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Tert-Butyl methacrylate (t-BMA) is a colorless liquid with an ester-like odor, characterized by a flash point below 141°F. It is less dense than water and insoluble in water, making it a versatile compound for various applications.

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  • 585-07-9 Structure
  • Basic information

    1. Product Name: tert-Butyl methacrylate
    2. Synonyms: TERTIARY-BUTYL METHACRYLATE;TERT-BUTYL METHACRYLATE;TERT-BUTYL METHACRYLATE MONOMER;TBMA;T-BUTYL METHACRYLATE;METHACRYLIC ACID TERT-BUTYL ESTER;METHACRYLIC ACID TERT-BUTYL ESTER MONOMER;(generic)2-propenoicacid,2-methyl-,1,1-dimethylethylester
    3. CAS NO:585-07-9
    4. Molecular Formula: C8H14O2
    5. Molecular Weight: 142.2
    6. EINECS: 209-548-7
    7. Product Categories: Medical Intermediates;Acrylic Monomers;C8 to C9Monomers;Carbonyl Compounds;Esters;Methacrylate
    8. Mol File: 585-07-9.mol
  • Chemical Properties

    1. Melting Point: -60°C
    2. Boiling Point: 132°C
    3. Flash Point: 81°F
    4. Appearance: colorless liquid with an ester like odor
    5. Density: 0.875
    6. Vapor Pressure: 2.82mmHg at 25°C
    7. Refractive Index: n20/D 1.415(lit.)
    8. Storage Temp.: 2-8°C
    9. Solubility: Insoluble in water
    10. Water Solubility: 464mg/L at 20℃
    11. CAS DataBase Reference: tert-Butyl methacrylate(CAS DataBase Reference)
    12. NIST Chemistry Reference: tert-Butyl methacrylate(585-07-9)
    13. EPA Substance Registry System: tert-Butyl methacrylate(585-07-9)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 10-38
    3. Safety Statements: 16
    4. RIDADR: 3272
    5. WGK Germany: 1
    6. RTECS: OZ3675500
    7. HazardClass: 3
    8. PackingGroup: III
    9. Hazardous Substances Data: 585-07-9(Hazardous Substances Data)

585-07-9 Usage

Uses

Used in Coatings Industry:
Tert-Butyl methacrylate is used as a monomer for the formation of homo and block copolymers through atom transfer radical polymerization (ATRP). These copolymers are utilized in the coatings industry due to their unique properties, such as enhanced durability, adhesion, and resistance to environmental factors.
Used in Biomaterials Industry:
In the biomaterials industry, tert-Butyl methacrylate is used as a key component in the synthesis of polymers with tailored properties. These polymers find applications in areas such as drug delivery systems, tissue engineering, and medical devices, where their biocompatibility and tunable characteristics are highly valued.
Used in Water Treatment Industry:
Tert-Butyl methacrylate is used as a monomer to produce flocculants, which are essential in the water treatment process. The flocculants help in the aggregation of suspended particles, making it easier to separate them from water, thus contributing to the purification process.
Used in Polymer Science:
Tert-Butyl methacrylate is also used in polymer science for the development of novel polymers with specific properties. These polymers can be tailored for various applications, such as in the automotive, electronics, and packaging industries, where their unique characteristics can provide advantages in terms of performance, durability, and cost-effectiveness.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

TERT-BUTYL METHACRYLATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Flammability and Explosibility

Flammable

Purification Methods

Purify as for butyl acrylate. [Beilstein 2 IV 1582.]

Check Digit Verification of cas no

The CAS Registry Mumber 585-07-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 5 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 585-07:
(5*5)+(4*8)+(3*5)+(2*0)+(1*7)=79
79 % 10 = 9
So 585-07-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H14O2/c1-6(2)7(9)10-8(3,4)5/h1H2,2-5H3

585-07-9 Well-known Company Product Price

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  • TCI America

  • (M0326)  tert-Butyl Methacrylate Monomer (stabilized with MEHQ)  >98.0%(GC)

  • 585-07-9

  • 25mL

  • 170.00CNY

  • Detail
  • TCI America

  • (M0326)  tert-Butyl Methacrylate Monomer (stabilized with MEHQ)  >98.0%(GC)

  • 585-07-9

  • 500mL

  • 650.00CNY

  • Detail
  • Aldrich

  • (463353)  tert-Butylmethacrylate  98%, contains 200 ppm monomethyl ether hydroquinone as inhibitor

  • 585-07-9

  • 463353-100ML

  • 721.89CNY

  • Detail
  • Aldrich

  • (463353)  tert-Butylmethacrylate  98%, contains 200 ppm monomethyl ether hydroquinone as inhibitor

  • 585-07-9

  • 463353-250ML

  • 691.47CNY

  • Detail

585-07-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-Butyl methacrylate

1.2 Other means of identification

Product number -
Other names TERT-BUTYL METHACRYLATE MONOMER

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:585-07-9 SDS

585-07-9Synthetic route

tert-butyl bromoisobutyrate
23877-12-5

tert-butyl bromoisobutyrate

methyl 5-chloro-2,4-dihydroxybenzoate
67828-69-7

methyl 5-chloro-2,4-dihydroxybenzoate

A

4-(1-tert-butoxycarbonyl-1-methylethoxy)-5-chloro-2-hydroxybenzoic acid methyl ester
1003567-14-3

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

B

tert-Butyl methacrylate
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
sodium t-butanolate
865-48-5

sodium t-butanolate

Methacryloyl chloride
920-46-7

Methacryloyl chloride

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

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

Methacryloyl chloride

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
With pyridine
With pyridine
Methacryloyl chloride
920-46-7

Methacryloyl chloride

magnesium bromide-tert-butylate

magnesium bromide-tert-butylate

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
With diethyl ether; hydroquinone
1,2-propanediene
463-49-0

1,2-propanediene

carbon monoxide
201230-82-2

carbon monoxide

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
dodecacarbonyl-triangulo-triruthenium at 80℃; under 22800 Torr; for 5h;36 % Chromat.
C15H21O4S
529495-12-3

C15H21O4S

A

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

B

toluene-4-sulfinyloxyl
19646-38-9

toluene-4-sulfinyloxyl

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

isobutene

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

isobutene
115-11-7

isobutene

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

2-methylpropenal
78-85-3

2-methylpropenal

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-Butyl methacrylate
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

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

A

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

B

Diethyl phosphonate
762-04-9, 123-22-8

Diethyl phosphonate

C

C18H38NO6P
1431319-34-4

C18H38NO6P

D

N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl
188526-94-5

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

Conditions
ConditionsYield
under 7.50075E-06 Torr; Kinetics;
poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
methacryloyl anhydride
760-93-0

methacryloyl anhydride

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
With tempol; 2,4-dimethyl-6-tert-butylphenol; 4-methoxy-phenol; magnesium bromide at 90℃; for 6h; Reagent/catalyst;
t-butyl pyruvate
76849-54-2

t-butyl pyruvate

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 2h;
Stage #2: t-butyl pyruvate In tetrahydrofuran; mineral oil at 0 - 20℃;
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethyl methacrylate
495417-67-9

2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethyl methacrylate

block-copoly{2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethyl methacrylate/tert-butyl methacrylate}, anionic polymerization, Mn = 18E3, Mw/Mn = 1.03; Monomer(s): 2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethyl methacrylate; tert-butyl methacrylate

block-copoly{2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethyl methacrylate/tert-butyl methacrylate}, anionic polymerization, Mn = 18E3, Mw/Mn = 1.03; Monomer(s): 2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethyl methacrylate; tert-butyl methacrylate

Conditions
ConditionsYield
Stage #1: 2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethyl methacrylate With diethylzinc; (diphenylmethyl)potassium In tetrahydrofuran at -78℃; for 2h;
Stage #2: tert-Butyl methacrylate In tetrahydrofuran at -78℃; for 1h;
100%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

2-[2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethoxy]ethyl methacrylate
495417-68-0

2-[2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethoxy]ethyl methacrylate

block-copoly{2-[2-[2-[(t-butyldimethylsilyl)oxy]ethoxy]ethoxy]ethyl methacrylate/tert-butyl methacrylate}, Mn = 9.0E3, Mw/Mn = 1.03; Monomer(s): 2-[2-[2-[(t-butyldimethylsilyl)oxy]ethoxy]ethoxy]ethyl methacrylate; tert-butyl methacrylate

block-copoly{2-[2-[2-[(t-butyldimethylsilyl)oxy]ethoxy]ethoxy]ethyl methacrylate/tert-butyl methacrylate}, Mn = 9.0E3, Mw/Mn = 1.03; Monomer(s): 2-[2-[2-[(t-butyldimethylsilyl)oxy]ethoxy]ethoxy]ethyl methacrylate; tert-butyl methacrylate

Conditions
ConditionsYield
Stage #1: 2-[2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethoxy]ethyl methacrylate With diethylzinc; (diphenylmethyl)potassium In tetrahydrofuran at -78℃; for 3h;
Stage #2: tert-Butyl methacrylate In tetrahydrofuran at -78℃; for 1h;
100%
poly(methyl methacrylate), 1,1-bis[3-(bromomethyl)phenyl]ethyl-terminated, Mn 1.23E4 Da by SEC, Mn 1.35E4 Da by osmometry, Mw/Mn 1.04; monomer(s): methyl methacrylate; 1,1-bis[3-(tert-butyldimethylsilyloxymethyl)phenyl]ethylene

poly(methyl methacrylate), 1,1-bis[3-(bromomethyl)phenyl]ethyl-terminated, Mn 1.23E4 Da by SEC, Mn 1.35E4 Da by osmometry, Mw/Mn 1.04; monomer(s): methyl methacrylate; 1,1-bis[3-(tert-butyldimethylsilyloxymethyl)phenyl]ethylene

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

poly[(methyl methacrylate)-b-(tert-butyl methacrylate)], asymmetric star-branched, 3-arm, Mw 3.33E4 Da, Mw/Mn 1.02; monomer(s): methyl methacrylate; 1,1-bis[3-(tert-butyldimethylsilyloxymethyl)phenyl]ethylene; tert-butyl methacrylate

poly[(methyl methacrylate)-b-(tert-butyl methacrylate)], asymmetric star-branched, 3-arm, Mw 3.33E4 Da, Mw/Mn 1.02; monomer(s): methyl methacrylate; 1,1-bis[3-(tert-butyldimethylsilyloxymethyl)phenyl]ethylene; tert-butyl methacrylate

Conditions
ConditionsYield
Stage #1: tert-Butyl methacrylate With (diphenylmethyl)potassium In tetrahydrofuran
Stage #2: poly(methyl methacrylate), 1,1-bis[3-(bromomethyl)phenyl]ethyl-terminated, Mn 1.23E4 Da by SEC, Mn 1.35E4 Da by osmometry, Mw/Mn 1.04; monomer(s): methyl methacrylate; 1,1-bis[3-(tert-butyldimethylsilyloxymethyl)phenyl]ethylene In tetrahydrofuran at -78℃; for 1h;
100%
poly(methyl methacrylate), with 3,97 3-(bromomethyl)phenyl end groups, Mn 1.24E4 Da by SEC, Mn 1.32E4 by osmometry, Mn 1.36E4 Da by NMR, Mw/Mn 1.03; monomer(s): methyl methacrylate; 1,1-bis[3-(tert-butyldimethylsilyloxymethyl)phenyl]ethylene

poly(methyl methacrylate), with 3,97 3-(bromomethyl)phenyl end groups, Mn 1.24E4 Da by SEC, Mn 1.32E4 by osmometry, Mn 1.36E4 Da by NMR, Mw/Mn 1.03; monomer(s): methyl methacrylate; 1,1-bis[3-(tert-butyldimethylsilyloxymethyl)phenyl]ethylene

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

poly[(methyl methacrylate)-b-(tert-butyl methacrylate)], asymmetric star-branched, 5-arm, Mw 6.27E4 Da, Mw/Mn 1.03; monomer(s): methyl methacrylate; 1,1-bis[3-(tert-butyldimethylsilyloxymethyl)phenyl]ethylene; tert-butyl methacrylate

poly[(methyl methacrylate)-b-(tert-butyl methacrylate)], asymmetric star-branched, 5-arm, Mw 6.27E4 Da, Mw/Mn 1.03; monomer(s): methyl methacrylate; 1,1-bis[3-(tert-butyldimethylsilyloxymethyl)phenyl]ethylene; tert-butyl methacrylate

Conditions
ConditionsYield
Stage #1: tert-Butyl methacrylate With (diphenylmethyl)potassium In tetrahydrofuran
Stage #2: poly(methyl methacrylate), with 3,97 3-(bromomethyl)phenyl end groups, Mn 1.24E4 Da by SEC, Mn 1.32E4 by osmometry, Mn 1.36E4 Da by NMR, Mw/Mn 1.03; monomer(s): methyl methacrylate; 1,1-bis[3-(tert-butyldimethylsilyloxymethyl)phenyl]ethylene In tetrahydrofuran at -78℃; for 1h;
100%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

3-bromo-2-methyl-acrylic acid tert-butyl ester
912809-59-7

3-bromo-2-methyl-acrylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: tert-Butyl methacrylate With bromine In tetrachloromethane at 25℃; for 2h;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrachloromethane at 25℃; for 5h;
100%
Multi-step reaction with 2 steps
1: bromine / tetrachloromethane / 0 - 20 °C / Inert atmosphere
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
View Scheme
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

polymer, Mn 6.30E4, PDI 1.95 by GPC; monomer(s): tert-butyl methacrylate

polymer, Mn 6.30E4, PDI 1.95 by GPC; monomer(s): tert-butyl methacrylate

Conditions
ConditionsYield
With potassium tert-butylate; triisobutylaluminum In hexane; toluene at 0 - 20℃; for 2h;100%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

4-bromo-2-methylbenzonitrile
67832-11-5

4-bromo-2-methylbenzonitrile

3-(4-cyano-3-methyl-phenyl)-2-methyl-acrylic acid tert-butyl ester
929202-11-9

3-(4-cyano-3-methyl-phenyl)-2-methyl-acrylic acid tert-butyl ester

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); N-Methyldicyclohexylamine; johnphos In 1,4-dioxane at 80℃; Heck coupling;100%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

tert-butyl 2,3-dibromo-2-methylpropanoate
854416-76-5

tert-butyl 2,3-dibromo-2-methylpropanoate

Conditions
ConditionsYield
With bromine In tetrachloromethane at 0 - 20℃; Inert atmosphere;100%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

pentan-3-one
96-22-0

pentan-3-one

methyl iodide
74-88-4

methyl iodide

2,2,4,6-Tetramethyl-cyclohexane-1,3-dione

2,2,4,6-Tetramethyl-cyclohexane-1,3-dione

Conditions
ConditionsYield
Stage #1: tert-Butyl methacrylate; pentan-3-one With potassium tert-butylate In tetrahydrofuran at 25℃; for 0.5h; Michael addition-Claisen condensation;
Stage #2: methyl iodide In tetrahydrofuran at 50℃; for 3h; Further stages.;
98%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

2-benzyloxycarbonyl-1-butene
219506-75-9

2-benzyloxycarbonyl-1-butene

poly(t-butyl methacrylate)-block-poly(benzyl-2-ethylacrylate)

poly(t-butyl methacrylate)-block-poly(benzyl-2-ethylacrylate)

Conditions
ConditionsYield
With 1,1-Diphenylpropyllithium In tetrahydrofuran at -78℃; for 15h;98%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

2-chloro-2-methyl-4-phenylbutane
4830-95-9

2-chloro-2-methyl-4-phenylbutane

tert-butyl 2,4,4-trimethyl-6-phenylhexanoate

tert-butyl 2,4,4-trimethyl-6-phenylhexanoate

Conditions
ConditionsYield
With Cp*TiCl3; triethylamine hydrochloride; zinc In ethyl acetate at 22℃; for 12h; Inert atmosphere; Glovebox;98%
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

4,4,6-trimethylcyclohexane-1,3-dione
104355-62-6

4,4,6-trimethylcyclohexane-1,3-dione

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 25℃; for 0.5h; Michael addition-Claisen condensation;97%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

diethyl (((diphenylmethylene)amino)methyl)phosphonate
122570-91-6

diethyl (((diphenylmethylene)amino)methyl)phosphonate

C26H36NO5P

C26H36NO5P

Conditions
ConditionsYield
Stage #1: diethyl N-(diphenylmethylene) aminomethyl phosphonate With C36H45NO9; sodium t-butanolate In toluene at -78℃; for 0.166667h; Michael Addition; Inert atmosphere;
Stage #2: tert-Butyl methacrylate In toluene at -78℃; for 1h; Michael Addition; Inert atmosphere; stereoselective reaction;
93%
2-ethyl-1-butene
760-21-4

2-ethyl-1-butene

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

2-((((benzyloxy)carbonyl)amino)oxy)-2-methylpropanoic acid

2-((((benzyloxy)carbonyl)amino)oxy)-2-methylpropanoic acid

tert-butyl 4-((((benzyloxy)carbonyl)amino)methyl)-4-ethyl-2-methylhexanoate

tert-butyl 4-((((benzyloxy)carbonyl)amino)methyl)-4-ethyl-2-methylhexanoate

Conditions
ConditionsYield
Stage #1: 2-((((benzyloxy)carbonyl)amino)oxy)-2-methylpropanoic acid With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 25℃; for 0.166667h; Schlenk technique; Inert atmosphere;
Stage #2: 2-ethyl-1-butene; tert-Butyl methacrylate With water In dichloromethane at 25℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; chemoselective reaction;
93%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

2-Methylcyclohexanone
583-60-8

2-Methylcyclohexanone

tert-butyl 3-(1-methyl-2-oxocyclohexyl)-2-methylpropanoate

tert-butyl 3-(1-methyl-2-oxocyclohexyl)-2-methylpropanoate

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 1.5h; Michael addition;92%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

para-iodoanisole
696-62-8

para-iodoanisole

(E)-tert-butyl 3-(4-methoxyphenyl)-2-methylacrylate
1415412-15-5

(E)-tert-butyl 3-(4-methoxyphenyl)-2-methylacrylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; Heck Reaction; Inert atmosphere;92%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

(2,2-dimethylcyclopropyl)(phenyl)methanone
5685-43-8

(2,2-dimethylcyclopropyl)(phenyl)methanone

tert-butyl (1R,2R)-2-benzoyl-1,4,4-trimethylcyclopentane-1-carboxylate

tert-butyl (1R,2R)-2-benzoyl-1,4,4-trimethylcyclopentane-1-carboxylate

Conditions
ConditionsYield
With manganese; C52H52Cl2F6N2O2Ti; triethylamine hydrochloride In ethyl acetate at 22℃; for 12h; Inert atmosphere; Sealed tube; stereoselective reaction;91%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

2-[(1E)-hex-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
126688-97-9

2-[(1E)-hex-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(2E,4E)-2-methylnona-2,4-dienenoic acid tert-butyl ester

(2E,4E)-2-methylnona-2,4-dienenoic acid tert-butyl ester

Conditions
ConditionsYield
With oxygen; palladium diacetate In N,N-dimethyl acetamide at 50℃; for 6h;90%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

tert-Butyl 2-(Phenylsulfonyl)acetate
138336-33-1

tert-Butyl 2-(Phenylsulfonyl)acetate

di-tertbutyl 2-methyl-4-(phenylsulfonyl)pentanedioate

di-tertbutyl 2-methyl-4-(phenylsulfonyl)pentanedioate

Conditions
ConditionsYield
With caesium carbonate In acetonitrile Michael Addition; Inert atmosphere; Reflux;90%
ethylenebis(triphenylphosphine)platinum(0)
12120-15-9

ethylenebis(triphenylphosphine)platinum(0)

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

Pt(P(C6H5)3)2(CH2C(CH3)COOC(CH3)3)
186495-03-4

Pt(P(C6H5)3)2(CH2C(CH3)COOC(CH3)3)

Conditions
ConditionsYield
In toluene byproducts: C2H4; N2-atmosphere; stirring equimolar amts. for 2 h; cooling to 0°C, pptn. on addn. of petroleum ether, collection (filtration), washing (petroleum ether), drying (vac.); elem. anal.;89%
iodobenzene
591-50-4

iodobenzene

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

(2E)-tert-butyl 2-methyl-3-phenylprop-2-enoate
98831-01-7

(2E)-tert-butyl 2-methyl-3-phenylprop-2-enoate

Conditions
ConditionsYield
With potassium carbonate at 80℃; Heck Reaction; Micellar solution;89%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

poly(tert-butyl methacrylate), atom transfer radical polymerization product, Mn: 47000, PDI: 1.14; monomer(s): tert-butyl methacrylate

poly(tert-butyl methacrylate), atom transfer radical polymerization product, Mn: 47000, PDI: 1.14; monomer(s): tert-butyl methacrylate

Conditions
ConditionsYield
With ethyl 2-bromoisobutyrate; [(1,3,5-iPr3C6H3)Ru(μ-Cl)3RuCl(C2H4)(PCy3)] In toluene at 35℃;88%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

poly(tert-butyl methacrylate), Mn = 12871, Mw/Mn = 1.28; Monomer(s): tert-butyl methacrylate

poly(tert-butyl methacrylate), Mn = 12871, Mw/Mn = 1.28; Monomer(s): tert-butyl methacrylate

Conditions
ConditionsYield
With Methyl 2-bromopropionate; N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper(I) bromide; copper(ll) bromide In acetone at 60℃; for 1.33333h;86%
rac-3-sulfanylpropane-1,2-diol
96-27-5

rac-3-sulfanylpropane-1,2-diol

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

6,7-dihydroxy-2-methyl-4-thiaheptanoic acid t-butyl ester
167768-11-8

6,7-dihydroxy-2-methyl-4-thiaheptanoic acid t-butyl ester

Conditions
ConditionsYield
With triethylamine for 0.5h; Ambient temperature;84%
With sodium bicarbonate; triethylamine; citric acid In water84%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

triethoxyphenylsilane
780-69-8

triethoxyphenylsilane

methyl-3-phenyl-propionic acid tert-butyl ester
70836-95-2, 107772-28-1, 126639-62-1

methyl-3-phenyl-propionic acid tert-butyl ester

Conditions
ConditionsYield
With sodium hydroxide; cyclo-octa-1,5-diene; [Rh(OH)(cod)]2 In 1,4-dioxane at 90℃; for 16h;84%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

carbon dioxide
124-38-9

carbon dioxide

para-thiocresol
106-45-6

para-thiocresol

4-(tert-butoxy)-3-methyl-4-oxo-3-(p-tolylthio)butanoic acid

4-(tert-butoxy)-3-methyl-4-oxo-3-(p-tolylthio)butanoic acid

Conditions
ConditionsYield
With iron(III) chloride; potassium tert-butylate In N,N-dimethyl acetamide at 25℃; under 760.051 Torr; for 12h; Glovebox; Schlenk technique; Irradiation; Sealed tube; regioselective reaction;84%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

tert-butyl ((1R,4R)-bornylideneamino)acetate
110269-68-6

tert-butyl ((1R,4R)-bornylideneamino)acetate

di-tert-butyl (2R)-2-<(1R,4R)-bornylideneamino>-4-methylglutamate
133445-88-2, 133521-71-8

di-tert-butyl (2R)-2-<(1R,4R)-bornylideneamino>-4-methylglutamate

Conditions
ConditionsYield
With n-butyllithium; tert-butyl alcohol In tetrahydrofuran; hexane at -78℃; for 18h;83%
(5,10,15,20-tetraphenylporphyrin)aluminum methyl

(5,10,15,20-tetraphenylporphyrin)aluminum methyl

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

C20N4H8(C6H5)4AlOCOCCH3C2H5CO2C4H9
136750-17-9

C20N4H8(C6H5)4AlOCOCCH3C2H5CO2C4H9

Conditions
ConditionsYield
With carbon dioxide In benzene under irradiation with visible light at 30°C for 3 h;; observed by NMR spectroscopy;;83%
tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

C12H20O3S3

C12H20O3S3

C30H56O6S3

C30H56O6S3

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 48h;82%
triethylsilane
617-86-7

triethylsilane

tert-Butyl methacrylate
585-07-9

tert-Butyl methacrylate

1-tert-butoxy-2-methyl-1-triethylsiloxypropene

1-tert-butoxy-2-methyl-1-triethylsiloxypropene

Conditions
ConditionsYield
Stage #1: triethylsilane With 1,3,5-trimethyl-2,4,6-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)benzene; tris(pentafluorophenyl)borate at 20℃; for 0.5h; Neat (no solvent);
Stage #2: tert-Butyl methacrylate at 3.5 - 6℃; for 5.5h; Neat (no solvent); Cooling with ice water;
81.5%

585-07-9Relevant articles and documents

Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates

Lou, Yixian,Qiu, Jian,Yang, Kai,Zhang, Feng,Wang, Chenglan,Song, Qiuling

supporting information, p. 4564 - 4569 (2021/06/28)

The transition-metal-catalyzed allylation reaction is an efficient strategy for the construction of new carbon-carbon bonds alongside allyl or homoallylic functionalization. Herein we describe a Ni-catalyzed reductive allylation of α-chloroboronates to efficiently render the corresponding homoallylic boronates, which could be readily converted into valuable homoallylic alcohols or amines or 1,4-diboronates. This reaction features a broad substrate scope with good functional group compatibility that is complementary to the existing methods for the preparation of homoallylic boronates.

Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route towardcontra-Thermodynamic Olefins

Zhao, Huaibo,McMillan, Alastair J.,Constantin, Timothée,Mykura, Rory C.,Juliá, Fabio,Leonori, Daniele

supporting information, p. 14806 - 14813 (2021/09/18)

We report here a mechanistically distinct tactic to carry E2-type eliminations on alkyl halides. This strategy exploits the interplay of α-aminoalkyl radical-mediated halogen-atom transfer (XAT) with desaturative cobalt catalysis. The methodology is high-yielding, tolerates many functionalities, and was used to access industrially relevant materials. In contrast to thermal E2 eliminations where unsymmetrical substrates give regioisomeric mixtures, this approach enables, by fine-tuning of the electronic and steric properties of the cobalt catalyst, to obtain high olefin positional selectivity. This unprecedented mechanistic feature has allowed access tocontra-thermodynamic olefins, elusive by E2 eliminations.

PREPARATION OF (METH)ACRYLIC ACID ESTERS

-

Page/Page column 16-17, (2020/03/05)

The invention relates to a method for preparation of (meth)acrylic acid esters from (meth)acrylic acid anhydrides.

PRODUCTION OF TERT-BUTYL ESTERS OF ETHYLENICALLY UNSATURATED CARBOXYLIC ACIDS

-

Paragraph 0163-0223, (2019/01/15)

A process for continuously preparing the tert-butyl ester of an ethylenically unsaturated carboxylic acid, by a) reacting an ethylenically unsaturated carboxylic acid with isobutene in the presence of an acidic catalyst to give an esterification mixture; b) removing the acidic catalyst; c) removing low-boiling components; and d) supplying a tert-butyl ester-comprising liquid to a distillation apparatus and subjecting it to purifying distillation in the distillation apparatus, where d1) in the distillation apparatus the tert-butyl ester-comprising liquid is separated into a tert-butyl ester-comprising gaseous top product and a carboxylic acid-comprising liquid bottom product; d2) the tert-butyl ester-comprising gaseous top product is at least partly condensed and the condensate is recycled partly as reflux to the distillation apparatus; d3) the carboxylic acid-comprising liquid bottom product is recycled at least partly to step a); d4) carboxylic acid-comprising liquid bottom product is drawn off and passed to a heater; a superheated, liquid recycle stream is taken from the heater; and the superheated recycle stream is let down into the distillatiuon apparatus; and d5) at least in the top region of the distillation apparatus, the distillation apparatus walls in contact with the vapor, at least in sub-regions, are heated and/or thermally insulated. In the course of the process, the separation of the tert-butyl ester from unreacted carboxylic acid is carried on with a particularly low level of accompanying polymerization both of the tert-butyl ester and of the carboxylic acid.

Method for the preparation of t-butyl methacrylate

-

Paragraph 0096-0124, (2020/03/04)

Of a typic a typa/aβaβbetaβbetaβbetaβbetaβbetaβbetaβbetaβbetaβbetaβbetaβbetaβbetaβbetaβbetaβbeta.beteq.a.sub .beteq.a.sub .beteq. t-a.sub .beteq.a.sub .beteq.a.sub .sub .beteq.a.sub .beteq.a.sub .beteq.a.sub .beteq.a.sub, t- t- t- t. (by machine translation)

Dehydrogenative Silylation of Alkenes for the Synthesis of Substituted Allylsilanes by Photoredox, Hydrogen-Atom Transfer, and Cobalt Catalysis

Yu, Wan-Lei,Luo, Yong-Chun,Yan, Lei,Liu, Dan,Wang, Zhu-Yin,Xu, Peng-Fei

supporting information, p. 10941 - 10945 (2019/07/17)

A synergistic catalytic method combining photoredox catalysis, hydrogen-atom transfer, and proton-reduction catalysis for the dehydrogenative silylation of alkenes was developed. With this approach, a highly concise route to substituted allylsilanes has been achieved under very mild reaction conditions without using oxidants. This transformation features good to excellent yields, operational simplicity, and high atom economy. Based on control experiments, a possible reaction mechanism is proposed.

METHOD FOR THE PRODUCTION PROCESS OF METHACRYL ACID ESTER

-

Paragraph 0045-0047, (2017/06/02)

The present invention relates to a method of preparing a methacrylic acid ester by performing a transesterification reaction while air blowing an alkyl methacrylic acid ester and an alcohol in the presence of a catalyst represented by chemical formula 1, to prepare a methacrylic acid ester. According to the present invention, a method of preparing a methacrylic acid ester may prevent a polymer from being generated and also increase yield when preparing a methacrylic acid ester without using an additional polymerization inhibitor.

H-transfer reaction during decomposition of N-(2-methylpropyl)- N-(1-diethylphosphono-2,2-dimethylpropyl)-N-oxyl (SG1)-based alkoxyamines

Edeleva, Mariya,Marque, Sylvain R.A.,Kabytaev, Kuanish,Guillaneuf, Yohann,Gigmes, Didier,Bagryanskaya, Elena

, p. 1323 - 1336 (2013/04/10)

Thermal decomposition of four tertiary N-(2-methylpropyl)-N-(1- diethylphosphono-2,2-dimethylpropyl)-N-oxyl (SG1)-based alkoxyamines (SG1-C(Me)2-C(O)-OR, R = Me, tBu, Et, H) has been studied at different experimental conditions using 1/su

PROCESS FOR THE PREPARATION OF CYCLIC SPIROPIPERIDINES

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Page/Page column 12-13, (2009/03/07)

The present invention relates to new processes for the preparation of compounds of formula I, especially the compound 2-{2-Chloro-5-{[(2S)-3-(5-chloro-1'H,3H-spiro[1- benzofuran-2,4'-piperidin]-1'-yl)-2-hydroxypropyl]oxy}-4-5 [(methylamino)carbonyl]phenoxy}-2-methylpropanoic acid and to new intermediates useful in the preparation thereof.

SPLROPIPERIDINE COMPOUNDS, A PROCESS OF THEIR PREPARATION, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND THEIR USE IN THE TREATMENT OF AIRWAY DISEASES, INFLAMMATORY DISEASES, COPD OR ASTHMA

-

Page/Page column 38, (2009/03/07)

The present invention relates to new polymorphs of compounds 2-{2-Chloro-5-{[(2S)-3-(5-chloro-1'H,3H-spiro[1-benzofuran-2,4'-piperidin]-1'-yl)-2-hydroxypropyl]oxy}-4- [(methylamino)carbonyl]phenoxy}-2-methylpropanoic acid, and the hydrochloride and sodium hydroxide salts thereof,and compound 2-{2-Chloro-5-{[(2R)-3-(5-chloro-1'H,3H-spiro[1-benzofuran-2,4'-piperidin]-1'-yl)-2-hydroxypropyl]oxy}-4- [(methylamino)carbonyl]phenoxy}-2-methylpropanoic acid. The invention further relates to pharmaceutical composition containing said compounds and to the use of said compounds in therapy. The present invention also relates to processes for the preparation of said compounds.

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