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| | 2,2'-Bis(trifluoromethyl)benzidine Basic information |
| Product Name: | 2,2'-Bis(trifluoromethyl)benzidine | | Synonyms: | 2,2'-Bis(trifluoroMethyl)-4,4'-diaMino biphenyl(TFMB/TFDB);2,2'-bis(trifluoromethyl)-[1,1‘-bibiphenyl]-4,4'-diamine;2,2'-Bis-trifluoromethyl-biphenyl-4,4'-diamine;2,2'-Bis(trifluorome;2,2'-Bis(trifluoroMethyl)-4,4'-diaMino biphenyl (TFMB);2,2 '- (trifluoroMethyl) -4,4' - diaMino diphenyl;ABL-21;4,4'-DIAMINO-2,2'-BIS(TRIFLUOROMETHYL)BIPHENYL | | CAS: | 341-58-2 | | MF: | C14H10F6N2 | | MW: | 320.23 | | EINECS: | 671-105-2 | | Product Categories: | Biphenyls (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials;341-58-2 | | Mol File: | 341-58-2.mol |  |
| | 2,2'-Bis(trifluoromethyl)benzidine Chemical Properties |
| Melting point | 183 °C | | Boiling point | 376.9±42.0 °C(Predicted) | | density | 1.415±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C(protect from light) | | solubility | soluble in Methanol | | pka | 3.23±0.10(Predicted) | | form | powder to crystal | | color | White to Light yellow to Light orange | | InChI | InChI=1S/C14H10F6N2/c15-13(16,17)11-5-7(21)1-3-9(11)10-4-2-8(22)6-12(10)14(18,19)20/h1-6H,21-22H2 | | InChIKey | NVKGJHAQGWCWDI-UHFFFAOYSA-N | | SMILES | C1(C2=CC=C(N)C=C2C(F)(F)F)=CC=C(N)C=C1C(F)(F)F | | CAS DataBase Reference | 341-58-2(CAS DataBase Reference) |
| | 2,2'-Bis(trifluoromethyl)benzidine Usage And Synthesis |
| Description | 2,2'-Bis(trifluoromethyl)benzidine (TFMB) is a fluorinated benzidine derivative with two trifluoromethyl substituents at the 2- and 2'-positions. 2,2'-Bis(trifluoromethyl)benzidine (TFMB) is a rigid and aromatic polyimide used in the synthesis of metal-organic frameworks (MOFs) and covalent organic frameworks (COFs) of high specific surface area.TFMB is also synthesised as UV-resistant and colourless polyimide thin films for optoelectronic applications. TFMB is also used to synthesise UV resistant and colourless polyimide films for optoelectronic applications. The two fluoromethyl groups have a strong electron-withdrawal effect, which reduces the electron dispersion in the π-orbitals of the fully conjugated polymer backbone. This effect results in a much higher transparency of the polyimide film compared to polyimide films containing methyl substituents. This polyimide can be used for the encapsulation of solar cells with MOFs cluster light diffusers. | | Chemical Properties | 2,2'-Bis(trifluoromethyl)benzidine is rigid and aromatic, the two fluoromethyl groups have strong electron withdrawing effect, reducing the electron delocalization of the π orbital on the fully conjugated polymer backbone. | | Uses | 2,2'-Bis(trifluoromethyl)benzidine is used for producing a high strength flexible transparent polyimide material. | | Hazard | 2,2'-Bis(trifluoromethyl)benzidine is harmful if swallowed, in contact with skin or if inhaled.
| | Synthesis | This 2,2′-bis(trifluoromethyl)-4,4′-dinitrobiphenyl crystal of 42.5 g, toluene of 127.5 g and 5% Pd/C (AER-TYPE: 50% water contained product) of 1.8 g manufactured by N.E. CHEMCAT Corp. were fed in an autoclave made of stainless steel, after the system was replaced sufficiently with hydrogen, pressured with hydrogen for a reaction pressure to be 1 MPa and reaction was carried out at a reaction temperate of 60 °C for 6 hours. After reaction, catalyst was filtered away, toluene in this reaction liquid was distilled away under reduced pressure, concentrated and crystallized, 2,2′-bis(trifluoromethyl)-4,4′-diaminobiphenyl of 28.5 g (purity converted) was obtained by solid-liquid separation. | | References | [1] Patent: CN105541637, 2016, A. Location in patent: Paragraph 0017; 0018
[2] Journal of the Chemical Society, 1951, p. 3459,3463
[3] Journal of the Chemical Society, 1954, p. 1071,1074
[4] Patent: EP2100874, 2009, A1. Location in patent: Page/Page column 7 |
| | 2,2'-Bis(trifluoromethyl)benzidine Preparation Products And Raw materials |
| Raw materials | 1,1'-Biphenyl, 4,4'-dinitro-2,2'-bis(trifluoromethyl)-->Hydrazine, 1,2-bis[3-(trifluoromethyl)phenyl]--->[1,1'-Biphenyl]-2,4'-diamine, 2',4-bis(trifluoromethyl)--->Diazene, bis[3-(trifluoromethyl)phenyl]- (9CI)-->2-(Trifluoromethyl)-1-iodo-4-nitrobenzene-->2-Amino-5-nitrobenzotrifluoride-->4-Nitro-2-(trifluoromethyl)acetanilide-->2-(Trifluoromethyl)acetanilide-->3-Nitrobenzotrifluoride-->Methanol |
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