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105-16-8

Basic Information
CAS No.: 105-16-8
Name: 2-(Diethylamino)ethyl methacrylate
Molecular Structure:
Molecular Structure of 105-16-8 (2-(Diethylamino)ethyl methacrylate)
Formula: C10H19NO2
Molecular Weight: 185.266
Synonyms: Methacrylicacid, 2-(diethylamino)ethyl ester (6CI,8CI);2-(N,N-Diethylamino)ethylmethacrylate;2-Diethylaminoethyl methacrylate;Daktose B;Diethyl[2-(methacryloyloxy)ethyl]amine;Diethylaminoethyl methacrylate;GE 710;Light Ester DE;N,N-Diethylaminoethyl methacrylate;NSC 14490;Polydeam;[2-(Methacryloyloxy)ethyl]diethylamine;b-(Diethylamino)ethyl methacrylate;b-(N,N-Diethylamino)ethylmethacrylate;
EINECS: 203-275-7
Density: 0.93 g/cm3
Melting Point: -60 °C
Boiling Point: 239.327 °C at 760 mmHg
Flash Point: 80.975 °C
Appearance: clear light colored liquid
Hazard Symbols: HarmfulXn
Risk Codes: 20-36/38-43
Safety: 26
PSA: 29.54000
LogP: 1.44750
Synthetic route
80-62-6

methacrylic acid methyl ester

100-37-8

2-(Diethylamino)ethanol

105-16-8

2-(diethylamino)ethyl methacrylate

Conditions
ConditionsYield
With 10H-phenothiazine; lithium hydroxide In hexane at 65 - 73℃; for 5h; Reagent/catalyst;94.1%
With hydroquinone; lithium hydroxide at 50 - 85℃; under 600 Torr; for 3.5h; Reagent/catalyst;94%
With sodium methylate; 1,4-phenylenediamine; benzene
105-16-8

2-(diethylamino)ethyl methacrylate

C14H17BrO5

C24H36NO7(1+)*Br(1-)

Conditions
ConditionsYield
With hydroquinone In acetonitrile at 70℃; for 10h;100%
5281-20-9

acetone hydrazone

105-16-8

2-(diethylamino)ethyl methacrylate

C13H25NO2

Conditions
ConditionsYield
With iodosylbenzene In ethyl acetate at 20℃; for 1h; Green chemistry;100%
31469-15-5

1-methoxy-2-methyl-1-trimethylsiloxy-1-propene

2867-47-2

2-(dimethylamino)ethyl methacrylate

105-16-8

2-(diethylamino)ethyl methacrylate

poly[2-(diethylamino)ethyl methacrylate]-block-poly[2-(dimethylamino)ethyl methacrylate], Mw 1.98E4 Da, PDI 1.23; monomer(s): 2-(diethylamino)ethyl methacrylate; 2-(dimethylamino)ethyl methacrylate; 1-methoxy-1-(trimethylsilyloxy)-2-methyl-1-propene

poly[2-(diethylamino)ethyl methacrylate]-block-poly[2-(dimethylamino)ethyl methacrylate], Mw 1.98E4 Da, PDI 1.23; monomer(s): 2-(diethylamino)ethyl methacrylate; 2-(dimethylamino)ethyl methacrylate; 1-methoxy-1-(trimethylsilyloxy)-2-methyl-1-propene

Conditions
ConditionsYield
Stage #1: 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene; 2-(diethylamino)ethyl methacrylate With tetra-n-butylammonium bibenzoate In tetrahydrofuran
Stage #2: 2-(dimethylamino)ethyl methacrylate With tetra-n-butylammonium bibenzoate In tetrahydrofuran
Stage #3: With methanol In tetrahydrofuran
98%
542-69-8

1-iodo-butane

105-16-8

2-(diethylamino)ethyl methacrylate

N-butyl-N,N-diethyl-N-[2-(methacryloyloxy)ethyl]ammonium iodide

Conditions
ConditionsYield
In acetonitrile at 60℃; for 72h; Inert atmosphere;97.5%
105-16-8

2-(diethylamino)ethyl methacrylate

75-03-6

ethyl iodide

6293-67-0

N,N,N-triethyl-N-[2-(methacryloyloxy)ethyl]ammonium iodide

Conditions
ConditionsYield
In acetonitrile at 45℃; for 24h; Inert atmosphere;96.4%
With hydroquinone
105-16-8

2-(diethylamino)ethyl methacrylate

638-45-9

1-Iodohexane

N,N-diethyl-N-hexyl-N-[2-(methacryloyloxy)ethyl]ammonium iodide

Conditions
ConditionsYield
In acetone at 56℃; for 120h; Solvent; Inert atmosphere;95.9%
105-16-8

2-(diethylamino)ethyl methacrylate

141-43-5

ethanolamine

polymer, Mn 2.5 kDa, PDI 1.3; monomer(s): 2-(N,N-diethylamino)ethyl methacrylate; 2-ethanolamine

polymer, Mn 2.5 kDa, PDI 1.3; monomer(s): 2-(N,N-diethylamino)ethyl methacrylate; 2-ethanolamine

Conditions
ConditionsYield
With Naphthalene anion ( K(1+) is the counterion) In tetrahydrofuran at 20℃; for 5h;93.4%
629-27-6

1-Iodooctane

105-16-8

2-(diethylamino)ethyl methacrylate

N,N-diethyl-N-[2-(methacryloyloxy)ethyl]-N-octylammonium iodide

Conditions
ConditionsYield
With 10H-phenothiazine In acetonitrile at 75℃; for 72h; Inert atmosphere;93.2%
105-16-8

2-(diethylamino)ethyl methacrylate

poly(ethylene oxide) bis(2-bromoisobutyrate), DP 45, Mn 3900 Da, Mw/Mn 1.05

poly(ethylene oxide) bis(2-bromoisobutyrate), DP 45, Mn 3900 Da, Mw/Mn 1.05

poly[(ethylene oxide)-block-(2-(diethylamino)ethyl methacrylate)], poly(ethylene oxide) block DP 45, Mn 7000 Da, Mw/Mn 1.19

poly[(ethylene oxide)-block-(2-(diethylamino)ethyl methacrylate)], poly(ethylene oxide) block DP 45, Mn 7000 Da, Mw/Mn 1.19

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper(I) bromide In methanol at 20℃; for 5h;93%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The 2-(Diethylamino)ethyl methacrylate, with the CAS registry number 105-16-8, is also known as 2-(N,N-Diethylamino)ethyl methacrylate. It belongs to the product categories of Monomer; Amine Photochemical Coinitiators Carbonyl Compounds; C10 to C11 Monomers; Acrylic Monomers; Esters; Methacrylate; Polymer Science; Polymerization Initiators. Its EINECS registry number is 203-275-7. This chemical's molecular formula is C10H19NO2 and molecular weight is 185.26. What's more, its IUPAC name is called 2-(Diethylamino)ethyl 2-methylprop-2-enoate. This chemical can be prepared by methacrylic acid with diethylaminoethanol. It can be used to prepare thermosetting coating, antistatic agents, dyeing additives, lubricant additives, adhesives, leather processing agents, combustion-supporting agent, and others. 

Physical properties about 2-(Diethylamino)ethyl methacrylate are: (1)ACD/LogP: 2.125; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.87; (4)ACD/LogD (pH 7.4): 0.36; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 5.88; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 29.54 Å2; (13)Index of Refraction: 1.449; (14)Molar Refractivity: 53.442 cm3; (15)Molar Volume: 199.233 cm3; (16)Polarizability: 21.186×10-24 cm3; (17)Surface Tension: 29.83 dyne/cm; (18)Density: 0.93 g/cm3; (19)Flash Point: 80.975 °C; (20)Enthalpy of Vaporization: 47.621 kJ/mol; (21)Boiling Point: 239.327 °C at 760 mmHg; (22)Vapour Pressure: 0.040 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and cause sensitisation by skin contact. It is harmful by inhalation and irritating to eyes and skin. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: CCN(CC)CCOC(=O)C(=C)C
(2) InChI: InChI=1S/C10H19NO2/c1-5-11(6-2)7-8-13-10(12)9(3)4/h3,5-8H2,1-2,4H3
(3) InChIKey: SJIXRGNQPBQWMK-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 12100mg/m3/2H (12100mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 51, 1982.
rat LC50 inhalation 11gm/m3/4H (11000mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 51, 1982.
rat LD50 oral 4696mg/kg (4696mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 51, 1982.