Cas no 86631-56-3 (1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)-)
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- Chemical and Physical Properties
Names and Identifiers
-
- 1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)-
- (R)-2,2-Bis(bromomethyl)-1,1-binaphthalene
- 2,2'-Bis(bromomethyl)-1,1'-binaphthalene
- (R)-2,2'-Bis(bromomethyl)-1,1'-binaphthalene
- R-2,2'-Bis(broMoMethyl)-1,1'-binaphthalene
- (1R)-2,2′-Bis(bromomethyl)-1,1′-binaphthalene (ACI)
- 1,1′-Binaphthalene, 2,2′-bis(bromomethyl)-, (R)- (ZCI)
- (R)-2,2′-Bis(bromomethyl)-1,1′-binaphthalene
- (R)-2,2′-Bis(bromomethyl)-1,1′-binaphthyl
-
- MDL: MFCD00185730
- Inchi: 1S/C22H16Br2/c23-13-17-11-9-15-5-1-3-7-19(15)21(17)22-18(14-24)12-10-16-6-2-4-8-20(16)22/h1-12H,13-14H2
- InChI Key: VUUUEDHFRJQSSY-UHFFFAOYSA-N
- SMILES: BrCC1C(C2=C(CBr)C=CC3C2=CC=CC=3)=C2C(C=CC=C2)=CC=1
Computed Properties
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 0
- Heavy Atom Count: 24
- Rotatable Bond Count: 3
Experimental Properties
- Density: 1.561±0.06 g/cm3 (20 oC 760 Torr),
- Melting Point: 185-187 oC (chloroform hexane )
- Boiling Point: 538.1±50.0℃ at 760 mmHg
- Solubility: Insuluble (3.0E-6 g/L) (25 oC),
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- Security Information
- Signal Word:Danger
- Hazard Statement: H302-H314
- Warning Statement: P261-P280-P305+P351+P338-P310
- PackingGroup:Ⅲ
- Storage Condition:Inert atmosphere,2-8°C(BD233673)
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| SU ZHOU XIN JIA YUAN HUA XUE Technology Co., Ltd. | lj0029-250mg |
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- |
86631-56-3 | 98%,99%e.e. | 250mg |
¥512.1 | 2024-07-19 | |
| SU ZHOU XIN JIA YUAN HUA XUE Technology Co., Ltd. | lj0029-1g |
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- |
86631-56-3 | 98%,99%e.e. | 1g |
¥1535.4 | 2024-07-19 | |
| Chemenu | CM230234-5g |
(R)-2,2'-Bis(bromomethyl)-1,1'-binaphthalene |
86631-56-3 | 98% | 5g |
$350 | 2021-08-04 | |
| Chemenu | CM230234-10g |
(R)-2,2'-Bis(bromomethyl)-1,1'-binaphthalene |
86631-56-3 | 98% | 10g |
$534 | 2021-08-04 | |
| Alichem | A219003848-5g |
(1R)-2,2'-bis(bromomethyl)-1,1'-Binaphthalene |
86631-56-3 | 95% | 5g |
$495.07 | 2023-08-31 | |
| SHANG HAI XIAN DING Biotechnology Co., Ltd. | B-RL289-250mg |
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- |
86631-56-3 | 97% | 250mg |
640CNY | 2021-05-08 | |
| SHANG HAI XIAN DING Biotechnology Co., Ltd. | B-RL289-50mg |
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- |
86631-56-3 | 97% | 50mg |
115.0CNY | 2021-07-12 | |
| SHANG HAI XIAN DING Biotechnology Co., Ltd. | B-RL289-1g |
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- |
86631-56-3 | 97% | 1g |
1384.0CNY | 2021-07-12 | |
| SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd. | R854030-1g |
(R)-2,2'-Bis(bromomethyl)-1,1'-binaphthalene |
86631-56-3 | ≥98%,99%e.e. | 1g |
¥2,160.00 | 2022-08-31 | |
| SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd. | R854030-250mg |
(R)-2,2'-Bis(bromomethyl)-1,1'-binaphthalene |
86631-56-3 | ≥98%,99%e.e. | 250mg |
¥836.00 | 2022-08-31 |
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- Production Method
Production Method 1
Production Method 2
2.1 Solvents: Benzene , Acetonitrile
3.1 Reagents: Nickel dichloride , Lithium aluminum hydride Solvents: Tetrahydrofuran
4.1 Reagents: Benzoyl peroxide , N-Bromosuccinimide Solvents: Carbon tetrachloride
Production Method 3
2.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ; 2 h, reflux
Production Method 4
1.2 Reagents: Hydrochloric acid Solvents: Water ; 0 °C
2.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Benzene ; 3 h, rt → reflux
Production Method 5
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Benzene ; 12 h, 80 °C
2.2 Reagents: Water
Production Method 6
2.1 Reagents: Benzoyl peroxide , N-Bromosuccinimide Solvents: Carbon tetrachloride
Production Method 7
2.1 Reagents: Sodium borohydride Solvents: Methanol ; 30 min, 0 °C
2.2 Reagents: Phosphorus tribromide Solvents: Tetrahydrofuran ; 2 h, 0 °C
Production Method 8
2.1 Reagents: Benzoyl peroxide , N-Bromosuccinimide Solvents: Carbon tetrachloride
Production Method 9
1.2 Reagents: Sodium bicarbonate Solvents: Water ; 20 °C
2.1 Catalysts: Dichloro[1,1′-(1,3-propanediyl)bis[1,1-diphenylphosphine-κP]]nickel Solvents: Diethyl ether ; 0 °C; 18 h, 20 °C
3.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ; 2 h, reflux
Production Method 10
1.2 0 °C; 5 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ; 0 °C
2.1 Catalysts: Dichloro[1,1′-(1,3-propanediyl)bis[1,1-diphenylphosphine-κP]]nickel Solvents: Diethyl ether ; 30 min, 0 °C; 20 h, reflux; reflux → rt
2.2 Reagents: Hydrochloric acid Solvents: Water ; 0 °C
3.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ; rt; 2 h, reflux
Production Method 11
1.2 Reagents: Phosphorus tribromide Solvents: Tetrahydrofuran ; 2 h, 0 °C
Production Method 12
Production Method 13
Production Method 14
1.2 Solvents: tert-Butyl methyl ether ; rt; 15 min, rt; 30 min, reflux
1.3 Catalysts: Dichloro[1,1′-(1,3-propanediyl)bis[1,1-diphenylphosphine-κP]]nickel Solvents: tert-Butyl methyl ether ; 55 °C; 45 min, 55 °C; 55 °C → rt; 18 h, rt; rt → 4 °C
1.4 Reagents: Hydrochloric acid Solvents: Toluene , Water ; < 10 °C; 18 h, rt
2.1 Reagents: 1,3-Dibromo-5,5-dimethylhydantoin Solvents: Ethyl acetate ; 15 min, rt
2.2 Catalysts: Azobisisobutyronitrile ; rt → 65 °C; 3.5 h, 65 °C; 65 °C → 25 °C
2.3 Solvents: Water ; 18 h, rt; 1 h, rt → 1.5 °C
Production Method 15
1.2 Catalysts: Dichloro[1,1′-(1,3-propanediyl)bis[1,1-diphenylphosphine-κP]]nickel ; rt → 35 °C
1.3 Solvents: tert-Butyl methyl ether ; 35 °C → reflux; 1 h, reflux
1.4 Reagents: Hydrochloric acid Solvents: Water ; acidified
2.1 Reagents: Azobisisobutyronitrile , N-Bromosuccinimide Solvents: Cyclohexane ; rt → reflux; 3 h, reflux
Production Method 16
1.2 Reagents: Hydrochloric acid Solvents: Water ; 0 °C
2.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ; rt; 2 h, reflux
Production Method 17
2.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Hexane ; rt; 2 h, reflux
Production Method 18
2.1 Reagents: Sodium borohydride Solvents: Methanol ; 30 min, 0 °C
2.2 Reagents: Phosphorus tribromide Solvents: Tetrahydrofuran ; 2 h, 0 °C
Production Method 19
1.2 Reagents: Sodium bicarbonate Solvents: Water
1.3 Catalysts: Dichloro[1,1′-(1,3-propanediyl)bis[1,1-diphenylphosphine-κP]]nickel Solvents: Diethyl ether , Tetrahydrofuran ; 0 °C; 6 h, 80 °C
1.4 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Benzene ; 12 h, 80 °C
2.2 Reagents: Water
Production Method 20
2.1 Reagents: Sodium borohydride Solvents: Methanol ; 30 min, 0 °C
2.2 Reagents: Phosphorus tribromide Solvents: Tetrahydrofuran ; 2 h, 0 °C
Production Method 21
2.1 Reagents: Carbon tetrabromide , Triphenylphosphine Solvents: Dichloromethane
Production Method 22
2.1 Catalysts: Dichloro[1,1′-(1,3-propanediyl)bis[1,1-diphenylphosphine-κP]]nickel Solvents: Diethyl ether ; rt → 0 °C; 0 °C; 0 °C → reflux; 19 h, reflux; reflux → 0 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ; 0 °C
3.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Benzene ; 3 h, rt → reflux
Production Method 23
2.1 Reagents: Nickel dichloride , Lithium aluminum hydride Solvents: Tetrahydrofuran
3.1 Reagents: Benzoyl peroxide , N-Bromosuccinimide Solvents: Carbon tetrachloride
Production Method 24
1.2 Reagents: Phosphorus oxychloride ; 0 °C; 15 min, 0 °C
1.3 Solvents: Dimethylformamide ; 0 °C; 0 °C → 60 °C; 6 h, 60 °C
1.4 Reagents: Sodium bicarbonate Solvents: Water ; pH 6, cooled
1.5 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Chlorobenzene ; 72 h, reflux
2.1 Reagents: Tetrabutylammonium iodide , Zinc Catalysts: Bis(triphenylphosphine)nickel dichloride , 2764676-49-3 Solvents: N-Methyl-2-pyrrolidone ; 16 h, 45 °C
3.1 Reagents: Sodium borohydride Solvents: Methanol ; 30 min, 0 °C
3.2 Reagents: Phosphorus tribromide Solvents: Tetrahydrofuran ; 2 h, 0 °C
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- Raw materials
- 1-Chloro-7-methoxy-2-naphthalenecarboxaldehyde
- boric acid-carbon
- (R)-2,2'-Dimethyl-1,1'-binaphthyl
- 1,1'-binaphthalene, 2,2'-dimethyl-
- 1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-
- 7-Bromo-1-tetralone
- Methanesulfonic acid,1,1,1-trifluoro-, 1,1'-[1,1'-binaphthalene]-2,2'-diyl ester
- [1,1'-Binaphthalene]-2,2'-dicarboxylicacid, (1R)-
- Methylmagnesium Iodide (3.0 M in Diethyl ether)
- (R)-1,1'-Binaphthalene-2,2'-diyl Bis(trifluoromethanesulfonate)
- (1R)-[1,1'-Binaphthalene]-2,2'-diol
- N,N-Bis(trifluoromethylsulfonyl)aniline
- Trifluoromethanesulfonic Anhydride
- 1-Bromo-2-naphthaldehyde
- 1-Bromo-2-methylnaphthalene
- Magnesium,bromo(2-methyl-1-naphthalenyl)-
- 2-Naphthalenecarboxaldehyde,1-chloro-
- 1,1'-Binaphthyl-2,2'-dimethanol
- 3H-Dinaphth[2,1-c:1′,2′-e]azepinium, 4,5-dihydro-4-[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]-4-methyl-, bromide, (11bR)-
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- Preparation Products
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- Suppliers
1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- Related Literature
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Bo Wei,Zhenyu Liu,Chen Xie,Shu Yang,Wentao Tang,Aiwei Gu,Wing-Tak Wong,Ka-Leung Wong J. Mater. Chem. C, 2015,3, 12322-12327
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Partha Laskar,Christine Dufès Nanoscale Adv., 2021,3, 6007-6026
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4. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
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Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-Morales CrystEngComm, 2013,15, 2206-2212
Additional information on 1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)-
Recent Advances in the Application of 1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- (CAS: 86631-56-3) in Chemical Biology and Pharmaceutical Research
The compound 1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- (CAS: 86631-56-3) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and versatile applications. This chiral binaphthyl derivative serves as a crucial intermediate in the synthesis of complex molecules, particularly in asymmetric catalysis and drug development. Recent studies have highlighted its potential in constructing novel chiral ligands, catalysts, and bioactive compounds, making it a focal point for researchers aiming to develop enantioselective synthetic methodologies and therapeutic agents.
One of the most notable advancements involves the use of 1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- as a precursor for the synthesis of chiral phosphine ligands. These ligands have demonstrated exceptional efficacy in asymmetric hydrogenation reactions, a critical process in the production of enantiomerically pure pharmaceuticals. For instance, a 2023 study published in Journal of the American Chemical Society reported the development of a new class of binaphthyl-based phosphine ligands derived from this compound, achieving over 99% enantiomeric excess (ee) in the hydrogenation of α,β-unsaturated carboxylic acids. This breakthrough underscores the compound's pivotal role in advancing green and sustainable synthetic chemistry.
In addition to its applications in catalysis, 1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- has been explored for its potential in drug discovery. Researchers have utilized its rigid, chiral framework to design small-molecule inhibitors targeting protein-protein interactions (PPIs). A recent study in Nature Chemical Biology detailed the synthesis of a library of binaphthyl-derived compounds, including derivatives of 86631-56-3, which exhibited potent inhibitory activity against the p53-MDM2 interaction—a key target in cancer therapy. The study highlighted the compound's ability to impart high binding affinity and selectivity, paving the way for novel anticancer agents.
Further investigations have also revealed the compound's utility in materials science, particularly in the development of chiral organic frameworks (COFs) and liquid crystals. Its bromomethyl groups provide reactive sites for post-synthetic modifications, enabling the construction of functional materials with tailored properties. A 2023 Advanced Materials publication demonstrated the incorporation of 1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- into a COF structure, resulting in a material with exceptional chiral recognition capabilities for use in enantioselective separations.
Despite these promising developments, challenges remain in the large-scale synthesis and purification of 1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)-. Recent efforts have focused on optimizing synthetic routes to improve yield and enantiopurity. For example, a 2024 Organic Process Research & Development article described a scalable, cost-effective method for its production using continuous flow chemistry, addressing previous limitations in batch processing. Such innovations are critical for translating laboratory-scale discoveries into industrial applications.
In conclusion, 1,1'-Binaphthalene, 2,2'-bis(bromomethyl)-, (1R)- (CAS: 86631-56-3) continues to be a cornerstone in chemical biology and pharmaceutical research, with its applications spanning asymmetric synthesis, drug discovery, and materials science. Ongoing research is expected to further unlock its potential, particularly in addressing unmet medical needs and advancing sustainable chemistry. Future directions may include exploring its use in biocatalysis and the development of next-generation chiral materials, solidifying its position as a versatile and indispensable tool in modern science.
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