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1,3-Bis(aminopropyl)tetramethyldisiloxane
Material Science
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Monomers
Polymers Organosilicon

[ CAS No. 2469-55-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 2469-55-8
Chemical Structure| 2469-55-8
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Quality Control of [ 2469-55-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 2469-55-8 ]

Product Details of [ 2469-55-8 ]

CAS No. :2469-55-8 MDL No. :MFCD00039786
Formula : C10H28N2OSi2 Boiling Point : -
Linear Structure Formula :- InChI Key :GPXCORHXFPYJEH-UHFFFAOYSA-N
M.W : 248.51 Pubchem ID :17181
Synonyms :

Calculated chemistry of [ 2469-55-8 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 8
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 72.42
TPSA : 61.27 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.1
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 2.11
Log Po/w (MLOGP) : 1.03
Log Po/w (SILICOS-IT) : -1.18
Consensus Log Po/w : 1.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.95
Solubility : 2.79 mg/ml ; 0.0112 mol/l
Class : Very soluble
Log S (Ali) : -2.64
Solubility : 0.565 mg/ml ; 0.00227 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.09
Solubility : 0.2 mg/ml ; 0.000805 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.62

Safety of [ 2469-55-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P210-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P370+P378-P403+P235-P405-P501 UN#:3267
Hazard Statements:H227-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 2469-55-8 ]

* 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 [ 2469-55-8 ]

[ 2469-55-8 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 18306-79-1 ]
  • [ 2469-55-8 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide
Reference： [1]Saam; Speier [Journal of Organic Chemistry, 1959, vol. 24, p. 119]
  • 2
  • [ 4743-17-3 ]
  • [ 2469-55-8 ]
  • 1,3-bis<3-(5-chloro-2-aminobenzamido)propyl>-1,1,3,3-tetramethyldisiloxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% In ethanol for 2h; Ambient temperature;
Reference： [1]Lafay, Jean; Latxague, Laurent; Lacroix, Christine; Deleris, Gerard [Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 102, # 1-4, p. 155 - 168] Delord; Guillorit; Lafay; Andreola; Tharaud; Tarrago-Litvak; Fleury; Deleris [European Journal of Medicinal Chemistry, 1996, vol. 31, # 2, p. 111 - 122]
  • 3
  • [ 118-48-9 ]
  • [ 2469-55-8 ]
  • 1,3-bis<3-(2-aminobenzamido)propyl>-1,1,3,3-tetramethyldisiloxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In ethanol for 2h; Ambient temperature;
Reference： [1]Lafay, Jean; Latxague, Laurent; Lacroix, Christine; Deleris, Gerard [Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 102, # 1-4, p. 155 - 168] Delord; Guillorit; Lafay; Andreola; Tharaud; Tarrago-Litvak; Fleury; Deleris [European Journal of Medicinal Chemistry, 1996, vol. 31, # 2, p. 111 - 122]
  • 4
  • [ 2469-55-8 ]
  • [ 10328-92-4 ]
  • 1,3-bis<3-(2-N-methylaminobenzamido)propyl>-1,1,3,3-tetramethyldisiloxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% In ethanol for 2h; Ambient temperature;
Reference： [1]Lafay, Jean; Latxague, Laurent; Lacroix, Christine; Deleris, Gerard [Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 102, # 1-4, p. 155 - 168] Delord; Guillorit; Lafay; Andreola; Tharaud; Tarrago-Litvak; Fleury; Deleris [European Journal of Medicinal Chemistry, 1996, vol. 31, # 2, p. 111 - 122]
  • 5
  • [ 2469-55-8 ]
  • [ 3770-97-6 ]
  • bis[(2,1-diazonaphthalenone-5-sulfonamido)dimethylpropyl]siloxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
61.2% With pyridine at 30 - 35℃; for 0.666667h;
Reference： [1]Rudaya, L. I.; Bogolyubova, S. S.; Klimova, N. V. [Russian Journal of Applied Chemistry, 1995, vol. 68, # 1part2, p. 96 - 99][Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1995, vol. 68, # 1, p. 110 - 113]
  • 6
  • [ 2469-55-8 ]
  • [ 36451-09-9 ]
  • bis[(2,1-diazonaphthalenone-4-sulfonamido)dimethylpropyl]siloxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.9% With pyridine at 30 - 35℃; for 0.666667h;
Reference： [1]Rudaya, L. I.; Bogolyubova, S. S.; Klimova, N. V. [Russian Journal of Applied Chemistry, 1995, vol. 68, # 1part2, p. 96 - 99][Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1995, vol. 68, # 1, p. 110 - 113]
  • 7
  • FGE(O-isopropyl methylphosphonylserine)AGAAS [ No CAS ]
  • [ 2469-55-8 ]
  • C43H75N11O14Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With barium dihydroxide; ammonium bicarbonate In water at 37℃; for 1h;
Reference： [1]Noort; Fidder; Van Der Schans; Hulst [Analytical Chemistry, 2006, vol. 78, # 18, p. 6640 - 6644]
  • 8
  • 4-[2-(2-amino-3-phenyl-propionylamino)-acetylamino]-4-[1-{1-[({1-[1-(1-carboxy-2-hydroxy-ethylcarbamoyl)-ethylcarbamoyl]-ethylcarbamoyl}-methyl)-carbamoyl]-ethylcarbamoyl}-2-(ethoxy-methyl-phosphinoyloxy)-ethylcarbamoyl]-butyric acid [ No CAS ]
  • [ 2469-55-8 ]
  • C43H75N11O14Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With barium dihydroxide; ammonium bicarbonate In water at 37℃; for 1h;
Reference： [1]Noort; Fidder; Van Der Schans; Hulst [Analytical Chemistry, 2006, vol. 78, # 18, p. 6640 - 6644]
  • 9
  • 4-[2-(2-amino-3-phenyl-propionylamino)-acetylamino]-4-{1-{1-[({1-[1-(1-carboxy-2-hydroxy-ethylcarbamoyl)-ethylcarbamoyl]-ethylcarbamoyl}-methyl)-carbamoyl]-ethylcarbamoyl}-2-[methyl-(1,2,2-trimethyl-propoxy)-phosphinoyloxy]-ethylcarbamoyl}-butyric acid [ No CAS ]
  • [ 2469-55-8 ]
  • C43H75N11O14Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With barium dihydroxide; ammonium bicarbonate In water at 37℃; for 1h;
Reference： [1]Noort; Fidder; Van Der Schans; Hulst [Analytical Chemistry, 2006, vol. 78, # 18, p. 6640 - 6644]
  • 10
  • [ 1823-59-2 ]
  • [ 2469-55-8 ]
  • [ 13080-86-9 ]
  • poly(imidesiloxane), prepared by polycondensation and thermal imidization, MN = 36137, PI = 1.63; monomer(s): 4,4'-oxydiphthalic dianhydride; 2,2-bis(4-[4-aminophenoxyl]phenyl)propane; 1,3-bis(3-aminopropyl)tetramethyldisiloxane, 10 wt % [ No CAS ]
Reference： [1]Macromolecules,2002,vol. 35,p. 5256 - 5266
  • 11
  • 1,19-bis(3-aminopropyl)icosamethyldecasiloxane [ No CAS ]
  • [ 1823-59-2 ]
  • [ 2469-55-8 ]
  • [ 13080-86-9 ]
  • poly(imidesiloxane), MN = 74898, PI = 2.06; monomer(s): 4,4'-oxydiphthalic dianhydride; 2,2-bis(4-[4-aminophenoxyl]phenyl)propane; 1,19-bis(3-aminopropyl)icosamethyldecasiloxane, 9 wt %; 1,3-bis(3-aminopropyl)tetramethyldisiloxane, 1 wt % [ No CAS ]
Reference： [1]Macromolecules,2002,vol. 35,p. 5256 - 5266
  • 12
  • 1,19-bis(3-aminopropyl)icosamethyldecasiloxane [ No CAS ]
  • [ 1823-59-2 ]
  • [ 2469-55-8 ]
  • [ 13080-86-9 ]
  • poly(imidesiloxane), MN = 68640, PI = 1.97; monomer(s): 4,4'-oxydiphthalic dianhydride; 2,2-bis(4-[4-aminophenoxyl]phenyl)propane; 1,19-bis(3-aminopropyl)icosamethyldecasiloxane, 7 wt %; 1,3-bis(3-aminopropyl)tetramethyldisiloxane, 3 wt % [ No CAS ]
Reference： [1]Macromolecules,2002,vol. 35,p. 5256 - 5266
  • 13
  • 1,19-bis(3-aminopropyl)icosamethyldecasiloxane [ No CAS ]
  • [ 1823-59-2 ]
  • [ 2469-55-8 ]
  • [ 13080-86-9 ]
  • poly(imidesiloxane), MN = 76005, PI = 2.10; monomer(s): 4,4'-oxydiphthalic dianhydride; 2,2-bis(4-[4-aminophenoxyl]phenyl)propane; 1,19-bis(3-aminopropyl)icosamethyldecasiloxane, 5 wt %; 1,3-bis(3-aminopropyl)tetramethyldisiloxane, 5 wt % [ No CAS ]
Reference： [1]Macromolecules,2002,vol. 35,p. 5256 - 5266
  • 14
  • 1,19-bis(3-aminopropyl)icosamethyldecasiloxane [ No CAS ]
  • [ 1823-59-2 ]
  • [ 2469-55-8 ]
  • [ 13080-86-9 ]
  • poly(imidesiloxane), MN = 130710, PI = 1.35; monomer(s): 4,4'-oxydiphthalic dianhydride; 2,2-bis(4-[4-aminophenoxyl]phenyl)propane; 1,19-bis(3-aminopropyl)icosamethyldecasiloxane, 3 wt %; 1,3-bis(3-aminopropyl)tetramethyldisiloxane, 7 wt % [ No CAS ]
Reference： [1]Macromolecules,2002,vol. 35,p. 5256 - 5266
  • 15
  • 1,19-bis(3-aminopropyl)icosamethyldecasiloxane [ No CAS ]
  • [ 1823-59-2 ]
  • [ 2469-55-8 ]
  • [ 13080-86-9 ]
  • poly(imidesiloxane), MN = 156320, PI = 1.44; monomer(s): 4,4'-oxydiphthalic dianhydride; 2,2-bis(4-[4-aminophenoxyl]phenyl)propane; 1,19-bis(3-aminopropyl)icosamethyldecasiloxane, 1 wt %; 1,3-bis(3-aminopropyl)tetramethyldisiloxane, 9 wt % [ No CAS ]
Reference： [1]Macromolecules,2002,vol. 35,p. 5256 - 5266
  • 16
  • [ 627-93-0 ]
  • [ 2469-55-8 ]
  • [ 67-56-1 ]
  • None [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 70℃; for 12h; Neat (no solvent); Heating / reflux; 12 Example 12 Analogous to Nylon, diamine [DISILOXANE] and dimethyl adipate were reacted with N435 as shown in the following diagram: . S R N435 N435 H2N (Si Si NHz + /-- Po beat 70'C 12 hours H I I H z0 < i ° if > 0* + CH30H il 0 0 The reaction was conducted with constant stirring (i. e. , magnetic stir bar) in a two-neck round-bottom flask attached to a Dean-Stark trap and a water-cooled condenser in a heated oil bath. The reaction was formulated with a [ORGANOSILICON] : organic mole ratio equal to 1: 1. The enzyme: monomer weight ratio was 1: 10. The dimethyl adipate was added to diamine disiloxane at [70°C.] After homogenization, dried lipase enzyme was added to the reaction mixture and heated for 12 hours. The reaction was monitored [BY 1H] NMR. After 12 hours, chloroform was added to the mixture to remove the contents from the flask and filter out the enzyme. Subsequently, the filtrate was evaporated on a rotary evaporator and dried in a vacuum oven overnight at-45 °C in order to isolate the product. The material was characterized [BY 1H AND 13C] NMR, MALDI TOF MS, FTIR, GPC-RI, TGA, and DSC. Fig. 12 illustrates the 1H NMR of the amidation. Based on the molecular characterization, lipase was observed to catalyze the formation of amide bonds during the synthesis of the [ORGANOSILICON] polyamide. The Mn and Mw values were calculated to be 2084 and 4566, respectively, with a 2.2 polydispersity. Based on the thermal analysis, the material experienced a critical mass loss at [394°C] vs. [107°C] of diamine [DISILOXANE.] The Tg was measured to be -21 °C. In comparison to the diamine [DISILOXANE,] Tg [=-110°C,] more energy was required to achieve molecular motion. During the first heating cycle, a crystalline phase was observed at [54°C] (Tm) with an energy equal to 9.6 J/g. No crystalline phases were observed in the diamine [DISILOXANE.] The crystalline phase provides evidence of regions of order within the material.
Reference： [1]Current Patent Assignee: NEW YORK UNIVERSITY; DOW INC - WO2004/16625, 2004, A2 Location in patent: Page 31-32
  • 17
  • [ 124-07-2 ]
  • [ 2469-55-8 ]
  • C26H56N2O3Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% In hexane at 70℃; for 144h; Heating / reflux; 10 Example 10 Subtilisin was used to catalyze the formation of amide bonds between 1,3- bis (3-aminopropyl)-tetramethyldisiloxane (i. e. diamine [DISILOXANE)] and octanoic acid as shown in the following diagram: 0 subtilisin HZN Si Si NHa + HO y op hexane 70°C 6 days H I I N . ^/N, I% SI. SI . N" + H20 0 0 The reaction was conducted using hexane as a solvent. The reaction was conducted with constant stirring (i. e. , magnetic stir bar) in a two-neck round- bottom flask attached to a Dean-Stark trap and a water-cooled condenser in a heated oil bath. The hexane reaction was formulated with [ORGANOSILICON] : organic and solvent : monomer mole ratios equal to 1: 1 and 10: 1, respectively. The enzyme: monomer weight ratio was 1: 10. The octanoic acid was added to the 1,3-bis (3-aminopropyl)- [TETRAMETHYLDISILOXANE] at [70°C.] After homogenization, dried subtilisin was added to the reaction mixture and heated for 12 hours. The refluxing reaction in hexane was conducted at [70°C] for 6 days. The completion of the reaction was monitored [BY 1H NMR OR TLC.] After the reaction, chloroform was added to the mixture to remove the contents from the flask and filter out the enzyme. Subsequently, the filtrate was evaporated on a rotary evaporator and dried in a vacuum oven overnight [AT ~45°C] in order to isolate the product. The reaction was characterized by [13C NMR.] Based on the spectral results, subtilisin was observed to catalyze the formation of an amide bond. The yield was estimated to be approximately 20%.
Reference： [1]Current Patent Assignee: NEW YORK UNIVERSITY; DOW INC - WO2004/16625, 2004, A2 Location in patent: Page 29-30
  • 18
  • silyl carbamate [ No CAS ]
  • [ 2627-95-4 ]
  • [ 7440-06-4 ]
  • [ 2469-55-8 ]
YieldReaction ConditionsOperation in experiment
84% 5 EXAMPLE 5 EXAMPLE 5 The silyl carbamate solution of Example 1 was combined with 1 ml. of a hydrosilation catalyst prepared from chloroplatinic acid and 3,3,5,5-tetramethyl-3,5-disila-4-oxa-1,6-heptadiene by the method disclosed in Example 10 of U.S. Pat. No. 3,814,730, said catalyst containing 5% platinum. The resulting solution contained platinum in the amount of 200 ppm. based on silyl carbamate. The mixture was heated slowly, with stirring, whereupon an exothermic reaction occurred and the temperature rose about 20° C. When the exotherm had subsided, the mixture was heated under reflux for 8 hours. Analysis then showed that all the silyl carbamate had reacted. The mixture was cooled and a 50% stoichiometric excess of water was added dropwise, with stirring, whereupon an exothermic reaction occurred. The rate of water addition was regulated so as to maintain a reaction temperature of about 50° C. When the exotherm had subsided, the mixture was heated under reflux for 15 hours. The toluene and solvent were then removed by distillation and the product was distilled; the desired 1,9-diamino-4,4,6,6-tetramethyl-5-oxa-4,6-disilanonane was recovered at 100° C./1 torr. The yield was 84% of theoretical, and the product contained about 20% trisiloxane and about 5% tetrasiloxane.
Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - US4631346, 1986, A
  • 19
  • [ 2469-55-8 ]
  • [ 530-62-1 ]
  • C18H32N6O3Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene at 20 - 23℃; 8 Example 8: Silicone-Urea-Azolide; At room temperature 32,42 g (0,20 Mole) CDI (FLUKA, > 97 %) are dispersed in 150 ml Toluene. At RT 24,85 g (0,10 Mole) 1,3,-Bis-(3-aminopropyl)-1,1,3,3-tetramethyl-disiloxane (Lancaster 97 %) are added to the suspension under stirring within 30 min. During addition temperature of the reaction mixture is kept at 23 ° C with an ice bath. After addition a clear two phase reaction mixture remains. The lower layer is separated and solvent is removed. Clear brownish yellow oil is obtained. Yield: 58,5 g (with imidazole and traces of toluene); 1H NMR δ (CH2-N(H)C(O)-): 3,50 ppm (vs. TMS in CDCl3).
Reference： [1]Current Patent Assignee: 3M CO - EP1780213, 2007, A1 Location in patent: Page/Page column 13
  • 20
  • [ 1293-79-4 ]
  • [ 2469-55-8 ]
  • {C5H5FeC5H4CONH(CH2)3Si(CH3)2}2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In toluene N2 atmosphere, room temp.; dropwise addn. of soln. of Fe complex (2 equiv.) to stirred soln. of substituted siloxane (1 equiv.) and Et3N (pptn.), stirring (15 min); filtration, chromy. (silanized silica/CH2Cl2:acetone = 10:1 v/v), solvent removal (vac.), recrystn. (slow diffusion of hexane to soln. in CH2Cl2); elem. anal.;
Reference： [1]Casado, Carmen M.; Morán, Moisés; Losada, José; Cuadrado, Isabel [Inorganic Chemistry, 1995, vol. 34, # 7, p. 1668 - 1680][Inorg. Chem.]
  • 21
  • [ 1273-94-5 ]
  • [ 2469-55-8 ]
  • [-Si(CH3)2(CH2)3NHC(O)(η(5)-C5H4)Fe(η(5)-C5H4)C(O)NH(CH2)3Si(CH3)O-]n [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With triethylamine In toluene N2 atmosphere; stirring (0°C, 15 min); filtration, treatment with CH3CN (overnight), extn. into CH2Cl2, concn., dropwise addn. to CH3CN (pptn.), washing (CH3CN), drying (vac.); elem.anal.;
Reference： [1]Casado, Carmen M.; Morán, Moisés; Losada, José; Cuadrado, Isabel [Inorganic Chemistry, 1995, vol. 34, # 7, p. 1668 - 1680][Inorg. Chem.]
  • 22
  • (chlorocarbonyl)cobaltocenium hexafluorophosphate [ No CAS ]
  • [ 2469-55-8 ]
  • [[(η(5)-C5H5)Co(η(5)-C5H4C(O)NH(CH2)3Si(CH3)2)]O][PF6]2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With triethylamine In chloroform byproducts: Et3NHCl; N2-atmosphere; stirring (overnight); filtering, washing (CHCl3), drying (vac.); elem. anal.;
Reference： [1]Cuadrado, Isabel; Casado, Carmen M.; Lobete, Francisco; Alonso, Beatriz; González, Blanca; Losada, José; Amador, Ulises [Organometallics, 1999, vol. 18, # 24, p. 4960 - 4969]
  • 23
  • 1,1'-bis(chlorocarbonyl)cobaltocenium hexafluorophosphate [ No CAS ]
  • [ 2469-55-8 ]
  • 2Co(3+)*2(C5H4C(O)NH(CH2)3Si(CH3)2)2O(2-)*2PF6(1-)=(Co(C5H4C(O)NH(CH2)3Si(CH3)2)2OPF6)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In chloroform byproducts: Et3NHCl; N2-atmosphere; stirring (overnight); filtering, washing (CHCl3), drying (vac.); elem. anal.;
Reference： [1]Cuadrado, Isabel; Casado, Carmen M.; Lobete, Francisco; Alonso, Beatriz; González, Blanca; Losada, José; Amador, Ulises [Organometallics, 1999, vol. 18, # 24, p. 4960 - 4969]
  • 24
  • [ 2469-55-8 ]
  • [ 40846-94-4 ]
  • [ 1026779-51-0 ]
YieldReaction ConditionsOperation in experiment
37% 2.3 3. Synthesis of N, N' - [ (1, 1, 3, 3-tetramethyldisiloxane- 1, 3-diyl) dipropane-3, 1-diyl] bis [5- (1, 2-dithiolan-3- yl) pentanamide]; The compound N, N' - [ (1, 1, 3, 3-tetramethyldisiloxane-l, 3- diyl) dipropane-3, 1-diyl] bis [5- (1, 2-dithiolan-3-yl) - pentanamide] was synthesized by introducing two equivalents of 1- { [5- (1, 2-dithiolan-3-yl) pentanoyl] - oxy}pyrrolidine-2 , 5-dione per 1 equivalent of 1, 3-bis (3-aminopropyl-l, 1,3, 3-tetramethyldisiloxane . Yield = 37%.The quasimolecular ions [M+H]+, [M+Na]+, [M-H]-, [M+Cl]- and the fragments [M+H-C13H27NO2S2Si] + and [M-H-C13H25NOS2Si] - of the expected molecule C26H52N2O3S4Si2, M = 624 are mainly detected. Detection of weak signals by ESI+ and ESI- in the mass range 65-800 possibly corresponding to impurities.Anal. Calculated for C26H52N2O3S4Si2 C 50.0, H 8.4, N 4.5, O 7.7, S 20.5, Si 9.0. Found: C(49.55); H(8.46); N(4.4); 1H NMR (DMSO-d6)
Reference： [1]Current Patent Assignee: L&apos;OREAL SA - WO2008/58999, 2008, A1 Location in patent: Page/Page column 46-47
  • 25
  • [ 2469-55-8 ]
  • [ 556-67-2 ]
  • None [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetramethyl ammoniumhydroxide at 130℃; for 42h; 2 PRACTICAL EXAMPLE 2; [0044] This example illustrates the utilization of the bis(aminopropyl)tetramethyldisiloxane endstopper from Practical Example 1 to prepare a low molecular weight bis(aminopropyl)polysiloxane. Into a 250 cc round bottom flask equipped with a magnetic stirrer, cold-finger distillation head, thermocouple connected to a temperature controller, nitrogen purge tube, and water ice plus dry ice traps on the vent, were charged 27.66 grams of 98.19% pure bis(aminopropyl)tetramethyldisiloxane, 81.12 grams of vacuum distilled and dehydrated octamethylcyclotetrasiloxane, and 0.23 grams of anhydrous tetramethylammonium hydroxide. The mixture was heated to 13O0C and held at that temperature for 22 hours. At that point, an additional 4.18 grams of bis(aminopropyl)tetramethyldisiloxane and 0.14 grains of anhydrous tetramethylammonium hydroxide was charged. The purpose of the second injection of the endstopper and catalyst was to force the equilibration to the low molecular weight. The mixture was then held at 1300C for 20 hours and then the catalyst was decomposed by heating at 16O0C for one hour. After removal of cyclic siloxanes and excess bis(aminopropyl)tetramethyldisiloxane by vacuum stripping, the molecular weight of the product was determined by amine content acid titration to be 900. Compared to the yellow color and strong odor of present commercial bis(aminopropyl)polysiloxane of similar molecular weight, the product prepared according to this Example was water-white and of low odor.
Reference： [1]Current Patent Assignee: MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC. - WO2008/115190, 2008, A1 Location in patent: Page/Page column 19
  • 26
  • [ 67-56-1 ]
  • [ 151565-10-5 ]
  • [ 59384-10-0 ]
  • [ 107-46-0 ]
  • [ 2469-55-8 ]
YieldReaction ConditionsOperation in experiment
94.1% for 2h; Heating / reflux; 1.C C. Alcoholysis Deprotection Reaction; [0036] Deprotection of the blocked amine was accomplished with alcohol. 234.27 grams of methanol was slowly charged to a reaction flask containing 842.79 grams of the product of the hydrosilation reaction of Step "B" while maintaining the reactor temperature below 500C. When all the methanol had been added and the exothermic reaction ceased, the reactor was heated to reflux and held for two hours. The reaction product was analyzed by gas chromatography and was found to contain 35.82% of the desired product, bis(aminopropyl)tetramethyldisiloxane and 32.48% of the byproduct hexamethyldisiloxane. Based on the charged amount of protected product, a yield of 91.9% was achieved. The product mixture was distilled using similar equipment as in the prior Step "A" distillation except vacuum conditions were employed. The distillation was accomplished with a pot temperature of 1800C and a pressure of 6 mm Hg. The distillation yield of bis(aminopropyl)tetramethyldisiloxane was 94.1%.
Reference： [1]Current Patent Assignee: MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC. - WO2008/115190, 2008, A1 Location in patent: Page/Page column 16
  • 27
  • [ 151565-10-5 ]
  • [ 59384-10-0 ]
  • [ 107-46-0 ]
  • [ 2469-55-8 ]
YieldReaction ConditionsOperation in experiment
92.7% With water at 78 - 80℃; for 1h; 1.C C. Hydrolysis Deprotection Reaction; [0041] Ion exchange treated water at room temperature was slowly fed via an addition funnel into a 2-liter round bottom flask containing 822.39 grams of the crude hydrosilation product. The reaction temperature was monitored and the addition of water was slow at first to prevent generated alcohol from boiling over. At 11% of the total water feed of 350.74 grams, the reaction had an exotherm to 78°C. After the remainder of the water was added, the reaction was held at 800C for 1 hour. The reactor contents were then charged to a separatory funnel and the water and product layers were decanted. 950.19 grams of crude product (top layer) was separated. By gas chromatograph analysis, the crude product was found to contain 395.47 grams of the desired deblocked product, bis(aminopropyl)tetramethyldi-siloxane which represents a hydrolysis reaction yield of 92.7%. The crude product was found to also contain 375.13 grams of the byproduct, hexamethyldisiloxane. The product mixture was distilled using similar equipment as in the prior Step "A" distillation except vacuum conditions were employed. The distillation was accomplished with a pot temperature of 1800C and a pressure of 8 mm Hg. The distillation yield of bis(aminopropyl)tetramethyldisiloxane was 97.7%.
Reference： [1]Current Patent Assignee: MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC. - WO2008/115190, 2008, A1 Location in patent: Page/Page column 18
  • 28
  • [ 85-44-9 ]
  • [ 2469-55-8 ]
  • C26H32N2O5Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% In 1-methyl-pyrrolidin-2-one at 0 - 20℃; for 24h; 4 In 50 mL of NMP was dissolved 8.389 g of 1,3-bis(3-aminopropyl)tetramethyldisiloxane. To the solution was dropped 10 g of phthalic anhydride under ice-cooling and the mixture was then stirred at room temperature for one day. 300 mL of ethyl acetate was added to the reaction mixture, and the mixture was washed with brine. The mixture was dried over magnesium sulfate and the solvent was evaporated off under a reduced pressure. In 80 mL of acetic anhydride was then dissolved 18.389 g of the solidified residue, and to the solution was added 8.309 g of sodium acetate, and the solution was reacted at 90° C. for 5 hours. After cooled, it was poured into iced water and stirred for 1 hour. The precipitated crystal was filtered, and the filtered crystal was washed with water. The obtained crystal was dissolved in 200 mL of ethyl acetate, and the solution was sequentially washed with 5% sodium carbonate, brine and water, and dried over magnesium sulfate. The solvent was evaporated off under a reduced pressure; 150 mL of hexane was added to the residue; and the mixture was stirred and washed. Furthermore, the mixture was re-precipitated with hexane/ethyl acetate (5/3) to obtain 8.68 g of the desired product (white solid, total yield: 71%).1H-NMR (THF-d8, δ): 0.81 (12H, s), 0.56-0.61 (4H, m), 1.67-1.75 (4H, m), 3.6-3.65 (4H, m), 7.72-7.76 (4H, m), 7.78-7.82 (4H, m).
Reference： [1]Current Patent Assignee: NEC CORPORATION - US2009/68587, 2009, A1 Location in patent: Page/Page column 17-18
  • 29
  • [ 2469-55-8 ]
  • [ 98-88-4 ]
  • [ 349607-63-2 ]
YieldReaction ConditionsOperation in experiment
58% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 24h; 5 In 80 mL of tetrahydrofuran were dissolved 7.467 g of 1,3-bis(3-aminopropyl)tetramethyldisiloxane and 9.71 g of N,N-diisopropylethylamine. To the solution was dropped 8.87 g of benzoyl chloride under ice-cooling and the mixture was then stirred at room temperature for one day. Water was poured into the reaction mixture, and an organic layer was extracted with 200 mL of diethyl ether. The obtained organic layer was sequentially washed with 0.2 N hydrochloric acid, brine, 3% aqueous sodium hydroxide solution and brine. The organic layer was then dried over magnesium sulfate and evaporated off under a reduced pressure to give 8 g of the desired product as viscous liquid (yield: 58%). The obtained product was solidified by leaving the product in a refrigerator.1H-NMR (CDCl3, δ): 0.06 (12H, s), 0.54-0.61 (4H, m), 1.62-1.70 (4H, m), 3.38-3.44 (4H, m), 6.78 (2H, br), 7.33-7.47 (6H, m), 7.74-7.81 (4H, m).
Reference： [1]Current Patent Assignee: NEC CORPORATION - US2009/68587, 2009, A1 Location in patent: Page/Page column 18
  • 30
  • [ 3277-26-7 ]
  • allylaminotrimethylsilane [ No CAS ]
  • [ 2469-55-8 ]
YieldReaction ConditionsOperation in experiment
58% With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex at 95 - 125℃; Inert atmosphere;
Reference： [1]Location in patent: experimental part Niu, Yuzhong; Lu, Haifeng; Wang, Dengxu; Yue, Yuanzhi; Feng, Shengyu [Journal of Organometallic Chemistry, 2011, vol. 696, # 2, p. 544 - 550]
  • 31
  • [ 2469-55-8 ]
  • [ 292638-85-8 ]
  • [ 1266558-39-7 ]
YieldReaction ConditionsOperation in experiment
99% In methanol at 50℃; for 48h;
96% In methanol at 50℃; for 48h;
95% In methanol at 50℃; for 48h; Inert atmosphere;
Reference： [1]Lu, Hang; Hu, Ziqi; Feng, Shengyu [Chemistry - An Asian Journal, 2017, vol. 12, # 11, p. 1213 - 1217]
[2]Lu, Hang; Feng, Linglong; Li, Shusheng; Zhang, Jie; Lu, Haifeng; Feng, Shengyu [Macromolecules, 2015, vol. 48, # 3, p. 476 - 482]
[3]Location in patent: experimental part Niu, Yuzhong; Lu, Haifeng; Wang, Dengxu; Yue, Yuanzhi; Feng, Shengyu [Journal of Organometallic Chemistry, 2011, vol. 696, # 2, p. 544 - 550]
  • 32
  • [ 2469-55-8 ]
  • [ 128-69-8 ]
  • [ 1272671-23-4 ]
YieldReaction ConditionsOperation in experiment
80% With zinc(II) acetate dihydrate In quinoline at 100 - 160℃; for 12h;
Reference： [1]Location in patent: experimental part Cazacu, Maria; Vlad, Angelica; Airinei, Anton; Nicolescu, Alina; Stoica, Iuliana [Dyes and Pigments, 2011, vol. 90, # 2, p. 106 - 113]
  • 33
  • [ 2469-55-8 ]
  • [ 75-59-2 ]
  • [ 114933-30-1 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran for 5h; Inert atmosphere; Reflux; Preparation of Anhydrous Tetramethylammonium 3-aminopropyldimethylsilanolate A 250 ml three-neck round-bottom flask equipped with a magnetic stirrer, argon inlet, and condenser with drying tube was charged with 12.4 g (0.05 mol) of 1,3-bis(3-aminopropyl)tetramethyldisiloxane, 18.1 (88.12 mmol) of tetramethylammonium hydroxide pentahydrate, and 30 ml of tetrahydrofuran. The mixture was heated under reflux in an inert gas atmosphere for 5 hours. In the course of slow cooling, a white, crystalline precipitate emerged from the yellow-brown mother liquor. The flask was placed in an ice bath and the solid was subsequently isolated by filtration with suction. This gave a colorless solid, which was dried for 5 hours under a pressure of 0.1 mbar. It was subsequently recrystallized from anhydrous THF and isolated by suction filtration on a Schlenk frit under inert gas. The hygroscopic product was stored at room temperature in a desiccator over blue indicator gel under argon.
Stage #1: 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane; tetramethyl ammoniumhydroxide With octamethylcyclotetrasiloxane In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; Stage #2: With N-((3-aminopropyl)-dimethylsilyl)-2,2-dimethyl-1-aza-2-silacyclopentane at 80 - 170℃; for 0.5h; 1 EXAMPLE 1A 1000 ml three-neck round-bottom flask with internal thermometer, mechanical stirrer, dropping funnel, and inert gas inlet was charged with 600 g (=4.73 mol) of octamethylcyclotetrasiloxane, 55.86 g (=0.22 mmol) of bis(3-aminopropyl)tetramethyldisiloxane, and 0.6 g (=3.3 mmol) of tetramethylammonium hydroxide pentahydrate. The contents of the flask were heated with an oil bath at 80° C. for 12 hours with stirring and under argon as inert gas.An Si-29-NMR of the mixture showed that the bis(3-aminopropyl)tetramethyldisiloxane had undergone 98% conversion. The amount of cyclosiloxanes in the reaction mixture was approximately 15% of the initial amount.The batch was then heated to 150° C. and stirred at that temperature for half an hour. Then, slowly and cautiously, a vacuum of 800 hPa was applied and volatile fractions were distilled off with slow reduction in pressure to 10 hPa. The batch was then cooled to room temperature and filtered at a pressure of 2 bar. Aminosiloxanes were obtained which had a viscosity of 50 mm2/s and a silanol content of 940 ppm by weight.Subsequently, 20 g (=87 mmol) of 3-[(2,2-dimethyl-1,2-azasilolidin-1-yl)(dimethyl)silyl]-1-propanamine (azacycle) were added to the batch, which was heated at 80° C. for 30 minutes. The contents of the flask were then devolatilized in a short-path evaporator at 170° C. under a pressure of 1 mbar.This gave 552 g of clear, colorless oil (84% of the theoretical yield). The molecular mass of the product, determined by Si-29-NMR, was 2854 g/mol (an average of 17.6 Si units). The silanol group content was 15 ppm by weight.
Reference： [1]Current Patent Assignee: WACKER CHEMIE AG - US2011/301374, 2011, A1 Location in patent: Page/Page column 6
[2]Current Patent Assignee: WACKER CHEMIE AG - US2011/301374, 2011, A1 Location in patent: Page/Page column 6
  • 34
  • [ 1070740-24-7 ]
  • [ 2469-55-8 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: bis(methylcarbamatopropyl)tetra-methyldisiloxane With water at 100℃; for 16h; Stage #2: With sodium hydroxide In water 3 EXAMPLE 3 2.00 g (5.49 mmol) of bis(methylcarbamatopropyl)tetra-methyldisiloxane are heated with 14 ml of 2N H2SO4 to 100° C. for 16 hours (complete conversion). The reaction mixture is made alkaline with 5M NaOH and extracted with MTBE and the organic phase is evaporated in vacuo. Yield 1.28 g (94%) of bis(aminopropyl)tetra-methyldisiloxane.
Reference： [1]Current Patent Assignee: WACKER CHEMIE AG - US2012/4436, 2012, A1 Location in patent: Page/Page column 3-4
  • 35
  • [ 2469-55-8 ]
  • [ 13818-44-5 ]
  • [ 1384895-93-5 ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 18.0h;Cooling with ice; Example 1; 1 ,3-Bis [3-([2-hydroxy-3-(methacryloyloxy)propoxy]carbonyl}amino)propyl] 1 ,1 ,3,3-tetramethyldisiloxane; To <strong>[13818-44-5]glycerol carbonate methacrylate</strong> (1.0 g, 5.4 mmol) cooled in an ice/water bath was added 1 ,3-bis(3-aminopropyl)-1 ,1 ,3,3-tetramethyldisiloxane (0.67 cm3, 2.4 mmol) dropwise with stirring. The reaction mixture was stirred for 2 h in the ice/water bath and then left to stand at room temperature for 16 h to give a thick, colourless oil.IR: (cm"1) 3357 (OH), 2955 (alkyl), 1705 (C=O), 1638 (C=C), 1532 (amide II), 1251 (Si-Me) 1043 (Si-O) and 775 (Si-Me).H NMR: (C2HCI3, 400 MHz) δΗ 0.04 (12 H, s, SiCH3), 0.44 - 0.51 (4 H, m, SiCH2), 1.46 - 1.56 (4 H, m, SiCH2CH2), 1.89 - 1.96 (6 H, m, CCH3), 3.08 - 3.16 (4 H, m, CH2N), 3.60 - 4.50 (10 H, m, 2 x CH2O and CHOH), 5.56 - 5.60 (2 H, m, CHtf=C) and 6.08 - 6.16 (2 H, m, CHH=C).
Reference： [1]Patent: WO2012/95293,2012,A2 .Location in patent: Page/Page column 23
  • 36
  • [ 2469-55-8 ]
  • 1,3-bis(3-ammonium-propyl)tetramethyldisiloxane-sulfate [ No CAS ]
YieldReaction ConditionsOperation in experiment
49.2% With vanadium (IV) oxide sulfate hydrate; salicylaldehyde In methanol; dichloromethane at 60℃; for 4h; 2.3.1. Procedure I General procedure: 0.1000 g (0.25 mmol) Fe2(SO4)3·xH2O dissolved in a solvent mixture formed by 4 ml methanol and 2 ml methylene chloride was added over the solution consisting in 0.1242 g (0.1326 mL, 0.50 mmol) 1,3-bis(3-aminopropyl)tetramethyldisiloxane and 0.0961 g (1 mmol) 4-imidazolecarboxaldehyde in 2.5 mL methanol in a 50 ml one-necked round-bottom flask. The reaction mixture was stirred for 4 h at 60 °C, after which was allowed to stay in a closed flask at room temperature. Formation of colorless prismatic crystals was observed after about 20 days. These were separated by filtration washed with diethyl ether, dried and analyzed (Yield: 0.062 g, 35.6%).
Reference： [1]Location in patent: experimental part Nistor, Alexandra; Soroceanu, Alina; Shova, Sergiu; Cazacu, Maria [Journal of Molecular Structure, 2012, vol. 1022, p. 1 - 7]
  • 37
  • [ 2469-55-8 ]
  • [ 552-30-7 ]
  • [ 915101-62-1 ]
YieldReaction ConditionsOperation in experiment
80% In N,N-dimethyl-formamide for 3h; Reflux;
Reference： [1]Cazacu, Maria; Vlad, Angelica; Turta, Constantin; Lisa, Gabriela [Central European Journal of Chemistry, 2012, vol. 10, # 4, p. 1079 - 1086]
  • 38
  • [ 1003-29-8 ]
  • [ 2469-55-8 ]
  • [ 1421633-91-1 ]
YieldReaction ConditionsOperation in experiment
91% In methanol at 20℃; for 3.16667h; Reflux;
Reference： [1]Vlad, Angelica; Turta, Constantin; Cazacu, Maria; Rusu, Elena; Shova, Sergiu [European Journal of Inorganic Chemistry, 2012, # 31, p. 5078 - 5084,7]
  • 39
  • [ 2469-55-8 ]
  • [ 129-64-6 ]
  • nadic anhydride [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.2% In N,N-dimethyl acetamide at 20℃; for 6h; Inert atmosphere;
Reference： [1]Singh, Ajit Shankar; Shukla, Shailendra Kumar; Alam, Sarfaraz [Journal of Thermal Analysis and Calorimetry, 2012, vol. 107, # 2, p. 509 - 517]
  • 40
  • [ 4997-36-8 ]
  • [ 2469-55-8 ]
  • [ 1417424-42-0 ]
YieldReaction ConditionsOperation in experiment
73% In N,N-dimethyl-formamide for 20h; Reflux;
Reference： [1]Zabulica, Andrei; Balan, Mihaela; Belei, Dalila; Sava, Mitica; Simionescu, Bogdan C.; Marin, Luminita [Dyes and Pigments, 2013, vol. 96, # 3, p. 686 - 698]
  • 41
  • [ 90-59-5 ]
  • [ 75-09-2 ]
  • [ 2469-55-8 ]
  • [ 6046-93-1 ]
  • C24H30Br4CuN2O3Si2*0.375CH2Cl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% In tetrahydrofuran; methanol at 60℃; for 3h;
Reference： [1]Soroceanu, Alina; Cazacu, Maria; Shova, Sergiu; Turta, Constantin; Kozisek, Jozef; Gall, Marian; Breza, Martin; Rapta, Peter; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.; Telser, Joshua; Dobrov, Anatolie A.; Arion, Vladimir B. [European Journal of Inorganic Chemistry, 2013, # 9, p. 1458 - 1474]
  • 42
  • [ 2469-55-8 ]
  • [ 95-01-2 ]
  • [ 648441-58-1 ]
YieldReaction ConditionsOperation in experiment
76.7% In methanol for 10h; Reflux;
Reference： [1]Soroceanu, Alina; Cazacu, Maria; Shova, Sergiu; Turta, Constantin; Kozisek, Jozef; Gall, Marian; Breza, Martin; Rapta, Peter; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.; Telser, Joshua; Dobrov, Anatolie A.; Arion, Vladimir B. [European Journal of Inorganic Chemistry, 2013, # 9, p. 1458 - 1474]
  • 43
  • copper(II) chloride monohydrate [ No CAS ]
  • [ 67-66-3 ]
  • [ 2469-55-8 ]
  • [ 97-51-8 ]
  • [ 1449239-04-6 ]
YieldReaction ConditionsOperation in experiment
22.9% In methanol; dichloromethane at 70℃; for 2h;
Reference： [1]Soroceanu, Alina; Cazacu, Maria; Shova, Sergiu; Turta, Constantin; Kozisek, Jozef; Gall, Marian; Breza, Martin; Rapta, Peter; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.; Telser, Joshua; Dobrov, Anatolie A.; Arion, Vladimir B. [European Journal of Inorganic Chemistry, 2013, # 9, p. 1458 - 1474]
  • 44
  • copper(II) chloride monohydrate [ No CAS ]
  • [ 2469-55-8 ]
  • [ 97-51-8 ]
  • [ 1449239-03-5 ]
YieldReaction ConditionsOperation in experiment
36.3% In methanol; dichloromethane at 70℃; for 2h;
Reference： [1]Soroceanu, Alina; Cazacu, Maria; Shova, Sergiu; Turta, Constantin; Kozisek, Jozef; Gall, Marian; Breza, Martin; Rapta, Peter; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.; Telser, Joshua; Dobrov, Anatolie A.; Arion, Vladimir B. [European Journal of Inorganic Chemistry, 2013, # 9, p. 1458 - 1474]
  • 45
  • copper(II) chloride monohydrate [ No CAS ]
  • [ 2469-55-8 ]
  • [ 635-93-8 ]
  • [ 1449239-05-7 ]
YieldReaction ConditionsOperation in experiment
35.5% In methanol; chloroform at 60℃; for 3h;
Reference： [1]Soroceanu, Alina; Cazacu, Maria; Shova, Sergiu; Turta, Constantin; Kozisek, Jozef; Gall, Marian; Breza, Martin; Rapta, Peter; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.; Telser, Joshua; Dobrov, Anatolie A.; Arion, Vladimir B. [European Journal of Inorganic Chemistry, 2013, # 9, p. 1458 - 1474]
  • 46
  • copper(II) chloride monohydrate [ No CAS ]
  • [ 2469-55-8 ]
  • [ 90-02-8 ]
  • [ 1449238-98-5 ]
YieldReaction ConditionsOperation in experiment
32% In methanol; dichloromethane at 60℃; for 3h;
Reference： [1]Soroceanu, Alina; Cazacu, Maria; Shova, Sergiu; Turta, Constantin; Kozisek, Jozef; Gall, Marian; Breza, Martin; Rapta, Peter; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.; Telser, Joshua; Dobrov, Anatolie A.; Arion, Vladimir B. [European Journal of Inorganic Chemistry, 2013, # 9, p. 1458 - 1474]
  • 47
  • [ 2469-55-8 ]
  • [ 6046-93-1 ]
  • [ 90-02-8 ]
  • [ 1449238-98-5 ]
YieldReaction ConditionsOperation in experiment
32.3% In methanol; dichloromethane at 60℃; for 3h;
Reference： [1]Soroceanu, Alina; Cazacu, Maria; Shova, Sergiu; Turta, Constantin; Kozisek, Jozef; Gall, Marian; Breza, Martin; Rapta, Peter; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.; Telser, Joshua; Dobrov, Anatolie A.; Arion, Vladimir B. [European Journal of Inorganic Chemistry, 2013, # 9, p. 1458 - 1474]
  • 48
  • [ 90-59-5 ]
  • zinc(II) nitrate hexahydrate [ No CAS ]
  • [ 2469-55-8 ]
  • C24H30Br4N2O3Si2Zn*0.21H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
9.9% Stage #1: 3,5-Dibromosalicylaldehyde; 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane In methanol; dichloromethane at 70℃; for 3h; Stage #2: zinc(II) nitrate hexahydrate In methanol; dichloromethane at 20℃; for 0.166667h; Synthesis of Zn(II) complex, 2 A solution containing 1 ml of 1,3-bis(3-aminopropyl)tetramethyldisiloxane (0.897 g, 3.61 mmol) in 20mL solvent mixture 1:1 methanol-methylene chloride wasadded under stirring at room temperature to the solution of3,5-dibromosalicylaldehyde (2.021 g, 7.22 mmol) in 20 mLsolvent mixture 1:1 methanol-methylene chloride. The mixturewas stirred at 70 °C for 3 h. Then, the orange solution wasadded to a solution of Zn(NO3)2·6H2O (1.189 g, 3.99 mmol) in10 mL methanol. The mixture was stirred at room temperaturefor 10 min. A clear yellow solution generated prismaticcrystals of good quality after 3-4 h at room temperature. Thesewere separated by filtration, washed with methanol and driedin air. Crystals yield: 0.3 g, 9.90 %. Calcd forC24H30.42Br4N2Zn1O3.21Si2 (Mr 839.19 g/mol), %: C, 34.32; H,3.62; N, 3.34. Found, %: C, 34.10; H, 3.50; N, 3.40. IRspectrum (KBr pellet), selected bands, νmax: 2930 m ν(C-Hfrom Si-CH3), 1617vs ν(C=N), 1506m ν(aromatic ring),1443vs ν(CH2), 1386s ν(CH3), 1254s ν(Si-CH3), 1071s ν(Si-O-Si), 840s ν(Si-CH3), 707s ν(Me-O), 482w ν(Me→N).1H-NMR (DMSO, 400.13 MHz, δ, ppm): 8.33 (-CH=N-),7.69-7.66, 7.51-7.40 (aromatic H), 3.27-3.30 (=N-CH2-CH2-CH2-Si), 1.49 (=N-CH2-CH2-CH2-Si), 0.26 (=N-CH2-CH2-CH2-Si), 0.03 ((CH3)2Si
Reference： [1]Soroceanu, Alina; Cazacu, Maria; Nistor, Alexandra; Shova, Sergiu [Revue Roumaine de Chimie, 2013, vol. 58, # 2-3, p. 209 - 216]
  • 49
  • [ 2469-55-8 ]
  • [ 124-38-9 ]
  • [ 3034-50-2 ]
  • [ 1498252-03-1 ]
YieldReaction ConditionsOperation in experiment
In methanol at 60℃; for 4h; A solution consisting in 0.1242 g (0.50 mmol) 1,3-bis(3 aminopropyl)tetramethyldisiloxane in 10 mL methanol was added to a solution of4-imidazolecarboxaldehyde 0.0961 g (1 mmol) in 2.5 mL methanol,in a 50mL one-necked round-bottom flask. The reactionmixturewasstirred for 4 h at 60 °C, after which was allowed to stay in a closedflask at room temperature. Formation of colorless crystals was observedafter about 5 days. These were separated by filtration washedwith diethyl ether, dried and analyzed further. Crystalline compoundwas labeled as APCO: C11H27N2O3Si2
Reference： [1]Bargan, Alexandra; Soroceanu, Alina; Alexandru, Mihaela; Stoica, Iuliana; Cazacu, Maria; Shova, Sergiu [Journal of Molecular Liquids, 2014, vol. 196, p. 319 - 325]
  • 50
  • [ 67-56-1 ]
  • [ 699-98-9 ]
  • copper(II) choride dihydrate [ No CAS ]
  • [ 2469-55-8 ]
  • [H2(1,3-bis(3-aminopropyl)tetramethyldisiloxane)]2[Cu(2,3-pyridinedicarboxylic acid)2]Cl2*2H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% Stage #1: Pyridine-2,3-dicarboxylic anhydride; 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane In N,N-dimethyl-formamide at 20 - 140℃; for 6h; Stage #2: methanol; copper(II) choride dihydrate at 20℃; for 0.0833333h; Procedure In a round bottom flask were loaded 1.073 g (7.2 mmol) ofPDCA, 1 mL (0.897 g, 3.6 mmol) AP0 and 10 mL of DMF. The mixturewas stirred at room temperature for 1 h and then heated for5 h at 140 C after which left in rest at room temperature. The nextday, the reaction mixture was distilled in vacuum to remove thesolvent and other volatile fraction, eventually. The rest solid wasdissolved in 12 mL methanol and then a solution consisting in0.613 g (3.6 mmol) copper chloride and 6 mL methanol was addedover it. The new resulting mixture was stirred for 5 min at roomtemperature and then was allowed to crystallize. Formation of blueprismatic crystals was observed after about two years. Thesewere separated by filtration washed with methanol, dried in airand further analyzed (compound 1), the rest being a complexmixture, amorphous, difficult to separate. Yield 1.153 g (32%).
Reference： [1]Soroceanu, Alina; Bargan, Alexandra; Shova, Sergiu; Avadanei, Mihaela; Cazacu, Maria [Journal of Molecular Structure, 2014, vol. 1083, p. 88 - 94]
  • 51
  • [ 2469-55-8 ]
  • 2',2'-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))bis(1,3-dicyclohexylguanidine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-carbodiimide S17 (G8): Synthesis of 2',2'-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))bis(1,3-dicyclohexylguanidine) A 250 ml four-necked flask equipped with KPG stirrer, reflux condenser, nitrogen blanketing, temperature sensor and heating hood was charged under inert conditions with 24.85 g (100 mmol) of 1,3-bis(3-aminopropyl)tetramethyldisiloxane, and 40.44 g (196 mmol) of N,N-dicyclohexylcarbodiimide were added. With continuing stirring, the reaction mixture was reacted at 90° C. for 6 hours, after which all of the volatile constituents were distilled off over 30 minutes under a diaphragm pump vacuum. This gave a clear, viscous product, which after analysis by means of 13C NMR showed complete conversion of the carbodiimide.
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - US2015/57412, 2015, A1 Location in patent: Page/Page column
  • 52
  • [ 2469-55-8 ]
  • [ 1266558-39-7 ]
  • C62H148N10O9Si10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In methanol at 50℃; for 168h;
In methanol
Reference： [1]Lu, Hang; Feng, Linglong; Li, Shusheng; Zhang, Jie; Lu, Haifeng; Feng, Shengyu [Macromolecules, 2015, vol. 48, # 3, p. 476 - 482]
[2]Lu, Hang; Hu, Ziqi; Feng, Shengyu [Chemistry - An Asian Journal, 2017, vol. 12, # 11, p. 1213 - 1217]
  • 53
  • [ 2469-55-8 ]
  • C94H196N10O25Si10 [ No CAS ]
  • C166H388N26O25Si26 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In methanol at 50℃; for 168h;
In methanol
Reference： [1]Lu, Hang; Feng, Linglong; Li, Shusheng; Zhang, Jie; Lu, Haifeng; Feng, Shengyu [Macromolecules, 2015, vol. 48, # 3, p. 476 - 482]
[2]Lu, Hang; Hu, Ziqi; Feng, Shengyu [Chemistry - An Asian Journal, 2017, vol. 12, # 11, p. 1213 - 1217]
  • 54
  • [ 2469-55-8 ]
  • [ 104-87-0 ]
  • {3-[1,1,3,3-tetramethyl-3-(3-[1-p-tolylmeth-(E)-ylidene]amino}propyl)disiloxanyl]propyl}-[1-p-tolylmeth-(E)-ylidene]amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With magnesium sulfate In dichloromethane at 20℃; Synthesis of {3-[1,1,3,3-tetramethyl-3-(3-[1-p-tolyl-meth-(E)-ylidene]-amino}-propyl)-disiloxanyl]-propyl}-[1-p-tolyl-meth-(E)-ylidene]-amine (7) p-Tolualdehyde (0.25g, 2.01mmol) and 3-bis-(3-aminopropyl)tetramethyldisiloxane (0.50g, 2.01mmol) were added to a stirred suspension of anhydrous magnesium sulphate in dichloromethane and the reaction stirred at room temperature until the IR spectrum revealed complete loss of starting material. The mixture was filtered and removal of excess dichloromethane afforded ( 7) as an orange-brown oil (Yield: 92%) with no further purification. Analysis, calcd for C26H40N2Si2O: C 69.0, H 8.9, N 6.2%, found C 68.8, H 8.8, N 6.2%. 1H NMR (300MHz, CDCl3): δ=8.14 (s, 1H, HC=N), 7.54 (d, J=8.0Hz, 2H, CH), 7.14 (d, J=8.0Hz, 2H, CH), 3.50 (t, J=7.0Hz, 2H, CH2N=CH), 2.30 (s, 3H, CCH3), 1.65 (m, 2H, SiCH2CH2), 0.48 (m, 2H, SiCH2CH2), 0.02 (s, 6H, SiCH3); 13C NMR (75MHz, CDCl3): δ=160.2 (HC=N), 140.2 (CH), 133.4 (CH), 128.9 (CH), 127.7 (CH), 64.5 (CH2N=CH), 24.5 (CCH3), 21.1 (SiCH2CH2), 15.7 (SiCH2CH2), -0.4 (SiCH3); 29Si NMR (60MHz, CDCl3): δ=7.7
Reference： [1]Smith, Douglas R.G.; Kociok-Köhn, Gabriele; Molloy, Kieran C.; Price, Gareth J.; Short, Rhys D. [Journal of Organometallic Chemistry, 2015, vol. 778, p. 29 - 34]
  • 55
  • copper(II) choride dihydrate [ No CAS ]
  • [ 2469-55-8 ]
  • [ 37942-07-7 ]
  • C40H66CuN2O3Si2*1.5H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.5% Stage #1: 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane; 3,5-di-tert-butyl-2-hydroxybenzaldehyde In methanol; dichloromethane at 70℃; for 3h; Stage #2: copper(II) choride dihydrate In methanol; dichloromethane at 20℃; for 0.5h;
Reference： [1]Cazacu, Maria; Shova, Sergiu; Soroceanu, Alina; Machata, Peter; Bucinsky, Lukas; Breza, Martin; Rapta, Peter; Telser, Joshua; Krzystek; Arion, Vladimir B. [Inorganic Chemistry, 2015, vol. 54, # 12, p. 5691 - 5706]
  • 56
  • [ 2469-55-8 ]
  • [ 37942-07-7 ]
  • [ 6156-78-1 ]
  • C42H69MnN2O5Si2*0.15H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
47.1% Stage #1: 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane; 3,5-di-tert-butyl-2-hydroxybenzaldehyde In methanol; dichloromethane at 70℃; for 3h; Stage #2: manganese (II) acetate tetrahydrate In methanol; ethanol; dichloromethane at 20℃;
Reference： [1]Cazacu, Maria; Shova, Sergiu; Soroceanu, Alina; Machata, Peter; Bucinsky, Lukas; Breza, Martin; Rapta, Peter; Telser, Joshua; Krzystek; Arion, Vladimir B. [Inorganic Chemistry, 2015, vol. 54, # 12, p. 5691 - 5706]
  • 57
  • [ 463-71-8 ]
  • [ 2469-55-8 ]
  • 1,3-bis(3-isothiocyanatopropyl)-1,1,3,3-tetramethyldisiloxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 2.5h; Reflux;
Reference： [1]Frański, Rafał; Gierczyk, Błazej; Markiewicz, Grzegorz; Kozik, Tomasz [Rapid Communications in Mass Spectrometry, 2015, vol. 29, # 23, p. 2272 - 2278]
  • 58
  • [ 12288-75-4 ]
  • [ 2469-55-8 ]
  • C22H36FeN4O3Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In chloroform; toluene at 20℃; for 24h; 2.3 Synthesis of ferrocenylsiloxane urea, FSU A 25mL toluene solution of 1,1′-diisocyanateferrocene (Fc(NCO)2) (1g, 3.7mmol) and a 25mL chloroform solution of 1,3-bis(3-aminopropyl)tetramethyldisiloxane (0.93g, 3.7mmol) were stirred together for 24h at room temperature. The solvent was removed under vacuum to yield a solid yellow product. The crude compound was purified by washing 3× with Et2O. The product was filtered, and dried under vacuum to give a yellow solid (1.2g, 65%). Suitable crystals for X-ray diffraction were obtained after crystallization in acetone. 1H NMR (DMSO-d6, 400MHz) δ (ppm): 0.07 (s, 12H, -Si(CH3)2-O-Si(CH3)2-), 0.51 (t, J=8.4Hz, 4H, -CH2-CH2-CH2-Si-), 1.49 (m, 4H, -CH2-CH2-CH2-Si-), 3.06 (q, J=6.2Hz, 4H, -CH2-CH2-CH2-Si-), 3.86, 4.27 (2s, 8H, Fc), 5.93 (t, J=4.4Hz, 2H, Fc-NH-CO-NH), 7.33 (s, 2H, Fc-NH-CO-NH). Anal. Calc. for dimer, according to XRD data C44H76Fe2N8O8Si4 (Mr 1069.19g/mol): C, 49.43; H, 7.16; N, 10.48. Found: C, 49.65; H, 7.27; N, 10.38%.
Reference： [1]Dascalu, Mihaela; Balan, Mihaela; Shova, Sergiu; Racles, Carmen; Cazacu, Maria [Polyhedron, 2015, vol. 102, p. 583 - 592]
  • 59
  • [ 527-69-5 ]
  • [ 2469-55-8 ]
  • C20H32N2O5Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With dmap; triethylamine In dichloromethane at 20℃; for 24h; Cooling with ice;
Reference： [1]Zhao, Jian; Xu, Rui; Luo, Gaoxing; Wu, Jun; Xia, Hesheng [Journal of Materials Chemistry B, 2016, vol. 4, # 5, p. 982 - 989]
  • 60
  • [ 2469-55-8 ]
  • [ 15859-67-3 ]
YieldReaction ConditionsOperation in experiment
60% With nickel(II) chloride heptahydrate; 4(5)formylimidazole In methanol; dichloromethane at 75℃; for 4h; Obtaining AP02*HCl, 1 0.119 g (0.50 mmol) NiCl2x7H2O dissolved in a solvent mixtureformed by 4 ml methanol and 2 ml methylene chloride wasadded over the solution consisting in 0.1326 ml (0.50 mmol) 1,3-bis(3-aminopropyl)tetramethyldisiloxane and 0.0961 g(1 mmol) 4-imidazolecarboxaldehyde in 2.5 ml methanol in a50 ml one-necked round-bottom flask. The reaction mixture wasstirred for 4 h at 75 °C, after which was allowed to stay in a closedflask at room temperature. Formation of colorless prismatic crystalswas observed after about 2 days.These were separated by filtration washed with diethyl ether,dried and analyzed. Yield 0.0964 g (60%). C10H30Cl2N2OSi2(321.44 g/mol): calcd. C 37.36, H 9.40, N 8.71; found C 37.24, H9.14, N 8.65.IR (KBr pellet, selected bands): 3436 (w), 3009 (w), 2954 (s),2923 (m, CAH from SiACH3), 2898 (m), 2876 (m), 2796 (vw),2708 (vw), 2542 (vw), 2448 (vw), 1643 (s), 1636 (s), 1600 (m),1576 (m), 1553 (m), 1507 (m), 1459 (m, CH2), 1407 (m), 1333(m), 1253 (vs, SiACH3), 1183 (m), 1058 (vs, SiAOASi), 944 (w),840 (vs), 795 (s, SiACH3), 771 (s), 704 (w), 632 (vw), 608 (w),568 (vw), 485 (vw), 456 (vw).
With hydrogenchloride In diethyl ether
Reference： [1]Bargan, Alexandra; Cazacu, Maria; Dascalu, Mihaela; Macsim, Ana-Maria; Macsim, Ioan Florin; Soroceanu, Alina [Polyhedron, 2020, vol. 179]
[2]Echalier, Cécile; Kalistratova, Aleksandra; Ciccione, Jérémie; Lebrun, Aurélien; Legrand, Baptiste; Naydenova, Emilia; Gagne, Didier; Fehrentz, Jean-Alain; Marie, Jacky; Amblard, Muriel; Mehdi, Ahmad; Martinez, Jean; Subra, Gilles [RSC Advances, 2016, vol. 6, # 39, p. 32905 - 32914]
  • 61
  • [ 2469-55-8 ]
  • [ 90-02-8 ]
  • C24H36N2O3Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% In methanol for 10h; Reflux; 1 2.2.1. H2L1 H2L1 was synthesized according to an already described procedure [32] , which consists in refluxing methanolic solution of a mixture of 1,3-bis(3-aminopropyl)tetramethyldisiloxane and 2-hydroxybenzaldehyde in a 1:2 molar ratio for 10 h. The reaction product, a yellow oil, was isolated by precipitation in water, decanting, washing with methanol and diethyl ether, and then drying. Yield: 95%; IR (KBr), νmax (cm-1): 3059 m, 3007w (aromatic C-H), 2949s, 2926s, (aliphatic -CH3), 2885s (aliphatic -CH2-), 1628vs (-CH=N-), 1252s (-Si-CH3), 1045vs (-Si-O-Si-), 833vs (-Si-CH3); 1H NMR (CDCl3), δ (ppm): 13.69 (s, 2H, -OH), 8.31 (s, 2H, -CH=N-), 7.32-7.23 (m, 4H, aromatic-H), 7.01-6.84 (m, 4H, aromatic-H), 3.61-3.55 (m, 4H, -CH2-CH2-CH2-Si-), 1.75-1.68 (m, 4H, -CH2-CH2-CH2-Si-), 0.69-0.55 (m, 4H, -CH2-CH2-CH2-Si-), 0.08 (s, 12H, Si-CH3) (Fig. 1S); UV-Vis (λmax, nm, DMF): 316 (11546), 402(365).
Reference： [1]Vlad, Angelica; Zaltariov, Mirela-Fernanda; Shova, Sergiu; Cazacu, Maria; Avadanei, Mihaela; Soroceanu, Alina; Samoila, Petrisor [Polyhedron, 2016, vol. 115, p. 76 - 85]
  • 62
  • zinc perchlorate [ No CAS ]
  • [ 2469-55-8 ]
  • [ 90-02-8 ]
  • C24H34N2O3Si2Zn [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: zinc perchlorate; salicylaldehyde In methanol at 20℃; for 0.333333h; Stage #2: With pyridine In methanol at 20℃; for 2h; Stage #3: 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane In methanol for 2h; Reflux; 2.3. Synthesis of the complexes General procedure: The zinc(II) and copper(II) complexes (ZnL1 and CuL2) were preparedby a template procedure. For this, a solution of the salt(Zn(ClO4)26H2O or Cu(ClO4)22H2O) (1mmol) in methanol (10 mL)was slowly added to a solution of aldehyde (salicylaldehyde oro-vanillin) (1 mmol) in methanol (30 mL). The mixture was stirredat room temperature for 20 min, then a solution of pyridine(2 mmol) in methanol (10 mL) was added dropwise and the resultantmixture was stirred for 2 h at room temperature. Finally, asolution of 1,3-bis(3-aminopropyl)tetramethyldisiloxane (1 mmol)in methanol (10 mL) was gradually added to the mixture and stirredwith refluxing for 2 h. Crystallization by slow evaporation ofthe solvent or from a DMF solution led to obtain ZnL1 or CuL2 singlecrystals, respectively.Crystals were also obtained when a solution of the metal saltwas added to a solution of the ligand in the presence of an excessof pyridine, followed by slow evaporation of the solvent. Similarstructures were determined from crystals obtained by bothmethods.2.3.1. ZnL1Color: yellow crystals; Yield: 68%; M.p.: 155 °C; IR (KBr), νmax(cm1): 3051w, 3026w (aromatic C-H), 2947m, 2924m (aliphatic-CH3), 2905m, 2878w (aliphatic -CH2-), 1626vs (-CHN-),1254vs (-Si-CH3), 1078vs (-Si-O-Si-), 837s (-Si-CH3), 465m(Zn-O), 386w (Zn-N) (Fig. 3S); 1H NMR (CDCl3), δ (ppm): 8.12 (s,2H, -CH = N-), 7.32-7.28 (m, 2H, aromatic-H), 7.15-7.13 (m, 2H,aromatic-H), 6.84 (d, 2H, aromatic-H), 6.63-6.59 (m, 2H, aromatic-H), 4.21-4.19 (m, 2H, -CH2-CH2-CH2-Si-), 3.15-3.09 (m,2H, -CH2-CH2-CH2-Si-), 1.88-1.72 (m, 2H, -CH2-CH2-CH2-Si-),1.71-1.53 (m, 2H, -CH2-CH2-CH2-Si-), 0.66-0.58 (m, 2H, -CH2-CH2-CH2-Si-), 0.27-0.18 (m, 2H, -CH2-CH2-CH2-Si-), 0.03 (s,12H, Si-CH3).Anal. Calc. for C24H34N2O3Si2Zn (Mr 520.08 g/mol): C, 55.37; H,6.53; N, 5.38. Found: C, 55.48; H, 6.36; N, 5.39; ESI-MS (methanol),positive: m/z 519.44 ([M]+), 541.32 ([M + Na]+), 1039.32 ([2M+]),1063.40 ([2M + Na]+), 1583.72 ([3M + Na]+) (Fig. 4S); UV-Vis(λmax, nm, DMF): 368 (11341).
Reference： [1]Vlad, Angelica; Zaltariov, Mirela-Fernanda; Shova, Sergiu; Cazacu, Maria; Avadanei, Mihaela; Soroceanu, Alina; Samoila, Petrisor [Polyhedron, 2016, vol. 115, p. 76 - 85]
  • 63
  • [ 2469-55-8 ]
  • [ 148-53-8 ]
  • C26H40N2O5Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% In methanol; chloroform at 20℃; for 8h; Reflux; 2 2.2.2. H2L2 The Schiff base H2L2 was prepared as follows. A solution of 1,3-bis(3-aminopropyl)tetramethyldisiloxane (0.5 mmol) in methanol-chloroform mixture (8 mL, 2:1 v/v) was slowly added to a solution of o-vanillin (1 mmol) in methanol-chloroform mixture (8 mL, 2:1 v/v). ;The reaction mixture was stirred at room temperature for 2 h and then refluxed for 6 h. After cooling at room temperature, the product was separated, washed with methanol and diethyl ether, and then dried. Color: red oil; Yield: 98%; IR (KBr), νmax (cm-1): 3059vw, 2999w (aromatic C-H), 2953m, 2932m (aliphatic -CH3), 2837m (aliphatic -CH2-), 1632s (-CH=N-), 1254vs (-Si-CH3), 1051s (-Si-O-Si-), 839s (-Si-CH3); 1H NMR (CDCl3), δ (ppm): 14.22 (s, 2H, -OH), 8.28 (s, 2H, -CH=N-), 6.90-6.84 (m, 4H, aromatic-H), 6.78-6.74 (m, 2H, aromatic-H), 3.88 (s, 6H, -CH3), 3.58-3.55 (m, 4H, -CH2-CH2-CH2-Si-), 1.73-1.65 (m, 4H, -CH2-CH2-CH2-Si-), 0.59-0.55 (m, 4H, -CH2-CH2-CH2-Si-), 0.05 (s, 12H, Si-CH3) (Fig. 2S); UV-Vis (λmax, nm, DMF): 330 (5738),420 (770).
Reference： [1]Vlad, Angelica; Zaltariov, Mirela-Fernanda; Shova, Sergiu; Cazacu, Maria; Avadanei, Mihaela; Soroceanu, Alina; Samoila, Petrisor [Polyhedron, 2016, vol. 115, p. 76 - 85]
  • 64
  • copper(II) perchlorate dihydrate [ No CAS ]
  • [ 2469-55-8 ]
  • [ 148-53-8 ]
  • C26H38CuN2O5Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% Stage #1: copper(II) perchlorate dihydrate; 3-methoxy-2-hydroxybenzaldehyde In methanol at 20℃; for 0.333333h; Stage #2: With pyridine In methanol at 20℃; for 2h; Stage #3: 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane In methanol for 2h; Reflux; 2.3. Synthesis of the complexes General procedure: The zinc(II) and copper(II) complexes (ZnL1 and CuL2) were preparedby a template procedure. For this, a solution of the salt(Zn(ClO4)26H2O or Cu(ClO4)22H2O) (1mmol) in methanol (10 mL)was slowly added to a solution of aldehyde (salicylaldehyde oro-vanillin) (1 mmol) in methanol (30 mL). The mixture was stirredat room temperature for 20 min, then a solution of pyridine(2 mmol) in methanol (10 mL) was added dropwise and the resultantmixture was stirred for 2 h at room temperature. Finally, asolution of 1,3-bis(3-aminopropyl)tetramethyldisiloxane (1 mmol)in methanol (10 mL) was gradually added to the mixture and stirredwith refluxing for 2 h. Crystallization by slow evaporation ofthe solvent or from a DMF solution led to obtain ZnL1 or CuL2 singlecrystals, respectively.Crystals were also obtained when a solution of the metal saltwas added to a solution of the ligand in the presence of an excessof pyridine, followed by slow evaporation of the solvent. Similarstructures were determined from crystals obtained by bothmethods.
Reference： [1]Vlad, Angelica; Zaltariov, Mirela-Fernanda; Shova, Sergiu; Cazacu, Maria; Avadanei, Mihaela; Soroceanu, Alina; Samoila, Petrisor [Polyhedron, 2016, vol. 115, p. 76 - 85]
  • 65
  • [ 1185-55-3 ]
  • [ 2469-55-8 ]
  • C16H45N3O3Si4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
43.9 kg With tetramethyl ammoniumhydroxide at 50℃; for 30h; Large scale; 1 Example 1 To a reaction vessel, add methyltrimethoxysilane 13.6Kg (100mol), 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane 124.3Kg (500mol), tetramethylammonium hydroxide 0.72Kg (8mol). Dissolve by heating. The temperature controlled at 50 deg.C. After reacting for 30 hours, heat to 140 deg.C, the catalyst deactivated. Vacuum distillation removed excess material to obtain triaminopropyl terminated cyclotetrasiloxane 43.9Kg (100mol). Add formic acid 13.8Kg (300mol). Use dichloromethane as solvent. At 50 deg.C, react for 5 hours. and the solvent was evaporated dichloromethane and excess raw materials, and vacuum dried to give the ionic liquid surfactant cyclotetrasiloxane 57.7Kg.
Reference： [1]Current Patent Assignee: CHANGSHU INSTITUTE OF TECHNOLOGY - CN105732686, 2016, A Location in patent: Paragraph 0029; 0030
  • 66
  • C26H32N2O5Si2 [ No CAS ]
  • [ 2469-55-8 ]
YieldReaction ConditionsOperation in experiment
11.9 g With hydrazine hydrate In ethanol at 70 - 110℃; for 4h; Inert atmosphere; 1 Synthesis of 1,3-bis(3'-aminopropyl)-1,1,3,3-tetramethyldisiloxane 250ml three neck flask was added N- allylbenzene imide 26.6g, 100ml of toluene, purged with argon, and then stirred isopropanol solution was added 1.0ml of chloroplatinic acid after the solid was dissolved, then add 1,1, 3,3-tetramethyldisiloxane 12.6g, heating temperature, and at 60 C ~ 130 Cmaintain 8h C, then cooled to 30 C C, at 110 , 1.3KPa distilled toluene and low viscosity, the solid obtained containing double phthalimide siloxane dimethylsiloxane structure, characteristic absorption peaks of an imide 1712,1770cm-1 , a Si-O absorption peak of a Si-1066cm -1 . 1L three-necked flask containing 17g of polydimethylsiloxane structure of a dual phthalimide silicone and 500ml of ethanol, then add 20g of hydrazine hydrate, which leads to N2And the temperature was raised to 70 C the C ~ 110 Cthe C maintained 4h, then cooled to room temperature, the solid was removed by filtration, the filtrate was evaporated under reduced pressure to give the solvent 11.9g1,3- bis (3'-aminopropyl) -1,1, 3,3-tetramethyldisiloxane liquid.
Reference： [1]Current Patent Assignee: Nanchang University; Liu, Feng; Wang, Xiulong; Qi, Haixia - CN102276639, 2016, B Location in patent: Paragraph 0033; 0034; 0036
  • 67
  • [ 2469-55-8 ]
  • [ 79-30-1 ]
  • N,N′-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))bis(2-methylpropanamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In dichloromethane at 0 - 20℃; for 1h; 33 N,N′-((1,1,3,3-Tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))bis(2-methylpropanamide) [Example 33] A solution of 48 3,3′-(1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propan-1-amine) (1 g, 4.03 mmol) in 88 DCM (10 mL) at 0° C. was charged with 49 triethyl amine (1.4 mL, 10.0 mmol) and 200 isobutyryl chloride (0.92 mL, 8.80 mmol) and stirred at room temperature for 1 h. The solid precipitated was filtered, washed with diethyl ether and the filtrate was concentrated in vacuo resulting in the crude 198 compound which was purified by column chromatography on silica gel eluting with 10-40% ethyl acetate in n-hexane to afford 1.25 g, 80% yield, of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=7.66 (br. s, 2H), 2.95 (d, J=6.36 Hz, 4H), 2.29 (t, J=6.60 Hz, 2H), 1.31-1.40 (m, 4H), 0.95 (d, J=6.85 Hz, 12H), 0.38-0.47 (m, 4H), 0.00 (s, 12H); MS-ELSD (ES+): m/z=411.00 [M+Na]+; LCMS: tR=2.72 min.
Reference： [1]Current Patent Assignee: BLINKBIO - US2017/202970, 2017, A1 Location in patent: Paragraph 0505; 0513; 0514
  • 68
  • [ 2469-55-8 ]
  • [ 383-63-1 ]
  • N,N′-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))bis(2,2,2-trifluoroacetamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 1h; 54 N,N′-((1,1,3,3-Tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))bis(2,2,2-trifluoroacetamide) (2) A solution of 48 3,3′-(1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propan-1-amine) (1 g, 4.03 mmol) was charged with 351 ethyl 2,2,2-trifluoroacetate (1.70 g, 12.09 mmol) and stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo until dryness to afford 1.76 g, 80% yield, of the title compound as colorless oil. The crude compound was used directly for next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ=9.40 (br. s, 2H), 3.13 (q, J=6.85 Hz, 4H), 1.47 (td, J=7.83, 15.65 Hz, 4H), 0.42-0.50 (m, 4H), 0.03 (s, 12H).
Reference： [1]Current Patent Assignee: BLINKBIO - US2017/202970, 2017, A1 Location in patent: Paragraph 0603; 0606; 0607
  • 69
  • [ 2469-55-8 ]
  • [ 75-36-5 ]
  • N,N’-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))diacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In diethyl ether at 0 - 20℃; for 1h; 18 N,N′-((1,1,3,3-Tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))diacetamide [Example 18] A solution of 48 3,3′-(1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propan-1-amine) (2 g, 8.04 mmol) in 15 diethyl ether (100 mL) at 0° C. was charged with 49 triethyl amine (2.8 mL, 20.1 mmol) and 50 acetyl chloride (1.4 mL, 19.2 mmol) and stirred at room temperature for 1 h. The 46 solid precipitated was filtered, washed with diethyl ether and the filtrate was concentrated in vacuo resulting in 2.67 g of the title compound as colorless oil. The crude compound was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ=7.77 (br. s, 2H), 2.94 (d, J=6.36 Hz, 4H), 1.69-1.83 (m, 6H), 1.35 (d, J=6.85 Hz, 4H), 0.36-0.50 (m, 4H), 0.00 (s, 12H), 1H NMR (400 MHz, CDCl3) δ=6.04 (br. s, 1H), 3.21 (q, J=6.68 Hz, 4H), 1.93-2.07 (m, 6H), 1.53 (td, J=7.83, 15.65 Hz, 4H), 0.46-0.55 (m, 4H), 0.05 (s, 12H); MS (ESMS+): m/z=355.05 [M+Na]+; ESMS: tR=0.13 min, m/z=377.00 [M+2Na]+; ESMS: tR=0.15 min; MS (ES+): m/z=333.00 [M+H]+; LCMS: tR=2.07 min.
With triethylamine In diethyl ether at 0 - 20℃; for 1h; 21 Example 21: N,N'-((1,1,3,3-Tetramethyldisiloxane-1,3-diyl)bis(propane-3,1- diyl))diacetamide Example 21: N,N'-((1,1,3,3-Tetramethyldisiloxane-1,3-diyl)bis(propane-3,1- diyl))diacetamide (0290) [00141] A solution of 3,3'-(1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propan-1-amine) (2 g, 8.04 mmol) in diethyl ether (100 mL) at 0 oC was charged with triethyl amine (2.8 mL, 20.1 mmol) and acetyl chloride (1.4 mL, 19.2 mmol) and stirred at room temperature for 1 h. The solid precipitated was filtered, washed with diethyl ether and the filtrate was concentrated in vacuo resulting in 2.67 g of the title compound as colorless oil. The crude compound was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ = 7.77 (br. s, 2 H), 2.94 (d, J = 6.36 Hz, 4 H), 1.69 - 1.83 (m, 6 H), 1.35 (d, J = 6.85 Hz, 4 H), 0.36 - 0.50 (m, 4 H), 0.00 (s, 12 H), 1H NMR (400 MHz, CDCl3) δ = 6.04 (br. s, 1 H), 3.21 (q, J = 6.68 Hz, 4 H), 1.93 - 2.07 (m, 6 H), 1.53 (td, J = 7.83, 15.65 Hz, 4 H), 0.46 - 0.55 (m, 4 H), 0.05 (s, 12 H); MS (ESMS+): m/z = 355.05 [M + Na]+; ESMS: tR = 0.13 min, m/z = 377.00 [M + 2Na]+; ESMS: tR = 0.15 min; MS (ES+): m/z = 333.00 [M + H]+; LCMS: tR = 2.07 min.
Reference： [1]Current Patent Assignee: BLINKBIO - US2017/202970, 2017, A1 Location in patent: Paragraph 0415; 0420; 0421
[2]Current Patent Assignee: BLINKBIO - WO2017/214491, 2017, A1 Location in patent: Paragraph 00141
  • 70
  • [ 2469-55-8 ]
  • [ 123-54-6 ]
  • C20H40N2O3Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium cerium (IV) nitrate In methanol at 20℃; 2. General procedure for the synthesis of symmetrical bispyrrole derivatives 1under solvent-free high-speed vibration milling (HSVM) conditions General procedure: The suitable ketone (1 mmol), N-iodosuccinimide (NIS, 1 mmol) and ptoluenesulphonic acid (PTSA, 10 mol %) were added to a commercially availablesnap closure grinding jar, along with a zirconium oxide ball. This ball mill vessel wasfitted to one of the horizontal vibratory arms of the ball mill, while the other arm wasoccupied with an empty vessel. The ball mill was set to vibrate at a frequency of20 s-1 for 60 min at room temperature. Then, a mixture of the corresponding diamine(0.85 mmol), the suitable -dicarbonyl compound (1.3 mmol) and cerium(IV)ammonium nitrate (CAN, 0.13 mmol) in 0.5 mL of methanol was stirred at roomtemperature during 30-60 min (judged by TLC), and the solvent was evaporated.The residue was transferred to the milling vessel with a Pasteur pipette or a spatulaand silver nitrate (1 mmol) was added. The reaction was subjected to the vibratorymovement at 20 s-1 for 60 min, affording a dark paste. Then, the reaction vessel wascleansed with ethyl acetate or dichloromethane and the suspension was filtered toremove the silver iodide precipitate. The organic layer was washed with water (2 mL),dried over anhydrous sodium sulfate and the solvent was removed under reducedpressure. Purification by flash column chromatography on silica gel eluting with agradient from petroleum ether to 8:2 petroleum ether-ethyl acetate afforded thedesired pyrrole derivatives. Compounds 1h, 1i and 1j were purified by flashchromatography eluting with a 98/2 dichloromethane/methanol mixture.
With ammonium cerium (IV) nitrate In methanol at 20℃; for 12h;
Reference： [1]Leonardi, Marco; Villacampa, Mercedes; Menéndez, J. Carlos [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1957 - 1962]
[2]Leonardi, Marco; Estévez, Verónica; Villacampa, Mercedes; Menéndez, J. Carlos [Advanced Synthesis and Catalysis, 2019, vol. 361, # 9, p. 2054 - 2074]
  • 71
  • [ 2469-55-8 ]
  • [ 105-45-3 ]
  • [ 83-33-0 ]
  • dimethyl 1,1'-[(1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl)]bis(2-methyl-1,4-dihydroindeno[1,2-b]pyrrole-3-carboxylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: inden-1-one With iodine; copper(II) oxide In methanol at 20℃; for 1h; Stage #2: 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane; acetoacetic acid methyl ester With ammonium cerium (IV) nitrate In methanol at 20℃; Stage #3: With silver nitrate for 1h; Milling;
Reference： [1]Leonardi, Marco; Villacampa, Mercedes; Menéndez, J. Carlos [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1957 - 1962]
  • 72
  • [ 2469-55-8 ]
  • [ 105-50-0 ]
  • C28H52N2O9Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium cerium (IV) nitrate In methanol at 20℃; 2. General procedure for the synthesis of symmetrical bispyrrole derivatives 1under solvent-free high-speed vibration milling (HSVM) conditions General procedure: The suitable ketone (1 mmol), N-iodosuccinimide (NIS, 1 mmol) and ptoluenesulphonic acid (PTSA, 10 mol %) were added to a commercially availablesnap closure grinding jar, along with a zirconium oxide ball. This ball mill vessel wasfitted to one of the horizontal vibratory arms of the ball mill, while the other arm wasoccupied with an empty vessel. The ball mill was set to vibrate at a frequency of20 s-1 for 60 min at room temperature. Then, a mixture of the corresponding diamine(0.85 mmol), the suitable -dicarbonyl compound (1.3 mmol) and cerium(IV)ammonium nitrate (CAN, 0.13 mmol) in 0.5 mL of methanol was stirred at roomtemperature during 30-60 min (judged by TLC), and the solvent was evaporated.The residue was transferred to the milling vessel with a Pasteur pipette or a spatulaand silver nitrate (1 mmol) was added. The reaction was subjected to the vibratorymovement at 20 s-1 for 60 min, affording a dark paste. Then, the reaction vessel wascleansed with ethyl acetate or dichloromethane and the suspension was filtered toremove the silver iodide precipitate. The organic layer was washed with water (2 mL),dried over anhydrous sodium sulfate and the solvent was removed under reducedpressure. Purification by flash column chromatography on silica gel eluting with agradient from petroleum ether to 8:2 petroleum ether-ethyl acetate afforded thedesired pyrrole derivatives. Compounds 1h, 1i and 1j were purified by flashchromatography eluting with a 98/2 dichloromethane/methanol mixture.
Reference： [1]Leonardi, Marco; Villacampa, Mercedes; Menéndez, J. Carlos [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1957 - 1962]
  • 73
  • [ 2469-55-8 ]
  • [ 105-45-3 ]
  • C20H40N2O5Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium cerium (IV) nitrate In methanol at 20℃; 2. General procedure for the synthesis of symmetrical bispyrrole derivatives 1under solvent-free high-speed vibration milling (HSVM) conditions General procedure: The suitable ketone (1 mmol), N-iodosuccinimide (NIS, 1 mmol) and ptoluenesulphonic acid (PTSA, 10 mol %) were added to a commercially availablesnap closure grinding jar, along with a zirconium oxide ball. This ball mill vessel wasfitted to one of the horizontal vibratory arms of the ball mill, while the other arm wasoccupied with an empty vessel. The ball mill was set to vibrate at a frequency of20 s-1 for 60 min at room temperature. Then, a mixture of the corresponding diamine(0.85 mmol), the suitable -dicarbonyl compound (1.3 mmol) and cerium(IV)ammonium nitrate (CAN, 0.13 mmol) in 0.5 mL of methanol was stirred at roomtemperature during 30-60 min (judged by TLC), and the solvent was evaporated.The residue was transferred to the milling vessel with a Pasteur pipette or a spatulaand silver nitrate (1 mmol) was added. The reaction was subjected to the vibratorymovement at 20 s-1 for 60 min, affording a dark paste. Then, the reaction vessel wascleansed with ethyl acetate or dichloromethane and the suspension was filtered toremove the silver iodide precipitate. The organic layer was washed with water (2 mL),dried over anhydrous sodium sulfate and the solvent was removed under reducedpressure. Purification by flash column chromatography on silica gel eluting with agradient from petroleum ether to 8:2 petroleum ether-ethyl acetate afforded thedesired pyrrole derivatives. Compounds 1h, 1i and 1j were purified by flashchromatography eluting with a 98/2 dichloromethane/methanol mixture.
With ammonium cerium (IV) nitrate In methanol at 20℃; for 12h;
Reference： [1]Leonardi, Marco; Villacampa, Mercedes; Menéndez, J. Carlos [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1957 - 1962]
[2]Leonardi, Marco; Estévez, Verónica; Villacampa, Mercedes; Menéndez, J. Carlos [Advanced Synthesis and Catalysis, 2019, vol. 361, # 9, p. 2054 - 2074]
  • 74
  • [ 2469-55-8 ]
  • [ 98-09-9 ]
  • N,N’-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))dibenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine In dichloromethane at 0 - 20℃; for 1h; 36 RRN 229N,N′-((1,1,3,3-Tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl)) dibenzenesulfonamide (2) A solution of 230 3 3,3′-(1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propan-1-amine) (1 g, 4.03 mmol) in 211 dichloromethane (50 mL) at 0° C. was charged with 49 triethyl amine (1.4 mL, 10.08 mmol) and 231 benzenesulfonyl chloride (1.56 g, 8.87 mmol) and stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo, diluted with diethyl ether and stirred for 15 min. The solid was filtered and the filtrate was concentrated in vacuo resulting in the crude 38 compound which was purified by column chromatography on silica gel eluting with 15-25% ethyl acetate in n-hexane to afford 1.89 g, 89% yield, of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=7.85 (d, J=7.34 Hz, 4H), 7.62-7.72 (m, 8H), 2.76 (q, J=6.68 Hz, 4H), 1.38 (td, J=7.83, 15.65 Hz, 4H), 0.39-0.47 (m, 4H), 0.00 (s, 12H).
Reference： [1]Current Patent Assignee: BLINKBIO - US2017/202970, 2017, A1 Location in patent: Page/Page column 0524; 0531; 0532
  • 75
  • [ 2469-55-8 ]
  • [ 28920-43-6 ]
  • bis-((9H-fluoren-9-yl)methyl)((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))dicarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; 45 Bis((9H-fluoren-9-yl)methyl)((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))dicarbamate (3) A solution of 48 3,3′-(1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propan-1-amine) (3 g, 12 mmol) in 88 DCM (60 mL) was charged with 58 DIPEA (4.68 g, 36 mmol) and 275 Fmoc-Cl (6.8 g, 26.6 mmol) and stirred at room temperature for 1 h. The reaction mixture was diluted with water and separated organic layer was dried over sodium sulphate. The organic layer was diluted with 10% methanol in DCM and concentrated in vacuo resulting in the crude 276 compound. The crude compound was stirred in methanol, filtered and dried to afford 7.96 g, 95% yield of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=7.89 (d, J=7.34 Hz, 4H), 7.68 (d, J=7.34 Hz, 4H), 7.38-7.44 (m, 4H), 7.32 (t, J=7.34 Hz, 4H), 4.29 (d, J=6.85 Hz, 4H), 4.21 (d, J=6.36 Hz, 2H), 4.04 (q, J=7.17 Hz, 2H), 2.95 (q, J=6.52 Hz, 4H), 1.41 (td, J=7.58, 15.16 Hz, 4H), 0.43-0.50 (m, 4H), 0.04 (s, 12H).
Reference： [1]Current Patent Assignee: BLINKBIO - US2017/202970, 2017, A1 Location in patent: Page/Page column 0552; 0557; 0558
  • 76
  • [ 2469-55-8 ]
  • [ 107-13-1 ]
  • C22H40N6OSi2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In methanol at 50℃; for 48h;
Reference： [1]Lu, Hang; Hu, Ziqi; Feng, Shengyu [Chemistry - An Asian Journal, 2017, vol. 12, # 11, p. 1213 - 1217]
  • 77
  • [ 2469-55-8 ]
  • 1-azido-3,6,9,12,15-pentaoxaoctadecan-18-oic acid [ No CAS ]
  • N,N'-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))bis(1-azido-3,6,9,12,15-pentaoxaoctadecan-18-amide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-azido-3,6,9,12,15-pentaoxaoctadecan-18-oic acid With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Stage #2: 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane
Reference： [1]Current Patent Assignee: BLINKBIO - WO2017/214491, 2017, A1 Location in patent: Paragraph 00182
  • 78
  • [ 3277-26-7 ]
  • [ 107-11-9 ]
  • [ 2469-55-8 ]
YieldReaction ConditionsOperation in experiment
80.56% at 80 - 110℃; for 6h; Inert atmosphere; 2 Example 2: In 1000mL stainless steel autoclave was added 125.4g (2.2mol) allylamine,134.3 g (1 mol) of tetramethyldisiloxane, 0.2 g of Carnar's reagent,Replace the reactor with nitrogen air 8 times, into the pressure of 0.5MPa nitrogen placed in the oil bath,Stirring and warming to 80 ° C for 3h, then warmed to 110 ° C for 3h,After the reaction is over, the mixture is cooled to room temperature; the distillate fraction (99-101 ° C / 2mmHg) is collected after distilling off the low boiler,200.2 g of product 1,3-bis (γ-aminopropyl) -1,1 ', 3,3'-tetramethyldisiloxane, purity of 98.9%The yield is 80.56%.
107.35 g With supported cis-dichlorobis(diethylsulfide)platinum (II) catalyst for 6.5h; Reflux; 1-4 (1) Dissolve 0.53g of cis-dichlorobis(diethylsulfide)platinum (II) in 15ml of ethanol, add 15.32g of white carbon black and stir evenly, then dry at 105°C to remove the solvent to obtain a supported cis -Dichlorobis(diethylsulfide)platinum(II) catalyst;(2) 128.45g allylamine, 120.88g 1,1,3,3-tetramethyldisiloxane and 0.58g supported cis-dichlorobis(diethylsulfide)platinum (II) catalyst Add to the flask with stirring and reflux device, react at reflux temperature for 6.5 hours, after the reaction, the reaction solution is lowered to room temperature, and the catalyst is filtered out;(3) The filtrate is distilled under reduced pressure, and the fraction with a top temperature of 132° C. under a pressure of 11 mm Hg (lit.) is collected to obtain 1,3-bis(3-aminopropyl)-1,1,3,3-tetrakis Methyldisiloxane 107.35g, the purity of the sample is 98.98% after testing.
Reference： [1]Current Patent Assignee: CHENGDU ZHENGWEI NEW MAT R D; CHINA ACADEMY OF ENGINEERING PHYSICS - CN106496261, 2017, A Location in patent: Paragraph 0020; 0021; 0022; 0023; 0024; 0025; 0026-0029
[2]Current Patent Assignee: JIANGXI BTL NEW MAT CO LTD - CN114292289, 2022, A Location in patent: Paragraph 0024-0041
  • 79
  • [ 2469-55-8 ]
  • [ 613-84-3 ]
  • C26H40N2O3Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In ethanol; chloroform for 4h; Reflux; 3.1. Preparation of the Schiff base ligand, H2L A mixture of 1,3-bis(3-aminopropyl)tetramethyldisiloxane(0.90 g, 4.00 mmol) and 5-methyl-2-hydroxy-benzaldehyde (0.33g, 2.00 mmol) in ethanol/chloroform (20 mL, 2:1 v/v) was stirredto reflux for 4 h and then cooled to room temperature. The solventwas removed at reduced pressure on a rotary evaporator, producinga yellow oil. This was washed with ethanol (10 mL) and diethylether (10 mL), and then dried in air. Yield: 1.05 g, 90%. Elementalanalysis, Calcd for C26H40N2O3Si2 (Mr 484.77): C, 64.42; H, 8.32;N, 5.78. Found: C, 64.46; H, 8.38; N, 5.72%. IR mmax (KBr), cm-1:3059w, 2953s, 2926s, 2864s, 1636vs, 1591s, 1493vs, 1445s,1402m, 1369m, 1342m, 1281s, 1254vs, 1226s, 1178s, 1130w,1057vs, 939m, 874s, 837vs, 818vs, 791vs, 737m, 706m, 665m,629w, 567m, 528vw, 515w, 459m, 401w. 1H NMR (CDCl3, 400MHz, ppm) d: 13.42 (s, 1H, -OH), 8.26 (s, 2H, -CHN), 7.12-7.09(m, 2H, Ar-H), 7.03-7.05 (d, 2H, Ar-H), 6.87-6.85 (d, 2H, Ar-H),3.57-3.54 (m, 4H, N-CH2-), 2.28 (s, 3H, -CH3), 1.74-1.66 (m, 4H,-CH2-), 0.58-0.54 (m, 4H, Si-CH2-), 0.06 (s, 12H, Si-CH3).
Reference： [1]Vlad, Angelica; Avadanei, Mihaela; Shova, Sergiu; Cazacu, Maria; Zaltariov, Mirela-Fernanda [Polyhedron, 2018, vol. 146, p. 129 - 135]
  • 80
  • [ 2469-55-8 ]
  • 3,3-diazidoindolin-2-one [ No CAS ]
  • 3,3'-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))bis(4-imino-3,4-dihydroquinazolin-2(1H)-one) [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 20h;
Reference： [1]Holzschneider, Kristina; Mohr, Fabian; Kirsch, Stefan F. [Organic Letters, 2018, vol. 20, # 22, p. 7066 - 7070]
  • 81
  • [ 2469-55-8 ]
  • [ 4181-05-9 ]
  • C48H54N4OSi2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% In dichloromethane at 20℃; for 24h; Molecular sieve; 1 Example 1 Synthesis of Fluorescent Probes Add aminopropyldisiloxane (1.24 g 5 mmol), 4-diphenylaminobenzaldehyde (2.73 g 10 mmol) dichloromethane (40.0 ml) to a 100 mL one-necked flask at a charge ratio of 1.0:2.0.Add appropriate amount of A4 molecular sieve to remove the water produced in the reaction, and stir at room temperature for 24 hours with a magnetic stirrer.After completion of the reaction, the excess impurities were removed by filtration through suction paper, and the excess solvent was removed by rotary evaporation to give Compound P1 (yield: 86%). A fluorescent probe Psi was prepared.
Reference： [1]Current Patent Assignee: UNIVERSITY OF JINAN (SHANDONG) - CN110066290, 2019, A Location in patent: Paragraph 0017
  • 82
  • [ 2469-55-8 ]
  • methyl 5-(1-methyl-1,4,5,6-tetrahydropyrimidin-2-yl)pentanecarboxylate [ No CAS ]
  • N,N'-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis-(propane-3,1-diyl))bis-(5-(1-methyl-1,4,5,6-tetrahydropyrimidin-2-yl))pentanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
9.8 g at 160℃; Amidine A6: methyl 5-(1-methyl-1,4,5,6-tetrahydropyrimidin-2-yl)pentanecarboxylate To an initial charge of 7.6 g (0.036 mol) of amidine A6, prepared as described above, in a round-bottom flask were added, while stirring, 4.5 g (0.018 mol) of bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane, and the mixture was heated gradually up to 160° C. under reduced pressure. After cooling to room temperature, 9.8 g of a dark-colored, odorless, low-viscosity liquid were obtained. FT-IR: 3307, 2926, 2861, 1737, 1645, 1605, 1549, 1437, 1403, 1364, 1309, 1250, 1185, 1137, 1040, 837, 792, 774, 698.
Reference： [1]Current Patent Assignee: SIKA AG - US2019/276412, 2019, A1 Location in patent: Paragraph 0280; 0281; 0282
  • 83
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  • [ 1262149-88-1 ]
  • C34H34N8O5Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol at 68℃; for 4h; Darkness; 1.2 (2) Weigh compound 2 (0.524 g, 2 mmol) obtained in step (1) and dissolve it in ethanol.Then aminopropyldisiloxane (0.249 g, 1 mmol) was added,The reaction was stirred at 68 ° C under reflux and protected from light for 4h.Then remove the ethanol from the reaction solution,Further purification was performed on a silica gel column with a volume ratio of 30: 1 dichloromethane and methanol as eluent to obtain compound 3.The obtained compound 3 was a fluorescent probe H-LDS.The 1H NMR spectrum is shown in Figure 1, and the 13C NMR spectrum is shown in Figure 2.
Reference： [1]Current Patent Assignee: UNIVERSITY OF JINAN (SHANDONG) - CN110372738, 2019, A Location in patent: Paragraph 0023-0025
  • 84
  • [ 2469-55-8 ]
  • 1,3-bis(3-ammoniumpropyl)tetramethyldisiloxane nitrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With copper(II) nitrate trihydrate; 4(5)formylimidazole In methanol; dichloromethane at 75℃; for 4h; Obtaining AP0*2NO3, 2 0.121 g (0.50 mmol) Cu(NO3)2x3H2O dissolved in a solventmixture formed by 4 ml methanol and 2 ml methylene chloridewas added over the solution consisting in 0.1326 ml (0.50 mmol)1,3-bis(3-aminopropyl)tetramethyldisiloxane and 0.0961 g(1 mmol) 4-imidazolecarboxaldehyde in 2.5 ml methanol in a50 ml one-necked round-bottom flask. The reaction mixture wasstirred for 4 h at 75 °C, after which was allowed to stay in a closedflask at room temperature. Formation of green prismatic crystalswas observed after about 4 days. These were separated by filtrationwashed with diethyl ether, dried and analyzed. Yield 0.1498 g(80%).C10H30N4O7Si2 (374.56 g/mol): calcd. C 32.06, H 8.07, N 14.96;found C 32.30, H 7.94, N 14.36.IR (KBr pellet, selected bands): 3527 (vw), 3442 (vw), 3386(vw), 3251 (vw), 3168 (w), 3111 (w), 3033 (w), 3018 (w), 3005(w), 2956 (m), 2929 (m, CAH from SiACH3), 2900 (w), 2858 (vw),2800 (vw), 2713 (vw), 2636 (vw), 2563 (vw), 2459 (vw), 2331(vw), 1733 (m), 1625 (w), 1606 (m), 1535 (w), 1382 (vs), 1359(vs), 1311 (s), 1251 (s, SiACH3), 1203 (m), 1164 (w), 1141 (w),1078 (s, SiAOASi), 1037 (s), 997 (m), 935 (m), 837 (s), 798 (s),767 (m), 732 (w), 705 (w), 663 (vw), 632 (w), 565 (vw), 528(vw), 462 (w), 393 (vw).
Reference： [1]Bargan, Alexandra; Cazacu, Maria; Dascalu, Mihaela; Macsim, Ana-Maria; Macsim, Ioan Florin; Soroceanu, Alina [Polyhedron, 2020, vol. 179]
  • 85
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  • [ 79-10-7 ]
  • C22H44N2O9Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 55℃; for 15h; Cooling with ice; Inert atmosphere; 2 Under ice-bath cooling, add 100g of dichloromethane to the dry round bottom flask, turn on the stirring,10g of 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane was added to dichloromethane, and then 25g of acrylic acid was slowly added dropwise to the mixed reaction system.After the addition is complete, the flask is transferred to an oil bath, the temperature is increased to 55°C, the condensed water is turned on, and the reflux reaction is continued for 15 hours under a nitrogen atmosphere.After the reaction is over, the reaction solution is cooled to room temperature, and most of the solvent and unreacted raw materials are removed by vacuum distillation.Finally, all residual impurities are removed in a vacuum drying oven, and a hard yellow solid at room temperature can be obtained.
Reference： [1]Current Patent Assignee: NANJING UNIVERSITY - CN111635424, 2020, A Location in patent: Paragraph 0062-0066
  • 86
  • [ 90-59-5 ]
  • [ 2469-55-8 ]
  • C24H32Br4N2O3Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% In dichloromethane at 20℃; for 1h; 2.3.2. Synthesis of the Schiff base H2L2 0.1 g (0.36mmol) 3,5-dibromosalicylaldehyde is dissolved in 10mLCH2Cl2, followed by 50 μL (0.18 mmol) of 1,3-bis(3-aminopropyl)tetramethyldisiloxane, and the reaction mixture immediately coloredin orange is stirred for 1 h at room temperature. After the specifiedtime, the solvent in the reaction mixture was removed by evaporationand the remaining cruel product was dissolved in a small amount ofCHCl3. For purification, the mixture is eluted trough the chromatographiccolumn with methanol. Yield 0,1379 g (95%). UV-vis (DMF,10-5 - 5 × 10-5 M), λmax, nm (ε, M-1 cm-1): 282 (36640), 333(7700), 421 (24188). IR (KBr), νmax, cm-1: 3419w, 2954s, 2925s,2854m, 2725w, 2553w, 2463w, 2044w, 1714w, 1635vs, 1556m,1516m, 1496w, 1444vs, 1375s, 1336m, 1284m, 1253vs, 1215m, 1170s,1134w, 1056vs, 962w, 947m, 862s, 840vs, 796vsm 779vs, 740s, 702s,688s, 632vw, 613vw, 597w, 559w, 459vw, 437vw. 1H NMR (DMSO-d6,400.13 MHz): δ (ppm) 14.69 (s, 2H, H-1, H-24), 8.53 (s, 2H, H-7, H-18), 7,79(d, 2H, J = 2.50 Hz, H-3, H-22), 7.54 (d, 2H, J = 2.50 Hz, H-5,H-20), 3,62 (t, 4H, J = 6.50 Hz, H-8, H-17), 1,67 (m, 4H, H-9, H-16),0.54 (m, 4H, H-10, H-15), 0.08 (s, 12H, H-11, H-12, H-13, H-14). 13CNMR (DMSO-d6, 100.6 MHz): δ (ppm) 165.21 (C-7, C-18), 138.10 (C-3, C-22), 134.08 (C-5, C-20), 116.94 (C-4/21, C-2/23-Br), 115.88 (C-4/21, C-2/23-Br), 103.44 (C-6, C-19), 55.80 (C-8, C-17), 23,73 (C-9, C-16), 14.68 (C-10, C-15), 0.21 (C-11, C-12, C-13, C-14).
Reference： [1]Cazacu, Maria; Damoc, Madalin; Dascalu, Mihaela; Macsim, Ana-Maria; Stoica, Alexandru-Constantin; Zaltariov, Mirela-Fernanda [Journal of Molecular Liquids, 2020, vol. 316]
  • 87
  • [ 2469-55-8 ]
  • [ 24677-78-9 ]
  • C24H36N2O5Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% In dichloromethane at 20℃; for 1h; 2.3.3. Synthesis of the Schiff base H2L3 0.1 g (0.72 mmol) 3-hydroxysalicylaldehyde is dissolved in 10 mLCH2Cl2, followed by addition of 100 μL (0.36 mmol) of 1,3-bis(3-aminopropyl)tetramethyldisiloxane, and the reaction mixture immediatelycolored in orange is stirred for 1 h at room temperature. After thespecified time, the solvent in the reaction mixture was removed by evaporation and the remaining cruel product was dissolved in a smallamount of CHCl3. Forpurification, themixture is eluted trough the chromatographiccolumn with methanol. Yield 0.1691 g (95%). UV-vis(DMF, 10-5 - 5 × 10-5 M), λmax, nm (ε, M-1 cm-1): 285 (12213),335 (2683), 423 (8350). IR (KBr), νmax, cm-1: 3352m, 3267m,3055vw, 3035w, 2952w, 2929m, 2916w, 2893w, 2875w, 2854w,1643vs, 1543s, 1521s, 1460s, 1390s, 1355s, 1255s, 1244s, 1222s,1184s, 1159m, 1064s, 1020s, 985m, 898m, 856m, 839s, 800 m, 781m,734m, 734s, 721m, 704s, 663m, 636w, 609w, 574w, 561w, 540vw,528vw, 505w, 482w, 395. 1H NMR (DMSO-d6, 400.13 MHz): δ (ppm)13.53 (s, 2H, H-1, H-24), 9.18 (s, 2H, H-2, H-23), 8.45 (s, 2H, H-7, H-18), 6.83 (dd, 4H, J = 1.4 Hz, 7.71 Hz H-6,H-4), 6,60 (t, 2H, J =7.75 Hz, H-4, H-21), 3.56 (t, 4H, J = 6.68 Hz, H-8, H-17), 1,64 (m, 4H,H-9, H-16), 0.55 (m, 4H, H-10, H-15), 0.65 (s, 12H, H-11, H-12, H-13,H-14). 13C NMR (DMSO-d6, 100.6 MHz): δ (ppm) 165.85 (C-7, C-18),153.28 (C-1, C-24), 146.27 (C-2, C-23), 121.78 (C-5, C-20), 117.39 (C-6, C-19), 117.06 (C-3, C-22), 116.79 (C-4, C-21), 59.35 (C-8, C-17),24.39 (C-9, C-16), 15.06 (C-10, C-15), 0.30 (C-11, C-12, C-13, C-14).
Reference： [1]Cazacu, Maria; Damoc, Madalin; Dascalu, Mihaela; Macsim, Ana-Maria; Stoica, Alexandru-Constantin; Zaltariov, Mirela-Fernanda [Journal of Molecular Liquids, 2020, vol. 316]

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