9-BROMOFLUORENE
- Product Name
- 9-BROMOFLUORENE
- CAS No.
- 1940-57-4
- Chemical Name
- 9-BROMOFLUORENE
- Synonyms
- 9-BROMO-9H-FLUORENE;9-bromo-fluoren;9-BROMOFLUORENE;AKOS BBS-00004423;9-Bromofluorene97%;Fluorene, 9-bromo-;9-FLUORENYL BROMIDE;9-Bromofluorene >9H-Fluorene, 9-bromo-;9-Bromofluorene, 98+%
- CBNumber
- CB3372043
- Molecular Formula
- C13H9Br
- Formula Weight
- 245.11
- MOL File
- 1940-57-4.mol
9-BROMOFLUORENE Property
- Melting point:
- 101-104 °C(lit.)
- Boiling point:
- 288.79°C (rough estimate)
- Density
- 1.4187 (rough estimate)
- refractive index
- 1.6290 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- form
- powder to crystal
- color
- White to Light yellow
- Water Solubility
- Insoluble in water.
- Sensitive
- Air Sensitive
- BRN
- 2047220
- CAS DataBase Reference
- 1940-57-4(CAS DataBase Reference)
- NIST Chemistry Reference
- 9H-fluorene, 9-bromo-(1940-57-4)
Safety
- Hazard Codes
- C
- Risk Statements
- 34-43
- Safety Statements
- 26-36/37/39-45
- RIDADR
- UN 1759 8/PG 2
- WGK Germany
- 3
- RTECS
- LL5890000
- HS Code
- 2903.99.8001
- HazardClass
- 8
- PackingGroup
- III
- Toxicity
- mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01610,
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H314Causes severe skin burns and eye damage
- Precautionary statements
-
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P363Wash contaminated clothing before reuse.
N-Bromosuccinimide Price
- Product number
- B66604
- Product name
- 9-Bromofluorene
- Purity
- 98%
- Packaging
- 10g
- Price
- $160
- Updated
- 2025/07/31
- Product number
- B66604
- Product name
- 9-Bromofluorene
- Purity
- 98%
- Packaging
- 25g
- Price
- $398
- Updated
- 2025/07/31
- Product number
- B1046
- Product name
- 9-Bromofluorene
- Purity
- >98.0%(T)
- Packaging
- 5g
- Price
- $42
- Updated
- 2025/07/31
- Product number
- B1046
- Product name
- 9-Bromofluorene
- Purity
- >98.0%(T)
- Packaging
- 25g
- Price
- $121
- Updated
- 2025/07/31
- Product number
- B683745
- Product name
- 9-Bromofluorene
- Packaging
- 10g
- Price
- $55
- Updated
- 2021/12/16
9-BROMOFLUORENE Chemical Properties,Usage,Production
Chemical Properties
yellow to beige-orange crystalline powder
Uses
9-Bromofluorene, is used to treat skin dermatological conditions and in pharmaceutical industry.
Synthesis Reference(s)
Journal of the American Chemical Society, 80, p. 4327, 1958 DOI: 10.1021/ja01549a053
Synthesis
86-73-7
1940-57-4
The general procedure for the synthesis of 9-bromofluorene from fluorene was as follows: free radical bromination of fluorene using N-bromosuccinimide (NBS) at room temperature was used as a baseline reaction for the evaluation of the initiator system of the present invention (Scheme 4). This was done as follows: fluorene (83 mg, 0.5 mmol, 1 eq.) and N-bromosuccinimide (98 mg, 0.55 mmol, 1.1 eq.) were dissolved in dichloromethane (5 mL) in a pre-oven dried Schlenk flask. The desired peroxide (0.025 mmol, 5 mol%) was added and the resulting mixture was degassed by freeze-pump-thaw cycle method (3 cycles). After recovery to room temperature, the acid catalyst was added under argon protection. After the reaction reached a predetermined time, the reaction mixture was quenched with triethylamine (250 μL) and dibromomethane (0.5 mmol) was added as an internal standard for analysis. Aliquots were taken for direct 1H NMR analysis, and the yield was determined by integrating the reference peak (5.9 ppm, s, 1H; determined from the actual sample) relative to the peak of dibromomethane. The reaction results are detailed in Table 1.The bromination reaction was efficiently carried out using peroxyacetone 1 (Trigonox 22, 50 wt% mineral oil solution) and different commercial solutions of Brownsted acid. Control experiments confirmed the necessity of the acid and peroxide, and no conversion was observed after 24 h if either component was omitted. The pKa values of the acid catalysts showed a clear trend: the stronger the acid, the faster the rate of conversion. The conversion of sulfuric acid and p-toluenesulfonic acid after 1 h was 72% and 28%, respectively (entries 1 and 2). Methanesulfonic acid had a slightly lower yield (45%; entry 3), whereas acids weaker than trifluoroacetic acid (22%, entry 5) or trichloroacetic acid (18%, entry 6) failed to initiate the reaction (entry 7). Nitric acid performed better than its pKa value predicted (96%; entry 4). Ultimately, high yields were obtained for all reactions (80-95% yield after 24-72 h) when the reaction time was extended to full conversion, indicating that the acid catalyst only affects the initiation rate. In addition, scandium(III) trifluoromethanesulfonate, a Lewis acid, was found to be catalytic (69%; entry 8). The efficiency of different commercial peroxydione solutions was evaluated using methanesulfonic acid as a standard catalyst of moderate reactivity. Peroxystrictone 2 (Trigonox? D; 50 wt%) was less efficient than 1 (45%; entry 3), with 1% product after 1 h and 76% after 48 h (entry 11). Peroxiredoxin 3 (Trigonox? 301; 41 wt%) showed low conversion after two days of reaction (8%, entry 15). Peroxiredoxin 4 (Luperox? DHD-9, 32 wt%) was more reactive than 3, yielding 12% product after 48 h (entry 16). A series of structurally different peroxides were evaluated based on the significant effect of the peroxydione structure on its reactivity. Compounds 11a and 11b demonstrated the effect of group X (formula I). 11b was less reactive than 1 (21%, entry 9), whereas 11a was more efficient, with 28% conversion after 1 h (entry 10). The aromatic substituents around the peroxide portion had a significant effect: 5 was more efficient than 2 (20%, entry 12 vs. entry 11), whereas 6 was much less efficient (33% after 48 h, entry 13). 9 was slightly more reactive than 1 (50%, entry 17), whereas 10 was the most efficient of the evaluated structures, with a conversion of 74% after 1 h of reaction (entry 28).
References
[1] Green Chemistry, 2011, vol. 13, # 4, p. 928 - 933
[2] Organic Letters, 2016, vol. 18, # 19, p. 4944 - 4947
[3] Patent: WO2017/108761, 2017, A1. Location in patent: Page/Page column 15-18
[4] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[5] Tetrahedron Letters, 2015, vol. 56, # 49, p. 6843 - 6845
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View Lastest Price from 9-BROMOFLUORENE manufacturers
- Product
- 9-BroMofluorene 1940-57-4
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 98%min
- Supply Ability
- 30tons/month
- Release date
- 2023-04-07
- Product
- 9-BROMOFLUORENE 1940-57-4
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20 mt
- Release date
- 2025-03-12
- Product
- 9-BROMOFLUORENE 1940-57-4
- Price
- US $101.00-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2023-12-28