4-(Dimethylamino)benzaldehyde

Base Information

• Chemical Name: 4-(Dimethylamino)benzaldehyde
• CAS No.: 100-10-7
• Molecular Formula: C9H11NO
• Molecular Weight: 149.192
• Hs Code.: 2922.30
• European Community (EC) Number: 202-819-0
• NSC Number: 5517
• UNII: V7E88PR1YB
• DSSTox Substance ID: DTXSID5021835
• Nikkaji Number: J4.002I
• Wikipedia: Para-Dimethylaminobenzaldehyde
• Wikidata: Q1225737
• Pharos Ligand ID: 6WKTAZF87VCK
• Metabolomics Workbench ID: 130690
• ChEMBL ID: CHEMBL3188333
• Mol file: 100-10-7.mol

Synonyms:4-(dimethylamino)benzaldehyde;4-(dimethylamino)benzaldehyde, hydrochloride;Ehrlich's reagent;p-dimethylaminobenzaldehyde;p-dimethylaminobenzaldehyde hydrochloride;para-dimethylaminobenzaldehyde

Chemical Property of 4-(Dimethylamino)benzaldehyde

Chemical Property:

• Appearance/Colour: White to off white crystalline powder
• Vapor Pressure: 0.000806mmHg at 25°C
• Melting Point: 72-75 °C(lit.)
• Refractive Index: n20/D 1.417
• Boiling Point: 266.5 °C at 760 mmHg
• PKA: pK1:1.647(+1) (25°C)
• Flash Point: 103.3 °C
• PSA: 20.31000
• Density: 1.072 g/cm³
• LogP: 1.56510
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: alcohol: passes test (APHA ≤60)
• Water Solubility.: 0.3 g/L (20 ºC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 149.084063974
• Heavy Atom Count: 11
• Complexity: 126

Purity/Quality:

98% ^*data from raw suppliers

4-(Dimethylamino)benzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xn,Xi
• Hazard Codes: C,Xn,Xi,F
• Statements: 36/37/38-52/53-22-67-41-37/38-10-66-37-34-20-20/21/22-36-11
• Safety Statements: 7-16-24/25-26-61-45-39-36/37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: CN(C)C1=CC=C(C=C1)C=O
• Uses: In the presence of oxygen, some bacteria, like E.coli, are able to split tryptophan into indole and alpha-aminopropionic acid. This reagent is for detecting the indole and identify the indole-positive and indole-negative microorganisms. Forms colored condensation products (Schiff bases) with pyrroles1 and primary amines.2 4-(Dimethylamino)benzaldehyde is used in Ehrlich's reagent for spectrophotometric determination of hydrazine as it reacts to form azo dyes. 4-(Dimethylamino)benzaldehyde is used for determination of u rine bilirubin and porphobilinogen. Used as derivitizing agent. 4-Dimethylaminobenzaldehyde is used to prepare colorful Schiff base adducts with amines, pyrroles and indoles. It is often used in the Ehrlich reaction, test for the presence of indoles in a sample containing alkaloids and determination of hydrazine.

Technology Process of 4-(Dimethylamino)benzaldehyde

There total 222 articles about 4-(Dimethylamino)benzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

N,N-dimethyl-aniline (121-69-7,77733-26-7) + Chloromethylene-dimethyl-ammonium; GENERIC INORGANIC ANION → 4-dimethylamino-benzaldehyde (100-10-7)

Guidance literature:

Reference yield: 74.0%

4-(N,N-dimethylamino)benzaldehyde N,N-dimethylhydrazone (32787-73-8) → 4-dimethylamino-benzaldehyde (100-10-7)

Guidance literature:

With 2,6-dimethylpyridine; trifluoroacetic anhydride; In chloroform; at 20 ℃; for 72h;

DOI:10.1021/jo00236a026

Reference yield: 60.0%

4-dimethylamino-4'-(N,N-dimethylamino)benzylideneaniline (10050-89-2) + 4-nitrobenzaldehdye (555-16-8) → N,N-dimethyl-N'-(4-nitro-benzylidene)-p-phenylenediamine (896-06-0) + 4-dimethylamino-benzaldehyde (100-10-7)

Guidance literature:

In ethanol; for 22h; Heating;

upstream raw materials:

diethyl ether

2-(4-(dimethylamino)phenyl)-2-oxoacetic acid

ethanol

sodium ethanolate

Downstream raw materials:

2-(4-dimethylamino-benzylidene)-2,3-dihydro-pyrido[3,2,1-ij]quinoline-1,7-dione

2.3-diphenyl-1c-(4-dimethylamino-phenyl)-propen-⁽¹⁾-one-⁽³⁾

p-dimethylaminocinnamic acid

4-dimethylamino-4'-nitrostilbene

Refernces

• 1、 Hattori, Tomohiro,Takakura, Ryoya,Ichikawa, Tomohiro,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao. "Switching the Cleavage Sites in Palladium on Carbon-Catalyzed Carbon-Carbon Bond Disconnection". . p. 2737 - 2743. Retrieved 2016.
• 2、 Ge, Wenlei,Zhu, Xun,Wei, Yunyang. "Iodine-catalyzed oxidative system for cyclization of primary alcohols with o-aminobenzamides to quinazolinones using DMSO as the oxidant in dimethyl carbonate". . p. 10817 - 10822. Retrieved 2013.
• 3、 Veisi, Hojat,Sedrpoushan, Alireza,Zolfigol, Mohammad Ali,Mohanazadeh, Farajollah,Hemmati, Saba. "Silica phenyl sulfonic acid as a solid acid heterogeneous catalyst for chemoselective thioacetalization of carbonyl compounds and dethioacetalization under mild conditions". . p. E204-E206. Retrieved 2013.
• 4、 Tang, Lin,Sun, Huayin,Li, Yunfeng,Zha, Zhenggen,Wang, Zhiyong. "Highly active and selective synthesis of imines from alcohols and amines or nitroarenes catalyzed by Pd/DNA in water with dehydrogenation". . p. 3423 - 3428. Retrieved 2012.
• 5、 Hamasaki, Akiyuki,Yasutake, Yutaro,Norio, Takafumi,Ishida, Tamao,Akita, Tomoki,Ohashi, Hironori,Yokoyama, Takushi,Honma, Tetsuo,Tokunaga, Makoto. "Cooperative catalysis of palladium nanoparticles and cobalt oxide support for formylation of aryl iodides under syngas atmosphere". . p. 146 - 152. Retrieved 2014.
• 6、 Glaser, Matthias,Arstad, Erik,Luthra, Sajinder K.,Robins, Edward G.. "Two-step radiosynthesis of [18F]N-succinimidyl-4-fluorobenzoate ([18F]SFB)". . p. 327 - 330. Retrieved 2009.
• 7、 Klaus, Stefan,Neumann, Helfried,Zapf, Alexander,Struebing, Dirk,Huebner, Sandra,Almena, Juan,Riermeier, Thomas,Gross, Peter,Sarich, Martin,Krahnert, Wolf-Ruediger,Rossen, Kai,Beller, Matthias. "A general and efficient method for the formylation of aryl and heteroaryl bromides". . p. 154 - 158. Retrieved 2006.
• 8、 Das, Asit Kumar,Nandy, Sneha,Bhar, Sanjay. "Chemoselective and ligand-free aerobic oxidation of benzylic alcohols to carbonyl compounds using alumina-supported mesoporous nickel nanoparticle as an efficient recyclable heterogeneous catalyst". . . Retrieved 2021.
• 9、 Sun, Haoran,DiMagno, Stephen G.. "Competitive demethylation and substitution in N,N,N-trimethylanilinium fluorides". . p. 806 - 812. Retrieved 2007.
• 10、 Adib, Mehdi,Karajabad, Morteza Akherati,Sheikhi, Ehsan. "Oxidation of Benzylic Alcohols to Aromatic Aldehydes by DMSO/Water/I2: A Chemoselective Oxidation". . . Retrieved 2020.