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tert-Butyl methacrylate

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Name

tert-Butyl methacrylate

EINECS 209-548-7
CAS No. 585-07-9 Density 0.875 g/cm3
PSA 26.30000 LogP 1.90420
Solubility insoluble in water Melting Point -60 °C
Formula C8H14O2 Boiling Point 156.9 °C at 760 mmHg
Molecular Weight 142.198 Flash Point 41.1 °C
Transport Information UN 3272 Appearance colorless liquid with an ester like odor
Safety 16 Risk Codes 10
Molecular Structure Molecular Structure of 585-07-9 (tert-Butyl methacrylate) Hazard Symbols R10:;
Synonyms

Methacrylicacid, tert-butyl ester (6CI,7CI,8CI);1,1-Dimethylethyl methacrylate;AcryesterTB;Acryester TBMA;Light Ester TB;NSC 20957;tert-Butyl 2-methylacrylate;tert-Butyl 2-methylpropenoate;tert-Butyl alcohol methacrylate;tert-Butylmethacrylate;tert-Butyl a-methacrylate;

Article Data 25

tert-Butyl methacrylate Synthetic route

23877-12-5

tert-butyl bromoisobutyrate

67828-69-7

methyl 5-chloro-2,4-dihydroxybenzoate

A

1003567-14-3

4-(1-tert-butoxycarbonyl-1-methylethoxy)-5-chloro-2-hydroxybenzoic acid methyl ester

B

585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
Stage #1: tert-butyl bromoisobutyrate; methyl 5-chloro-2,4-dihydroxybenzoate With tetrabutylammomium bromide; potassium carbonate In 1-methyl-pyrrolidin-2-one at 60 - 65℃; for 16h;
Stage #2: With hydrogenchloride In 1-methyl-pyrrolidin-2-one; water pH=~ 4;
A 72.2%
B n/a
Stage #1: tert-butyl bromoisobutyrate; methyl 5-chloro-2,4-dihydroxybenzoate With potassium carbonate; tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one at 60 - 65℃; for 16h;
Stage #2: With hydrogenchloride In 1-methyl-pyrrolidin-2-one; water pH=~ 4;
A 72.2%
B n/a
With tetrabutylammomium bromide; potassium carbonate In 1-methyl-pyrrolidin-2-one at 60 - 65℃; for 16h;A 72.2%
B n/a
865-48-5

sodium t-butanolate

920-46-7

Methacryloyl chloride

585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
With Petroleum ether; tert-butyl alcohol
920-46-7

Methacryloyl chloride

75-65-0

tert-butyl alcohol

585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
With pyridine
With pyridine
920-46-7

Methacryloyl chloride

magnesium bromide-tert-butylate

magnesium bromide-tert-butylate

585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
With diethyl ether; hydroquinone
463-49-0

1,2-propanediene

201230-82-2

carbon monoxide

75-65-0

tert-butyl alcohol

585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
dodecacarbonyl-triangulo-triruthenium at 80℃; under 22800 Torr; for 5h;36 % Chromat.
529495-12-3

C15H21O4S

A

585-07-9

tert-Butyl methacrylate

B

19646-38-9

toluene-4-sulfinyloxyl

Conditions
ConditionsYield
With pentamethylbenzene, at 19.85℃; Kinetics;
115-11-7

isobutene

585-07-9

tert-Butyl methacrylate

79-41-4

poly(methacrylic acid)

115-11-7

isobutene

585-07-9

tert-Butyl methacrylate

78-85-3

2-methylpropenal

75-65-0

tert-butyl alcohol

585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
Stage #1: 2-methylpropenal With tert-butylhypochlorite In tetrachloromethane at 20 - 50℃; for 5.5 - 6.5h;
Stage #2: tert-butyl alcohol With triethylamine In tetrachloromethane at 0 - 20℃; for 19.5h;

2-{N-tert-butyl-N-[1-(diethyl-phosphoryl)-2,2-dimethyl-propyl]-aminooxy}-2-methyl-propionic acid tert-butyl ester

A

585-07-9

tert-Butyl methacrylate

B

762-04-9, 123-22-8

Diethyl phosphonate

C

1431319-34-4

C18H38NO6P

D

188526-94-5

N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl

Conditions
ConditionsYield
under 7.50075E-06 Torr; Kinetics;

tert-Butyl methacrylate Specification

The tert-Butyl methacrylate, with the CAS registry number 585-07-9, is also known as 1,1-Dimethylethyl 2-methyl-2-propenoate. It belongs to the product categories of Medical Intermediates; Acrylic Monomers; C8 to C9Monomers; Carbonyl Compounds; Esters; Methacrylate. Its EINECS registry number is 209-548-7. This chemical's molecular formula is C8H14O2 and molecular weight is 142.19556. Its IUPAC name is called tert-butyl 2-methylprop-2-enoate. What's more, this chemical's classification codes are Drug / Therapeutic Agent; TSCA Flag P [A commenced PMN (Premanufacture Notice) substance]. When you are using this chemical, please be cautious about it. It is flammable. You should keep it away from sources of ignition - No smoking.

Physical properties of tert-Butyl methacrylate: (1)ACD/LogP: 2.57; (2)ACD/LogD (pH 5.5): 2.57; (3)ACD/LogD (pH 7.4): 2.57; (4)ACD/BCF (pH 5.5): 53.22; (5)ACD/BCF (pH 7.4): 53.22; (6)ACD/KOC (pH 5.5): 598.63; (7)ACD/KOC (pH 7.4): 598.63; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.422; (11)Molar Refractivity: 40.42 cm3; (12)Molar Volume: 159 cm3; (13)Surface Tension: 24.9 dyne/cm; (14)Density: 0.894 g/cm3; (15)Flash Point: 41.1 °C; (16)Enthalpy of Vaporization: 39.36 kJ/mol; (17)Boiling Point: 156.9 °C at 760 mmHg; (18)Vapour Pressure: 2.82 mmHg at 25°C.

Uses of tert-Butyl methacrylate: it can be used to produce 4,4,6-trimethyl-cyclohexane-1,3-dione with 3-methyl-butan-2-one at temperature of 25 °C. This reaction is a kind of Michael addition-Claisen condensation. It will need reagent t-BuOK and solvent tetrahydrofuran with reaction time of 0.5 hours. The yield is about 97%.

tert-Butyl methacrylate can be used to produce 4,4,6-trimethyl-cyclohexane-1,3-dione with 3-methyl-butan-2-one

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(=C)C(=O)OC(C)(C)C
(2)InChI: InChI=1S/C8H14O2/c1-6(2)7(9)10-8(3,4)5/h1H2,2-5H3
(3)InChIKey: SJMYWORNLPSJQO-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 8549mg/kg (8549mg/kg)   Toxicology Letters. Vol. 11, Pg. 125, 1982.

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