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2-{(E)-[4-(Dimethylamino)benzylidene]amino}benzoic acid is a Schiff base that can exist as a zwitterion stabilized by an intramolecular ionic hydrogen bond. It forms co-crystals with metal complexes, such as drum-type butylstannoxane aggregates, and exhibits notable dielectric properties when combined with urea in a 1:2 intermolecular compound (IMC). The IMC displays a high dielectric constant (~0.9 × 103) and moderate electrical conductivity (~5 × 10-6 S m-1) due to excited-state intramolecular proton transfer and unique hydrogen-bonded motifs. Additionally, the compound exhibits strong fluorescence in solution with a high quantum yield (0.99).

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  • 159805-67-1 Structure
  • Basic information

    1. Product Name: 2-{(E)-[4-(dimethylamino)benzylidene]amino}benzoic acid
    2. Synonyms: 2-{(E)-[4-(dimethylamino)benzylidene]amino}benzoic acid
    3. CAS NO:159805-67-1
    4. Molecular Formula:
    5. Molecular Weight: 268.315
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 159805-67-1.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 2-{(E)-[4-(dimethylamino)benzylidene]amino}benzoic acid(CAS DataBase Reference)
    10. NIST Chemistry Reference: 2-{(E)-[4-(dimethylamino)benzylidene]amino}benzoic acid(159805-67-1)
    11. EPA Substance Registry System: 2-{(E)-[4-(dimethylamino)benzylidene]amino}benzoic acid(159805-67-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 159805-67-1(Hazardous Substances Data)

159805-67-1 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 159805-67-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,9,8,0 and 5 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 159805-67:
(8*1)+(7*5)+(6*9)+(5*8)+(4*0)+(3*5)+(2*6)+(1*7)=171
171 % 10 = 1
So 159805-67-1 is a valid CAS Registry Number.

159805-67-1Downstream Products

159805-67-1Relevant articles and documents

Perceptive variation of carboxylate ligand and probing the influence of substitution pattern on the structure of mono- and di-butylstannoxane complexes

Basu Baul, Tushar S.,Dutta, Dhrubajyoti,Duthie, Andrew,Guedes da Silva, M. Fátima C.

, p. 627 - 637 (2017)

By reacting 2- and 3-aminobenzoic acids (HL1and HL2, respectively), as well as 2-, 3- and 4-{(E)-2-[4-(dimethylamino)phenyl]diazenyl}benzoic acids (HL3, HL4and HL5, in this order) with a n-butyltin(IV) source [nBuSn(O)OH ornBu2SnO], the drum-type butylstannoxane complexes of general composition [nBu6Sn6O6(Ln)6] [Ln?=?L1(1), L2(2) and L3(3)] and the ladder-type compounds [nBu8Sn4O2(Ln)4] [Ln?=?L3(5), L4(6) and L5(7)] were obtained and fully characterized. By reacting 1 with 2-{(E)-[4-(dimethylamino)benzylidene]amino}benzoic acid (HL6), a co-crystal (4) was achieved which comprises the metal complex aggregate found in 1 and the neutral HL6molecule. The solution properties of the compounds were assessed from1H and13C NMR studies and, for the metal complexes, also from119Sn NMR. The molecular structures of 1, 2, 4–7 were confirmed by single-crystal X-ray diffraction. Compounds 1–3 and the complex moiety of 4 display hexameric Sn6O6clusters with drum-like structures, but 5–7 reveal Sn4O2cores with ladder-type structural motifs. Besides the observed relationship between the ligand N-functional group and obtained (drum- or ladder-type) assemblies, the relative position of the carboxylate group in the ligand itself influences its coplanarity.

The zwitterion of N-(2-carboxyphenyl)-4-dimethylaminebenzylideneimine

Trzesowska-Kruszynska, Agata

, p. 131 - 138 (2010)

The crystal and molecular structures of N-(2-carboxyphenyl)-4-dimethylaminebenzylideneimine and its protonated form have been determined. The Schiff base exists as the zwitterion, which is stabilized by the intramolecular ionic hydrogen bond. According to

Remarkable dielectric properties of 1:2 inter-molecular compound of 2-(4-(dimethylamino) benzylideneamino) benzoic acid and urea due to excited-state intramolecular proton transfer

Rai,Singh, Manjeet,Rai

, p. 34382 - 34391 (2017)

The phase diagram of 2-(4-(dimethylamino) benzylideneamino) benzoic acid (DMABAB)-urea (U) gives two eutectics E1 (mp 107.0 °C) and E2 (mp 138.0 °C) with 0.01 and 0.86 mole fractions of urea, respectively, and a 1:2 inter-molecular compound (IMC) with a congruent melting point of 219.0 °C, which has a high dielectric constant (? = 0.9 × 103) and reasonable electrical conductivity in the order ~5 × 10-6 S m-1. This is due to the remarkable packing of U molecules in the IMC, where it shows coupling of two different types of cyclic hydrogen-bonded motifs alternating to form a corrugated sheet or chain of rings extending along the b axis via N-H?O hydrogen bonding interactions. In the presence of an electric field, an inter-molecular proton transfer process occurs in the NH?O bonds of the chain of the U molecules, which leads to disproportionate defects and the formation of polar domains on the macroscopic scale. An appropriate quantity of the IMC is synthesized via a green synthetic method, which has a monoclinic crystal system with the P21/c centrosymmetric space group. Additionally, its crystal data and hydrogen bonding parameters are determined. According to powder X-ray diffraction, spectral and thermal characterization, the eutectics are a mechanical mixture of the IMC and pure components, although the IMC behaves as a pure compound. The IMC shows a broad emission band in the range of 350 to 580 nm with a quantum yield of almost 1 (0.99) upon excitation at the λmax absorption (300 nm) in MeOH solution at a concentration of 1 × 10-5 M.

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