9-VINYLANTHRACENE Chemical Properties

Melting point:

62-65 °C (lit.)

Boiling point:

61-66 °C/10 mmHg (lit.)

Density 

1.1570 (estimate)

refractive index 

1.5000 (estimate)

Flash point:

61-66°C/10mm

storage temp. 

Store below +30°C.

form 

powder to crystal

color 

White to Yellow to Orange

BRN 

2041641

InChI

InChI=1S/C16H12/c1-2-14-15-9-5-3-7-12(15)11-13-8-4-6-10-16(13)14/h2-11H,1H2

InChIKey

OGOYZCQQQFAGRI-UHFFFAOYSA-N

SMILES

C1=C2C(C=C3C(=C2C=C)C=CC=C3)=CC=C1

CAS DataBase Reference

2444-68-0(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2902 90 00

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

9-VINYLANTHRACENE Usage And Synthesis

Chemical Properties

yellow to green crystalline solid

Uses

9-Vinylanthracene (cas# 2444-68-0) is a compound useful in organic synthesis.

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 4035, 1991 DOI: 10.1021/jo00012a043
Synthesis, p. 319, 1981

Synthesis

General method C: Preparation of compounds A17-A24 by catalytic Wittig reaction. catalyst Aid (0.2 mmol, 20 mol%) and base A2 (2.0-3.5 mmol, 2.0-3.5 eq.) were added to a 1-dram vial fitted with a stirrer in air. If a solid aldehyde (1.0-1.2 mmol, 1.0-1.2 eq.) is used, it is added together at this point. The vial is then sealed with a septum and the air in the vial is replaced with argon. Toluene (1.4 mL) and the liquid reagents: aldehydes (1.2 mmol, 1.2 eq.) and organic halides (1.0 mmol, 1.0 eq.) were added sequentially. Diphenylsilane (1.2 mmol, 1.2 eq.) was then added and the septum was replaced with a PTFE-lined screw cap under an inert atmosphere. The reaction mixture was heated at 140°C or 150°C for 24-48 hours. After the reaction has been carried out for 24 hours, the base and halide are added additionally and the reaction is continued up to 48 hours. After completion of the reaction, the crude product was filtered through Celite, concentrated under reduced pressure and finally purified by fast column chromatography. Synthesis of 9-vinylanthracene (A23): In toluene (0.7 mL), 9-anthracenecarboxaldehyde (128 mg, 0.6 mmol, 1.2 eq.), iodomethane (31 μL, 0.5 mmol, 1.0 eq.), and diphenylsilane (112 μL, 0.6 mmol, 1.2 eq.) were added to the reaction with catalyst A3b (30 mg, 20 mol%) and base A2 (210 mg, 1.5 mmol, 3.0 eq.) were added, and the reaction was carried out at 140 °C for 24 hours. During the reaction, iodomethane and A2 were added twice at 0 h and 4 h. The crude product was purified by fast column chromatography (eluent: hexane, Rf = 0.35) to afford 9-vinylanthracene (A23, 66 mg, 65% yield) in yellow liquid form.1H NMR (400 MHz, CDCl3) δ: 5.68 (d, J = 18.0 Hz, 1H), 6.06 (d, J = 18.0 Hz, 1H), 6.06 (d, J = 18.0 Hz, 1H) 6.06 (d, J = 11.5 Hz, 1H), 7.48-7.60 (m, 5H), 8.00-8.08 (m, 2H), 8.35-8.40 (m, 2H).

Purification Methods

Purify it by vacuum sublimation. It has also been purified by chromatography on silica gel with cyclohexane as eluent, and recrystallised from EtOH [Werst et al. J Am Chem Soc 109 32 1987]. [Beilstein 5 IV 2415.]

References

[1] Angewandte Chemie - International Edition, 2014, vol. 53, # 47, p. 12907 - 12911
[2] Angew. Chem., 2014, vol. 126, # 47, p. 13121 - 13125,5
[3] Patent: WO2014/140353, 2014, A1. Location in patent: Page/Page column 59; 68; 69; 70

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