Phenylsodium

Phenylsodium
Names
	IUPAC name Sodium benzenide
	Other names Sodium benzenide, Sodium phenyl, sodiobenzene
Identifiers
CAS Number	1623-99-0 ;
3D model (JSmol)	Interactive image;
Abbreviations	NaPh, PhNa
ChemSpider	9183013 ;
PubChem CID	11007827;
UNII	SNA8TW8V4T;
CompTox Dashboard (EPA)	DTXSID301316871 ;
	InChI InChI=1S/C6H5.Na/c1-2-4-6-5-3-1;/h1-5H;/q-1;+1 Key: KSMWLICLECSXMI-UHFFFAOYSA-N;
	SMILES [Na]C1=CC=CC=C1;
Properties
Chemical formula	C6H5Na
Molar mass	100.096 g·mol−1
Appearance	Yellowish-white powder
Solubility in water	Reacts
Solubility	Insoluble in hydrocarbons, reacts with ether
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Corrosive, pyrophoric in air
Related compounds
Related compounds	Phenyllithium, Phenylcopper, Phenylcobalt
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Phenylsodium C₆H₅Na is an organosodium compound. Solid phenylsodium was first isolated by Nef in 1903. Although the behavior of phenylsodium and phenyl magnesium bromide are similar, the organosodium compound is very rarely used.^[2]

^ Schlenk, W.; Holtz, Johanna (January 1917). "Über die einfachsten metallorganischen Alkaliverbindungen". Berichte der Deutschen Chemischen Gesellschaft. 50 (1): 262–274. doi:10.1002/cber.19170500142.
^ Cite error: The named reference DS was invoked but never defined (see the help page).

[schlenk-1] Schlenk, W.; Holtz, Johanna (January 1917). "Über die einfachsten metallorganischen Alkaliverbindungen". Berichte der Deutschen Chemischen Gesellschaft. 50 (1): 262–274. doi:10.1002/cber.19170500142.

[DS-2] Cite error: The named reference DS was invoked but never defined (see the help page).

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