Bis-(4-chloro-phenyl)-diazene

• CAS: 1602-00-2
• Catalog Number: ACM1602002
• Category: Main Products
• Molecular Weight: 251.10
• Molecular Formula: C₁₂H₈Cl₂N₂
• Synonyms: DCAB, Bis-(4-chloro-phenyl)-diazene, 1602-00-2, Diazene, bis(4-chlorophenyl)-, 4,4-DICHLOROAZOBENZENE, p,p-Dichloroazobenzene, Azobenzene, 4,4-dichloro-, HSDB 2720, NSC 59160, BRN 0745559, Azobenzene,4-dichloro-, bis(4-chlorophenyl)diazene, AC1L25OT, bis(4-chlorophenyl)-diazene, 1,2-Bis(4-chlorophenyl)diazene, CTK0J7286, CTK4D0374, (E)-bis(4-chlorophenyl)-diazene, MolPort-003-911-095, NSC59160
• IUPAC Name: bis(4-chlorophenyl)diazene
• Canonical SMILES: C1=CC(=CC=C1N=NC2=CC=C(C=C2)Cl)Cl
• InChI Key: XHQLXCFUPJSGOE-UHFFFAOYSA-N
• Boiling Point: 375.2ºC at 760mmHg
• Flash Point: 180.7ºC
• Density: 1.27g/cm³
• Exact Mass: 250.00600
• H-Bond Acceptor: 2
• H-Bond Donor: 0

Case Study

Gold Nanoparticle-Catalyzed cis-trans Isomerization of Azobenzenes such as 4,4'-Dichloroazobenzene

Hallett-Tapley, Geniece L., et al. Chemical Communications, 2013, 49(86), 10073-10075.

Ablated "pseudo-naked" gold nanoparticles (AuNPs) can catalyze the cis-trans isomerization of substituted azobenzenes. This work examined the AuNP-mediated isomerization of para-substituted azobenzenes 2 (4-methoxyazobenzene), 3 (4,4'-dichloro), and 4 (4,4'-dimethylazobenzene) to investigate the role of the substituent in the isomerization reaction.
· The UV-visible spectra depicted in the figure indicate that, following the addition of AuNPs to the reaction mixture, the maximum absorption for (a) 4-methoxy, (b) 4,4'-dichloro, and (c) 4,4'-dimethyl substituted azobenzenes shifts from its initial position.
· For azobenzene 2, the primary absorption peak moves from 320 nm to 345 nm.
· In contrast, azobenzene 3 does not exhibit a significant shift; instead, the trans isomer is suggested to form due to the appearance of a shoulder absorption peak at 390 nm, as compared to standard samples.
· The isomerization of azobenzene 4 reflects the loss of the 305 nm cis isomer absorption, paired with an increase in absorption at 385 nm, attributed to the trans isomer.

Synthetic Use

Upstream Synthesis Route 1

• 68230-00-2

• 94-97-3
• 106-47-8
• 120-92-3
• 1602-00-2

Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 825 - 827

Upstream Synthesis Route 2

• 68230-01-3

• 94-97-3
• 108-94-1
• 106-47-8
• 1602-00-2

Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 825 - 827

Upstream Synthesis Route 3

• 68230-02-4

• 94-97-3
• 106-47-8
• 1602-00-2
• 502-42-1

Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 825 - 827

Upstream Synthesis Route 4

• 6831-82-9
• 100-00-5

• 100-02-7
• 26455-31-2
• 106-47-8
• 614-26-6
• 1602-00-2

Reference: [1]Bassani, Alberto; Prato, Maurizio; Rampazzo, Paolo; Quintily, Ugo; Scorrano, Gianfranco
[Journal of Organic Chemistry, 1980, vol. 45, # 11, p. 2263 - 2264]

Upstream Synthesis Route 5

• 68230-00-2

• 94-97-3
• 106-47-8
• 120-92-3
• 1602-00-2

Reference: [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 825 - 827