1-Bromonaphthalene

1-Bromonaphthalene.svg 180px 1-Bromonaphthalene α-Bromonaphthalene 90-11-9 correct CAS correct FDA 976Y53P08P 201-965-2 7001 6735 c1ccc2c(c1)cccc2Br 1/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H DLKQHBOKULLWDQ-UHFFFAOYAA 1S/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H DLKQHBOKULLWDQ-UHFFFAOYSA-N C108222 10 7 1 Colorless liquid 1.48 g/mL 1-2 132–135 °C at 12 mm; 145–148 °C at 20 mm 1-Bromonaphthalene is an organic compound with the formula C10H7Br. thumb|1-Bromonaphthalene It is one of two isomeric bromonaphthalenes, the other being 2-bromonaphthalene. Under normal conditions, the substance is a colorless liquid. Synthesis and reactions It is prepared by treatment of naphthalene with bromine: 10.15227/orgsyn.001.0035 free α-Bromonaphthalene Organic Syntheses 1921 1 35 H. T. Clarke M. R. Brethen C10H8 + Br2 → C10H7Br + HBr The compound exhibits many reactions typical of aryl bromides. Bromide can be displaced by cyanide to give the nitrile. It forms a Grignard reagent 10.15227/orgsyn.011.0080 free α-Naphthoic Acid Organic Syntheses 1931 11 80 Henry Gilman Nina B. St. John F. Schulze. and organolithium compound. Analogous to the synthesis of phenyllithium is the conversion of 1-bromonaphthalene to 1-lithionaphthalene, by lithium–halogen exchange: C10H7Br + BuLi → C10H7Li + BuBr (Bu = butyl) The resulting 1-lithionaphthalene undergoes a second lithiation, in contrast to the behavior of phenyllithium. The 1,8-dilithio derivative is a precursor to a host of peri-naphthalene derivatives. van Soolingen J, de Lang RJ, den Besten R, Klusener PA, Veldman N, Spek AL, Brandsma L 3 1995 A simple procedure for the preparation of 1,8-bis(diphenylphosphino)naphthalene Synthetic Communications 25 11 1741–1744 10.1080/00397919508015858 Applications The compound is also used as a precursor to various substituted naphthalenes, but substituted bromonaphthalenes are more important commercially.Gerd Collin Hartmut Höke Helmut Greim Naphthalene and Hydronaphthalenes 2003 doi10.1002/14356007.a17_001.pub2. Because of its high refractive index (1.656-1.659nD),https://www.chemsrc.com/en/cas/90-11-9_897096.html 1-Bromonaphthalene 1-bromonaphthalene is used as an embedding agent in microscopy and for determining the refraction of crystals. See also 2-Bromonaphthalene 1-Chloronaphthalene 1-Fluoronaphthalene References Category:Bromoarenes Category:1-Naphthyl compounds