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Chemical Structure| 111-33-1 Chemical Structure| 111-33-1

Structure of 111-33-1

Chemical Structure| 111-33-1

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Product Citations

Product Citations

Li, Bowen ; Manan, Rajith Singh ; Liang, Shun-Qing ; Gordon, Akiva ; Jiang, Allen ; Varley, Andrew , et al.

Abstract: The expanding applications of nonviral genomic medicines in the lung remain restricted by delivery challenges. Here, leveraging a high-throughput platform, we synthesize and screen a combinatorial library of biodegradable ionizable lipids to build inhalable delivery vehicles for mRNA and CRISPR-Cas9 gene editors. Lead lipid nanoparticles are amenable for repeated intratracheal dosing and could achieve efficient gene editing in lung epithelium, providing avenues for gene therapy of congenital lung diseases.

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Product Details of [ 111-33-1 ]

CAS No. :111-33-1
Formula : C5H14N2
M.W : 102.18
SMILES Code : CNCCCNC
MDL No. :MFCD00008292
InChI Key :UQUPIHHYKUEXQD-UHFFFAOYSA-N
Pubchem ID :66978

Safety of [ 111-33-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H314
Precautionary Statements:P210-P280-P305+P351+P338-P310
Class:3(8)
UN#:2733
Packing Group:

Application In Synthesis of [ 111-33-1 ]

* 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 [ 111-33-1 ]

[ 111-33-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 111-33-1 ]
  • [ 4263-52-9 ]
  • [ 185305-85-5 ]
YieldReaction ConditionsOperation in experiment
79% With N-ethyl-N,N-diisopropylamine; In ethanol; water; at 20℃; Example 8 (Method 8): Preparation of 1 ,1 ,5,9-tetramethyl-2-hydroxy-5,9- bis(2-sulfoethyl)- 1 ,5,9-triazanonane di-inner salt (82, fw=419.57).Step 1 (Method 8a):N,N'-dimethyl- N,N'- bis(2-sulfoethyl)- 1 ,3-propanediamine, di-inner salt(fw=318.42, [185305-85-5])102.18 g freshly distilled N,N'-dimethyl- 1 ,3-propanediamine (1 .0 mole, fw=102.18, [1 1 1 -33- 1]) and 1500 mL ethanol/water (70/30 v/v) are placed in a 3 L Erlenmeyer flask that is equipped with a mechanical stirrer and a thermometer. 258.5 g Diisopropylethylamine (2.0 mole, fw=129.25) and 422.1 g 2-bromoethanesulfonic acid, sodium salt (2.0 mole, fw=21 1 .01 ) are added portionwise over a period of about seven (7) hours to the vigorously stirring diamine solution. The reaction mixture is stirred at room temperature for about 42 hours and monitored periodically by HPLC. The reaction rate is limited by the solubility of the sodium salt of the sulfonic acid. Once the reaction is come to completion (-42 hours) and the bromoethylsulfonate is consumed, the amount of additional alkylating agent that is needed to complete the reaction is estimated from the HPLC data. Then additional diisopropylethylamine (0.3 mole, -39 g) and bromoethylsulfonate (0.3 mole, -64 g) are added because some bromoethylsulfonate is lost to hydrolysis. The reaction mixture is stirred again at room temperature for about 22 hours. This process is repeated until all of the starting amine has been cleanly dialkylated with little evidence of trialkylation. The reaction mixture is heated to 60C for about 1 hour and then filtered to remove any solids. The solvent (water, ethanol) is removed under vacuum until the residue is nearly dry. The residue is dissolved/suspended in 1500 ml_ absolute ethanol, the pH is verified to be basic (pH>10.0, pH paper), the mixture is stirred at 70C for about 3 hours and then allowed to cool to room temperature while stirring. The reaction mixture is filtered again to remove solids, and then methanesulfonic acid (-220 g, fw=96.1 1 ) is added portionwise to the stirring mixture until it becomes acidic (pH<2.0, pH paper). During acidification, the product comes out of solution, initially as a sticky solid and then as fine white crystals. The mixture is then stirred at room temperature for 3 hours and overnight (18 hours) at 4C. The reaction mixture is filtered through sintered-glass under a blanket of N2 or dry air, washed with absolute ethanol and acetone and dried on the filter.The product is recrystallized by suspending the solid in 1200 ml_ stirring absolute ethanol and adding enough base (Et3N) until most is dissolved. The solution is filtered to remove solids and enough acid (methanesulfonic acid or gaseous HCI) is added to the filtrate in a portionwise manner until the pH is acidic (pH<2.0, pH paper). Addition of acid causes a mass of white microcrystals to come out of solution. The mixture is stirred at room temperature overnight (18 hours), filtered through sintered-glass under a blanket of dry N2 or dry air, washed with absolute ethanol and acetone and dried on the filter. The solid is fully dried by placing it in a vacuum oven overnight (50C, 15 torr). The yield is 252 g (79%) of a dry white microcrystalline solid that has no detectable impurity (>99%, HPLC).
  • 2
  • [ 1709-71-3 ]
  • [ 111-33-1 ]
  • C25H42N2O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 80℃; for 2h;Cooling with ice; (2) 30.6 g of N,N'-dimethyl-1,3-propanediamine was added dropwise to the reaction system under ice bath conditions, and after the completion of the dropwise addition, the temperature was raised to 80 C, and the reaction was continued for 2 hours; (3) After the reaction is completed, the temperature is lowered to room temperature, and the product is washed 2-3 times with deionized water, and then washed 2-3 times with a 1 wt% aqueous NaOH solution.Finally, it is washed with deionized water to neutrality, transferred to a beaker, added with an appropriate amount of anhydrous sodium sulfate, dried for 24 hours, and filtered to obtain a methacrylate monomer for a dental restorative material
 

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