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EC number: 223-228-4 | CAS number: 3775-90-4
Endpoint summary
Administrative data
Link to relevant study record(s)
Description of key information
There is not specific information available on the absorption, metabolism and excretion of 2-tert-butylaminoethyl methacrylate. There is limited in formation on the read across substance 2-dimethylaminoethyl methacrylate that is considered to also be applicable to 2-tery-butylaminoethyl methacrylate.
Key value for chemical safety assessment
- Bioaccumulation potential:
- low bioaccumulation potential
- Absorption rate - oral (%):
- 50
- Absorption rate - dermal (%):
- 50
- Absorption rate - inhalation (%):
- 100
Additional information
Molecular chemical profile and estimated properties:
|
2-tert-butylaminoethyl methacrylate (TBAEMA) |
2-dimethylaminoethyl methacrylate (DMAEMA) |
CAS |
3775-90-4 |
2867-47-2 |
Physical state |
Colourless liquid |
Colourless liquid |
SMILES |
C(NCCOC(=O)C(=C)C)(C)(C)C |
O(C(C(C)=C)=O)CCN(C)C |
Structure |
||
Molecular formula |
C10H19O2N |
C8H15O2N |
Molecular weight |
185.2634 |
157.2102 |
Solubility: avgLogS (g/L) |
-1.69 (3.78 g/L) |
-0.36 (68.6 g/L) |
Solubility (meas) |
(not possible due to hydrolysis) |
50 g/L (BASF info) |
Hydrolysis |
cross-read DMAEMA |
t½ at 25°C: at pH 9 = 3.3h; pH 7=4.5 days; Stable at 50°C and pH 4 (OECD) |
Density (25 °C) |
0.914 g/cm3(BASF info) |
0.933 g/cm3 (BASF info) 974.75 kg/m³ (ECHA) |
pKa: neutral: 1+: |
9.57 > 99% at pH 11.5 > 99% at pH < 7.6 |
8.42 > 99% at pH 10.4 > 99% at pH < 6.5 |
logPow(ALOGPS 2.1) (KOWWIN v1.68) |
1.72 (±0.19) 2.1233 |
0.97 (±0.26) 0.9723 |
logPow (meas) |
(not possible due to hydrolysis) |
1.13 (OECD SIDS) |
logD (Chemaxon) |
pH logD 1,700 -1,245 4,600 -1,237 5,500 -1,184 7,400 -0,136 |
pH logD 1,700 -2,175 4,600 -2,004 5,500 -1,491 7,400 0,270 |
Mp (EPIWIN) |
13.11°C |
-20.45°C |
bp (EPIWIN) |
220.73°C |
183.13°C |
Vp (EPIWIN) |
16.8 Pa |
96.1 Pa |
Mp (meas) |
No mp between -130 °C - 450 °C |
– 30 °C (BASF info/ ECHA) |
bp (meas) |
215 ºC. |
201 °C (BASF info) 182 -192 °C (ECHA) |
Vp (meas) |
6 Pa |
1.33 hPa (BASF info) 0.58 hPa at 20 °C (ECHA) |
Reactivity |
DNA:Michael addition - Polarised Alkenes-Michael addition (Alpha, beta- unsaturated esters) Protein:Michael addition mechanism; GSH slightly reactive; DPRA Cysteine peptide depletion: moderate reactive |
DNA:Michael addition - Polarised Alkenes-Michael addition (Alpha, beta- unsaturated esters); SN1 mechanism - iminium formation (aliphatic tertiary amine) Protein:Michael addition mechanism; GSH slightly reactive; DPRA Cysteine peptide depletion: moderate reactive |
HOMO LUMO (difference (GAP) |
-9.4(-9.66;-9.15) eV 0.165(-0.029;0.506) eV 9.57(9.12;10.1) eV |
-9.15(-9.38;-9.02) eV 0.244(-0.00042;0.74) eV 9.39(9.07;9.98) eV |
Dermal penetration coefficient Kp (est) |
0.00066 cm/hr |
0.0000445 cm/hr
|
Max. dermal absorption |
2.05E-4 mg/cm2/h |
3.08E-3mg/cm2/h |
Human Intestinal absorption (HIA) |
91.7% |
89.5% |
Absorption
2-tert-butylaminoethyl methacrylate and the read across substance 2-dimethylaminoethyl methacrylate both would be expected to be rapidly absorbed from the gastrointestinal tract; the modelling (Epiwin) information predicts 91.7% and 89.5% respectively. Both would also be assumed to be readily absorbed in the lungs, although this is highly unlikely route of exposure. 2-tert-butylaminoethyl methacrylate would be expected to somewhat more readily absorbed through the skin due to it higher octanol water partition coefficient, in reality both substances are corrosive to skin and would therefore destroy the barrier with prolonged exposure so similar higher than might be predicted absorption would be expected.
Metabolism
There is no specific information on the metabolism of 2-tert-butylaminoethyl methacrylate, however there is information in the OECD SIDS dossier for the read across substance 2-dimethylaminoethyl methacrylate that is relevant.Small quantities of methacrylates may readily be metabolized by saponification into the alcohol and methacrylic acid. The latter may form an acetyl-CoA derivative, which then enters the normal lipid metabolism [Clayton/Patty, 1993-1994]. The substance (2-dimethylaminoethyl methacrylate) was rapidly hydrolysed to methacrylic acid (MAA) and N,N-dimethylaminoethanol (DMAE) when incubated with simulated saliva or simulated intestinal fluidin vitro. 90 % degradation was observed in simulated saliva after 4 hrs at 37 °C, 86 % degradation after incubation with simulated intestinal fluid for 4 hrs at 37 °C. Degradation was below 8% after incubation with simulated gastric fluid for 4 hours at 37 °C [Atochem, 1994]. However, noin vivostudy is available.
Based on the available information on 2-dimethylaminoethyl methacrylate it is expected that the same hydrolysis would take place such that the 2-tert-butylaminoethyl methacrylate would be initially metabolised to methacrylic acid (MAA) and 2-(tert-Butylamino)ethanol CAS No 4620-70-6..Then the MAA may form an acetyl-CoA derivative, which then enters the normal lipid metabolism. No information is available concerning the further metabolism of the 2-(tert-butylamino)ethanol. Information from the water solubility experiment is that 2-tert-butylaminoethyl methacrylate undgoes rapid hydrolysis in water, which supports a similar metabolism to the 2-diemthylaminoethyl methacrylate.
Excretion
The urine would be expected to be the main route of excretion of the conjugated waste products from the metabolism of the 2-(tert-butylamino)ethanol. It is possible the nitrogen would be excreted in the form of urea.
References:
Molecular formula, molecular weight, pKa and logD were all calculated using ChemAxon MarvinSketch (v.5.4.0.1).
Melting point, boiling point, vapour pressure and logPow were estimated by EPI Suite (v4.1).
Solubility and logPow are estimated using ALOGPS 2.1 (VCCLAB, Virtual Computational Chemistry Laboratory,http://www.vcclab.org, 2005)
Reactivity: QSAR Toolbox v.3.0: profiling: DNA binding (OASIS v1.1; OECD); Protein binding (OASIS v1.1; OECD)
HOMO/LUMO Energy, [eV], quantum-chemical descriptor (the energy of the highest occupied resp. lowest unoccupied molecular orbital), calculated in OASIS software, based on MOPAC 7.
(a large difference between HOMO and LUMO energies implies high stability and thus low reactivity)
Absorption properties:
- dermal: EpiSuite v. 4.1; (water:0.0005 cm/hr): (logD at pH5.5 as basis)
- intestinal: HIA: QSAR toolbox (version 3.1) (Human Intestinal Absorption)
Max. dermal absorption: IH Skin Perm v1.03 from AIHA
Atochem (1994), Hydrolysis studies on dimethylaminoethyl methacrylate, SA 006/94
Clayton GD., Patty's Industrial Hygiene and Toxicology Vol. 2A, 2B, 2C, 2D, 2E, 2F,
Toxicology 4th ed. New York, NY, John Wiley & Sons Inc., 3008, 1993-1994
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