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Chemical Structure| 102-54-5
Chemical Structure| 102-54-5
Structure of 102-54-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 102-54-5 ]

CAS No. :102-54-5 MDL No. :MFCD00001427
Formula : Fe(C5H5)2 Boiling Point : -
Linear Structure Formula :- InChI Key :KTWOOEGAPBSYNW-UHFFFAOYSA-N
M.W : 186.03 Pubchem ID :7611
Synonyms :

Calculated chemistry of [ 102-54-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.12
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -1.67
Log Po/w (WLOGP) : 1.4
Log Po/w (MLOGP) : 3.08
Log Po/w (SILICOS-IT) : 1.98
Consensus Log Po/w : 0.96

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.12
Solubility : 233.0 mg/ml ; 1.32 mol/l
Class : Highly soluble
Log S (Ali) : 2.18
Solubility : 26700.0 mg/ml ; 152.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -2.24
Solubility : 1.02 mg/ml ; 0.00578 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.59

Safety of [ 102-54-5 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P210-P260-P280-P301+P312+P330-P370+P378 UN#:1325
Hazard Statements:H228-H302+H332-H361-H373-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 102-54-5 ]

* 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 [ 102-54-5 ]
  • Downstream synthetic route of [ 102-54-5 ]

[ 102-54-5 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 102-54-5 ]
  • [ 1079-66-9 ]
  • [ 12150-46-8 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 39, p. 12267 - 12277
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  • [ 68-12-2 ]
  • [ 1271-48-3 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 20℃; for 18 h; Inert atmosphere; Schlenk technique
Stage #2: at 0 - 20℃; for 2 h; Inert atmosphere; Schlenk technique
The literature procedure [26b] for the preparation of 9 was modified as follows: To a room temperature solution of ferrocene (10 g, 0.054 mol) in dry hexane (200 mL) was added n-butyl lithium solution (67 mL, 1.6 M in hexanes, 0.10 mol) dropwise followed by addition of tetramethylene ethylenediamine (TMEDA) (14.7 g, 0.25 mol).
No difference in yields was detected if the additions were made at -50 °C.
After stirring the reaction mixture for 18 h at room temperature, dilithiated ferrocene has precipitated as an orange solid.
The suspension was cooled to 0 °C, DMF (7.85 g, 0.11 mol, 8.3 mL) was added, and the stirring continued for further 2 h at room temperature.
56%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 20℃;
Stage #2: at -78℃;
To a solution of ferrocene (6 g, 32 mmol) in hexane (100 mL) was addedtetramethylethylenediamine (TMEDA) (10.6 mL, 71 mmol) and n-butyllithium (46.4 mL,74 mmol) and the mixture stirred overnight at room temperature. The reaction was cooledto -78° C and a solution of DMF (5.5 mL, 71 mmol) in Et2O (100 mL) was added. Themixture was allowed to warm to room temperature and stirred for 4 h. The reaction wasquenched with brine (100 mL) and extracted with CH2Cl2( 100 mL). The organic phasewas dried over MgSO4 and the solvent removed in vacuo. The product was purified bycolumn chromatography on silica gel using hexane/ether followed by hexane/ether/ethylacetate. Yield 4.3 g, 56 percent.
48%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 20℃; for 20 h;
Stage #2: at -78℃; for 2 h;
1 g (5.37 mmol) of ferrocene, dissolved in 12 ml of anhydrous ethyl ether, was treated with 7.2 ml (11.56 mmol) of n-BuLi (1.6M solution in hexane) and by addition of 1.74 ml (11.56 mmol) of N,N,N',N'-tetramethylethylenediamine. The reaction was left under argon and with stirring at ambient temperature for 20 hours. 1.33 ml (17.20 mmol) of DMF were added at -78° C. After stirring at -78° C. for 2 hours, the reaction mixture was hydrolyzed (15 ml of water). The aqueous phase was extracted with dichloromethane (3.x.15 ml). The resulting organic phase was dried over MgSO4 and was then concentrated. The residue was purified on silica gel with a pentane/ethyl acetate (50:50) mixture. [0152] 0.62 g (2.56 mmol, 48percent) of compound 1 was obtained in the form of a brown paste. [0153] 1H NMR (CDCl3): 4.62 (d, J=9 Hz, 4H, H2H3-H2'H3'), 4.83 (d, J=8.7 Hz, 4H, H1H4-H1'H4'), 9.89 (m, 2H, 2CHO) [0154] 13C NMR (CDCl3): 70.9 (C2H5), 74.20 (C3C4), 80.4 (C1), 192.9 (C6). [0155] MS: 185 (60), 243 (M+, 95).
3.363 g
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 20℃; for 17 h;
Stage #2: at 20℃; for 0.5 h; Cooling with ice
To a dry Schlenk flask was added 3.100 g (16.6 mmol) of vacuum dried ferrocene and 12.0 mL of n-hexane,Stirred to a suspension; then 25.0 mL of n-butyllithium (1.6 M, 40.0 mmo1)Then, 6.0 mL of tetramethylethylenediamine (40.0 mmo1) was added dropwise over a period of about 60 min,The reaction was continued for 16 h at room temperature; the resulting mixture was filtered,The resulting orange-red powder was washed three times with 15.0 mL of n-hexane, i.e., about 15.0 mmo1 of 1,1'-bis-lithium ferrocene,To this was added 35.0 mL of n-hexane,Stirred to a suspension; another 12 mL of anhydrous ether was added 2.8 mL (36.0 mmo1) of dimethylformamide,The solution was added dropwise to the suspension (about 30 min) under ice-water bath cooling. After the dropwise addition, the ice-water bath was removed and allowed to warm to room temperature and stirred for about 30 minutes.Add 50.0 mL (4.0 M, 0.2 mol) of hydrochloric acid,Continue to react for 15 min after static, set stratification,The aqueous layer was extracted three times with 15.0 mL of dichloromethane,A dark red solid ferrocene dialdehyde was obtained 3.363 g.

Reference: [1] Journal of Organometallic Chemistry, 1993, vol. 463, # 1-2, p. 163 - 168
[2] Journal of Organometallic Chemistry, 2013, vol. 740, p. 61 - 69
[3] Journal of Organometallic Chemistry, 2009, vol. 694, # 13, p. 2020 - 2028
[4] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 10, p. 1551 - 1557
[5] European Journal of Inorganic Chemistry, 2014, vol. 2014, # 36, p. 6212 - 6219
[6] Journal of Organometallic Chemistry, 1991, vol. 412, # 3, p. 381 - 382
[7] Journal of Organometallic Chemistry, 2017, vol. 846, p. 251 - 262
[8] Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11445 - 11450[9] Angew. Chem., 2018, vol. 130, p. 11616 - 11621,6
[10] Patent: US2005/38234, 2005, A1, . Location in patent: Page/Page column 11
[11] Chemical Physics Letters, 2015, vol. 624, p. 47 - 52
[12] Inorganica Chimica Acta, 2015, vol. 438, p. 42 - 51
[13] Tetrahedron Asymmetry, 2015, vol. 26, # 23, p. 1307 - 1313
[14] Patent: CN105777817, 2016, A, . Location in patent: Paragraph 0105
[15] Patent: CN103665053, 2016, B, . Location in patent: Paragraph 0040-0044
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  • [ 68-12-2 ]
  • [ 12093-10-6 ]
  • [ 1271-48-3 ]
Reference: [1] Journal of Organometallic Chemistry, 1993, vol. 463, # 1-2, p. 163 - 168
[2] Journal of Organometallic Chemistry, 1996, vol. 512, # 1-2, p. 219 - 224
[3] Organometallics, 2013, vol. 32, # 20, p. 5784 - 5797
[4] Journal of Organometallic Chemistry, 1996, vol. 512, # 1-2, p. 219 - 224
[5] Journal of Organometallic Chemistry, 1996, vol. 512, # 1-2, p. 219 - 224
[6] Journal of Organometallic Chemistry, 1996, vol. 512, # 1-2, p. 219 - 224
  • 4
  • [ 2591-86-8 ]
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  • [ 1271-48-3 ]
Reference: [1] Inorganica Chimica Acta, 2009, vol. 362, # 6, p. 2068 - 2070
  • 5
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  • [ 1271-48-3 ]
Reference: [1] New Journal of Chemistry, 2004, vol. 28, # 1, p. 134 - 144
  • 6
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  • [ 93-61-8 ]
  • [ 12093-10-6 ]
  • [ 1271-48-3 ]
Reference: [1] Chemistry and Industry (London, United Kingdom), [2] Chemistry and Industry (London, United Kingdom), 1957, p. 72 - 72
[3] , Gmelin Handbook: Fe: Org.Verb.A1, 2.5.7.7, page 161 - 162,
  • 7
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  • [ 68-12-2 ]
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Reference: [1] Journal of Organometallic Chemistry, 1996, vol. 512, # 1-2, p. 219 - 224
  • 8
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  • [ 1293-65-8 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 39, p. 12267 - 12277
[2] Chemical Communications, 2016, vol. 52, # 48, p. 7553 - 7555
[3] Journal of Organometallic Chemistry, 1996, vol. 509, # 2, p. 131 - 134
  • 9
  • [ 79-27-6 ]
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  • [ 1293-65-8 ]
Reference: [1] Dalton Transactions, 2013, vol. 42, # 8, p. 2813 - 2816
[2] Chemistry - A European Journal, 2014, vol. 20, # 51, p. 16899 - 16912
  • 10
  • [ 102-54-5 ]
  • [ 124-73-2 ]
  • [ 1293-65-8 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1261 - 1266
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  • [ 98-88-4 ]
  • [ 12180-80-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 10, p. 1551 - 1557
[2] Journal of Organometallic Chemistry, 2001, vol. 637-639, p. 698 - 709
[3] Thermochimica Acta, 1981, vol. 48, p. 333 - 342
[4] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9563 - 9569
[5] Acta Crystallographica Section C: Crystal Structure Communications, 1997, vol. 53, # 11, p. 1772 - 1775
  • 12
  • [ 102-54-5 ]
  • [ 98-88-4 ]
  • [ 1272-44-2 ]
  • [ 12180-80-2 ]
Reference: [1] Journal of the Chemical Society - Dalton Transactions, 1999, # 1, p. 63 - 66
[2] Journal of the Chemical Society - Dalton Transactions, 1999, # 1, p. 63 - 66
[3] Chemistry - A European Journal, 2012, vol. 18, # 39, p. 12267 - 12277
  • 13
  • [ 102-54-5 ]
  • [ 85-44-9 ]
  • [ 12180-80-2 ]
Reference: [1] , Gmelin Handbook: Fe: Org.Verb.A1, 2.5.7.6.5, page 156 - 161,
[2] Journal of the American Chemical Society, 1952, vol. 74, p. 3458 - 3459
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YieldReaction ConditionsOperation in experiment
80% With aluminum (III) chloride In dichloromethane at 20℃; for 9 h; Reflux 1) Adding anhydrous 0.1-0.18 mol of aluminum trichloride and 30-60 mL of dichloromethane, stir well, then slowly add a mixture of ferrocene 0.03-0.06 mol, dichloromethane 80-100 mL and acetyl chloride 0.1-0.16 mol, and add dropwise. The reaction is first carried out at room temperature for 3-5 h, then refluxed for 3-4 h, the reaction is stopped, and aluminum trichloride is slowly hydrolyzed with 70-100 mL of distilled water to prevent splashing. After the hydrolysis is completed, it is extracted with dichloromethane, and the lower layer product is separated in a separating funnel. The upper aqueous solution is extracted three times with a small amount of CH 2 Cl 2 and combined into the product. Dry over anhydrous MgSO4, filter MgSO4, dry The crude product was recrystallized from water to give a red needle crystal, 1,1'-diacetylferrocene (a) yield: 80percent.
72%
Stage #1: With aluminum (III) chloride In 1,2-dichloro-ethaneCooling with ice
Stage #2: at 40℃; Cooling with ice
To a 250 mL round bottom reaction flask was added 5.36 g of aluminum trichloride and 15 mL of dichloroethane,Under ice-cooling, 2.8 mL (i.e., 38 mmol) of acetyl chloride was added dropwise,Continue to stir until the basic solution of aluminum trichloride.In another 250 mL round bottom reaction flask,3.00 g (i.e., 16 mmol) of ferrocene was added,And completely dissolved with 20 mL of dichloroethane.Ice water cooling,The ferrocene dichloroethane solution was slowly added dropwise to a solution of aluminum trichloride and acetyl chloride using a constant pressure dropping funnel,Continue stirring in the ice bath for 3 hours.After returning to room temperature,The reaction was complete at 40 ° C until the reaction was complete (using thin layer chromatography).The reaction is poured into ice water,Separate the organic phase, followed by water,5percent sodium carbonate solution and water,Dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure,To give a dark brown oil,Recrystallization to obtain orange-red needle-like crystals of 1,1'-diacetyl ferrocene,The yield was 72percent.
68.8%
Stage #1: With aluminum (III) chloride In dichloromethaneCooling with ice
Stage #2: at 10 - 20℃; for 4 h;
In a three-neck flask, add fine aluminum trichloride 8.9738g/67.3mmol and dichloromethane 20ml,A solution of acetyl chloride (6.7 ml/94.2 mmol) in dichloromethane was added with stirring under ice-cooling and stirred until the aluminum trichloride was substantially dissolved. A solution of ferrocene 5g/26.9 mmol in dichloromethane (20 ml) was then added, and the mixture was stirred overnight at 10° C. for 1 h and then stirred at room temperature until evolution of hydrogen chloride (about 3 h). The system was transferred to ice until all ice had melted. The organic phase was separated off with a funnel. The aqueous phase was extracted with chloroform. The organic phases were combined, washed successively with water and saturated sodium bicarbonate solution, and dried over anhydrous sodium sulfate. The solvent was distilled off to give a crude orange-yellow solid diacetylferrocene. The crude product was purified by silica column chromatography with CHCl3/CH3OH=50/1 as eluent in a yield of 68.8percent.
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[2] Patent: CN108530493, 2018, A, . Location in patent: Paragraph 0032; 0038; 0044; 0049
[3] Patent: CN107226829, 2017, A, . Location in patent: Paragraph 0022; 0026; 0030
[4] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9563 - 9569
[5] Patent: CN104292274, 2017, B, . Location in patent: Paragraph 0057
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[13] Russian Journal of Applied Chemistry, 2017, vol. 90, # 12, p. 2016 - 2018[14] Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2018, vol. 90, # 12, p. 2016 - 2018,3
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Reference: [1] Thermochimica Acta, [2] Thermochimica Acta, 1981, vol. 48, p. 333 - 342
[3] Chemistry and Industry (London, United Kingdom), [4] Chemistry and Industry (London, United Kingdom), 1956, p. 1456 - 1456
[5] Journal of the American Chemical Society, [6] Journal of the American Chemical Society, 1958, vol. 80, p. 5443 - 5449
[7] Journal of Organometallic Chemistry, 1970, vol. 21, p. 195 - 201
[8] Chemistry and Industry (London, United Kingdom), [9] Chemistry and Industry (London, United Kingdom), 1956, p. 1456 - 1456
[10] Journal of the American Chemical Society, [11] Journal of the American Chemical Society, 1958, vol. 80, p. 5443 - 5449
[12] Journal of Organometallic Chemistry, 1970, vol. 21, p. 195 - 201
[13] , Gmelin Handbook: Fe: Org.Verb.A1, 2.5.7.6.2, page 144 - 147,
[14] , Gmelin Handbook: Fe: Org.Verb.A1, 2.5.7.6.2, page 144 - 147,
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[3] , Gmelin Handbook: Fe: Org.Verb.A1, 2.5.7.6.5, page 156 - 161,
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[5] Journal of the American Chemical Society, [6] Journal of the American Chemical Society, 1957, vol. 79, p. 3416 - 3420
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Reference: [1] Journal of the Chemical Society - Dalton Transactions, 1999, # 1, p. 63 - 66
[2] Journal of the Chemical Society - Dalton Transactions, 1999, # 1, p. 63 - 66
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  • [ 1273-97-8 ]
Reference: [1] Journal of General Chemistry USSR (English Translation), 1983, vol. 53, p. 2297 - 2301[2] Zhurnal Obshchei Khimii, 1983, vol. 53, p. 2548 - 2552
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[3] Journal of General Chemistry USSR (English Translation), 1982, vol. 52, p. 2108 - 2109[4] Zhurnal Obshchei Khimii, 1982, vol. 52, p. 2369 - 2370
[5] Journal of General Chemistry USSR (English Translation), 1982, vol. 52, p. 2108 - 2109[6] Zhurnal Obshchei Khimii, 1982, vol. 52, p. 2369 - 2370
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