113597-81-2

Basic information

• Product Name: diazomethane
• Synonyms: diazomethane
• CAS NO: 113597-81-2
• Molecular Weight: 304.44
• Mol File: 113597-81-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: diazomethane(CAS DataBase Reference)
• NIST Chemistry Reference: diazomethane(113597-81-2)
• EPA Substance Registry System: diazomethane(113597-81-2)

Safety Data

• Hazardous Substances Data: 113597-81-2(Hazardous Substances Data)

Upstream product

• 116889-36-2 C--N-(trimethylsilyl)nitrilimine 
• 113533-22-5 C--N-nitrilimine 
• 116889-37-3 C--N-(triphenylsilyl)nitrilimine 

Downstream Products

• 133549-07-2 (diazo)methane 
• 133549-10-7 C₃₄H₅₀F₉N₅P₂S 
• 133549-09-4 C₂₈H₃₇F₉N₄OP₂S 
• 116889-39-5 C₃₅H₄₉N₄O₂PSSi 
• 133549-08-3 C--N-<(phenyl)<2,4,6-tris(trifluoromethyl)phenyl>phosphanyl>nitrilimine 
• 116889-37-3 C--N-(triphenylsilyl)nitrilimine 

Relevant articles and documents

N-Phosphino- and N-Phosphonionitrilimines: From Nucleophilic to Electrophilic 1,3-Dipoles

N-[Bis(diisopropylamino)phosphino]-C-[bis(diisopropylamino) thioxophosphoranyl]nitrilimine (1) reacts with electron-poor dipolarophiles such as maleimide, methyl vinyl ketone, and 1,4-naphthoquinone via HOMO(dipole)-controlled [2+3] cycloadditions, while N-[bis(diisopropylamino)(methyl)phosphonio]-C-[bis(diisopropylamino) thioxophosphoranyl]nitrilimine (2a) reacts with electron-rich dipolarophiles such as norbornadiene and ethyl trans-pyrrolineacrylate via LUMO(dipole)-controlled [2+3] cycloadditions. Carbon disulfide reacts with 1 via a formal [4+2] cycloaddition leading to phosphazene containing heterocycle 11 in 75% yield. Dipole 1 is cleaved by HCl, giving the corresponding (thioxophosphoranyl)diazomethane 15, while addition of HCl to 2a leads to hydrazonoyl chloride 16, in 70% isolated yield. Hydrazone 17′ (95%) and phosphazine 18 (80%) are obtained by a 1,3-addition of BuLi to 1 and PhOLi to 2a, respectively. Trimethylphosphine reacts with 2a by a phosphine - carbene coupling reaction, giving the ylide 20 which is isolated in 75% yield.