4-Dimethylamino-4'-nitrostilbene

Base Information

• Chemical Name: 4-Dimethylamino-4'-nitrostilbene
• CAS No.: 2844-15-7
• Deprecated CAS: 211565-05-8
• Molecular Formula: C16H16N2O2
• Molecular Weight: 268.315
• European Community (EC) Number: 634-782-5,679-843-7
• DSSTox Substance ID: DTXSID6049303
• Nikkaji Number: J421.728D,J236.519G
• Wikidata: Q27122685,Q76305843
• Metabolomics Workbench ID: 57808
• ChEMBL ID: CHEMBL84003
• Mol file: 2844-15-7.mol

Synonyms:4-Dimethylamino-4'-nitrostilbene;4584-57-0;n,n-dimethyl-4-(4-nitrostyryl)aniline;DANS;2844-15-7;Amino-Nitrostilbene;N,N-dimethyl-4-[2-(4-nitrophenyl)vinyl]aniline;N,N-Dimethyl-4-[(E)-2-(4-nitrophenyl)ethenyl]aniline;Benzenamine, N,N-dimethyl-4-(2-(4-nitrophenyl)ethenyl)-;(E)-N,N-dimethyl-4-(4-nitrostyryl)aniline;DTXSID6049303;1,4-Dimethylamino-4-nitrostilbene;1,4-Dimethylamino-4'-nitrostilbene;4,-Dimethylamino -4'-nitrostilbene;CCRIS 2642;4-Stilbenamine, N,N-dimethyl-4'-nitro-;N,N-dimethyl-4-[2-(4-nitrophenyl)ethenyl]aniline;Benzenamine, N,N-dimethyl-4-[2-(4-nitrophenyl)ethenyl]-;N,N-Dimethyl-4-(2-(4-nitrophenyl)ethenyl)aniline;CHEMBL84003;SCHEMBL531104;DTXCID8029159;p-Dimethylamino-p'-nitrostilbene;CHEBI:51615;4-nitro-4'-dimethylaminostilbene;N1,N1-dimethyl-4-((E)-2-(4-nitrophenyl)-1-ethenyl)aniline;4-(Dimethylamino)-4'-nitrostilbene;4-Nitro-4'-(dimethylamino)stilbene;Tox21_202918;MFCD00041877;AKOS001483337;AKOS015894994;N,N-Dimethyl-4'-nitro-4-stilbenamine;4-Dimethylamino-4'-nitrostilbene, 98%;NCGC00260464-01;(E)-4-(Dimethylamino)-4'-nitrostilbene;BS-44047;CAS-4584-57-0;CS-0373809;D2505;4-Dimethylamino-4'-nitrostilbene, >=99.8% (T);A912625;SR-01000389581;J-017070;SR-01000389581-1;Q27122685;Benzenamine, N,N-dimethyl-4-[2-(4-nitrophenyl)vinyl]-;(E)-dimethyl-{4-[2-(4-nitro-phenyl)-vinyl]-phenyl}-amine;Dimethyl-pyrrol4-[2-(4-nitrophenyl)-vinyl]-phenylmorpho-amin;N,N-dimethyl-N-{4-[(E)-2-(4-nitrophenyl)vinyl]phenyl}amine

Chemical Property of 4-Dimethylamino-4'-nitrostilbene

Chemical Property:

• Melting Point: 256-259oC
• Boiling Point: 411.7oC at 760 mmHg
• PKA: 4.12±0.15(Predicted)
• Flash Point: 202.8oC
• PSA: 49.06000
• Density: 1.206g/cm3
• LogP: 4.35440
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 268.121177757
• Heavy Atom Count: 20
• Complexity: 333

Purity/Quality:

98% ^*data from raw suppliers

4-Dimethylamino-4''-nitrostilbene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 1379389
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: CN(C)C1=CC=C(C=C1)C=CC2=CC=C(C=C2)[N+](=O)[O-]
• Isomeric SMILES: CN(C)C1=CC=C(C=C1)/C=C/C2=CC=C(C=C2)[N+](=O)[O-]
• Uses: 4-Dimethylamino-4''-nitrostilbene is a useful standard for the correction of emission of fluorescence spectrometers.

Technology Process of 4-Dimethylamino-4'-nitrostilbene

There total 23 articles about 4-Dimethylamino-4'-nitrostilbene 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%

diethyl p-nitrobenzylphosphonate (2609-49-6) + 4-dimethylamino-benzaldehyde (100-10-7) → N,N-dimethyl-4-[(E)-2-(4-nitrophenyl)vinyl]aniline (2844-15-7,211565-05-8)

Guidance literature:

diethyl p-nitrobenzylphosphonate; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; for 0.25h;

4-dimethylamino-benzaldehyde; In N,N-dimethyl-formamide; mineral oil; for 1h;

DOI:10.1021/acs.inorgchem.0c01520

Reference yield: 89.0%

4-nitrobenzeneacetic acid (104-03-0) + 4-dimethylamino-benzaldehyde (100-10-7) → N,N-dimethyl-4-[(E)-2-(4-nitrophenyl)vinyl]aniline (2844-15-7,211565-05-8)

Guidance literature:

With piperidine; Inert atmosphere;

DOI:10.1039/c6cc10066j

Reference yield: 82.0%

1-methyl-4-nitrobenzene (99-99-0) + 4-dimethylamino-benzaldehyde (100-10-7) → N,N-dimethyl-4-[(E)-2-(4-nitrophenyl)vinyl]aniline (2844-15-7,211565-05-8)

Guidance literature:

With potassium carbonate; at 100 ℃; for 3h; stereoselective reaction; neat (no solvent);

DOI:10.3184/030823410X12814419570511

upstream raw materials:

1-methyl-4-nitrobenzene

4-dimethylamino-benzaldehyde

4-nitrobenzeneacetic acid

chloro-trimethyl-silane

Downstream raw materials:

trans-4′-(N,N′-dimethylamino)-4-aminostilbene

C₁₆H₂₀N₂

4-(dimethylamino)-2-((4-((E)-2-(4-(dimethylamino)styryl))phenylamino)methyl)phenol

4-amino-4′-(N,N-dimethylamino)stilbene

Refernces

• 1、 Cullinane, Carleen,Donnelly, Paul S.,Hayne, David J.,Lim, SinChun,McLean, Catriona A.,Noor, Asif,Roselt, Peter D.,Van Zuylekom, Jessica K.,White, Jonathan M.. "Copper Bis(thiosemicarbazonato)-stilbenyl Complexes That Bind to Amyloid-β Plaques". . p. 11658 - 11669. Retrieved 2020/08/24.
• 2、 Papper, Vladislav,Wu, Yuanyuan,Kharlanov, Vladimir,Sukharaharja, Ayrine,Steele, Terry W. J.,Marks, Robert S.. "Theoretical and Experimental Studies of N,N-Dimethyl-N′-Picryl-4,4′-Stilbenediamine". . p. 13 - 19. Retrieved 2015/02/19.