883-40-9

Basic information

• Product Name: Diphenyldiazomethane
• Synonyms: (diazo-phenyl-methyl)benzene;1,1'-(Diazomethylene)bisbenzene;Diazodiphenylmethane;INTERMEDIATEOFCEFOSELISSULFATE;Bis(phenyl)diazomethane;(3R)-tert-butyl 3-(3-bromo-2-oxopyrrolidin-1-yl)pyrrolidine-1-carboxylate;Benzene, 1,1'-(diazoMethylene)bis-;3,3-diphenyldiazirine
• CAS NO: 883-40-9
• Molecular Formula: C₁₃H₁₀N₂
• Molecular Weight: 194.23
• Mol File: 883-40-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 29-30 °C
• Boiling Point: 320.68°C (rough estimate)
• Appearance: black and red crystals
• Density: 1.1579 (rough estimate)
• Refractive Index: 1.5014 (estimate)
• Storage Temp.: -20°C, Light sensitive
• Solubility: Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Possibly shock sensitive
• CAS DataBase Reference: Diphenyldiazomethane(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenyldiazomethane(883-40-9)
• EPA Substance Registry System: Diphenyldiazomethane(883-40-9)

Safety Data

• Hazardous Substances Data: 883-40-9(Hazardous Substances Data)

Usage

Description

Diphenyldiazomethane, also known as 1,1-Diphenyldiazomethane, is an organic compound with the chemical formula C15H14N2. It is a yellow crystalline solid that is highly reactive and sensitive to light and heat. Diphenyldiazomethane is known for its ability to act as a methylating agent and a carbene transfer reagent in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
Diphenyldiazomethane is used as a synthetic reagent for the synthesis of tartaric acid analogs of FR258900, which are glycogen phosphorylase inhibitors. These inhibitors have potential applications in the development of drugs for the treatment of type 2 diabetes and other metabolic disorders.
In the pharmaceutical industry, Diphenyldiazomethane plays a crucial role in the synthesis of complex organic molecules, including potential drug candidates. Its ability to act as a methylating agent and a carbene transfer reagent allows for the efficient construction of specific molecular structures, which can be further optimized for therapeutic applications.
Additionally, Diphenyldiazomethane can be used in other chemical industries for the synthesis of various organic compounds, such as pharmaceuticals, agrochemicals, and specialty chemicals. Its versatility as a synthetic reagent makes it a valuable tool in the development of new and innovative chemical products.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 351, 1955The Journal of Organic Chemistry, 60, p. 4725, 1995 DOI: 10.1021/jo00120a013

Synthetic route

diazodiphenylmethane (908093-98-1) → Diphenyldiazomethane Radical Anion (883-40-9)

Conditions	Yield
With solvat. electrons In isopropyl alcohol Rate constant; Irradiation;

Upstream product

• 908093-98-1 diazodiphenylmethane 

Relevant articles and documents

Spectroscopic and Kinetic Characterization of Diphenyldiazomethane Radical Anion

Diphenyldiazomethane radical anion (Ph2CN2.-) has been generated by radiolytic reduction of diphenyldiazomethane (Ph2CN2) in both protic and aprotic solvents.The absolute kinetics of formation and reactivity of Ph2CN2.- were obtained by monitoring its transient absorption (λmax = 355-370 nm) following nanosecond pulse radiolysis.In isopropylalcohol, reaction of the solvated electron with Ph2CN2 forms Ph2CN2.- (λmax =355 nm), which subsequently protonates to form Ph2C.N2H), as detected by a sharp absorption band at 330 nm.In aprotic solvents and in the ab sence of added quenchers, Ph2CN2.- decays primarily by pseudo-first-order reaction with Ph2CN2.With added weak organic acids protonation of Ph2CN2.- also occurs.Ph2CN2.- reacts with molecular oxygen with a near diffusion-controlled rate; however, it demonstrates no reactivity toward hydrogen atom donors, and no evidence of thermal loss of N2 to produce diphenylcarbene radical anion was observed.