19016-92-3

Basic information

• Product Name: phenylchlorodiazomethane
• Synonyms: phenylchlorodiazomethane
• CAS NO: 19016-92-3
• Molecular Weight: 152.583
• Mol File: 19016-92-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: phenylchlorodiazomethane(CAS DataBase Reference)
• NIST Chemistry Reference: phenylchlorodiazomethane(19016-92-3)
• EPA Substance Registry System: phenylchlorodiazomethane(19016-92-3)

Safety Data

• Hazardous Substances Data: 19016-92-3(Hazardous Substances Data)

Upstream product

• 4460-46-2 3-chloro-3-phenyl-3H-diazirine 
• 1670-14-0 benzamidine monohydrochloride 

Downstream Products

• 20420-98-8 (CH₃CH₂CH₂CH₂)3SnCHClC₆H₅ 
• 83320-85-8 C₃₅H₂₆O 
• 19807-41-1 chlorophenylcarbene 
• 83320-84-7 9-Chlor-exo-9-phenylbicyclo<6.1.0>nona-2,4,6-trien 
• 83320-84-7 exo-9-Chlor-endo-9-phenylbicyclo<6.1.0>nona-2,4,6-trien 
• 5082-83-7 C₁₅H₁₃Cl 
• 5082-83-7 C₁₅H₁₃Cl 

Relevant articles and documents

Direct observation of carbene and diazo formation from aryldiazirines by ultrafast infrared spectroscopy

Ultrafast laser flash photolysis (λex = 270 nm) of phenyldiazirine produces transient infrared absorptions at 2040 and 1582 cm-1. The first band is assigned to phenyldiazomethane, and the second is assigned to singlet phenylcarbene. This assignment is consistent with DFT calculations. Diazo band integration reveals that photoisomerization from diazirine to diazo occurs within a few picoseconds of the laser pulse. The majority of carbene produced is also formed instantaneously. Copyright

1,2,4,6-CYCLOHEPTATETRAENE: THE KEY INTERMEDIATE IN ARYLCARBENE INTERCONVERSIONS AND RELATED C7H6 REARRANGEMENTS

Thermolysis or photolysis of phenyldiazomethane (2) produces phenylmethylene (3), which ring-expands to give 1,2,4,6-cycloheptatetraene (6).Spectroscopic and chemical evidence rule out bicyclo(4.1.0)hepta-2,4,6-triene (4), cycloheptatrienylidene (5), and bicyclo(3.2.0)hepta-1,3,6-triene (11) intermediates.The strained allene in cycloheptatetraene (6) exhibits infrared absorption at 1824 and 1816 cm-1.Deuterium substitution produces the expected 10-cm-1 shift in the allene absorption.Fluorine or chlorine substitution substantially enhances the allene absorption intensity.Deuterium labeling studies reveal that the intramolecular chemistry of cycloheptatetraene (6) involves reversible thermal or photochemical equilibriation with phenylmethylene (3).The intermolecular chemistry of 6 involves dimerization.At temperatures as low as 10 K, 6 forms a labile (2+2) dimer,7, which undergoes thermally allowed, electrocyclic ring opening to give heptafulvalene (8) upon warming to room temperature.The rearrangements of 7-acetoxynorbornadiene (9), 2-diazobicyclo(3.2.0)hepta-3,6-diene (31), and 8-diazobicyclo(2.2.2)octa-2,5-dien-7-one (33) all involve cycloheptatetraene (6) intermediates.