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[ CAS No. 107934-68-9 ] {[proInfo.proName]}

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Chemical Structure| 107934-68-9
Chemical Structure| 107934-68-9
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Product Details of [ 107934-68-9 ]

CAS No. :107934-68-9 MDL No. :MFCD10000948
Formula : C25H18Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :CIZUMWWHWPJAAK-UHFFFAOYSA-N
M.W : 417.33 Pubchem ID :21872159
Synonyms :

Safety of [ 107934-68-9 ]

Signal Word:Danger Class:9
Precautionary Statements:P264-P270-P273-P280-P301+P312+P330-P302+P352+P312-P305+P351+P338+P310-P332+P313-P391-P501 UN#:3077
Hazard Statements:H302+H312-H315-H318-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 107934-68-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 107934-68-9 ]

[ 107934-68-9 ] Synthesis Path-Downstream   1~5

YieldReaction ConditionsOperation in experiment
94% 63 Preparation of 9,9-Bis(4-amino-3-chlorophenyl)fluorene EXAMPLE 63 Preparation of 9,9-Bis(4-amino-3-chlorophenyl)fluorene The procedure of Example 39 is repeated except that 0.537 mole of 2-chloroaniline is used in place of the aniline and, after stirring at 60° C., the temperature is raised to 175° C. 9,9-Bis(4-amino-3-chlorophenyl)fluorene (abbreviated BACPF) has a molecular weight of 404 (as determined by mass spectroscopy) and a melting point of 235°-236° C., and is prepared in 94 percent yield. Results are shown in Table 8.
The aminophenylfluorene curing agent according to claim 12 selected from the group consisting of 9,9-bis(3-methyl-4-aminophenyl)fluorene, 9,9-bis(3,5-dimethyl-4-aminophenyl)fluorene, 9,9-bis(3-chloro-4-aminophenyl)fluorene, and 9,9-bis(3,5-diethyl-4-aminophenyl)fluorene.
  • 2
  • [ 107934-68-9 ]
  • [ 140-89-6 ]
  • 9,9-bis(2-mercaptobenzothiazol-6-yl)fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
14.2% In N,N-dimethyl-formamide at 135℃; for 7h; 2 Comparative Example 2 General procedure: A glass reactor equipped with a stirrer and a thermometer was charged with 25.0 g (0.05 mol) of 9,9'-bis (3-bromo-4-aminophenyl) fluorene obtained in Example 1, 34.0 g (0.21 mol) of potassium xanthate and 57.5 g of DMF were charged and heated to 135 ° C. After reaction for 7 hours at the same temperature, the reaction mass was analyzed by HPLC, and it was found that 87.5% of 9,9'-bis (2-mercaptobenzothiazol-6-yl) fluorene had been formed. After the reaction, the reaction solution was cooled to room temperature, 161 g of DMF, 250 g of water, 22.6 g of 35% hydrochloric acid were added, the precipitated solid was filtered, and the precipitated solid was washed three times with 100 g of 10% aqueous methanol To obtain crude crystals. The obtained crude crystals were added to 188.8 g of DMF and dissolved at 90 ° C., followed by crystallization. The precipitated solid was filtered and dried to obtain 9,9'-bis (2-mercaptobenzothiazol-6-yl) 69.4 g (yield: 74.6%, purity: 98.8%) of fluorene as white crystals
  • 3
  • [ 15499-84-0 ]
  • [ 107934-68-9 ]
YieldReaction ConditionsOperation in experiment
23.7% With aluminum (III) chloride; N-chloro-succinimide; In N,N-dimethyl-formamide; at 0℃; for 6h; In a glass reactor equipped with a stirrer and a thermometer,10.0 g (0.03 mol) of 9,9'-bis (4-aminophenyl) fluorene, salt0.96 g (0.01 mol) of aluminum (AlCl 3),30 g of DMF was charged, and the internal temperature was cooled to 0 ° C. Next, 7.86 g (0.06 mol) of N-chlorosuccinimide was added at the same temperature, and the reaction was further carried out at 0 ° C. for 6 hours.Analysis of the obtained reaction mass by HPLC revealed that 9,9'-bis (3-chloro-4-aMinophenyl) fluorene was produced at 68.6percent.Ethyl acetate, water and a saturated aqueous solution of sodium bicarbonate were added to the obtained reaction mixture, and the mixture was stirred.The aqueous layer was removed by phase separation.Wash with water twice ·After liquid separation, the obtained organic layer was concentrated to obtain crude crystals.Thereafter, purification was carried out by silica gel column chromatography (developing solution: hexane / ethyl acetate = 2: 1) to obtain white crystals of 9,9'-bis (3-chloro-4-aminophenyl) fluorene .7percent, LC purity 99.3percent).
  • 4
  • [ 107934-68-9 ]
  • 9,9-bis(3-chlorophenyl)fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 9,9-bis(3-chloro-4-aminophenyl)fluorene With hydrogenchloride; acetic acid; sodium nitrite In water at 20℃; Stage #2: With hypophosphorous acid In water for 24h; Synthesis of 9,9-Bis(3-chlorophenyl)fluorene (m-BCF). A 300 mL one neck round-bottomed flask equipped with a magnetic stirrer bar was charged with 9,9-bis(4-amino-3-chlorophenyl)fluorene (10.0 g, 24.0 mmol), acetic acid (88mL), deionized water (38 mL) and concentrated hydrochloric acid (10 mL). To this white suspension, sodium nitrite (3.91 g,56.7 mmol) aqueous solution (12.6 mL) was added. The mixture was stirred at room temperature and the solid was gradually dissolved to afford an orange solution. To the resulting diazonium salt solution, phosphinic acid (3234%, 70 mL) was added. During the addition of phosphinic acid, an orange solid was precipitated with an evolution of gas. After stirring for 24 hours, the resulting solid was recovered by filtration and dissolved in EtOAc. This EtOAc solution was washed with saturated aqueous solution of sodium hydrogen carbonate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/EtOAc = 19/1) to afford m-BFC as a white solid (7.01 g, 76% yield). 1H and 13C NMR spectra of obtained solid are shown in Figure S2. 1H NMR (500 MHz, CDCl3): 7.09 (m, 2H), 7.12(m, 2H), 7.17 (dd, J = 7.8, 7.8 Hz, 2H), 7.20 (m, 2H), 7.29 (dd,J = 7.3, 7.3 Hz, 2H), 7.37 (d, J = 7.3 Hz, 2H), 7.39 (dd, J =7.3, 7.3 Hz, 2H), 7.77 (d, J = 7.3 Hz, 2H). 13C NMR (125 MHz,CDCl3): 64.9, 120.4, 126.0, 126.3, 127.1, 127.9, 128.0 (C*2),129.6, 134.2, 140.0, 147.4, 149.6.
  • 5
  • [ 486-25-9 ]
  • [ 95-51-2 ]
  • [ 107934-68-9 ]
YieldReaction ConditionsOperation in experiment
92.8% Stage #1: o-chloroaniline With sulfuric acid In ethylene glycol at 20 - 50℃; for 0.5h; Stage #2: 9-fluorenone In ethylene glycol at 140℃; 2 This example is a method for preparing 9,9-bis[2-chloro-4-aminophenyl]fluorene, which is as follows: General procedure: Add 36.0g (0.28mol) of 3-chloroaniline and 50mL of ethylene glycol to a 250mL three-necked flask equipped with mechanical stirring. After mixing well, slowly add 4.9g of concentrated sulfuric acid at a temperature of ≤50 ° C, and stir at room temperature for 0.5h. Then, add 18.0g (0.1mol) of 9-fluorenone, mix at room temperature first, then raise the temperature to 150 ± 1 ° C to conduct the condensation reaction. The reaction ends when the 9-fluorenone content is <0.1%. After the reaction, the reaction system was cooled to room temperature, 36 mL of a 40 wt% sodium hydroxide aqueous solution was added, stirred for 1.5 h, and filtered. The filter cake was slurried with 36 mL of water at room temperature, filtered, and the cake was dried to obtain 41.0 g of crude product and 50 mL of toluene. Recrystallization, filtration, and drying of the filter cake gave 39.8 g of the target product 9,9-bis [2-chloro-4-aminophenyl] fluorene with a yield of 95.4% and a purity of 99.5%.
With methanesulfonic acid In 1,2-dichloro-benzene at 175℃; for 12h; 1-2 In Example 1 of the method present invention, fluorenone (1.000 pbw), excess 2-chloroaniline (4.162 pbw), methylsulfonic acid (0.261 pbw), and in ortho-dichlorobenzene (2.650 pbw) were each charged to acontinuously stirred tank reactor, sparged with N2 for 0.5 hour, heated to 175°C, and then held at 175°C, while removing water formed in the reaction of the fluorenone and 2-chloroaniline, for 12.0 hours to form a crude product mixture comprising CAF, methyl sulfonic acid and 2-chloroaniline in ortho dichlorobenzene. The crude product mixture was cooled to 85°C and solid CAF seed crystals (0.1 pbw) were introduced to the mixture. The CAF was then recrystallized from the mixture by allowing the mixture to cool to 5°C.The crystalline CAF was separated from the cooled mixture by filtration, washed once with ortho-dichlorobenzene (1.300 pbw), and then washed three times in succession with volumes (9.000 pbw, 6.000 pbw, and 6.000 pbw, respectively) of a mixture isopropyl alcohol in water (50 pbw isopropyl alcohol /50 pbw water). The method of Example 1 yielded 1 .702 pbw CAF and 28.672 pbw of waste comprising 2-chloroaniline, ortho-dichlorobenzene, isopropyl alcohol, and water. The washed CAF comprised 75 ppm methyl sulfonic acid, 4839 ppm 2-chloraniline, and 2050 ppm ortho-diclorobenzene. The global yield of CAF was 75%.
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