃; for 5.5h;75%
2,2,2-trichloro-1-(4-diethylamino-phenyl)-ethanol

2,2,2-trichloro-1-(4-diethylamino-phenyl)-ethanol

alcoholic potash

alcoholic potash

A

chloroform
67-66-3

chloroform

B

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

N,N-diethylaniline
91-66-7

N,N-diethylaniline

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

Conditions
ConditionsYield
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

aniline

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

Conditions
ConditionsYield
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-aniline

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

N,N-dimethyl-formamide

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

Conditions
ConditionsYield
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

(trifluoromethyl)trimethylsilane

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

diethyl-[4-(2,2,2-trifluoro-1-trimethylsilanyloxy-ethyl)-phenyl]-amine

diethyl-[4-(2,2,2-trifluoro-1-trimethylsilanyloxy-ethyl)-phenyl]-amine

Conditions
ConditionsYield
With cesium fluoride In 1,2-dimethoxyethane for 3h;100%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

1-(4-diethylaminophenyl)-1-pentanol

1-(4-diethylaminophenyl)-1-pentanol

Conditions
ConditionsYield
In tetrahydrofuran; hexane at -78 - 20℃;100%
propylamine
107-10-8

propylamine

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

p-Diaethylamino-N-n-propylimino-methylbenzol

p-Diaethylamino-N-n-propylimino-methylbenzol

Conditions
ConditionsYield
at 20℃; for 12h;100%
4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

isopropylamine
75-31-0

isopropylamine

p-Diaethylamino-N-isopropylimino-methylbenzol

p-Diaethylamino-N-isopropylimino-methylbenzol

Conditions
ConditionsYield
at 20℃; for 12h;100%
4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

methylamine
74-89-5

methylamine

Diethyl-{4-[(E)-methyliminomethyl]-phenyl}-amine
72617-24-4

Diethyl-{4-[(E)-methyliminomethyl]-phenyl}-amine

Conditions
ConditionsYield
at 20℃; for 12h;100%
4,4'-dimethyl-2,2'-bipyridines
1134-35-6

4,4'-dimethyl-2,2'-bipyridines

4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

4-{2-[4-(diethylamino)phenyl]-2-hydroxyethyl}-4'-methyl-2,2'-bipyridine
478550-41-3

4-{2-[4-(diethylamino)phenyl]-2-hydroxyethyl}-4'-methyl-2,2'-bipyridine

Conditions
ConditionsYield
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%

120-21-8Relevant articles and documents

Aggregation induced emission in the rotatable molecules: The essential role of molecular interaction

Yu, Zhipeng,Duan, Yaya,Cheng, Longhuai,Han, Zhili,Zheng, Zheng,Zhou, Hongping,Wu, Jieying,Tian, Yupeng

, p. 16927 - 16932 (2012)

Aggregation-induced emission (AIE) compounds, dye2 and dye3, with a rotatable N-N single bond and aza-crown-ether, have been synthesized. The fluorescence intensities of both dyes are very weak in THF, while become extraordinarily strong in a mixture of H2O-THF (v/v 95%). They are increased by 88.9 and 70.7 times, respectively, indicating enhanced blue-green fluorescence emissions. The λem of these two compounds in different states has been well studied. Besides this, dye1 and dye2 were characterized by single crystal X-ray structural determination. The results show that molecular interactions are formed in the particles, which considerably restrict the intramolecular vibration and rotation. The Royal Society of Chemistry 2012.

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

Li, Dandan,Zhang, Qiong,Wang, Xuchun,Li, Shengli,Zhou, Hongping,Wu, Jieying,Tian, Yupeng

, p. 175 - 183 (2015)

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

-

Paragraph 0178-0180, (2021/02/05)

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.

Detection living body Fe2 + Double-photon fluorescence probe as well as preparation method and application thereof

-

Paragraph 0042-0045; 0051-0054; 0060-0063, (2021/11/19)

The invention relates to a pyrimidine-based dye which can be quickly regulated and controlled by light. Sensitive detection living body Fe2 + A double-photon fluorescence probe belongs to the field of organic fluorescent probes. The fluorescent probe is PyFe fluorescence probe, and the structural formula of PyFe fluorescence probe is as shown in formula (I). Fe In vivo can be accurately detected by the fluorescent probe. 2 + , Interference of other ionic amino acids in the cells is avoided. The probe has very fast response rate and high ion selectivity, can realize naked eye detection in vitro and also has good biocompatibility. The fluorescence confocal imaging experiment shows that the probe has good cell permeability, does not have toxic or side effects on cells and organisms, and has dual photonicity, so that the depth imaging of living animals or tissues can be realized.

Continuous-flow Synthesis of Aryl Aldehydes by Pd-catalyzed Formylation of Aryl Bromides Using Carbon Monoxide and Hydrogen

Hone, Christopher A.,Lopatka, Pavol,Munday, Rachel,O'Kearney-McMullan, Anne,Kappe, C. Oliver

, p. 326 - 337 (2018/11/23)

A continuous-flow protocol utilizing syngas (CO and H2) was developed for the palladium-catalyzed reductive carbonylation of (hetero)aryl bromides to their corresponding (hetero)aryl aldehydes. The optimization of temperature, pressure, catalyst and ligand loading, and residence time resulted in process-intensified flow conditions for the transformation. In addition, a key benefit of investigating the reaction in flow is the ability to precisely control the CO-to-H2 stoichiometric ratio, which was identified as having a critical influence on yield. The protocol proceeds with low catalyst and ligand loadings: palladium acetate (1 mol % or below) and cataCXium A (3 mol % or below). A variety of (hetero)aryl bromides at a 3 mmol scale were converted to their corresponding (hetero)aryl aldehydes at 12 bar pressure (CO/H2=1:3) and 120 °C reaction temperature within 45 min residence time to afford products mostly in good-to-excellent yields (17 examples). In particular, a successful scale-up was achieved over 415 min operation time for the reductive carbonylation of 2-bromo-6-methoxynaphthalene to synthesize 3.8 g of 6-methoxy-2-naphthaldehyde in 85 % isolated yield. Studies were conducted to understand catalyst decomposition within the reactor by using inductively coupled plasma–mass spectrometry (ICP–MS) analysis. The palladium could easily be recovered using an aqueous nitric acid wash post reaction. Mechanistic aspects and the scope of the transformation are discussed.

Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl) methane

Betterley, Nolan M.,Kongsriprapan, Sopanat,Chaturonrutsamee, Suppisak,Deelertpaiboon, Pramchai,Surawatanawong, Panida,Pohmakotr, Manat,Soorukram, Darunee,Reutrakul, Vichai,Kuhakarn, Chutima

, p. 2033 - 2040 (2018/03/21)

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.

A process for preparing a broad pH fluorescent probe of the organic compound and use thereof (by machine translation)

-

Paragraph 0130; 0131, (2018/04/03)

The present invention discloses a process for the preparation of a wide range of fluorescent probe in the pH of the organic compound, the organic compound can be produced according to the actual need to carry out any proportion of combination, and can be fixed in the hydrophilic high polymer further preparing and detecting water environment acidity and alkalinity of the product. The product can be realized to the pH value of the continuous measuring, thereby greatly improving the efficiency, sensitivity and repeatability. (by machine translation)

Design, Synthesis, and Structure–Activity Relationship Analysis of Thiazolo[3,2-a]pyrimidine Derivatives with Anti-inflammatory Activity in Acute Lung Injury

Chen, Lingfeng,Jin, Yiyi,Fu, Weitao,Xiao, Siyang,Feng, Chen,Fang, Bo,Gu, Yugui,Li, Chenglong,Zhao, Yunjie,Liu, Zhiguo,Liang, Guang

supporting information, p. 1022 - 1032 (2017/07/11)

Acute lung injury (ALI) has a high lethality rate, and interleukin-6 (IL-6) and tumor necrosis factor-α (TNF-α) contribute most to tissue deterioration in cases of ALI. In this study, we designed and synthesized a new series of thiazolo[3,2-a]pyrimidine derivatives based on a previously identified lead compound, and we evaluated their anti-inflammatory activities. Structure–activity relationship studies led to the discovery of two highly potent inhibitors. The two promising compounds were found to inhibit lipopolysaccharide (LPS)-induced IL-6 and TNF-α release in a dose-dependent manner in mouse primary peritoneal macrophages (MPMs). Furthermore, administration of these compounds resulted in lung histopathological improvements and attenuated LPS-induced ALI in vivo. Taken together, these data indicate that these novel thiazolo[3,2-a]pyrimidine derivatives could be developed as candidate drugs for the treatment of ALI.

FTC-containing molecules: large second-order nonlinear optical performance and excellent thermal stability, and the key development of the “Isolation Chromophore” concept

Chen, Pengyu,Yin, Xiuyang,Xie, Yujun,Li, Shufang,Luo, Shiyu,Zeng, Huiyi,Guo, Guocong,Li, Qianqian,Li, Zhen

supporting information, p. 11474 - 11481 (2016/12/18)

A series of second-order nonlinear optical (NLO) molecules, M1-M5, were designed and successfully synthesized through the convenient ‘‘click chemistry’’ reaction, which contain two different types of chromophore moieties, the FTC chromophore and nitro-based azo ones, according to the concept of “Isolation Chromophore”. All these five molecules possess excellent thermal stability and very large NLO performance, with an ultrahigh d33 value of 384 pm V?1 at the wavelength of 1950 nm achieved for M1, furthering the rational design of excellent NLO materials.

Monocarboxylate transporter 1 inhibitors as potential anticancer agents

Gurrapu, Shirisha,Jonnalagadda, Sravan K.,Alam, Mohammad A.,Nelson, Grady L.,Sneve, Mary G.,Drewes, Lester R.,Mereddy, Venkatram R.

supporting information, p. 558 - 561 (2015/05/27)

Potent monocarboxylate transporter 1 inhibitors (MCT1) have been developed based on α-cyano-4-hydroxycinnamic acid template. Structure-activity relationship studies demonstrate that the introduction of p-N, N-dialkyl/diaryl, and o-methoxy groups into cyanocinnamic acid has maximal MCT1 inhibitory activity. Systemic toxicity studies in healthy ICR mice with few potent MCT1 inhibitors indicate normal body weight gains in treated animals. In vivo tumor growth inhibition studies in colorectal adenocarcinoma (WiDr cell line) in nude mice xenograft models establish that compound 27 exhibits single agent activity in inhibiting the tumor growth.

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