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Inaccessible (Haz class 6.1), International USD 150+
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Chemical Structure| 102-54-5 Chemical Structure| 102-54-5

Structure of Ferrocene
CAS No.: 102-54-5

Chemical Structure| 102-54-5

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Product Details of [ 102-54-5 ]

CAS No. :102-54-5
Formula : Fe(C5H5)2
M.W : 186.03
SMILES Code : [CH]12=[CH]3[CH-]4[CH]5=[CH]1[Fe+2]32546789[CH]%10=[CH]6[CH-]7[CH]8=[CH]%109
MDL No. :MFCD00001427
InChI Key :KTWOOEGAPBSYNW-UHFFFAOYSA-N
Pubchem ID :7611

Safety of [ 102-54-5 ]

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

Computational Chemistry of [ 102-54-5 ] Show Less

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 ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-1.67
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.4
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

3.08
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.98
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.96

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

0.12
Solubility 233.0 mg/ml ; 1.32 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

2.18
Solubility 26700.0 mg/ml ; 152.0 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.24
Solubility 1.02 mg/ml ; 0.00578 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-8.56 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

3.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

3.59

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.

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

[ 102-54-5 ] Synthesis Path-Downstream   1~30

  • 2
  • [ 102-54-5 ]
  • [ 38414-01-6 ]
  • [ 80937-33-3 ]
  • [ 12125-80-3 ]
  • [ 14172-90-8 ]
  • 3
  • [ 102-54-5 ]
  • [ 14172-90-8 ]
  • [ 80937-33-3 ]
  • [ 12125-80-3 ]
  • [ 38414-01-6 ]
  • 4
  • [ 1273-73-0 ]
  • [ 102-54-5 ]
References: [1]Doklady Akademii nauk SSSR,1964,vol. 154/159,p. 1213 - 1216.
    Doklady Akademii Nauk SSSR,1964,vol. 159,p. 591 - 594.
[2]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 808 - 812.
[3]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 808 - 812.
[4]Doklady Akademii nauk SSSR,1964,vol. 154/159,p. 30 - 32.
    Doklady Akademii Nauk SSSR,1964,vol. 154,p. 158 - 159.
[5]Nippon Kagaku Zasshi,.
    Nippon Kagaku Zasshi,1970,vol. 91,p. A 33 - A 33.
[6]Journal of Organic Chemistry,1961,vol. 26,p. 1034 - 1037.
[7]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 2.1.3, page 24 - 28.
[8]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 2.1.3, page 24 - 28.
[9]Doklady Akademii nauk SSSR,1964,vol. 154/159,p. 30 - 32.
    Doklady Akademii Nauk SSSR,1964,vol. 154,p. 158 - 159.
[10]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 597 - 603.
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 667 - 674.
[11]Journal of Organic Chemistry,1961,vol. 26,p. 1802 - 1805.
[12]Bulletin of the Chemical Society of Japan,1969,vol. 42,p. 1976 - 1981.
[13]Bulletin of the Chemical Society of Japan,1969,vol. 42,p. 1976 - 1981.
[14]Doklady Akademii nauk SSSR,1965,vol. 160/165,p. 1121 - 1123.
    Doklady Akademii Nauk SSSR,1965,vol. 165,p. 575 - 577.
[15]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 5.1.2.1.5, page 372 - 380.
[16]Doklady Akademii nauk SSSR,1964,vol. 154/159,p. 765 - 768.
    Doklady Akademii Nauk SSSR,1964,vol. 157,p. 922 - 925.
  • 5
  • [ 29786-93-4 ]
  • [ 1273-73-0 ]
  • [ 15599-91-4 ]
  • [ 102-54-5 ]
  • N3P3F5(η-C5H4)Fe(η-C5H5) [ No CAS ]
  • [ 84462-68-0 ]
  • 6
  • [ 29786-93-4 ]
  • [ 1273-73-0 ]
  • [ 14700-00-6 ]
  • [ 102-54-5 ]
  • N4P4F7(η-C5H4)Fe(η-C5H5) [ No CAS ]
  • [ 89179-01-1 ]
  • 7
  • [ 126-33-0 ]
  • [ 102-54-5 ]
  • 1-cyanoferrocene [ No CAS ]
  • 9
  • [ 1273-73-0 ]
  • C5H5FeC5H4NHC6H5 [ No CAS ]
  • [ 102-54-5 ]
  • ((C5H5)Fe(C5H4))2N(C6H5) [ No CAS ]
  • 10
  • [ 1273-73-0 ]
  • [ 102-54-5 ]
  • methoxyferrocene [ No CAS ]
  • 11
  • [ 1273-73-0 ]
  • [ 4388-22-1 ]
  • [ 102-54-5 ]
  • diferrocenyl sulfide [ No CAS ]
  • 12
  • [ 1293-65-8 ]
  • 1-ethyl-1'-bromoferrocene [ No CAS ]
  • [ 102-54-5 ]
  • 1-ethylferrocene [ No CAS ]
  • 1',1'''-diethylbiferrocene [ No CAS ]
  • [ 211239-38-2 ]
  • 13
  • [ 102-54-5 ]
  • [ 6287-82-7 ]
  • [ 7646-85-7 ]
  • [ 926885-52-1 ]
  • 14
  • [ 102-54-5 ]
  • [ 6287-82-7 ]
  • [ 7646-85-7 ]
  • [ 887343-60-4 ]
  • 15
  • [ 102-54-5 ]
  • [ 191980-54-8 ]
  • [ 936484-37-6 ]
  • 16
  • [ 102-54-5 ]
  • [ 18995-35-2 ]
  • [ 143-66-8 ]
  • (η6-4-chlorophenyl-tert-butyl ether)(η5-cyclopentadienyl)iron(II) tetraphenylborate [ No CAS ]
  • 17
  • [ 102-54-5 ]
  • [ 23351-91-9 ]
  • [ 1075734-59-6 ]
  • 19
  • [ 1293-65-8 ]
  • [ 7732-18-5 ]
  • [ 102-54-5 ]
  • [ 1273-73-0 ]
  • 20
  • [ 79-27-6 ]
  • [ 1293-65-8 ]
  • [ 102-54-5 ]
  • [ 238413-86-0 ]
  • 24
  • [ 102-54-5 ]
  • [ 72040-64-3 ]
  • 6-biotinamidohexanoylferrocene [ No CAS ]
  • 25
  • [ 102-54-5 ]
  • [ 89889-51-0 ]
  • 6-(6-biotinamidohexanamido)hexanoylferrocene [ No CAS ]
  • 26
  • [ 102-54-5 ]
  • [ 124-73-2 ]
  • [ 1293-65-8 ]
  • 27
  • [ 102-54-5 ]
  • [ 174508-31-7 ]
  • 2,5-Diferrocenyl-3,4-ethylenedioxythiophene [ No CAS ]
  • 28
  • [ 1532-71-4 ]
  • [ 102-54-5 ]
  • [ 879559-36-1 ]
  • 29
  • [ 102-54-5 ]
  • [ 171243-30-4 ]
  • 3-fluoro-5-(trifluoromethyl)benzoyl ferrocene [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With aluminum (III) chloride; In dichloromethane; at 20℃; for 2.83333h;Cooling; General procedure: A thoroughly dried two-necked round bottom flask was equipped with a mechanical stirrer. The system was maintained under pressure via dry nitrogen. The flask was charged with fer- rocene, fluorine/tri-fluoromethyl benzoyl chloride in 1:1 equiva- lent ratio and 11 ml of dichloride methane. The resulting mixture was stirred and the flask was immersed in an ice bath. When the solution has been thoroughly cooled, anhydrous AlCl 3 was added slowly for a period of about 20 min. A deep blue color indicates that the reaction has occurred and after its formation, stirring is continued for another 30 min with ice cooling. This is continued further for another 2 h at room temperature to ensure comple- tion of reaction. The reaction mixture was cooled again in ice, fol- lowed by continuous addition of 20 ml of water. The resulting two- phase mixture was stirred vigorously for 30 min. After transfer- ring the mixture to a separatory funnel, the layers are separated and the aqueous layer is extracted with two 20 ml portions of dichloromethane. The combined DCM solution was washed with 20 ml water, twice with 10 ml portions of 10% aq. NaOH and dried over anhydrous Na 2 SO 4 . The resulting solution was evapo- rated to dryness at reduced pressure, yielding the final product. The amount/volume of starting materials taken and the amount of the final synthesized compounds obtained is given in Table S1. The yields and obtained melting points (from DSC) are as follows: : 76%; 105 0 C; : 84%; 110 0 C; : 84%; 100 0 C; : 73%; 100 0 C; : 65%; 145 0 C ; : 70%; 65 0 C;
  • 30
  • [ 60-35-5 ]
  • [ 1273-73-0 ]
  • [ 102-54-5 ]
  • 1-(acetylamino)ferrocene [ No CAS ]
 

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