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
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)
Safety
- Safety Statements
- 22-24/25
- WGK Germany
- 3
- HS Code
- 2902 90 00
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.
N-Bromosuccinimide Price
- Product number
- 8.24593
- Product name
- 9-Vinylanthracene
- Purity
- for synthesis
- Packaging
- 0.5g
- Price
- $97.7
- Updated
- 2024/03/01
- Product number
- V1708
- Product name
- 9-Vinylanthracene
- Purity
- 97%
- Packaging
- 1g
- Price
- $128
- Updated
- 2023/06/20
- Product number
- V1708
- Product name
- 9-Vinylanthracene
- Purity
- 97%
- Packaging
- 5g
- Price
- $404
- Updated
- 2023/06/20
- Product number
- V0130
- Product name
- 9-Vinylanthracene
- Packaging
- 1G
- Price
- $63
- Updated
- 2025/07/31
- Product number
- V0130
- Product name
- 9-Vinylanthracene
- Packaging
- 5G
- Price
- $184
- Updated
- 2025/07/31
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
Preparation Products
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View Lastest Price from 9-VINYLANTHRACENE manufacturers
- Product
- 9-VINYLANTHRACENE 2444-68-0
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2024-10-24
- 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
- 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