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924-50-5

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924-50-5 Usage

Chemical Properties

Colorless liquid

Uses

Methyl 3,3-dimethylacrylate is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 3214, 1949 DOI: 10.1021/ja01177a079

General Description

Methyl 3-methyl-2-butenoate is an α,β-unsaturated ester. It is reported as overripe fruity, ethereal odorant, responsible for the aroma of snake fruit. Rate coefficients for the reaction between the NO3 radical and methyl 3-methyl-2-butenoate has been evaluated.

Check Digit Verification of cas no

The CAS Registry Mumber 924-50-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 4 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 924-50:
(5*9)+(4*2)+(3*4)+(2*5)+(1*0)=75
75 % 10 = 5
So 924-50-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O2/c1-5(2)4-6(7)8-3/h4H,1-3H3

924-50-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (M2052)  Methyl 3,3-Dimethylacrylate  >98.0%(GC)

  • 924-50-5

  • 25g

  • 690.00CNY

  • Detail
  • Alfa Aesar

  • (L19731)  Methyl 3,3-dimethylacrylate, 98%   

  • 924-50-5

  • 10g

  • 452.0CNY

  • Detail
  • Alfa Aesar

  • (L19731)  Methyl 3,3-dimethylacrylate, 98%   

  • 924-50-5

  • 50g

  • 1733.0CNY

  • Detail

924-50-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,3-Dimethylacrylic Acid Methyl Ester

1.2 Other means of identification

Product number -
Other names methyl 3-methylbut-2-enoate

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:924-50-5 SDS

924-50-5Synthetic route

methanol
67-56-1

methanol

3-Methylbutenoic acid
541-47-9

3-Methylbutenoic acid

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

Conditions
ConditionsYield
With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate for 3h; Reflux; Green chemistry;97.8%
With sulfuric acid95%
With sulfuric acid for 16h; Heating;92%
tert-butyl(1-methoxyvinyl)dimethylsilane
105245-42-9

tert-butyl(1-methoxyvinyl)dimethylsilane

acetone
67-64-1

acetone

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

Conditions
ConditionsYield
Stage #1: tert-butyl(1-methoxyvinyl)dimethylsilane; acetone With C40H61Al3O3 In acetonitrile at 0 - 5℃; for 72h; Mukaiyama Aldol Addition;
Stage #2: With hydrogenchloride In water; acetonitrile at 20℃; for 3h; Mukaiyama Aldol Addition;
90%
methanol
67-56-1

methanol

C9H18ClNO3
135765-56-9

C9H18ClNO3

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

β-(N-methoxy-N-isopropoxyamino)-isovaleric acid methyl ester
82004-48-6

β-(N-methoxy-N-isopropoxyamino)-isovaleric acid methyl ester

Conditions
ConditionsYield
With triethylamine 1.) -20 deg C, 6 h, 2.) 20 deg C, 1 h;A 14%
B 86%
(E)-4-bromo-3-methyl-2-butenoic acid methyl ester
27652-13-7, 50465-52-6, 19041-17-9

(E)-4-bromo-3-methyl-2-butenoic acid methyl ester

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

(E)-5-Isopropenyl-3-methyl-hex-2-enedioic acid dimethyl ester
91664-11-8

(E)-5-Isopropenyl-3-methyl-hex-2-enedioic acid dimethyl ester

Conditions
ConditionsYield
With zinc In dimethyl sulfoxide for 4h;A 10%
B 68%
(Z)-methyl-β-bromomethyl-β-methylacrylate
27652-13-7

(Z)-methyl-β-bromomethyl-β-methylacrylate

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

(Z)-5-Isopropenyl-3-methyl-hex-2-enedioic acid dimethyl ester
91664-12-9

(Z)-5-Isopropenyl-3-methyl-hex-2-enedioic acid dimethyl ester

Conditions
ConditionsYield
With zinc In dimethyl sulfoxide for 4h;A 10%
B 67%
β-(N-chloro-N-methoxyamino)-isovaleric acid methyl ester
70569-70-9

β-(N-chloro-N-methoxyamino)-isovaleric acid methyl ester

isobutene
115-11-7

isobutene

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

β-isovaleric acid methyl ester
135765-48-9

β-isovaleric acid methyl ester

Conditions
ConditionsYield
With sulfur dioxide 1.) 7 deg C, 24 h, 2.) 20 deg C, 2 h;A 13%
B 67%
2,2,3,3-tetracyano-4,4-dimethylcyclopentanone dimethyl acetal
76430-13-2

2,2,3,3-tetracyano-4,4-dimethylcyclopentanone dimethyl acetal

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

methyl 3,3-dimethyl-4,5,5-tricyano-4-pentenoate
76430-21-2

methyl 3,3-dimethyl-4,5,5-tricyano-4-pentenoate

C

methyl 3,3-dimethyl-4,4,5,5-tetracyanopentanoate
76430-18-7

methyl 3,3-dimethyl-4,4,5,5-tetracyanopentanoate

Conditions
ConditionsYield
With water In acetonitrile at 80℃; for 12h;A n/a
B n/a
C 63%
(2-Trifluoromethanesulfonyl-pentane-2-sulfonyl)-acetic acid methyl ester
101146-22-9

(2-Trifluoromethanesulfonyl-pentane-2-sulfonyl)-acetic acid methyl ester

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water62%
β-(N,N-dimethoxyamino)-isovaleric acid methyl ester
70569-71-0

β-(N,N-dimethoxyamino)-isovaleric acid methyl ester

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

3-(2-Methoxycarbonyl-1,1-dimethyl-ethyl-NNO-azoxy)-3-methyl-butyric acid methyl ester
80552-91-6

3-(2-Methoxycarbonyl-1,1-dimethyl-ethyl-NNO-azoxy)-3-methyl-butyric acid methyl ester

Conditions
ConditionsYield
With triethylamine hydrochloride In chloroform for 126h; Product distribution; Heating; various acyclic N,N-dialkoxyamines;A 15%
B 51.9%
methyl 2-diazo-3-methylbutanoate
63282-42-8

methyl 2-diazo-3-methylbutanoate

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

Conditions
ConditionsYield
at 400℃; under 0.001 - 0.1 Torr;47%
methanol
67-56-1

methanol

4,4-dimethyl-2-(2-propylidene)-3-thietanone
74966-50-0

4,4-dimethyl-2-(2-propylidene)-3-thietanone

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane
74966-53-3

4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane

Conditions
ConditionsYield
In methanol for 3h; Irradiation;A 28%
B 22%
3-diazo-2,2,5,5-tetramethylthiolan-4-one
74966-46-4

3-diazo-2,2,5,5-tetramethylthiolan-4-one

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

2,2,4,4-Tetramethyl-thietane-3-carboxylic acid methyl ester
74966-52-2

2,2,4,4-Tetramethyl-thietane-3-carboxylic acid methyl ester

C

4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane
74966-53-3

4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane

Conditions
ConditionsYield
In methanol Irradiation;A 19%
B 28%
C 14%
4,4-dimethyl-2-(2-propylidene)-3-thietanone
74966-50-0

4,4-dimethyl-2-(2-propylidene)-3-thietanone

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane
74966-53-3

4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane

Conditions
ConditionsYield
In methanol Irradiation;A 28%
B 22%
methanol
67-56-1

methanol

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

2,2,4,4-Tetramethyl-thietane-3-carboxylic acid methyl ester
74966-52-2

2,2,4,4-Tetramethyl-thietane-3-carboxylic acid methyl ester

C

4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane
74966-53-3

4-Isopropylidene-5-methoxy-2,2-dimethyl-[1,3]oxathiolane

Conditions
ConditionsYield
Irradiation;A 19%
B 27.8%
C 14%
β-(N-chloro-N-methoxyamino)-isovaleric acid methyl ester
70569-70-9

β-(N-chloro-N-methoxyamino)-isovaleric acid methyl ester

acetonitrile
75-05-8

acetonitrile

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

methyl β-(Nacetylamino)isovalerate
43135-04-2

methyl β-(Nacetylamino)isovalerate

Conditions
ConditionsYield
With silver fluoride at -78℃; for 15h;A n/a
B 27.8%
methyl 2-bromo-3-methylbutanoic ester
69367-52-8, 70332-52-4, 114528-93-7, 26330-51-8

methyl 2-bromo-3-methylbutanoic ester

A

2-pyrrolidinon
616-45-5

2-pyrrolidinon

B

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

C

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

Conditions
ConditionsYield
With N-trimethylsilyl-pyrrolidin-2-one at 165 - 195℃; for 3h; Yields of byproduct given;A n/a
B 27%
C n/a
methyl (2,2-dimethyl-3-oxocyclobutyl)acetate
27830-36-0

methyl (2,2-dimethyl-3-oxocyclobutyl)acetate

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

methyl 2-(2,2-dimethyl-5-oxotetrahydrofuran-3-yl)acetate
38306-10-4

methyl 2-(2,2-dimethyl-5-oxotetrahydrofuran-3-yl)acetate

C

Methyl 2,2-dimethyl-4,5-dihydro-3-furanacetate
121757-31-1

Methyl 2,2-dimethyl-4,5-dihydro-3-furanacetate

D

Methyl 2,2-dimethyl-5-(2,2-dimethyltetrahydro-3-(methoxycarbonyl)furan-5-ylidene)tetrahydro-3-furanacetate
121757-32-2

Methyl 2,2-dimethyl-5-(2,2-dimethyltetrahydro-3-(methoxycarbonyl)furan-5-ylidene)tetrahydro-3-furanacetate

Conditions
ConditionsYield
With 4 A molecular sieve In dichloromethane for 72h; Irradiation; Further byproducts given;A 16%
B n/a
C 12%
D 22%
methanol
67-56-1

methanol

Bromoform
75-25-2

Bromoform

acetone
67-64-1

acetone

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzonitrile; acetonitrile at 20℃; for 5h;22%
3,3-dimethyl-4-oxo-oxetane-2-carboxylic acid methyl ester

3,3-dimethyl-4-oxo-oxetane-2-carboxylic acid methyl ester

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

Conditions
ConditionsYield
bei der Destillation im Vakuum ueber eine rotgluehende Platinspirale;
diethyl ether
60-29-7

diethyl ether

3,4-Dibromo-3-methyl-butan-2-one
85526-21-2

3,4-Dibromo-3-methyl-butan-2-one

sodium methylate
124-41-4

sodium methylate

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

β-methoxy-isovaleric acid methyl ester
56830-25-2

β-methoxy-isovaleric acid methyl ester

methyl 3-methyl-3-butenoate
25859-52-3

methyl 3-methyl-3-butenoate

sodium methylate
124-41-4

sodium methylate

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

β-methoxy-isovaleric acid methyl ester
56830-25-2

β-methoxy-isovaleric acid methyl ester

Conditions
ConditionsYield
With diethyl ether
3,4-Dibromo-3-methyl-butan-2-one
85526-21-2

3,4-Dibromo-3-methyl-butan-2-one

sodium methylate
124-41-4

sodium methylate

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

β-methoxy-isovaleric acid methyl ester
56830-25-2

β-methoxy-isovaleric acid methyl ester

Conditions
ConditionsYield
With diethyl ether anfangs unter Kuehlung;
With diethyl ether
methyl 2-bromo-3-methylbutanoic ester
69367-52-8, 70332-52-4, 114528-93-7, 26330-51-8

methyl 2-bromo-3-methylbutanoic ester

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

Conditions
ConditionsYield
With N,N-diethylaniline
methanol
67-56-1

methanol

ethyl 2-acetyl-3-methylbut-2-enoate
35044-52-1

ethyl 2-acetyl-3-methylbut-2-enoate

methyl iodide
74-88-4

methyl iodide

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

Conditions
ConditionsYield
With sodium methylate
methanol
67-56-1

methanol

isopropylideneketene
63364-70-5

isopropylideneketene

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

Conditions
ConditionsYield
at -196.1℃;
methanol
67-56-1

methanol

methyl (2,2-dimethyl-3-oxocyclobutyl)acetate
27830-36-0

methyl (2,2-dimethyl-3-oxocyclobutyl)acetate

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

(2,2-Dimethyl-cyclopropyl)-essigsaeuremethylester
20602-89-5

(2,2-Dimethyl-cyclopropyl)-essigsaeuremethylester

Methyl (3R*,5S*)-5-methoxy-2,2-dimethyltetrahydro-3-furanacetate
113371-55-4, 113371-56-5

Methyl (3R*,5S*)-5-methoxy-2,2-dimethyltetrahydro-3-furanacetate

Methyl (3R*,5R*)-5-methoxy-2,2-dimethyltetrahydro-3-furanacetate
113371-55-4, 113371-56-5

Methyl (3R*,5R*)-5-methoxy-2,2-dimethyltetrahydro-3-furanacetate

Conditions
ConditionsYield
for 16h; Irradiation; Yield given. Yields of byproduct given;
3-methyl-but-2-enal dimethyl acetal
31525-65-2

3-methyl-but-2-enal dimethyl acetal

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

C

3-Dimethoxymethyl-2,2-dimethyl-oxirane
87128-47-0

3-Dimethoxymethyl-2,2-dimethyl-oxirane

Conditions
ConditionsYield
With potassium fluoride; sodium fluoride; 3-chloro-benzenecarboperoxoic acid In dichloromethane 1.) 15 h, RT; 2.) 1 h, RT;
β,β-Di(3>methyl)acrylsaeure-methylester
100342-98-1

β,β-Di(3>methyl)acrylsaeure-methylester

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

Conditions
ConditionsYield
With potassium hydroxide In methanol
methyl tert-butyl(pivaloyl)acetate
144864-97-1

methyl tert-butyl(pivaloyl)acetate

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

methyl 3,3-dimethylbutyrate
10250-48-3

methyl 3,3-dimethylbutyrate

Conditions
ConditionsYield
at 900℃; under 8E-05 Torr; Product distribution;
methyl tert-butyl(pivaloyl)acetate
144864-97-1

methyl tert-butyl(pivaloyl)acetate

A

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

B

methyl 3,3-dimethylbutyrate
10250-48-3

methyl 3,3-dimethylbutyrate

C

Methyl 4,4-dimethyl-3-oxopentanoate
55107-14-7

Methyl 4,4-dimethyl-3-oxopentanoate

D

isobutene
115-11-7

isobutene

E

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
at 600℃; under 8E-05 Torr; Product distribution; other temperatures;
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

nonylmagnesium bromide
39691-62-8

nonylmagnesium bromide

methyl 3,3-dimethyldodecanoate

methyl 3,3-dimethyldodecanoate

Conditions
ConditionsYield
With copper(l) iodide; chloro-trimethyl-silane In tetrahydrofuran; diethyl ether at -15 - 20℃;100%
With chloro-trimethyl-silane; copper(l) iodide In tetrahydrofuran at -15 - 20℃;
With copper(l) iodide; chloro-trimethyl-silane In tetrahydrofuran at -15 - 20℃;
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

5,5-dimethylpyrazolidin-3-one
42953-82-2

5,5-dimethylpyrazolidin-3-one

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 20℃; for 5h; Reflux;99%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

Methyl 3-mercaptopropionate
2935-90-2

Methyl 3-mercaptopropionate

3-(2-methoxycarbonyl-ethylsulfanyl)-3-methylbutyric acid methyl ester

3-(2-methoxycarbonyl-ethylsulfanyl)-3-methylbutyric acid methyl ester

Conditions
ConditionsYield
Stage #1: Methyl 3,3-dimethylacrylate With piperidine; N-benzyl-trimethylammonium hydroxide In methanol at 0℃; Inert atmosphere;
Stage #2: Methyl 3-mercaptopropionate at 60℃; for 24h; Inert atmosphere;
97.23%
With piperidine; N-benzyl-trimethylammonium hydroxide In methanol at 0 - 60℃; for 24h; Inert atmosphere;97%
With piperidine; N-benzyl-trimethylammonium hydroxide In methanol at 60℃; for 24h; Michael addition;75%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

4,4,5,7-tetramethyl-3,4-dihydrocoumarin
40662-14-4

4,4,5,7-tetramethyl-3,4-dihydrocoumarin

Conditions
ConditionsYield
With methanesulfonic acid at 70℃; for 6h;96%
With sulfuric acid Michael Addition; Reflux;93%
With methanesulfonic acid at 20 - 70℃; for 17h;92%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

tert-butylhydrazine
32064-67-8

tert-butylhydrazine

3-(N'-tert-Butyl-hydrazino)-3-methyl-butyric acid methyl ester

3-(N'-tert-Butyl-hydrazino)-3-methyl-butyric acid methyl ester

Conditions
ConditionsYield
In Dimethyl ether for 168h;96%
methanol
67-56-1

methanol

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

methyl 2-iodo-3-methoxy-3-methylbutanoate

methyl 2-iodo-3-methoxy-3-methylbutanoate

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; iodine at 50℃; for 15h;96%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

3,3,5,7-tetramethylchroman-2-one

3,3,5,7-tetramethylchroman-2-one

Conditions
ConditionsYield
With methanesulfonic acid at 70℃;96%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

n-decyl magnesium bromide
17049-50-2

n-decyl magnesium bromide

methyl 3,3-dimethyltridecanoate

methyl 3,3-dimethyltridecanoate

Conditions
ConditionsYield
With copper(l) iodide; chloro-trimethyl-silane In tetrahydrofuran; 2-methyltetrahydrofuran at -15 - 20℃; Inert atmosphere;96%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

isononanoyl chloride
36727-29-4

isononanoyl chloride

3,7,9,9-tetramethyl-2-decen-5-onic acid methyl ester

3,7,9,9-tetramethyl-2-decen-5-onic acid methyl ester

Conditions
ConditionsYield
With aluminum (III) chloride; tin(IV) chloride at 40℃; for 5h; Time; Cooling with ice; Reflux;95.4%
Stage #1: isononanoyl chloride With aluminum (III) chloride In dichloromethane at 30℃; for 0.666667h;
Stage #2: Methyl 3,3-dimethylacrylate In dichloromethane at 38℃; for 1h; Temperature;
Stage #1: isononanoyl chloride With aluminum (III) chloride In dichloromethane for 5h;
Stage #2: Methyl 3,3-dimethylacrylate In dichloromethane at 40℃; for 10h; Time;
Stage #1: isononanoyl chloride With anhydrous aluminum chloride, anhydrous lanthanum chloride, anhydrous lithium perchlorate on silica gel catalyst In dichloromethane at 0℃; for 1h;
Stage #2: Methyl 3,3-dimethylacrylate In dichloromethane at 25 - 40℃; for 11h; Temperature;
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

(+/-)-lavandulol
58461-27-1

(+/-)-lavandulol

A

2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate
23960-07-8

2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate

B

2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-3-butenoate

2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-3-butenoate

Conditions
ConditionsYield
With titanium(IV) isopropylate In toluene at 100℃; Temperature; Reagent/catalyst;A 94.9%
B n/a
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

2,3-dibromo-3-metyl-butenoate
63881-44-7

2,3-dibromo-3-metyl-butenoate

Conditions
ConditionsYield
With bromine In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Schlenk technique;94%
With bromine In dichloromethane at 0℃; for 10h;73%
With tetrachloromethane; bromine
With bromine
With bromine In neat (no solvent) for 48h; from -50 deg C to -70 deg C;
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

2,4-Xylenol
105-67-9

2,4-Xylenol

4,4,6,8-tetramethyldihydrocoumarin
249629-60-5

4,4,6,8-tetramethyldihydrocoumarin

Conditions
ConditionsYield
With methanesulfonic acid at 70℃; Condensation; cyclization;93%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

allyl bromide
106-95-6

allyl bromide

2-(prop-1-en-2-yl)pent-4-en-1-ol
99799-91-4

2-(prop-1-en-2-yl)pent-4-en-1-ol

Conditions
ConditionsYield
Stage #1: Methyl 3,3-dimethylacrylate With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 0℃; for 1.83333h; Inert atmosphere; Cooling with acetone-dry ice;
Stage #2: allyl bromide In tetrahydrofuran at -78 - 0℃; for 15h; Inert atmosphere; Cooling with acetone-dry ice;
Stage #3: With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Inert atmosphere;
93%
Stage #1: Methyl 3,3-dimethylacrylate; allyl bromide With lithium diisopropyl amide Inert atmosphere;
Stage #2: With lithium aluminium tetrahydride Inert atmosphere;
93%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

methyl 3-hydroxy-3-methyl-2-iodobutanoate

methyl 3-hydroxy-3-methyl-2-iodobutanoate

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; water; iodine In acetonitrile at 50℃; for 9h; Reagent/catalyst;93%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

methyl 3-methylbutanoate
556-24-1

methyl 3-methylbutanoate

Conditions
ConditionsYield
With zinc copper In methanol for 24h; Heating;88%
With magnesium In methanol at 10℃; for 2.5h;78%
With platinum(IV) oxide Hydrogenation;
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

methyllithium
917-54-4

methyllithium

2,4-dimethyl-3-penten-2-ol
56763-70-3

2,4-dimethyl-3-penten-2-ol

Conditions
ConditionsYield
In diethyl ether at 0℃; for 1h;88%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

Trimethylhydroquinone
700-13-0

Trimethylhydroquinone

6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
40662-76-8

6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Conditions
ConditionsYield
With methanesulfonic acid87%
With methanesulfonic acid at 70℃; for 3h;81.2%
With methanesulfonic acid at 70℃; for 2h;80%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyl-(1-methoxy-3-methyl-buta-1,3-dienyloxy)-dimethyl-silane

tert-butyl-(1-methoxy-3-methyl-buta-1,3-dienyloxy)-dimethyl-silane

Conditions
ConditionsYield
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 20℃; for 1.5h;87%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

methyl 3-amino-3-methyl-butanoate
29637-56-7

methyl 3-amino-3-methyl-butanoate

Conditions
ConditionsYield
With ammonia In methanol at 120℃; for 4h; Inert atmosphere; Microwave irradiation;87%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

<(phenylsuilfonyl)methylene>dilithium
59807-81-7

<(phenylsuilfonyl)methylene>dilithium

1-benzenesulfonyl-4-methylpent-3-en-2-one
107006-44-0

1-benzenesulfonyl-4-methylpent-3-en-2-one

Conditions
ConditionsYield
86%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

2,6-dimethyl-4-(2'-methyl-2'-propenyl)-1,5-heptadien-4-ol

2,6-dimethyl-4-(2'-methyl-2'-propenyl)-1,5-heptadien-4-ol

Conditions
ConditionsYield
With magnesium In tetrahydrofuran Heating;86%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

[1,1-(2)H2]-3-methyl-2-buten-1-ol

[1,1-(2)H2]-3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With lithium aluminium deuteride at 20℃; for 2h;86%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

[1,1-2H2]-3-methyl-2-butenol
6158-92-5

[1,1-2H2]-3-methyl-2-butenol

Conditions
ConditionsYield
With lithium aluminium deuteride86%
With lithium aluminium deuteride In diethyl ether at 0℃; for 1h; Inert atmosphere; Reflux;76%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

(R)-1-methyl-4-(1-(phenylsulfonyl)propan-2-yl)benzene

(R)-1-methyl-4-(1-(phenylsulfonyl)propan-2-yl)benzene

(6R)-2-methyl-5-(phenylsulfonyl)-6-p-tolylhept-2-en-4-one

(6R)-2-methyl-5-(phenylsulfonyl)-6-p-tolylhept-2-en-4-one

Conditions
ConditionsYield
Stage #1: (R)-1-methyl-4-(1-(phenylsulfonyl)propan-2-yl)benzene With n-butyllithium In tetrahydrofuran at -78 - -50℃; Inert atmosphere; Glovebox; Schlenk technique;
Stage #2: With magnesium bromide ethyl etherate In tetrahydrofuran at -78 - 20℃; for 0h; Inert atmosphere; Glovebox; Schlenk technique;
Stage #3: Methyl 3,3-dimethylacrylate In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Glovebox; Schlenk technique;
85%
Stage #1: (R)-1-methyl-4-(1-(phenylsulfonyl)propan-2-yl)benzene With n-butyllithium In tetrahydrofuran; hexane at -50℃; Inert atmosphere;
Stage #2: With magnesium bromide ethyl etherate In tetrahydrofuran; diethyl ether; hexane at -78 - 0℃; for 0.166667h; Inert atmosphere;
Stage #3: Methyl 3,3-dimethylacrylate In tetrahydrofuran; diethyl ether; hexane at -78 - 20℃; Inert atmosphere; enantioselective reaction;
77%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

7-methyl-3-methylene-7-octen-1-ol
73945-79-6

7-methyl-3-methylene-7-octen-1-ol

7-methyl-3-methylene-7-octenyl senecioate

7-methyl-3-methylene-7-octenyl senecioate

Conditions
ConditionsYield
With titanium(IV) isopropylate Inert atmosphere; Heating;84.7%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

(4-(tert-butyldimethylsilyloxy)butyl)magnesium chloride

(4-(tert-butyldimethylsilyloxy)butyl)magnesium chloride

C15H30O2Si

C15H30O2Si

Conditions
ConditionsYield
Stage #1: (4-(tert-butyldimethylsilyloxy)butyl)magnesium chloride With zirconocene dichloride In tetrahydrofuran; toluene at 0℃; for 3h;
Stage #2: Methyl 3,3-dimethylacrylate In tetrahydrofuran; toluene at 0 - 20℃;
84%
piperazine
110-85-0

piperazine

Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

dimethyl 3,3'-(piperazine-1,4-diyl)bis-(3-methylbutanoate)
1260115-90-9

dimethyl 3,3'-(piperazine-1,4-diyl)bis-(3-methylbutanoate)

Conditions
ConditionsYield
In tetrahydrofuran; methanol at 20℃; for 24h; Aza-Michael addition; hyperbaric;84%

924-50-5Relevant articles and documents

Hagens et al.

, p. 3682,3684 (1970)

Cardemie,Cori

, p. 15 (1973)

Effect of Differential Geminal Substitution of γAmino Acid Residues at the (i + 2) Position of αγTurn Segments on the Conformation of Template β-Hairpin Peptides

Chatterjee, Sunanda,Debnath, Swapna,Ghosh, Suvankar,Pandit, Gopal,Satpati, Priyadarshi

supporting information, p. 11310 - 11323 (2021/09/07)

The effect of insertion of three geminally dimethyl substituted γamino acid residues [γ2,2 (4-amino-2,2-dimethylbutanoic acid), γ3,3 (4-amino-3,3-dimethylbutanoic acid), and γ4,4 (4-amino-4,4-dimethylbutanoic acid)] at the (i + 2) position of a two-residue αγC12 turn segment in a model octapeptide sequence Leu-Phe-Val-Aib-Xxx-Leu-Phe-Val (where Xxx = γamino acid residues) has been investigated in this study. Solution conformational studies (NMR, CD, and IR) and ab initio calculations indicated that γ3,3 and γ4,4 residues were well accommodated in the β-hairpin nucleating αγC12 turns, which gave rise to well-registered hairpins, in contrast to γ2,2, which was unable to form a tight C12 β-hairpin nucleating turn and promote a well-registered β-hairpin. Geminal disubstitution at the Cα carbon in γ2,2 led to unfavorable steric contacts, disabling its accommodation in the αγC12 hairpin nucleating turn unlike the γ3,3 and γ4,4 residues. Geminal substitutions at different carbons along the backbone constrained backbone torsion angles for the three γamino acid residues differently, generating diverse conformational preferences in them. Folded hairpins were energetically more stable (~8 to 9 kcal/mol) than the unfolded peptides. Conformational preference of the peptides was independent of the N-terminal protecting group. Such fundamental understanding will instrumentalize the future directed design of foldamers.

Engineering Catalysts for Selective Ester Hydrogenation

Dub, Pavel A.,Batrice, Rami J.,Gordon, John C.,Scott, Brian L.,Minko, Yury,Schmidt, Jurgen G.,Williams, Robert F.

, p. 415 - 442 (2020/03/04)

The development of efficient catalysts and processes for synthesizing functionalized (olefinic and/or chiral) primary alcohols and fluoral hemiacetals is currently needed. These are valuable building blocks for pharmaceuticals, agrochemicals, perfumes, and so forth. From an economic standpoint, bench-stable Takasago Int. Corp.'s Ru-PNP, more commonly known as Ru-MACHO, and Gusev's Ru-SNS complexes are arguably the most appealing molecular catalysts to access primary alcohols from esters and H2 (Waser, M. et al. Org. Proc. Res. Dev. 2018, 22, 862). This work introduces economically competitive Ru-SNP(O)z complexes (z = 0, 1), which combine key structural elements of both of these catalysts. In particular, the incorporation of SNP heteroatoms into the ligand skeleton was found to be crucial for the design of a more product-selective catalyst in the synthesis of fluoral hemiacetals under kinetically controlled conditions. Based on experimental observations and computational analysis, this paper further extends the current state-of-the-art understanding of the accelerative role of KO-t-C4H9 in ester hydrogenation. It attempts to explain why a maximum turnover is seen to occur starting at 25 mol % base, in contrast to only 10 mol % with ketones as substrates.

Cyanide-Free One-Pot Synthesis of Methacrylic Esters from Acetone

Koyama, Minoru,Kawakami, Takafumi,Okazoe, Takashi,Nozaki, Kyoko

, p. 10913 - 10917 (2019/08/02)

Methacrylic esters, represented by methyl methacrylate (MMA), are widely used as commodity chemicals. Here, the one-pot synthesis of methacrylic esters from acetone, a haloform and alcohols in the presence of an organic base is described. Using DBU as the organic base for the reaction of acetone, chloroform and methanol in acetonitrile afforded MMA in 66 % yield. When the solvent was replaced by benzonitrile, the product MMA was successfully purified by distillation. Applicability of this process to various alcohols was also investigated to show ethyl, phenyl, CF3CH2, and n-C6F13CH2CH2 esters were obtained in moderate yields. The use of bromoform instead of chloroform resulted in the improvement of the yield, for example, methyl and n-C6F13CH2CH2 esters up to 81 and 70 %, respectively. The reaction with deuterated starting materials acetone-d6 and MeOH-d4, with DBU in acetonitrile afforded deuterated MMA (MMA-d8) in 70 % yield.

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