trans-4-(Diethylamino)cinnamaldehyde

Base Information

• Chemical Name: trans-4-(Diethylamino)cinnamaldehyde
• CAS No.: 22411-59-2
• Molecular Formula: C13H17NO
• Molecular Weight: 203.284
• Hs Code.: 2922399090
• European Community (EC) Number: 806-301-0
• NSC Number: 166362
• DSSTox Substance ID: DTXSID90418751
• Nikkaji Number: J307.761F
• Wikidata: Q72469086
• Mol file: 22411-59-2.mol

Synonyms:trans-4-(Diethylamino)cinnamaldehyde;22411-59-2;(E)-3-[4-(diethylamino)phenyl]prop-2-enal;4-(diethylamino)cinnamaldehyde;p-diethylaminocinnamaldehyde;NSC166362;(E)-3-(4-(diethylamino)phenyl)acrylaldehyde;DTXSID90418751;JXXOTBSUZDDHLT-AATRIKPKSA-N;AKOS022622923;NSC-166362;3-[4-(diethylamino)phenyl]prop-2-enal;AS-78741;trans-4-(Diethylamino)cinnamaldehyde, 98%;CS-0348279;D93403;EN300-1851948;(2E)-3-[4-(Diethylamino)phenyl]-2-propenal #;J-014694;194099-39-3;InChI=1/C13H17NO/c1-3-14(4-2)13-9-7-12(8-10-13)6-5-11-15/h5-11H,3-4H2,1-2H3/b6-5

Chemical Property of trans-4-(Diethylamino)cinnamaldehyde

Chemical Property:

• Vapor Pressure: 3.14E-05mmHg at 25°C
• Melting Point: 74-76℃
• Refractive Index: 1.577
• Boiling Point: 355.4 °C at 760 mmHg
• Flash Point: 136.2 °C
• PSA: 20.31000
• Density: 1.022 g/cm³
• LogP: 2.74490
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 203.131014166
• Heavy Atom Count: 15
• Complexity: 201

Purity/Quality:

99% ^*data from raw suppliers

trans-4-(Diethylamino)cinnamaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-27-36/37/39-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN(CC)C1=CC=C(C=C1)C=CC=O
• Isomeric SMILES: CCN(CC)C1=CC=C(C=C1)/C=C/C=O

Technology Process of trans-4-(Diethylamino)cinnamaldehyde

There total 15 articles about trans-4-(Diethylamino)cinnamaldehyde 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: 74.0%

1-(4-N,N-diethylaminophenyl)butadiene → p-diethylamino-cinnamaldehyde (22411-59-2)

Guidance literature:

With iron(III) sulfate hydrate; oxygen; In water; acetonitrile; at 45 ℃; for 21h; regioselective reaction;

DOI:10.1021/acs.orglett.9b03562

Reference yield: 68.0%

(Z)-1-bromo-2-ethoxyethene (23521-49-5) + 4-Diethylaminobenzaldehyde (120-21-8) → p-diethylamino-cinnamaldehyde (22411-59-2)

Guidance literature:

(Z)-1-bromo-2-ethoxyethene; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.666667h;

4-Diethylaminobenzaldehyde; In tetrahydrofuran; pentane; at -78 ℃; for 2h;

DOI:10.1039/b608391a

Reference yield: 55.0%

N,N-diethylaniline (91-66-7) + 3-dimethylaminoacrolein (927-63-9) → p-diethylamino-cinnamaldehyde (22411-59-2)

Guidance literature:

With trichlorophosphate; In chloroform; at -10 - 60 ℃;

DOI:10.3390/molecules26144360

upstream raw materials:

4-Diethylaminobenzaldehyde

p-Diaethylamino-zimtsaeure-methylester

N-ethylidenecyclohexylamine

[4-((E)-2-[1,3]Dioxolan-2-yl-vinyl)-phenyl]-diethyl-amine

Downstream raw materials:

2-benzoyl-5-(4-diethylamino-phenyl)-penta-2,4-dienenitrile

3-(4-(diethylamino)phenyl)acrylic acid

Refernces

• 1、 Bhowmik, Amit,Fernandes, Rodney A.. "Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes". supporting information. p. 9203 - 9207. Retrieved 2019/11/14.
• 2、 Kim, Eunha,Koh, Minseob,Lim, Byung Joon,Park, Seung Bum. "Emission wavelength prediction of a full-color-tunable fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one". . p. 6642 - 6649. Retrieved 2011/06/19.