5117-12-4 Usage
Chemical Properties
4-Acryloylmorpholine has a melting point of ?35 °C and is clear liquid at room
temperature. At 25 °C, it has a density of 1.122 g/mL. It needs to be
stored at 2-8°C.
Uses
4-Acryloylmorpholine is used in adhesives, UV curable resins, industrial coatings, UV printing ink, oil recovery polymer, medicinal and commodity chemicals.
Flammability and Explosibility
Nonflammable
Synthesis
A
solution of 0.04 mol of the corresponding amine in 20 ml of anhydrous
methylene chloride was slowly added at 0-5°C to 0.02 mol of acryloyl
chloride in 20 ml of anhydrous methylene chloride. The mixture was
stirred for 3 h at room temperature in an inert atmosphere, and the
precipitate was filtered off and washed with methylene chloride (2 × 10
ml). The organic layer was washed in succession with 5 ml of water and 5
ml of a saturated solution of NaHCO3 and dried over Na2SO4, the solvent
was removed under reduced pressure, and the residue was purified by
column chromatography on silica gel using hexane-ethyl acetate (5 : 1 to
1 : 1) as eluent. 4-Acryloylmorpholine, Yield 1.78 g (63%).
IR spectrum, ν, cm-1: 2857, 1647, 1612, 1439, 1263, 1238, 1115, 1038,
953. 1H NMR spectrum, δ, ppm: 3.51-3.73 m (8H, NCH2CH2O),
5.72 d.d (1H, 3-Hcis, 3J = 10.6, 2J = 1.9 Hz), 6.29 d.d (1H, 3-Htrans,
3J = 16.7, 2J = 1.9 Hz), 6.57 d.d (1H, 2-H, J = 16.7, 10.6 Hz). 13C NMR
spectrum, δC, ppm: 41.74 and 45.66 (CH2N), 66.22 (CH2O), 126.64 (C2),
127.69 (C3), 164.92 (C1). Mass spectrum, m/z (Irel, %): 141 (36) [M]+,
140 (12), 126 (58), 112 (22), 111 (15), 110 (15), 109 (12), 98 (10), 96
(26), 86 (72), 83 (13), 70 (14), 68 (14), 57 (17), 56 (86), 55 (100),
42 (23).Fig. The synthetic method 2 of 4-Acryloylmorpholine
Check Digit Verification of cas no
The CAS Registry Mumber 5117-12-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,1,1 and 7 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 5117-12:
(6*5)+(5*1)+(4*1)+(3*7)+(2*1)+(1*2)=64
64 % 10 = 4
So 5117-12-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H12N2O2/c1-7-4-3-5-9(6-7)10(14)12-11-8(2)13/h3-6H,1-2H3,(H,11,13)(H,12,14)
5117-12-4Relevant articles and documents
Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights
Kurouchi, Hiroaki,Sai, Masahiro
supporting information, p. 3585 - 3591 (2021/06/27)
We report herein the first KHMDS-catalyzed Michael additions of allylic alcohols to α,β-unsaturated amides through allylic isomerization. The reaction proceeds smoothly in the presence of only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations, including experimental and computational studies, reveal that the KHMDS-catalyzed in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is the key to the success of this transformation. (Figure presented.).
Method for catalytically synthesizing acrylamide compound by MOFs-derived zirconium-based ternary oxide solid acid
-
Paragraph 0063-0064, (2021/11/14)
The invention provides a catalytic synthesis of acrylamide compounds with zirconium-based ternary oxide solid acid as a catalyst, and the low-temperature activity is good. In the synthesis process, the acid is small, the reaction conditions are mild and controllable, the byproducts are few, the reaction yield is effectively improved, the purity is high, the quality is good, and the method is suitable for large-scale production.
Copper-Catalyzed Propargylation of Nitroalkanes
Kim, Raphael S.,Dinh-Nguyen, Linh V.,Shimkin, Kirk W.,Watson, Donald A.
supporting information, p. 8106 - 8110 (2020/11/02)
Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α-functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N-heterocycles such as pyrroles and 2-pyrrolines.
