Name: 1271-86-9|(Dimethylaminomethyl)ferrocene|98%
Brand: Ambeed
SKU: A371697
Price: 7.0 USD
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1
[ 102-54-5 ]
[ 51-80-9 ]
[ 1271-86-9 ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 3065 - 3072
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 2.5.7.10, page 166 - 167
[3]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 2.5.7.10, page 166 - 167
[4]Organic Syntheses,1960,vol. 40,p. 31 - 33
[5]Journal of Organic Chemistry,1957,vol. 22,p. 355 - 358
[6]Journal of Organic Chemistry,1964,vol. 29,p. 2028 - 2030
[7]Tetrahedron,1973,vol. 29,p. 1575 - 1584
[8]Tetrahedron,1973,vol. 29,p. 1575 - 1584
[9]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 942 - 949
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 1036 - 1045
[10]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 942 - 949
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 1036 - 1045
[11]Dissertation abstracts, Diss. Purdue Univ. 1963,1964,vol. 24,p. 2687
[12]Angewandte Chemie - International Edition,2015,vol. 54,p. 1494 - 1498
    Angew. Chem.,
[13]Patent: DE2543999,1977,A1
    C.A.,1977,vol. 87,p. 67314

2
[ 29786-93-4 ]
[ 1271-86-9 ]
[α-(N,N-dimethylaminomethyl)ferrocenyl]lithium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane;Inert atmosphere; Schlenk technique;	From rac-2-lithio<strong>[1271-86-9](dimethylaminomethyl)ferrocene</strong> (prepared from <strong>[1271-86-9]N,N-dimethylaminomethylferrocene</strong> (0.97g, 4.0mmol) and n-BuLi (2.75mL, 1.60M in hexanes, 4.40mmol) in Et2O (25mL) at room temperature for 16h) [39] and iododicarbonyl(pentamethylcyclopentadienyl)iron (1.20g, 3.20mmol) in Et2O (10mL), 0.67g (43%) of orange needles were obtained.

Reference： [1]Journal of Organometallic Chemistry,1973,vol. 51,p. 1
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 2.5.7.14, page 172 - 173
[3]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.3.2.3, page 45 - 48
[4]Organometallics,2000,vol. 19,p. 1013 - 1022
[5]Inorganic Chemistry Communications,2004,vol. 7,p. 1049 - 1052
[6]Journal of Organometallic Chemistry,2013,vol. 741-742,p. 47 - 58

3
[ 1271-86-9 ]
(η-C5H5)Fe(η-C5H4CH2NMe2)(1+) [ No CAS ]

Reference： [1]Analytical Chemistry,1970,vol. 42,p. 535 - 536
[2]Journal of Organometallic Chemistry,
    Journal of Organometallic Chemistry,1970,vol. 25,p. C 74 - C 76
[3]Zhurnal Analiticheskoi Khimii,1974,vol. 29,p. 1298 - 1301
    Zhurnal Analiticheskoi Khimii,1974,vol. 29,p. 1497 - 1502
[4]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.3.2.3, page 45 - 48
[5]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.3.2.3, page 45 - 48
[6]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.3.2.3, page 45 - 48
[7]Doklady Akademii nauk SSSR,1962,vol. 142/147,p. 346 - 349
    Doklady Akademii Nauk SSSR,1962,vol. 143,p. 1351 - 1354

4
[ 1271-86-9 ]
methyl ferrocene [ No CAS ]

Reference： [1]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.1.4.1, page 253 - 255
[2]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1967,p. 159 - 162
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1967,p. 171 - 175
[3]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1967,p. 159 - 162
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1967,p. 171 - 175
[4]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.1.1, page 245 - 248
[5]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.3.2.3, page 45 - 48

5
[ 1271-86-9 ]
FeC₁₀H₉CH₂NO(CH₃)2 [ No CAS ]

Reference： [1]Zhurnal Obshchei Khimii,1978,vol. 48,p. 1311
Zhurnal Obshchei Khimii,1978,vol. 48,p. 1427
[2]Zhurnal Obshchei Khimii,1978,vol. 48,p. 1311
Zhurnal Obshchei Khimii,1978,vol. 48,p. 1427

6
[ 1271-86-9 ]
[ 882-33-7 ]
1-{(dimethylamino)methyl}-2-(phenylthio)ferrocene [ No CAS ]

Reference： [1]Organometallics,1988,vol. 7,p. 1297 - 1302
[2]Organometallics,1986,vol. 5,p. 482 - 490
[3]Research on Chemical Intermediates,2017,vol. 43,p. 5293 - 5303

7
[ 1271-86-9 ]
[ 143-15-7 ]
n-dodecyldimethylferrocenylmethylammonium bromide [ No CAS ]

Reference： [1]Journal of Physical Chemistry,1995,vol. 99,p. 6986 - 6993
[2]Journal of applied chemistry of the USSR,1988,vol. 61,p. 300 - 303
Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1988,vol. 61,p. 336 - 340
[3]ChemMedChem,2021,vol. 16,p. 467 - 471
[4]Journal of the American Chemical Society,1985,vol. 107,p. 6865 - 6868

8
[ 1271-86-9 ]
[ 110-06-5 ]
1-{(dimethylamino)methyl}-2-(tert-butylthio)ferrocene [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 11992 - 12004
[2]Organometallics,1988,vol. 7,p. 1297 - 1302
[3]Patent: WO2013/190328,2013,A1 .Location in patent: Page/Page column 37

9
N,N,N-(ferrocenylmethyl)trimethylammonium iodide [ No CAS ]
methyl ferrocene [ No CAS ]
[ 1271-86-9 ]

Reference： [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 950 - 953
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 1045 - 1049
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.4.3, page 80 - 89
[3]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.1.4.1, page 253 - 255
[4]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 950 - 953
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 1045 - 1049
[5]Journal of Organometallic Chemistry,1974,vol. 72,p. 227 - 237
[6]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 5.1.1.1.1, page 245 - 248
[7]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.4.3, page 80 - 89

10
[ 12093-10-6 ]
[ 124-40-3 ]
[ 1271-86-9 ]

Reference： [1]Chemistry - A European Journal,2022,vol. 28
[2]Journal of the American Chemical Society,1957,vol. 79,p. 3416 - 3420

11
[ 1271-86-9 ]
[ 74-88-4 ]
N,N,N-(ferrocenylmethyl)trimethylammonium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In acetone; at 20℃; for 2h;Inert atmosphere;	The synthesis method is: completely dissolve 2.430 g (10 mmol) of dimethylaminomethylferrocene in 10 mL of acetone.In a 250 mL round-bottomed flask, 1.970 g (14 mmol) of iodomethane was added dropwise, and a yellow precipitate formed immediately. Pass N2, stir the reaction for 2 hours at room temperature, suction filter, filter cake was washed with diethyl ether 2 or 3 times, and placed in a vacuum. Drying in a dry box at 45[deg.] C. for 48 hours gave compound B in a yield of 85%.
	In acetone; at 20℃; for 8h;	The formula of the ferrocenyl methyl quaternary ammonium salt in this example is as follows: It was synthesized according to the literature method by a specific synthesis method: 2.383g (9.8mmol) of dimethylamine methyl ferrocene was completely dissolved in 50mL round bottom flask containing 10mL of acetone, and then 1.94g (1.2mmol) Methyl iodide, immediately generated yellow precipitate, the reaction was stirred at room temperature for 8 hours, suction filtration, the filter cake washed with ether 2 to 3 times, placed in a vacuum oven at 50 for 24 hours to obtain a quaternary ferrocenyl methyl ammonium salt.

Reference： [1]Chemistry - A European Journal,2021,vol. 27,p. 15501 - 15507
[2]Journal of Coordination Chemistry,2018,vol. 71,p. 2584 - 2603
[3]Journal of Organometallic Chemistry,1999,vol. 589,p. 59 - 65
[4]New Journal of Chemistry,2011,vol. 35,p. 893 - 901
[5]Inorganic Chemistry,2018,vol. 57,p. 15247 - 15261
[6]Journal of the Electrochemical Society,2014,vol. 161,p. H161-H165
[7]Patent: CN106336436,2017,A .Location in patent: Paragraph 0103; 0104; 0105
[8]Journal of Organometallic Chemistry,1995,vol. 489,p. C87 - C89
[9]Electrochimica Acta,1997,vol. 42,p. 1325 - 1335
[10]Angewandte Chemie - International Edition,2015,vol. 54,p. 1494 - 1498
Angew. Chem.,
[11]Patent: CN104876975,2017,B .Location in patent: Paragraph 0038; 0039; 0040

12
[ 74-96-4 ]
[ 1271-86-9 ]
(ferrocenylmethyl)ethyldimethylammonium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; at 20℃; for 24h;Schlenk technique; Inert atmosphere;	In a 250 mL N2 purged Schlenk flask, <strong>[1271-86-9](ferrocenylmethyl)dimethylamine</strong> (10 g, 41.13 mmol) was combined with bromoethane (4.48 g, 41.13 mmol) in 25 mL CH3CN, and stirred at 25 C. for 24 h. The resulting orange precipitate was filtered and washed with 2*25 mL diethyl ether and dried under vacuum. The orange powder [FcNEt]Br product was stored in a dry desiccator. 1H NMR (D2O, 25 C., 500 MHz): δ (ppm), 1.24 (triplet 3H), 2.78 (singlet 6H), 3.15 (quartet 2H), 4.21 (singlet 5H), 4.29 (singlet 2H), 4.36 (singlet 2H), 4.43 (singlet 2H) (See ). Elemental Analysis for C15H22BrFeN, Calculated: C, 51.17, H, 6.30, N, 3.98. Found: C, 50.97, H, 6.17, N, 4.16.

Reference： [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1961,p. 1850 - 1852
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1961,p. 1982 - 1985
[2]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1961,p. 1850 - 1852
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1961,p. 1982 - 1985
[3]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1961,p. 1850 - 1852
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1961,p. 1982 - 1985
[4]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1961,p. 1850 - 1852
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1961,p. 1982 - 1985
[5]Patent: US3322804,1967,A
    C.A.,1967,vol. 67,p. 64547
[6]Patent: US3322804,1967,A
    C.A.,1967,vol. 67,p. 64547
[7]Patent: US3322804,1967,A
    C.A.,1967,vol. 67,p. 64547
[8]Patent: US3322804,1967,A
    C.A.,1967,vol. 67,p. 64547
[9]Patent: US2018/72669,2018,A1 .Location in patent: Paragraph 0256; 0263
[10]Chemical Communications,2019,vol. 55,p. 14127 - 14130

13
[ 1271-86-9 ]
[ 624-92-0 ]
1-[(dimethylamino)methy1]-2-(methylthio)ferrocene [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 11992 - 12004
[2]Organometallics,1986,vol. 5,p. 482 - 490

14
[ 1271-86-9 ]
[ 88-89-1 ]
ferrocenylmethyldimethylammonium picrate [ No CAS ]

Reference： [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2016,vol. 642,p. 1095 - 1103
[2]Bulletin de la Societe Chimique de France,
Bulletin de la Societe Chimique de France,1969,p. 2158 - 2164
[3]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.3.2.4, page 48 - 52

15
[ 1271-86-9 ]
(ferrocenylmethyl)-n-butyldimethyl-ammonium iodide [ No CAS ]

Reference： [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 942 - 949
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 1036 - 1045
[2]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 942 - 949
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 1036 - 1045
[3]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 942 - 949
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 1036 - 1045
[4]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 942 - 949
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1963,p. 1036 - 1045

16
[ 1120-71-4 ]
[ 1271-86-9 ]
dimethyl-3-sulfopropyl(ferrocenylmethyl)ammonium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In ethyl acetate; for 19h;	25.00 g (102.8 mmol) of (dimethylamino)methylferrocene and 13.82 g (113.1 mmol) of 1,3-propanesultone were stirred together in .-500 mE of ethyl acetate. After 19 hours, the reaction mixture was filtered, and the collected solid was rinsed with ethyl acetate, acetone, then MTBE. Prolonged drying in vacuo at 50 C. gave the pure product. Yield: 37.55 g (100.0%) of an orange-yellow powder.1H NMR (500 MHz, DMSO-d5) ö 4.51 (m, 2H),4.37 (m, 4H), 4.23 (s, 5H), 3.25 (m, 2H), 2.82 (s, 6H), 2.43 (t, 2H), 2.02 (m, 2H).

Reference： [1]Patent: US2020/373599,2020,A1 .Location in patent: Paragraph 0082
[2]Journal of general chemistry of the USSR,1991,vol. 61,p. 1068 - 1071
J.Gen.Chem.USSR (Engl.Transl.),1991,vol. 61,p. 1174 - 1178

17
trans-dichloroplatinum(II)(DMSO){{(N,N-dimethylamino)methyl}ferrocene} [ No CAS ]
[ 14056-88-3 ]
[ 1271-86-9 ]

Reference： [1]Organometallics,1994,vol. 13,p. 500 - 510

18
[ 1271-86-9 ]
[ 4253-89-8 ]
[ 100113-90-4 ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 11992 - 12004
[2]Organometallics,1986,vol. 5,p. 482 - 490

19
[ 1271-86-9 ]
[ 420-37-1 ]
(ferrocenylmethylene)trimethylammonium tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.8%	In dichloromethane; at 20℃; for 2h;	0.4863 g (2.00 mmol) of (dimethylamino)methylferrocene was dissolved in 10 mE of anhydrous CH2C12. 0.2958 g (2.00 mmol) of trimethyloxonium tetrafluoroborate was added as a solid and the reaction stirred at room temperature for 2 hours. Thereafter, the reaction mixture was diluted with .50 mE of methyl tert-butyl ether (MTBE) and allowed to stand for 15 minutes. The precipitate was filtered off, rinsed with MTBE, then hexane, then dried in vacuo. Yield: 0.5710 g (82.8%) of an orange-yellow powder.

Reference： [1]Patent: US2020/373599,2020,A1 .Location in patent: Paragraph 0081
[2]Inorganic Chemistry,1994,vol. 33,p. 4098 - 4104

20
[ 1271-86-9 ]
[ 33513-42-7 ]
[ 162762-18-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With n-butyllithium; In diethyl ether; at 20℃; for 0.00583333h;Schlenk technique;	Example 2: Synthesis of N-(2-hydroxymethyl)ferrocenyl)-4-((trifluoromethyl)thio)benzamide (compound 3) The proposed synthetic pathway is depicted in Scheme 5. 30 Scheme 5: (a) -BuLi, DMF, Et20, 0.35 min, r.t., 98%; (b) acetic anhydride, reflux, 2 h, 74%; (c) NaOH, hydroxylamine chlorhydrate, EtOH, reflux, 3 h, 78%; (d) LiAIH4, THF, overnight, r.t., 51 %; (e) NEt3, 4-(trifluoromethylthio)benzoyl chloride, THF, overnight, r.t., 40%, (f) NaH, 3-fluoro-4-(trifluoromethyl)benzonitrile, THF, overnight, 0C→r.t, 79%. Compound 8 is producible with the same reaction. The compounds 6 and 8 can be separate by column chromatography.2-(<strong>[1271-86-9]N,N-dimethylaminomethylferrocene</strong>)carboxaldehyde (27) 2-(/V,/V-dimethylaminomethylferrocene)carboxaldehyde (27) was prepared following the procedure reported by Picart-Goethgheluck et al (Picart-Goetgheluck, S.; Delacroix, O.; Maciejewski, L; Brocard, J. Synthesis 2000, 2000, 1421 ).The spectroscopic data matched those reported by Picart-Goethgheluck et al.
72%		(Diaminomethyl)methylferrocene (lg, 5mmol) was dissolved in Et20, n - butyl lithium (2.51mL, 6.25mmol) was added slowly and the reaction mixture was stirred at room temperature for 16hrs.After 16 hrs, the reaction mixture was quenched with DMF (0.4mL, 6.25mmol) and stirred again at room temperature for 4hrs. Water (15mL) was then added to the reaction. The organic phase was then extracted with ether (2x25mL). The combined organic phases were dried with magnesium sulphate, filtered and the solvent was removed under vacuum to afford the product in an 72% yield (dark red/brown oil). 1H NMR (300MHz, CDC13) δ 9.81 (1H, s, CHO), 4.21 (2H, s, Cp), 4.14 (5H, s, Cp), 3.64 (2H, s, CH2), 2.08 (6H, s, NMe2) 13C NMR (75.5 Hz, CDC13) δ 193.2, 86.7, 83.4, 77.8, 77.5, 77.0, 76.62, 75.8, 71.8, 70.3, 70.2, 70.0, 68.4, 68.0, 59.2, 56.6, 44.8, 44.7. HRMS (ESI) calculated for CMHjgNjOjFe. m/z 272.0737 found 272.0731Ref: Biot, C, Glorian, G., Maciejewski, L. A., Brocard, J. S., Domarle, O., Blampain, G., Millet, P., Georges, A. J., Abessolo, H., Dive, D., Lebibi, J. J. Med. Chem. 1997, 40, 3715- 3718.(b) Synthesis of Label B
60%		Under a nitrogen atmosphere, 5.00 g (20.6 mmol) of N, N-dimethylaminomethylferrocene was dissolved in dehydrated diethyl ether (100 ml). 19 ml (30.9 mmol) of t-butyllithium (1.63 M, pentane solution) was added dropwise at room temperature and the mixture was stirred for 15 minutes. Next, 2.26 g (30.9 mmol) of dehydrated DMF was added dropwise and the mixture was further stirred for 15 minutes. Water was added to the reaction solution, and the aqueous phase and the organic phase were separated. The obtained organic phase was washed successively with water and saturated brine. The organic phase after washing was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 3.34 g (12.3 mmol, yield 60%) of compound (IIIb).

		1. Preparation of the compounds of formula (III)Preparation of 1 -[(dimethylamino)methyl]-2-formyl-ferrocene.Charge an inertized reactor with 39.6 g of 1-[(dimethylamino)methyl]-ferrocene and 360 ml of MTBE. Distil about 160 ml of MTBE (4V) at atmospheric pressure. Cool the solution to -10C and slowly add 98.2 ml of a solution of t-BuLi in heptane (titer 16%). Stir the reaction mixture at -10C for 2 hours and then at 0C, slowly add 25.2 ml of DMF. Continue stirring the reaction mixture at 20C for 2 hours then at 5C, slowly add 135 ml of 1 .5N aqueous HCI. Continue stirring the reaction mixture at 5C for 30 min, then at 20C for 30 min. Leave the reaction mixture to settle and withdraw the aqueous phase then the MTBE phase. Counter-extract the aqueous phase with 125 ml of MTBE. Filter the combined MTBE phases on activated charcoal then concentrate to 120 ml under vacuum. Add 80 ml of isopropanol then distil 420 ml of solvent to constant volume, under vacuum, by regular addition of isopropanol. At the end of distillation, dilute the reaction mixture to 280 ml with isopropanol. 39.9 g of the expected compound is obtained in solution in isopropanol.
39.9 g		1. Preparation of the Compounds of Formula (III) Preparation of 1-[(dimethylamino)methyl]-2-formyl-ferrocene. Charge an inertized reactor with 39.6 g of 1-[(dimethylamino)methyl]-ferrocene and 360 ml of MTBE. Distill about 160 ml of MTBE (4V) at atmospheric pressure. Cool the solution to -10 C. and slowly add 98.2 ml of a solution of t-BuLi in heptane (titer 16%). Stir the reaction mixture at -10 C. for 2 hours and then at 0 C., slowly add 25.2 ml of DMF. Continue stirring the reaction mixture at 20 C. for 2 hours then at 5 C., slowly add 135 ml of 1.5N aqueous HCl. Continue stirring the reaction mixture at 5 C. for 30 min, then at 20 C. for 30 min. Leave the reaction mixture to settle and withdraw the aqueous phase then the MTBE phase. Counter-extract the aqueous phase with 125 ml of MTBE. Filter the combined MTBE phases on activated charcoal then concentrate to 120 ml under vacuum. Add 80 ml of isopropanol then distill 420 ml of solvent to constant volume, under vacuum, by regular addition of isopropanol. At the end of distillation, dilute the reaction mixture to 280 ml with isopropanol. 39.9 g of the expected compound is obtained in solution in isopropanol.

Reference： [1]ChemMedChem,2015,vol. 10,p. 2099 - 2110
[2]Patent: WO2015/44397,2015,A1 .Location in patent: Page/Page column 81; 88
[3]Organometallics,2016,vol. 35,p. 3369 - 3377
[4]Angewandte Chemie - International Edition,2018,vol. 57,p. 5544 - 5547
Angew. Chem.,2018,vol. 130,p. 5643 - 5646,4
[5]Patent: WO2012/85591,2012,A1 .Location in patent: Page/Page column 24-25
[6]Patent: JP2018/203652,2018,A .Location in patent: Paragraph 0059; 0060; 0061
[7]Journal of the Chemical Society, Dalton Transactions,2002,p. 4426 - 4433
[8]Patent: WO2011/154923,2011,A1 .Location in patent: Page/Page column 11
[9]Patent: US2013/96306,2013,A1 .Location in patent: Paragraph 0095
[10]Journal of Organometallic Chemistry,2015,vol. 788,p. 1 - 8

21
[ 1271-86-9 ]
[ 112-72-1 ]
[ 178943-51-6 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 6707 - 6715

22
[ 1271-86-9 ]
[ 629-41-4 ]
[ 178943-60-7 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 6707 - 6715

23
[ 1271-86-9 ]
[ 5675-51-4 ]
[ 178943-56-1 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 6707 - 6715

24
[ 1271-86-9 ]
[ 36653-82-4 ]
[ 178943-52-7 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 6707 - 6715

25
[ 112-92-5 ]
[ 1271-86-9 ]
[ 178943-53-8 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 6707 - 6715

26
[ 50-00-0 ]
[ 1271-86-9 ]
[ 157811-78-4 ]

Yield	Reaction Conditions	Operation in experiment
		Part (I)Preparation of l-hydroxymethyl-2-dimethylaminomethyl ferrocene <n="95"/>n-Butyl lithium (Aldrich, 1.6 molar in diethyl ether, 5.14 ml, 8.24 mmol) is added to a solution of 1-dimethylaminomethyl ferrocene (Aldrich, 1. Og, 4.12mmol) in diethyl ether (2OmL) under argon. The reaction is stirred for 3 hours and developes a reddish colour. The solution is then cooled in a dry ice/acetone bath, calcined para-formaldehyde (0.247g, 2 times excess) added and the resultant mixture stirred overnight at room temperature. The reaction is then quenched with water, extracted with diethyl ether, dried over MgSO4, and filtered over celite. The solvent is removed in vacuo to yield crude title compound. The crude product is applied to a neutral alumina column, which is eluted with petrol/diethyl ether (9:1 ratio) to remove the starting material, 1-dimethylaminomethyl ferrocene. The column is then eluted with substantially pure ethyl acetate to elute the title compound. The ethyl acetate is removed in vacuo, to yield the title compound as an orange oil/crystalline mass.1H NMR (250 MHz; CDCl3) 52.131 (s, 6 H), δ2.735 (d, 1 H, 12.512 Hz), δ3.853 (d, 1 H, 12.512 Hz), δ3.984 (dd, 1 H, 2.156 Hz), 54.035 (s, 5 H), 54.060 (dd, 1 H, 2.136 Hz) 54.071 (d, 1 H, 12.207 Hz), 54.154 (m, 1 H), 54.73 (d, 1 H, 12.207 Hz).13C NMR (61 MHz; CDCl3) 57.688, 584.519, 570.615, 568.871, 568.447, 565.369, 560.077, 558.318, 544.414COSY 2D 1H NMRPartly obscured doublet at 4.071ppm and its coupling to the doublet at 4.73 ppm confirmed. Infrared spectra (CHCl3) (c.a. 0.06g / 0.8mL)2953.8 cm"1 , 2860.6 cm"1, 2826.0 cm"1, 2783.4 cm"1, 1104.9 cm"1
		n-Butyl lithium (Aldrich, 1.6 molar in 31 diethyl ether, 5.14 ml, 8.24 mmol) is added to a solution of 93 1-dimethylaminomethyl ferrocene (Aldrich, 1.0 g, 4.12 mmol) in diethyl ether (20 mL) under argon. The reaction is stirred for 3 hours and develops a reddish colour. The solution is then cooled in a dry ice/acetone bath, calcined 94 para-formaldehyde (0.247 g, 2 times excess) added and the resultant mixture stirred overnight at room temperature. (0524) The reaction is then quenched with water, extracted with diethyl ether, dried over MgSO4, and filtered over celite. The solvent is removed in vacuo to yield crude title compound. The crude product is applied to a neutral alumina column, which is eluted with petrol/diethyl ether (9:1 ratio) to remove the starting material, 1-dimethylaminomethyl ferrocene. The column is then eluted with substantially pure ethyl acetate to elute the title compound. The ethyl acetate is removed in vacuo, to yield the 95 title compound as an orange oil/crystalline mass. (0525) 1H NMR (250 MHz; CDCl3) δ2.131 (s, 6H), δ2.735 (d, 1H, 12.512 Hz), δ3.853 (d, 1H, 12.512 Hz), δ3.984 (dd, 1H, 2.156 Hz), δ4.035 (s, 5H), δ4.060 (dd, 1H, 2.136 Hz) δ4.071 (d, 1H, 12.207 Hz), δ4.154 (m, 1H), δ4.73 (d, 1H, 12.207 Hz). (0526) 13C NMR (61 MHz; CDCl3) δ7.688, δ84.519, δ70.615, δ68.871, δ68.447, δ865.369, δ60.077, δ58.318, δ44.414 (0527) COSY 2D 1H NMR (0528) Partly obscured doublet at 4.071 ppm and its coupling to the doublet at 4.73 ppm confirmed. (0529) Infrared spectra (CHCl3) (c.a. 0.06 g/0.8 mL) (0530) 2953.8 cm-1, 2860.6 cm-1, 2826.0 cm-1, 2783.4 cm-1, 1104.9 cm-1

Reference： [1]Inorganic Chemistry Communications,2004,vol. 7,p. 923 - 928
[2]Patent: WO2008/65448,2008,A1 .Location in patent: Page/Page column 93-94
[3]Patent: US9802185,2017,B2 .Location in patent: Page/Page column 46

27
[ 16853-85-3 ]
[ 1271-86-9 ]
[ 814-49-3 ]
[ 858126-71-3 ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 2965 - 2969

28
[ 75-77-4 ]
[ 1271-86-9 ]
[ 198766-23-3 ]

Yield	Reaction Conditions	Operation in experiment
84%		Part (I) Preparation of l-dimethylaminomethyl-2, 1' -bis-trimethylsilyl ferroceneTo dimethylaminomethylferrocene (3Og, 123.39mmol) (Aldrich) in dry diethyl ether (200ml) was added n-butyllithium (123.39ml, 308.48mmol, 2.5eq) and TMEDA (20.48ml, 135.73mmol, l.leq) and the reaction was stirred under N2 for 12 hours at room temperature. The solution was then cooled to -780C (dry ice/acetone bath) and quenched with chlorotrimethylsilane (34.45ml, 271.46mmol, 2.2eq) . The solution was then allowed to warm up to room temperature and further stirred for twelve hours resulting in an orange solution.The reaction was then quenched with water, and stirred for a further fifteen minutes. The ethereal layer, containing product <n="88"/>was separated and the aqueous layer was further extracted several times with diethyl ether. The combined ether fractions were dried over magnesium sulphate and filtered through celite. The ether solvent was removed by rotary evaporator (resulting in red oil) . The product was purified by column chromatography (large scale column) . Small amounts of starting material were removed with petrol (5% triethylamine) and the product was then obtained with 1:1 petrol/Et2θ (5% triethylamine) . The resulting red oil was finally dried under vacuum: (4Og, 84% yield)

Reference： [1]Patent: WO2008/65448,2008,A1 .Location in patent: Page/Page column 86-87

29
[ 1271-86-9 ]
[ 33797-51-2 ]
[ 32717-10-5 ]

Yield	Reaction Conditions	Operation in experiment
52%		Preparation of 1 , 2-bis- (dimethylaminomethyl) ferrocenen-Butyllithium (Aldrich, 2.5 molar in hexane, 24 ml, 54 mmol) is added to a solution of (dimethylaminomethyl ) ferrocene (Aldrich, 13.13 g, 10.69 ml, 48.97 mmol) in diethyl ether (80 ml) under nitrogen at a temperature of 25C and the reaction mixture stirred for 4 hours. The resulting red solution is then cooled to approximately -700C in a dry ice/acetone bath and Eschenmosers salt (ICH2NMe2) (Aldrich, 10 g, 54 mmol) is added. The reaction is allowed to warm to room temperature and stirred overnight .The resultant solution is quenched with excess aqueous sodium hydroxide and the resulting product extracted with diethyl ether (3 x 80 ml) dried over anhydrous magnesium sulfate, filtered over celite, and volatiles removed in vacuo to yield the crude title compound as a light orange crystalline solid. The crude product is recrystallised from light petrol with cooling to -17C and the recrystallised product washed with cold petrol to yield the title compound as a light orange solid (13.2 g, 74%). The compound can be further purified by sublimation to give 8.5 g (52%) of the Part (I) title compound (mpt 74C) .1H NMR(250 MHz; CDCl3 ) : 54.23 (brd, 2H) ; 4.11-4.10 (t, IH) ; 4.04(s, 5H) ; 3.43, 3.38, 3.23, 3.18 (AB quartet, 2H) ; 2.22(s, 6H) . <n="94"/>13C NMR (63 MHz; CDCl3 ): 583.81 ; 70.40; 69.25; 66.84; 57.35; 45.23.Elemental analysis: Found: C 63.7%; H 8.9%; N 9.5% Calculated: C 64.0%; H 8.1%; N 9.4%
52%		n-Butyllithium (Aldrich, 2.5 molar in 82 hexane, 24 ml, 54 mmol) is added to a solution of 83 <strong>[1271-86-9](dimethylaminomethyl)ferrocene</strong> (Aldrich, 13.13 g, 10.69 ml, 48.97 mmol) in 31 diethyl ether (80 ml) under nitrogen at a temperature of 25 C. and the reaction mixture stirred for 4 hours. The resulting red solution is then cooled to approximately -70 C. in a dry ice/acetone bath and Eschenmosers salt (ICH2NMe2) (Aldrich, 10 g, 54 mmol) is added. The reaction is allowed to warm to room temperature and stirred overnight. (0510) The resultant solution is quenched with excess aqueous sodium hydroxide and the resulting product extracted with diethyl ether (3×80 ml) dried over anhydrous magnesium sulfate, filtered over celite, and volatiles removed in vacuo to yield the crude title compound as a light orange crystalline solid. The crude product is recrystallised from light petrol with cooling to -17 C. and the recrystallised product washed with cold petrol to yield the 84 title compound as a light orange solid (13.2 g, 74%). The compound can be further purified by sublimation to give 8.5 g (52%) of the title compound (mpt 74 C.). (0511) 1H NMR (250 MHz; CDCl3): δ4.23 (brd, 2H); 4.11-4.10 (t, 1H); 4.04 (s, 5H); 3.43, 3.38, 3.23, 3.18 (AB quartet, 2H); 2.22 (s, 6H). (0512) 13C NMR (63 MHz; CDCl3): δ83.81; 70.40; 69.25; 66.84; 57.35; 45.23. (0513) Elemental analysis: Found: C, 63.7%; H, 8.9%; N, 9.5%. (0514) Calculated: C, 64.0%; H, 8.1%; N, 9.4%.

Reference： [1]Patent: WO2008/65448,2008,A1 .Location in patent: Page/Page column 92-93
[2]Patent: US9802185,2017,B2 .Location in patent: Page/Page column 46

30
[ 1271-86-9 ]
[ 76-86-8 ]
[ 1029696-99-8 ]

Yield	Reaction Conditions	Operation in experiment
68%		Part (I)Preparation of l-dimethylaminomethyl-2, 1' -bis-triphenylsilyl ferroceneTo dimethylaminomethylferrocene (2Og, 82.26mmol) in dry diethyl ether (300ml) was added n-butyllithium (82.26ml, 205.65mmol, 2.5eq) and TMEDA (13.66ml, 90.49mmol, l.leq) and the reaction was stirred under N2 for 12 hours at room temperature. The solution was then cooled to -780C (dry ice/acetone bath) and quenched with chlorotriphenylsilane (50.94g, 172.75mmol, 2. leq) dissolved in dry THF (200ml) . The solution was then allowed to <n="79"/>warm up to room temperature and further stirred for twelve hours resulting in a red solution.The reaction was then quenched with water, and stirred for a further fifteen minutes. The ethereal layer, containing product was separated and the aqueous layer was further extracted several times with diethyl ether. The combined ether fractions were dried over magnesium sulphate and filtered through celite. The ether solvent was removed by rotary evaporator (resulting in red oil) . The product was purified by layering the oil with petrol and Et2θ and leaving to crystallize overnight. The liquid residue was decanted and the orange/red crystals were dried under vacuum. A second crop of orange/red crystals were obtained with the layering of the decanted liquid and repeating the process: (42.75g, 68% yield).

Reference： [1]Patent: WO2008/65448,2008,A1 .Location in patent: Page/Page column 77-78

31
[ 1271-86-9 ]
[ 76-86-8 ]
[ 937168-67-7 ]

Yield	Reaction Conditions	Operation in experiment
62%		Part (I)Preparation of l-dimethylaminomethyl-2-triphenylsilyl ferrocene <n="81"/>To dimethylaminomethylferrocene (2Og, 82.26mmol) in dry diethyl ether (300ml) was added n-butyllithium (41.13ml, 102.82mmol, 1.25eq) and TMEDA (13.66ml, 90.49mmol, 1. leq) and the reaction was stirred under N2 for 12 hours at room temperature. The solution was then cooled to -780C (dry ice/acetone bath) and quenched with chlorotriphenylsilane (25.48g, 86.38mmol, 1.05eq) dissolved in dry THF (200ml). The solution was then allowed to warm up to room temperature and further stirred for twelve hours resulting in a red solution.The reaction was then quenched with water, and stirred for a further fifteen minutes. The ethereal layer, containing product was separated and the aqueous layer was further extracted several times with diethyl ether. The combined ether fractions were dried over magnesium sulphate and filtered through celite. The ether solvent was removed by rotary evaporator (resulting in red oil) . The product was purified by layering the oil with petrol and Et2U and leaving to crystallize overnight. The liquid residue was decanted and the orange/red crystals were dried under vacuum. A second crop of orange/red crystals were obtained with the layering of the decanted liquid and repeating the process: (25.63g, 62% yield).

Reference： [1]Patent: WO2008/65448,2008,A1 .Location in patent: Page/Page column 79-80

32
sodium tetrachloropalladate(II) [ No CAS ]
[ 1271-86-9 ]
(Rp)-bis(μ-chloro)bis(2-dimethylaminomethylferrocenyl)-N-dipalladium [ No CAS ]

Reference： [1]Organometallics,2009,vol. 28,p. 5833 - 5836
[2]Organometallics,2009,vol. 28,p. 5833 - 5836
[3]Organometallics,2009,vol. 28,p. 5833 - 5836
[4]Organometallics,2009,vol. 28,p. 5833 - 5836
[5]Organometallics,2009,vol. 28,p. 5833 - 5836
[6]Chemical Communications,2014,vol. 50,p. 7893 - 7896

33
[ 1271-86-9 ]
[ 32316-92-0 ]
[ 1416696-45-1 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 86 - 89

34
[ 1271-86-9 ]
[ 98-80-6 ]
[ 1416696-01-9 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 86 - 89

35
[ 1271-86-9 ]
[ 17933-03-8 ]
[ 1416696-36-0 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 86 - 89

36
[ 1271-86-9 ]
[ 5525-40-6 ]
[ 1427217-91-1 ]