meso-Stilbene dibromide

*meso*-Stilbene dibromide
Names
	Preferred IUPAC name 1,1′-[(1R,2S)-1,2-Dibromoethane-1,2-diyl]dibenzene
	Other names Stilbene dibromide; meso-1,2-dibromo-1,2-diphenyl ethane
Identifiers
CAS Number	13440-24-9;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3115205;
ChemSpider	2279317;
ECHA InfoCard	100.162.977
PubChem CID	2753450;
	InChI InChI=1S/C14H12Br2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14H/t13-,14+ Key: GKESIQQTGWVOLH-OKILXGFUSA-N;
	SMILES C1=CC=C(C=C1)[C@H]([C@H](C2=CC=CC=C2)Br)Br;
Properties
Chemical formula	C14H12Br2
Molar mass	340.058 g·mol−1
Appearance	White solid
Melting point	241 °C (466 °F; 514 K)
Dipole moment	0.4-0.9
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H314
Precautionary statements	P260, P264, P270, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P332+P313, P337+P313, P362, P363, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

meso-Stilbene dibromide is an organic compound with a formula of (C₆H₅CH(Br))₂.^[3] It is one of three isomeric stilbene dibromides, the others being the pair of enantiomers. All are white solids.^[4]

Synthesis and reactions

meso-Stilbene dibromide can be prepared by treatment of (E)-stilbene with bromine.^[5]

Reaction of stilbene dibromide with base gives diphenylacetylene.^[4]

References

^ Weissberger, A. (1945). "Dipole Moment and Structure of Organic Compounds. XVII.[1] The Electric Moments of α- and β-Stilbene Dibromide and of p-Diacetylbenzene". J. Am. Chem. Soc. 67 (5): 778–779. doi:10.1021/ja01221a025.
^ Kulangiappar, K.; Ramaprakash, M.; Vasudevan, D.; Raju, T. (2016). "Electrochemical bromination of cyclic and acyclic enes using biphase electrolysis". Synthetic Communications. 46 (2): 145–153. doi:10.1080/00397911.2015.1125498. S2CID 101806740.
^ Schroth, Werner; Zeitschrift für Chemie 1977, V17(2), P56 CAPLUS
^ ^a ^b Smith, Lee Irvin; Falkov, M. M. (1942). "Diphenylacetylene". Org. Synth. 22: 50. doi:10.15227/orgsyn.022.0050.
^ Gilbert, J.C.; Martin, S.F. (2002). Experimental Organic Chemistry: A Miniscale and Macroscale Approach, third edition. London: Thomson. pp. 348–353. ISBN 978-0-03-034048-2.

[1] Weissberger, A. (1945). "Dipole Moment and Structure of Organic Compounds. XVII.[1] The Electric Moments of α- and β-Stilbene Dibromide and of p-Diacetylbenzene". J. Am. Chem. Soc. 67 (5): 778–779. doi:10.1021/ja01221a025.

[2] Kulangiappar, K.; Ramaprakash, M.; Vasudevan, D.; Raju, T. (2016). "Electrochemical bromination of cyclic and acyclic enes using biphase electrolysis". Synthetic Communications. 46 (2): 145–153. doi:10.1080/00397911.2015.1125498. S2CID 101806740.

[3] Schroth, Werner; Zeitschrift für Chemie 1977, V17(2), P56 CAPLUS

[OS-4] Smith, Lee Irvin; Falkov, M. M. (1942). "Diphenylacetylene". Org. Synth. 22: 50. doi:10.15227/orgsyn.022.0050.

[5] Gilbert, J.C.; Martin, S.F. (2002). Experimental Organic Chemistry: A Miniscale and Macroscale Approach, third edition. London: Thomson. pp. 348–353. ISBN 978-0-03-034048-2.

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