5822-69-5

Basic information

• Product Name: 6-chloro-5-[(E)-(4-chlorophenyl)diazenyl]pyrimidine-2,4-diamine
• CAS NO: 5822-69-5
• Molecular Formula: C₁₀H₈Cl₂N₆
• Molecular Weight: 283.1167
• Mol File: 5822-69-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 587.8°C at 760 mmHg
• Flash Point: 309.3°C
• Density: 1.68g/cm³
• Vapor Pressure: 8.52E-14mmHg at 25°C
• Refractive Index: 1.756
• CAS DataBase Reference: 6-chloro-5-[(E)-(4-chlorophenyl)diazenyl]pyrimidine-2,4-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-5-[(E)-(4-chlorophenyl)diazenyl]pyrimidine-2,4-diamine(5822-69-5)
• EPA Substance Registry System: 6-chloro-5-[(E)-(4-chlorophenyl)diazenyl]pyrimidine-2,4-diamine(5822-69-5)

Safety Data

• Hazardous Substances Data: 5822-69-5(Hazardous Substances Data)

Usage

Functional groups

two chloro groups, one phenyldiazenyl group

Potential applications

pharmaceuticals, agrochemicals
Versatile structure
Potential biological activity
Further research needed for fully understanding properties and potential uses

Upstream product

• 156-83-2 6-chloro-pyrimidine-2,4-diyldiamine 
• 2028-74-2 p-chlorobenzenediazonium chloride 
• 106-47-8 4-chloro-aniline 
• 56-06-4 2,6-diaminopyrimidin-4-ol 

Downstream Products

• 108622-61-3 5-(4-chloro-phenylazo)-6-morpholino-pyrimidine-2,4-diyldiamine 
• 100793-47-3 6-(2-ethoxy-ethoxy)-5-(4-chloro-phenylazo)-pyrimidine-2,4-diyldiamine 
• 105339-10-4 5-(4-chloro-phenylazo)-N⁴,N⁴-dimethyl-pyrimidine-2,4,6-triyltriamine 
• 100721-75-3 5-(4-chloro-phenylazo)-N⁴,N⁴-bis-(2-hydroxy-ethyl)-pyrimidine-2,4,6-triyltriamine 
• 104857-00-3 N-(4-chlorophenyl)glycine 2-<2,6-diamino-5-<(4-chlorophenyl)azo>-4-pyrimidinyl>hydrazide hemihydrate 
• 27078-97-3 2,6-diamino-4-piperidino-5-p-chlorophenylazopyrimidine 
• 108622-61-3 2,6-diamino-4-morpholino-5-p-chlorophenylazopyrimidine 
• 247913-69-5 2,6-diamino-4-piperidino-5-p-chlorophenylazopyrimidine 
• 247913-67-3 2,6-diamino-4-diethylamino-5-p-chlorophenylazopyrimidine 
• 247913-68-4 2,6-diamino-4-dibenzylamino-5-p-chlorophenylazopyrimidine 
• 1173827-25-2 2,6-diamino-4-[(4-methoxycarbonylphenyl)methylamino]-5-(p-chlorophenyl)azopyrimidine 
• 929073-66-5 (S)-diethyl 2-{4-[2,6-diamino-5-[2-(4-chlorophenyl)-diazenyl]pyrimidin-ylamino]benzamido}pentanedioate 
• 1194-78-1 6-chloropyrimidine-2,4,5-triamine 

Relevant articles and documents

Photoswitchable Intramolecular Hydrogen Bonds in 5-Phenylazopyrimidines Revealed By In Situ Irradiation NMR Spectroscopy

NMR spectroscopy with in situ irradiation uncovered unique photoswitchable intramolecular hydrogen bonds (IMHBs) in 5-phenylazopyrimidines with two hydrogen bond donors. These compounds form two stable rotamers, each with one IMHB, and the rotamer ratio changes reversibly upon UV or visible light irradiation. Strong substituent dependence of photoinduced structural changes was observed; using suitable substituents, orthogonal photoswitching can be achieved. For example, whereas UV irradiation caused switching between the two rotamers of the trans isomer of a compound with electron-donating methoxy substituent, visible light enabled to obtain the cis photoisomer. No cis isomer was detected for compounds with electro-neutral or electron-accepting substituents, but photoswitching between the two trans isomers was observed. On the other hand, compounds without hydrogen-bond donors or with one donor only formed stable cis isomers. A mechanism of the photoswitching was proposed by DFT computations.

COMPOUNDS FOR IMPROVING MRNA SPLICING

Provided herein are compounds useful for improving mRNA splicing in a cell. Exemplary compounds provided herein are useful for improving mRNA splicing in genes comprising at least one exon ending in the nucleotide sequence CAA. Methods for preparing the compounds and methods of treating diseases of the central nervous system are also provided.

Synthesis and biological activities of 2,4-diaminopteridine derivatives

Substituted 2,4-diaminopteridine derivatives 10a-10l were prepared in moderate to good yield. Their structures were confirmed by 1H-NMR and MS spectroscopy, as well as by elemental analysis. Their inhibitory properties against inducible nitric oxide synthase (iNOS) were evaluated in vitro. Biological tests indicated that compound 10a, 10d, 10e, 10h, 10i, and 10l showed potent inhibitory activities similar to that of methotrexate (MTX), while the activities of compound 10b, 10c, 10f, 10g, 10j, and 10k are stronger than MTX. Two compounds, i. e., 10b (IC50 = 18.85 μM) and 10i (IC 50 = 24.08 μM) were further studied for their effect on septic shock in rats and immunologically liver injured mice (in vivo). The results demonstrated that 10b and 10i had the capacity to increase the blood pressure in septic shock and showed notable protective activities on immunological hepatic injury.