ChemicalBook > CAS DataBase List > 9-VINYLANTHRACENE

9-VINYLANTHRACENE

Product Name
9-VINYLANTHRACENE
CAS No.
2444-68-0
Chemical Name
9-VINYLANTHRACENE
Synonyms
Anthracene, 9-ethenyl-;9-Ethenyl anthracene;9-VINYLANTHRACENE;9-Ethenylanthracen;10-vinylanthracene;9-Vinylanthracene,97%;9-Vinylanthracene 97%;9-vinyl-anthracene radical cation
CBNumber
CB9248029
Molecular Formula
C16H12
Formula Weight
204.27
MOL File
2444-68-0.mol
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9-VINYLANTHRACENE Property

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)
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
HS Code 
2902 90 00
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.24593
Product name
9-Vinylanthracene
Purity
for synthesis
Packaging
0.5g
Price
$97.7
Updated
2024/03/01
Sigma-Aldrich
Product number
V1708
Product name
9-Vinylanthracene
Purity
97%
Packaging
1g
Price
$128
Updated
2023/06/20
Sigma-Aldrich
Product number
V1708
Product name
9-Vinylanthracene
Purity
97%
Packaging
5g
Price
$404
Updated
2023/06/20
TCI Chemical
Product number
V0130
Product name
9-Vinylanthracene
Packaging
1G
Price
$63
Updated
2025/07/31
TCI Chemical
Product number
V0130
Product name
9-Vinylanthracene
Packaging
5G
Price
$184
Updated
2025/07/31
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9-VINYLANTHRACENE Chemical Properties,Usage,Production

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

642-31-9

74-88-4

2444-68-0

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

9-VINYLANTHRACENE Preparation Products And Raw materials

Raw materials

Anthrone Sodium acetate Potassium tert-butoxide p-Toluenesulfonic acid Sodium azide Ethanol 3-Chloro-1-propanol N,N-Dimethylformamide 2-Pyrrolidinone Acetyl chloride Anisole 9-Anthraldehyde Phosphorus oxitrichloride Sodium borohydride Aluminum chloride Tosyl chloride DBU Vinylmagnesium bromide Tetrahydrofuran 1,2-Dichloroethane Anthracene Acetic acid Methanol Oxalyl chloride Triphenylphosphine Methyl bromide Iodomethane Potassium bisulfate 1,2-Dichlorobenzene

Preparation Products

polyvinyl anthracene
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View Lastest Price from 9-VINYLANTHRACENE manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
Product
9-VINYLANTHRACENE 2444-68-0
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-24
Hebei Yanxi Chemical Co., Ltd.
Product
9-VINYLANTHRACENE 2444-68-0
Price
US $20.00-1.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20 tons
Release date
2023-10-23
Pharmahands (Taizhou) Co., Ltd.
Product
9-vinylanthracene 2444-68-0
Price
US $10.00/g
Min. Order
1g
Purity
99%
Supply Ability
100kg/month
Release date
2020-09-15

2444-68-0, 9-VINYLANTHRACENERelated Search:

9-VINYLANTHRACENE TRANS-9-STYRYLANTHRACENE HYPOCRELLIN A Anthracene 9-(2-nitrovinyl)anthracene (9-ANTHRYLMETHYLENE)MALONONITRILE benz(j)aceanthrylene ISOVIOLANTHRENE benz(e)aceanthrylene aceanthrylene benz(l)aceanthrylene 2-VINYLANTHRACENE,2-VINYLANTHRACENE, 97+% 1-vinylanthracene BENZ(K)ACEANTHRYLENE naphtho(2,1,8-hij)acephenanthrylene 3-(9-ANTHRYL)-1-(4-METHYLPHENYL)PROP-2-EN-1-ONE (5E)-5-(9-ANTHRYLMETHYLENE)-3-(4-METHOXYPHENYL)-2-THIOXO-1,3-THIAZOLIDIN-4-ONE 3-(9-ANTHRYL)-1-(2-NAPHTHYL)PROP-2-EN-1-ONE

  • 9-Ethenyl anthracene
  • 9-VINYLANTHRACENE
  • 10-vinylanthracene
  • 9-Ethenylanthracen
  • 9-Vinylanthracene 97%
  • 9-Vinylanthracene,97%
  • Anthracene, 9-ethenyl-
  • 9-vinyl-anthracene radical cation
  • 2444-68-0
  • ALKENE
  • Organic Building Blocks
  • Alkenes
  • Acyclic
  • Building Blocks
  • Styrenes
  • Photoluminescent Materials > Fluorescent MonomersPolymer Science
  • Monomers
  • Photonic and Optical Materials
  • Styrene and Functionalized Styrene MonomersPolymer Science
  • Vinyl Halides, Amines, Amides, and Other Vinyl Monomers