[ CAS No. 15499-84-0 ] {[proInfo.proName]}

Name: 15499-84-0|4,4'-(9H-Fluorene-9,9-diyl)dianiline|98%
Brand: Ambeed
SKU: A256550
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Quality Control of [ 15499-84-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 15499-84-0 ]

SDS Specification

Alternatived Products of [ 15499-84-0 ]

Product Details of [ 15499-84-0 ]

CAS No. :	15499-84-0	MDL No. :	MFCD00039156
Formula :	C₂₅H₂₀N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KIFDSGGWDIVQGN-UHFFFAOYSA-N
M.W :	348.44	Pubchem ID :	631552
Synonyms :

Calculated chemistry of [ 15499-84-0 ]

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.04
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	2.0
Molar Refractivity :	112.55
TPSA :	52.04 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-4.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.75
Log Po/w (XLOGP3) :	5.31
Log Po/w (WLOGP) :	5.23
Log Po/w (MLOGP) :	4.63
Log Po/w (SILICOS-IT) :	5.17
Consensus Log Po/w :	4.62

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-5.87
Solubility :	0.000469 mg/ml ; 0.00000134 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.15
Solubility :	0.000244 mg/ml ; 0.000000701 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.45
Solubility :	0.000000123 mg/ml ; 0.0000000004 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.11

Safety of [ 15499-84-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H312-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 15499-84-0 ]

* 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.

Upstream synthesis route of [ 15499-84-0 ]
Downstream synthetic route of [ 15499-84-0 ]

[ 15499-84-0 ] Synthesis Path-Upstream 1~4

1
[ 486-25-9 ]
[ 62-53-3 ]
[ 15499-84-0 ]

Yield	Reaction Conditions	Operation in experiment
93.4%	With sodium hydrogensulfite In toluene at 125 - 150℃; for 6 h;	72 g of 9-fluorenone , 155.4 g of aniline hydrochloride, 10 g of sodium bisulfite, and 72 g of a 9-fluorenone, were added to the reaction apparatus equipped with a water trap.145 g of aniline and 100 g of toluene are heated to 125-130° C. under stirring, and incubated at 125-130° C. for 3 hours, and the generated water passes through. Toluene was brought to the trap. Then, the temperature was raised slowly to 145-150 for 3 hours. After the reaction is over, cool down to 95°C. At this temperature, 10percent sodium hydroxide solution was added dropwise until the pH of the feed solution was approximately , 95° C., and the mixture was neutralized for 3 hours. Thermal stratification was performed at 95° C., the aqueous layer was separated, and the upper oil layer was collected and added to the flask. Under stirring, the temperature was gradually lowered to 20 to 30°C, and the mixture was sufficiently stirred at 20 to 30°C for 1 hour to be sufficiently crystallized. filter,About 185.6g after drying. 185.6 g of 9,9-bis(4-aminophenyl)fluorene and 300 g of xylene were added to the biscuit, 20 to 30Fully beaten at °C, filter,The product had a wet weight of 170 g, 141 g after drying, and a purity of 99.5percent (HPLC normalized content).Obtained above was 141 g of 9,9-bis(4-aminophenyl)fluorene, 2800 g of deionized water, 49.3 g of 33percent hydrochloric acid and 28 g ofActivated carbon was added to the flask, and the temperature was raised to 65-70°C to defocus for 2 hours. Heat filtration at 70°C. Add filtrate to burnIn the bottle, add 10percent ammonia water and feed solution at pH 60 to 65°C to pH 9 to 10. Stir at 60-65°C for 3 hours.Make it fully neutralized. After the end of the neutralization,After cooling down to 20 to 30°C, filtering and drying the 130g product, the yield is 93.4percent, the appearance is pure white solid,The purity is 99.7percent.

Reference： [1] Patent: CN107892649, 2018, A, . Location in patent: Paragraph 0023-0042
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 23, p. 240

2
[ 76123-68-7 ]
[ 15499-84-0 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 9, p. 2592 - 2596

3
[ 486-25-9 ]
[ 15499-84-0 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 9, p. 2592 - 2596

4
[ 103-84-4 ]
[ 15499-84-0 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 9, p. 2592 - 2596

[ 15499-84-0 ] Synthesis Path-Downstream 1~88

1
[ 486-25-9 ]
[ 62-53-3 ]
[ 15499-84-0 ]

Yield	Reaction Conditions	Operation in experiment
93.4%	With sodium hydrogensulfite; In toluene; at 125 - 150℃; for 6h;	72 g of 9-fluorenone , 155.4 g of aniline hydrochloride, 10 g of sodium bisulfite, and 72 g of a 9-fluorenone, were added to the reaction apparatus equipped with a water trap.145 g of aniline and 100 g of toluene are heated to 125-130° C. under stirring, and incubated at 125-130° C. for 3 hours, and the generated water passes through. Toluene was brought to the trap. Then, the temperature was raised slowly to 145-150 for 3 hours. After the reaction is over, cool down to 95°C. At this temperature, 10percent sodium hydroxide solution was added dropwise until the pH of the feed solution was approximately , 95° C., and the mixture was neutralized for 3 hours. Thermal stratification was performed at 95° C., the aqueous layer was separated, and the upper oil layer was collected and added to the flask. Under stirring, the temperature was gradually lowered to 20 to 30°C, and the mixture was sufficiently stirred at 20 to 30°C for 1 hour to be sufficiently crystallized. filter,About 185.6g after drying. 185.6 g of 9,9-bis(4-aminophenyl)fluorene and 300 g of xylene were added to the biscuit, 20 to 30Fully beaten at °C, filter,The product had a wet weight of 170 g, 141 g after drying, and a purity of 99.5percent (HPLC normalized content).Obtained above was 141 g of 9,9-bis(4-aminophenyl)fluorene, 2800 g of deionized water, 49.3 g of 33percent hydrochloric acid and 28 g ofActivated carbon was added to the flask, and the temperature was raised to 65-70°C to defocus for 2 hours. Heat filtration at 70°C. Add filtrate to burnIn the bottle, add 10percent ammonia water and feed solution at pH 60 to 65°C to pH 9 to 10. Stir at 60-65°C for 3 hours.Make it fully neutralized. After the end of the neutralization,After cooling down to 20 to 30°C, filtering and drying the 130g product, the yield is 93.4percent, the appearance is pure white solid,The purity is 99.7percent.
93%	With phosphotungstic acid; 3-mercaptopropionic acid; In chlorobenzene; for 6h;Inert atmosphere; Reflux;	Will 108g 9-fluorenone,180.0 g aniline,84g supported phosphotungstic acid catalyst (25percent),3g 3-mercaptopropionic acid,1000g of chlorobenzene was added to the mechanical stirrer in turn,Thermometer and 2L three-necked flask with condenser;N2 protection,Turn on the agitation,Heat back to reflux and separate water,Reaction for 6 hours,After the reaction, filter it hot.The filter residue-supported phosphotungstic acid is recovered for the next reaction.The filtrate is cooled to about 20 ° C and then filtered for half an hour to obtain a brown-red crude product.The solvent that can be used for the next reaction after the filtrate is recovered;The crude product was recrystallized from toluene-dioxane (volume ratio 1:1).9,9-bis(4-aminophenyl)phosphonium white solid 194.2 g, yield 93percent,The HPLC purity was 99.6percent.

Reference： [1]Patent: CN107892649,2018,A .Location in patent: Paragraph 0023-0042
[2]Patent: CN108863807,2018,A .Location in patent: Paragraph 0034-0040; 0058-0060
[3]Patent: DE638534,1935,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 23,p. 240

3
[ 15499-84-0 ]
[ 128406-10-0 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,2000,vol. 65,p. 1403 - 1418
[2]Chemistry - A European Journal,2011,vol. 17,p. 2592 - 2596
[3]Macromolecules,2004,vol. 37,p. 4496 - 4504
[4]Chemistry - A European Journal,2011,vol. 17,p. 2592 - 2596

4
[ 118-45-6 ]
[ 15499-84-0 ]
4,4'-bis(4-chlorophthalimido)diphenyl-9-fluorenylidene [ No CAS ]

Reference： [1]Macromolecules,2003,vol. 36,p. 5559 - 5565

5
[ 117-21-5 ]
[ 15499-84-0 ]
4,4'-bis(3-chlorophthalimido)diphenyl-9-fluorenylidene [ No CAS ]

Reference： [1]Macromolecules,2003,vol. 36,p. 5559 - 5565

6
[ 15499-84-0 ]
[ 128143-89-5 ]
9,9-bis[4-(2,2':6',2''-terpyridin-4'-yl)aminophenyl]fluorene [ No CAS ]

Reference： [1]Synthesis,2004,p. 869 - 874

7
[ 15499-84-0 ]
[ 474115-76-9 ]

Yield	Reaction Conditions	Operation in experiment
59%		A total of 25.5 g (73.18 mmol) of <strong>[15499-84-0]9,9-bis(4-aminophenyl)fluorene</strong> from TCI (Japan) was dissolved in a mixture of 250 ml of water and 45 ml (0.456 mol, 6 eg.) of concentrated HCI. This mixture was placed in a 1 L three- neck round bottom flask equipped with an overhead stirrer, a thermocouple, an addition funnel, and a cooling ice/methanol bath. The flask's contents were cooled to O0C, and a cold solution of NaNO2 (10.6 g, 153.6 mmol, 2 eq.) in 40 ml of water was added dropwise to the solution under vigorous stirring. The resulting yellow solution was further stirred at O0C for 30 minutes. This solution was transferred to a jacketed addition funnel with a jacket filled with ice in order to maintain the prepared diazonium salt at a temperature of O0C. A solution of this salt was slowly added to a solution of Kl (48.3 g, 0.291 mol, 4 eq.) in 250 ml of water at ~10°C under vigorous stirring. After completing the addition, the resulting dark mixture was maintained at a temperature of 6O0C and stirred for 6 hours. The mixture was cooled to room temperature, and the organic material was extracted with dichloromethane (3x0.5 L), washed with water (1 L), dried over Na2SO4, and concentrated on a rotary evaporator to give 45 g of black foam. This crude material was purified on CombiFlash (33Og column, hexane) to give 24.7 g (59percent yield) of 9,9-bis-(4-iodophenyl)- fluorene 10 as a white solid with Rf = 0.33 (in hexane).
47%		H2O (287 ml), <strong>[15499-84-0]9,9-bis(4-aminophenyl)fluorene</strong> (25.0 g, 71.8 mmol), hydrochoric acid (45 ml, 540.0 mmol) were added around bottom flask and were cooled to 0 °C. Sodium nitrite (10.1 g, 147.1 mmol) in H2O (54 ml) was slowly added.Stirring was continued for half an hour at the same temperature. Diazonium salts were got. Potassium iodide (42.9 g,258.3 mmol) and H2O (287 ml) contained in a round bottom flask were cooled to 0 °C. Diazonium salts were slowlyintroduced into the flask at 0 °C. Stirring was continued for four hours at room temperature. The mixture was washedwith chloroform and water two times, subsequently the residue was purified by chromatography on silica gel (eluent:chloroform: hexane = 1: 10) to afford BIPF (19.1 g, 47percent) as white powder:

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2004,vol. 60,p. 3029 - 3032
[2]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2005,vol. 61,p. 1171 - 1174
[3]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2005,vol. 61,p. 2505 - 2509
[4]Patent: WO2010/43693,2010,A1 .Location in patent: Page/Page column 22
[5]Tetrahedron,2007,vol. 63,p. 10161 - 10168
[6]Chemistry Letters,2016,vol. 45,p. 283 - 285

8
[ 108-78-1 ]
[ 15499-84-0 ]
[ 117-61-3 ]
[ 81-30-1 ]
polymer, molar percentage of fluorenyl groups 27 percent, M_n 5,27E₄ Da, M_W 1.365E₅; monomer(s): 1,4,5,8-naphthalenetetracarboxylic dianhydride; 4,4\-diamino-2,2\-biphenyldisulfonic acid; 4,4\-(fluorenylidene)dianiline; melamine [ No CAS ]