Stibabenzene

Stibabenzene^[1] is an organic chemical compound. Stibabenzene has the chemical formula C₅H₅Sb. The molecule is a derivative of benzene, with one of the carbon atoms in the 6-membered ring replaced by an antimony (Sb) atom. Stibabenzene is a molecule that is considered to be an organoantimony compound due to it containing carbon, hydrogen, and antimony atoms.

Bond lengths and angles of benzene, pyridine, phosphorine, arsabenzene, stibabenzene, and bismabenzene^{[clarification needed]}

Stibabenzene

The white balls represent hydrogens, the light gray balls represent carbons, and the dark gray ball represents antimony
Names
Preferred IUPAC name Stibinine
Other names Antimonin; Stibinin
Identifiers
CAS Number	289-75-8
3D model (JSmol)	Interactive image
ChemSpider	119914
PubChem CID	136137
CompTox Dashboard (EPA)	DTXSID90183098
InChI InChI=1S/C5H5.Sb/c1-3-5-4-2;/h1-5H; Key: JRKNFVZITCJKDC-UHFFFAOYSA-N
SMILES C1=CC=[Sb]C=C1
Properties
Chemical formula	C5H5Sb
Molar mass	186.855 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Laboratory synthesis

The synthesis of stibabenzene can be accomplished in a three step process. The final product can be isolated, even though the molecule is highly labile. The first step of this synthesis involves the treatment of penta-1,4-diyne with dibutylstannane as shown in the figure below.^[2]

C₅H₄ + Bu₂SnH₂ → C₁₃H₂₄Sn

The second step of the synthesis involves reacting the product of the first step, 1,1-dibutyl-1,4-dihydrostannine, with antimony trichloride, to yield 1-chloro-1-stibacyclohexa-2,5-diene.^[1]

C₁₃H₂₄Sn + SbCl₃ → C₅H₆SbCl

The final step of the synthesis of stibabenzene involves treating 1-chloro-1-stibacyclohexa-2,5-diene with a base, such as DBN, to yield the final product of stibabenzene.

C₅H₆SbCl + DBN → C₅H₆Sb

Similar compounds

It is noted that other benzene derivatives with one carbon replaced with a group 15 element can be synthesized via a similar synthetic pathway to that which stibabenzene is synthesized. The reaction of 1,1-dibutyl-1,4-dihydrostannine with arsenic trichloride, phosphorus tribromide, or bismuth trichloride can yield arsabenzene, phosphabenzene, or 1-chloro-1-bismacyclohexa-2,5-diene respectively. Treatment of 1-chloro-1-bismacyclohexa-2,5-diene with a base, such as DBN, can yield the product bismabenzene.^[3]

The four different reaction pathways possible from 1,1-dibutyl-1,4-dihydrostannin to form the products arsabenzene, phosphabenzene, bismabenzene, and stibabenzene.

See also

• 6-membered aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium