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142-90-5

Basic Information
CAS No.: 142-90-5
Name: Dodecyl 2-methylacrylate
Article Data: 13
Molecular Structure:
Molecular Structure of 142-90-5 (Dodecyl 2-methylacrylate)
Formula: C16H30O2
Molecular Weight: 254.413
Synonyms: 1-Dodecyl methacrylate;Methacrylicacid, dodecyl ester (6CI,8CI);Acryester L;Ageflex FM246;Dodecyl 2-methyl-2-propenoate;Dodecyl methacrylate;GE 410;LAMA;Lauryl methacrylate;Light Ester L;MA 13;MA13 (methacrylate);NSC 5188;Rocryl 320;GE 410 (methacrylate);Exceparl L-MA;SR 313E;Sipomer LMA;n-Dodecyl methacrylate;SR 313;
EINECS: 205-570-6
Density: 0.874 g/cm3
Melting Point: -7 °C(lit.)
Boiling Point: 322.7 °C at 760 mmHg
Flash Point: 133.8 °C
Solubility: insoluble in water
Appearance: clear colorless to yellowish liquid
Hazard Symbols: IrritantXi, DangerousN
Risk Codes: 36/37/38-50/53
Safety: 26-28-60-61-28B
Transport Information: UN 3082 9/PG 3
PSA: 26.30000
LogP: 5.02660
Synthetic route
79-41-4

poly(methacrylic acid)

112-53-8

1-dodecyl alcohol

142-90-5

n-dodecyl methacrylate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;86%
With phosphoric acid; (p-tolueneslfonic acid, sulfosalicylic acid, resin KU-2x8); hydroquinone In toluene Heating;
112-53-8

1-dodecyl alcohol

31978-13-9

3-(2-methylpropenoyl)-oxazolidin-2-one

142-90-5

n-dodecyl methacrylate

Conditions
ConditionsYield
With ytterbium(III) triflate In acetonitrile at 90℃; for 48h; Sealed tube; Inert atmosphere;79%
112-53-8

1-dodecyl alcohol

80-62-6

methacrylic acid methyl ester

142-90-5

n-dodecyl methacrylate

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; dibutyltin dilaurate; zirconium(IV) acetylacetonate Reagent/catalyst; Autoclave; Reflux; Large scale;70.99%
at 60 - 70℃;
Stage #1: 1-dodecyl alcohol; methacrylic acid methyl ester With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy for 1h; Heating / reflux;
Stage #2: titanium tetramethoxide at 111 - 129℃; for 3 - 6.5h; Product distribution / selectivity;
96 - 98.5 %Chromat.
With sulfuric acid at 110 - 150℃;
α-hydroxy-isobutyric acid dodecyl ester

α-hydroxy-isobutyric acid dodecyl ester

142-90-5

n-dodecyl methacrylate

Conditions
ConditionsYield
With phosphorus pentoxide; 1,2-dichloro-ethane
142-90-5

n-dodecyl methacrylate

6624-71-1

dodecyl isobutyrate

Conditions
ConditionsYield
With Dimethylphenylsilane; copper(l) chloride In various solvent(s) for 6h; Ambient temperature;95%
With hydrogen In water; toluene for 3h; pH=3 - 7;>= 99 %Chromat.
142-90-5

n-dodecyl methacrylate

dodecyl methacrylate-d5

Conditions
ConditionsYield
With platinum on carbon; water-d2; hydroquinone; isopropyl alcohol at 120℃; for 24h; Sealed tube;69%
142-90-5

n-dodecyl methacrylate

622837-75-6

dansyl iodide

lauryl 2-(dansylmethyl)acrylate

Conditions
ConditionsYield
Stage #1: n-dodecyl methacrylate; dansyl iodide In tetrachloromethane at 20℃; for 24h;
Stage #2: With triethylamine In tetrachloromethane for 24h; Heating;
60%
142-90-5

n-dodecyl methacrylate

85557-24-0

Sodium; 2-dodecyloxycarbonyl-propane-1-sulfonate

Conditions
ConditionsYield
With sodium hydrogensulfite In ethanol at 80 - 100℃; under 1520 - 2280 Torr; Yield given;
100-43-6

4-vinylpyridine

142-90-5

n-dodecyl methacrylate

polymer; monomer(s): dodecyl methacrylate; 4-vinylpyridine; ethylene dimethacrylate

polymer; monomer(s): dodecyl methacrylate; 4-vinylpyridine; ethylene dimethacrylate

Conditions
ConditionsYield
at 20℃; for 72h; Irradiation;
142-90-5

n-dodecyl methacrylate

79-41-4

poly(methacrylic acid)

polymer; monomer(s): dodecyl methacrylate; methacrylic acid; ethylene dimethacrylate

polymer; monomer(s): dodecyl methacrylate; methacrylic acid; ethylene dimethacrylate

Conditions
ConditionsYield
at 20℃; for 72h; Irradiation;
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of Dodecyl methacrylate is dodecyl 2-methylprop-2-enoate. With the CAS registry number 142-90-5 and EINECS 205-570-6, it is also named as 2-Methyl-2-propenoic acid, dodecyl ester. The product's category is Functional Monomer. It is clear colorless to yellowish liquid which is flammable.  When heated to decomposition it emits acrid smoke and irritating fumes. So the storage environment should be well-ventilated, low-temperature and dry. Keep Dodecyl methacrylate separate from oxidant.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 7.19; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.19; (4)ACD/LogD (pH 7.4): 7.19; (5)ACD/BCF (pH 5.5): 171679.08; (6)ACD/BCF (pH 7.4): 171679.08; (7)ACD/KOC (pH 5.5): 194351.14; (8)ACD/KOC (pH 7.4): 194351.14; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 13; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.445; (14)Molar Refractivity: 77.51 cm3; (15)Molar Volume: 291 cm3; (16)Polarizability: 30.73×10-24 cm3; (17)Surface Tension: 29.5 dyne/cm; (18)Density: 0.874 g/cm3; (19)Flash Point: 133.8 °C; (20)Enthalpy of Vaporization: 56.46 kJ/mol; (21)Boiling Point: 322.7 °C at 760 mmHg; (22)Vapour Pressure: 0.000274 mmHg at 25°C.

Uses of Dodecyl methacrylate: It is used in the manufacture of lubricant additives, deodorant, paper processing agents, adhesives and so on. It also can be used to produce Dodecyl isobutyrate. This reaction needs reagents dimethylphenylsilane, copper(I) chloride and various solvent(s) at ambient temperature. The reaction time is 6 hours. The yield is 95%.

Dodecyl methacrylate can be used to produce Dodecyl isobutyrate

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. And it is aery toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, wash immediately with plenty of soap-suds. Besides, this material and its container must be disposed of as hazardous waste. Avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C(OCCCCCCCCCCCC)\C(=C)C
2. InChI:InChI=1/C16H30O2/c1-4-5-6-7-8-9-10-11-12-13-14-18-16(17)15(2)3/h2,4-14H2,1,3H3
3. InChIKey:GMSCBRSQMRDRCD-UHFFFAOYAN

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 1240uL/kg (1.24mL/kg)   Journal of Pharmaceutical Sciences. Vol. 63, Pg. 376, 1974.
mouse LD50 intraperitoneal 25gm/kg (25000mg/kg)   Journal of Pharmaceutical Sciences. Vol. 62, Pg. 778, 1973.
rat LD50 intraperitoneal 12gm/kg (12000mg/kg)   Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 36, Pg. 58, 1975.