meso-Stilbene dibromide

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meso-Stilbene dibromide
Meso-stilbene dibromide.svg
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.162.977 Edit this at Wikidata
  • 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
  • C1=CC=C(C=C1)[C@H]([C@H](C2=CC=CC=C2)Br)Br
Properties
C14H12Br2
Molar mass 340.058 g·mol−1
Appearance White solid
Melting point 241 °C (466 °F; 514 K)[2]
0.4-0.9[1]
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H314
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).

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[edit]

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

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

References[edit]

  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
  4. ^ a b 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.