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759-24-0 Usage

Uses

Diethyl tert-butylmalonate is used in the preparation of enantiomers of 4-tert-butyl-3-isopropyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-sulfide.

Purification Methods

Dissolve it in Et2O, wash with aqueous NaHCO3, H2O, dry (MgSO4), filter, evaporate and distil the residue. Identify by hydrolysis to the acid and determine the neutralisation equivalent (theor: 80.0). The acid has m 155-157o effervescence [Hauser et al. J Am Chem Soc 64 2715 1942, Bush & Beauchamp J Am Chem Soc 75 2949 1953]. [Beilstein 2 IV 2027.]

Check Digit Verification of cas no

The CAS Registry Mumber 759-24-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,5 and 9 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 759-24:
(5*7)+(4*5)+(3*9)+(2*2)+(1*4)=90
90 % 10 = 0
So 759-24-0 is a valid CAS Registry Number.
InChI:InChI=1/C11H20O4/c1-6-14-9(12)8(11(3,4)5)10(13)15-7-2/h8H,6-7H2,1-5H3

759-24-0 Well-known Company Product Price

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  • Alfa Aesar

  • (L09131)  Diethyl tert-butylmalonate, 97%   

  • 759-24-0

  • 1g

  • 341.0CNY

  • Detail
  • Alfa Aesar

  • (L09131)  Diethyl tert-butylmalonate, 97%   

  • 759-24-0

  • 5g

  • 1227.0CNY

  • Detail
  • Alfa Aesar

  • (L09131)  Diethyl tert-butylmalonate, 97%   

  • 759-24-0

  • 25g

  • 5360.0CNY

  • Detail

759-24-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name diethyl 2-tert-butylpropanedioate

1.2 Other means of identification

Product number -
Other names diethyl 2-(t-butyl)-malonate

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:759-24-0 SDS

759-24-0Synthetic route

diethyl isopropylidenemalonate
6802-75-1

diethyl isopropylidenemalonate

methyl iodide
74-88-4

methyl iodide

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: methyl iodide With magnesium In diethyl ether at 0℃; Inert atmosphere;
Stage #2: diethyl isopropylidenemalonate With copper(l) chloride In diethyl ether for 1.5h; Inert atmosphere; Cooling with ice;
93%
With magnesium; copper(l) chloride 1) ether, 2) ether, 30 min, heating; Yield given. Multistep reaction;
diethyl isopropylidenemalonate
6802-75-1

diethyl isopropylidenemalonate

methyl manganese chloride
89984-56-5

methyl manganese chloride

A

isopropenyl-malonic acid diethyl ester
38806-12-1

isopropenyl-malonic acid diethyl ester

B

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Product distribution; 1.) 0 deg C, 2.) 20 deg C; var organomanganeses.;A 10%
B 82%
In tetrahydrofuran for 2h; 1.) 0 deg C, 2.) 20 deg C,;A 10%
B 82%
diethyl 1,1-dimethylethyl(methylsulfonyl)malonate
1214319-97-7

diethyl 1,1-dimethylethyl(methylsulfonyl)malonate

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: diethyl 1,1-dimethylethyl(methylsulfonyl)malonate With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 20℃; for 8h; Reflux;
Stage #2: With water
68%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

diethyl isopropylidenemalonate
6802-75-1

diethyl isopropylidenemalonate

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: methyl magnesium iodide; diethyl isopropylidenemalonate With copper(l) chloride In diethyl ether at 20℃; for 0.5h;
Stage #2: With sulfuric acid; water In diethyl ether
60%
With diethyl ether anfangs unter Kuehlen, zuletzt bei kurzem Erhitzen;
With diethyl ether
lithium dimethylcuprate
15681-48-8

lithium dimethylcuprate

diethyl (1,3-dithian-2-ylidene)-1-propanedioate
19723-88-7

diethyl (1,3-dithian-2-ylidene)-1-propanedioate

A

diethyl isopropylidenemalonate
6802-75-1

diethyl isopropylidenemalonate

B

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
In diethyl ether 1.) 0 deg C, 0.25 h; 2.) 23 deg C, 0.5 h.;A 5%
B 15%
diethyl isopropylidenemalonate
6802-75-1

diethyl isopropylidenemalonate

methylmagnesium chloride
676-58-4

methylmagnesium chloride

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
In tetrahydrofuran 1.) -30 deg C, 2.) 20 deg C,;3%
t-butyl bromide
507-19-7

t-butyl bromide

diethyl malonate
105-53-3

diethyl malonate

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
With sodium ethanolate at 5℃; dann bei Raumtemperatur;
With sodium ethanolate at 5℃; in der Siedehitze;
Stage #1: diethyl malonate With sodium ethanolate In ethanol for 2h; Reflux;
Stage #2: t-butyl bromide In ethanol for 6h; Reflux;
diethyl ether
60-29-7

diethyl ether

ethyl 3,3-dimethylbutanoate
5340-78-3

ethyl 3,3-dimethylbutanoate

triphenylmethyl sodium
4303-71-3

triphenylmethyl sodium

Diethyl carbonate
105-58-8

Diethyl carbonate

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

methyl magnesium iodide
917-64-6

methyl magnesium iodide

diethyl [bis(methylthio)methylene]malonate
55084-15-6

diethyl [bis(methylthio)methylene]malonate

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
With copper(I) bromide In diethyl ether
t-butyl bromide
507-19-7

t-butyl bromide

Difluorborsaeureester d. Enols v. Malonsaeurediethylester

Difluorborsaeureester d. Enols v. Malonsaeurediethylester

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
With silver perchlorate In nitromethane at 0℃;
diethyl isopropylidenemalonate
6802-75-1

diethyl isopropylidenemalonate

lithium dimethylcuprate
15681-48-8

lithium dimethylcuprate

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
In diethyl ether
diethyl isopropylidenemalonate
6802-75-1

diethyl isopropylidenemalonate

methyllithium
917-54-4

methyllithium

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
With copper(l) iodide In diethyl ether
tertiary butyl chloride
507-20-0

tertiary butyl chloride

diethyl malonate
105-53-3

diethyl malonate

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
(i) BF3, (ii) /BRN= 1730872/, CS2, ClCH2CH2Cl; Multistep reaction;
methyl magnesium iodide
917-64-6

methyl magnesium iodide

diethyl isopropylidenemalonate
6802-75-1

diethyl isopropylidenemalonate

A

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

B

ethyl 2-ethoxycarbonyl-2-methyl-3-butenoate
64770-16-7

ethyl 2-ethoxycarbonyl-2-methyl-3-butenoate

Conditions
ConditionsYield
With copper(l) cyanide In tetrahydrofuran
1,3-diethyl 2-diazopropanedioate
5256-74-6

1,3-diethyl 2-diazopropanedioate

Isobutane
75-28-5

Isobutane

A

(2-methylpropyl)-propanedioic acid, diethyl ester
10203-58-4

(2-methylpropyl)-propanedioic acid, diethyl ester

B

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
Product distribution; Irradiation; with and without benzophenone, different temperatures;
2-tert-butyl-5-hydroxy-1,4-benzoquinone
4857-70-9

2-tert-butyl-5-hydroxy-1,4-benzoquinone

ethyl iodide
75-03-6

ethyl iodide

A

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

B

α-tert-butyl-β-hydroxy-succinic acid diethyl ester
77292-40-1

α-tert-butyl-β-hydroxy-succinic acid diethyl ester

C

2,3-epoxy-3-tert-butyl-4-oxy-pentanoic acid ethyl ester
77292-41-2

2,3-epoxy-3-tert-butyl-4-oxy-pentanoic acid ethyl ester

Conditions
ConditionsYield
With sodium hydroxide; sodium silicate; diethylenetriaminopentaacetic acid; dihydrogen peroxide 1.) water, 40 deg C, 60 min, pH 11.0, 2) methylene chloride, reflux, 2 h; Yield given. Multistep reaction. Yields of byproduct given;
methyl magnesium iodide
917-64-6

methyl magnesium iodide

acetone
67-64-1

acetone

diethyl malonate
105-53-3

diethyl malonate

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Diethyl carbonate
105-58-8

Diethyl carbonate

tert-butylacetic acid ethyl ester

tert-butylacetic acid ethyl ester

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
With diethyl ether; triphenylmethyl sodium
diethyl malonate
105-53-3

diethyl malonate

6-ethoxy-4-cyano-5-methyl-hex-2ξ-enoic acid ethyl ester

6-ethoxy-4-cyano-5-methyl-hex-2ξ-enoic acid ethyl ester

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ZnCl2 / acetic anhydride
2: 2.) H3O+
View Scheme
diethyl malonate
105-53-3

diethyl malonate

diazotized 3-bromo-4-methyl-aniline

diazotized 3-bromo-4-methyl-aniline

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) BF3, CH2Cl2, (ii) aq. NaHCO3
2: AgClO4 / nitromethane / 0 °C
View Scheme
diethyl malonate
105-53-3

diethyl malonate

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: zinc(II) chloride; acetic anhydride / 24 h / Reflux
2.1: magnesium / diethyl ether / 0 °C / Inert atmosphere
2.2: 1.5 h / Inert atmosphere; Cooling with ice
View Scheme
tert-Butylacetic acid
1070-83-3

tert-Butylacetic acid

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: methanesulfonic acid
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 14.5 h / -78 - 20 °C / Inert atmosphere
View Scheme
ethyl 3,3-dimethylbutanoate
5340-78-3

ethyl 3,3-dimethylbutanoate

Diethyl carbonate
105-58-8

Diethyl carbonate

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: ethyl 3,3-dimethylbutanoate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: Diethyl carbonate In tetrahydrofuran at -78 - 20℃; for 14.5h; Inert atmosphere;
methanethiosulfonic acid S-methyl ester
2949-92-0

methanethiosulfonic acid S-methyl ester

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

t-BuCSMe(CO2Et)2
1214319-95-5

t-BuCSMe(CO2Et)2

Conditions
ConditionsYield
Stage #1: tert-butylmalonic acid diethyl ester With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: methanethiosulfonic acid S-methyl ester In tetrahydrofuran at 20℃; for 2h;
89%
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

2-tert-butylpropane-1,3-diol
2819-05-8

2-tert-butylpropane-1,3-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether 1) 2 h, reflux, 2) overnight;84.8%
With lithium aluminium tetrahydride In diethyl ether66%
With lithium aluminium tetrahydride In diethyl ether Inert atmosphere; Cooling with ice; Reflux;66%
ethyl bromide
74-96-4

ethyl bromide

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

diethyl t-butylethylmalonate
18149-55-8

diethyl t-butylethylmalonate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 3h; Ambient temperature;82%
With ethanol; sodium ethanolate
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

pivalamidine hydrochloride
18202-73-8

pivalamidine hydrochloride

2,5-di-t-butylpyrimidine-4,6-diol
128939-54-8

2,5-di-t-butylpyrimidine-4,6-diol

Conditions
ConditionsYield
With sodium ethanolate In ethanol 1.) RT, 10 h, 2.) reflux, 3 h;80%
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

allyl bromide
106-95-6

allyl bromide

diethyl allyl t-butylmalonate
59726-42-0

diethyl allyl t-butylmalonate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 8h;79%
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine
5807-14-7

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine

C14H21N3O2

C14H21N3O2

Conditions
ConditionsYield
In various solvent(s) for 6h; Heating;77%
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C14H26O5

C14H26O5

Conditions
ConditionsYield
Stage #1: tert-butylmalonic acid diethyl ester With sodium hydride In N,N-dimethyl acetamide at 25℃; for 1h;
Stage #2: ethyl chloromethyl ether In N,N-dimethyl acetamide at 0 - 25℃;
73%
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

2-(tert-butyl)malonic acid
4379-33-3

2-(tert-butyl)malonic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 10h; Heating;67%
With potassium hydroxide
With water; sodium hydroxide In tetrahydrofuran at 30℃; for 2h;
formaldehyd
50-00-0

formaldehyd

tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

diethyl tert-butyl(hydroxymethyl)malonate
82515-42-2

diethyl tert-butyl(hydroxymethyl)malonate

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide for 5h; Ambient temperature;66%
With benzyltrimethylammonium chloride; potassium carbonate In dimethyl sulfoxide at 80℃; for 12h; Alkylation;33%
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

2-tert-butyl-malonic acid monoethyl ester
83096-36-0

2-tert-butyl-malonic acid monoethyl ester

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 10h; Heating;58%
With potassium hydroxide In ethanol
hydrolysis;
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

urea
57-13-6

urea

5-tert-butylbarbituric acid
90197-63-0

5-tert-butylbarbituric acid

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 70℃; for 8h;56%
With sodium ethanolate
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

urea
57-13-6

urea

5-tert-Butyl-6-hydroxy-1H-pyrimidine-2,4-dione
90197-63-0

5-tert-Butyl-6-hydroxy-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 6h; Heating / reflux;48%
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

propargyl bromide
106-96-7

propargyl bromide

2-tert-butyl-2-prop-2-ynylmalonic acid diethyl ester
745071-77-6

2-tert-butyl-2-prop-2-ynylmalonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: tert-butylmalonic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 16h;
47%
Stage #1: tert-butylmalonic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 16h;
47%
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

tetra(n-butyl)ammonium hydroxide
2052-49-5

tetra(n-butyl)ammonium hydroxide

tetrabutylammonium diethyl-2-tert-butylmalonate

tetrabutylammonium diethyl-2-tert-butylmalonate

Conditions
ConditionsYield
20%
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

tert-Butylacetic acid
1070-83-3

tert-Butylacetic acid

Conditions
ConditionsYield
With potassium hydroxide
Multi-step reaction with 2 steps
1: alcoholic KOH
View Scheme
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

diethyl allyl t-butylmalonate
59726-42-0

diethyl allyl t-butylmalonate

Conditions
ConditionsYield
With sodium ethanolate; Diethyl carbonate beim Abdestillieren des Alkohols und allmaehlichen Erhitzen mit Allylbromid auf 100-105grad;
tert-butylmalonic acid diethyl ester
759-24-0

tert-butylmalonic acid diethyl ester

diphenyl hydrazine
122-66-7

diphenyl hydrazine

4-tert-butyl-1,2-diphenyl-pyrazolidine-3,5-dione
568-74-1

4-tert-butyl-1,2-diphenyl-pyrazolidine-3,5-dione

Conditions
ConditionsYield
With sodium ethanolate at 160℃;

759-24-0Relevant articles and documents

Tautomerism in bis(oxazoline)s

Walli, Adam,Dechert, Sebastian,Meyer, Franc

, p. 7044 - 7049 (2013)

Bis(oxazoline)s (BOXs) are a privileged ligand class and have found widespread use in catalysis. Herein, the tautomerism of selected BOX ligands was evidenced by X-ray diffractometry as well as by NMR and IR spectroscopy and supported by DFT calculations. In CDCl3 solution at room temperature, the new 1,1-bis(4,4-dimethyl-1,3-oxazolin-2-yl)-1-phenylmethane ( Ph,HBOX-Me2) ligand is present as a 1:1 mixture of the diimine and iminoenamine tautomers. Thermodynamic and kinetic data for the tautomeric equilibrium were determined, which allowed comparison with related bidentate ligand classes. The other BOXs studied, H,HBOX-Me 2, Me,HBOX-Me2, and tBu,HBOX-Me 2, are largely present in the diimine form under similar conditions. IR spectroscopy was identified as a valuable tool for detecting the presence of the iminoenamine form as a minor component. Tautomerism in the prominent bis(oxazoline) ligand class is evidenced by X-ray diffractometry as well as by NMR and IR spectroscopy and supported by DFT calculations. Thermodynamic and kinetic data for the tautomeric equilibrium are determined for a specific example, which allows comparison with related bidentate ligand classes. Copyright

A amide alkaloid fully synthetic method

-

Paragraph 0056; 0057, (2017/08/25)

The invention discloses a total synthesis method of amides alkaloid, and belongs to the technical field of the chemistry of natural products. The total synthesis method comprises the following steps: carrying out the synthesis by adopting malonate and 2-bromopropane or 2-bromopropane derivative as raw materials, thereby obtaining isopropyl malonate; (2) carrying out the synthesis by adopting 2-aminopyrrolidine as a raw material, thereby obtaining mid-body 2-amino tetralin pyrrolidine; and (3) synthesizing amides alkaloid 3-isopropyl-nafoxidine[1,2-alpha]pyrimidine-2,4(1H,3H)-diketone and a derivative by adopting the isopropyl malonate and the 2-2-amino tetralin pyrrolidine as a raw material. By adopting the total synthesis method, the defect that the extraction separation process in the natural product is complicated and the yield is low can be overcome, and the demand of perople for further researching the natural product can be satisfied; moreover, the synthesis method is simple in route, raw materials are cheap and easy to obtain, and the yield is relatively high.

METHOD OF PRODUCING 3-ETHOXY-2-TERT-BUTYL ALKYL PROPIONATE

-

Paragraph 0039; 0040, (2016/12/22)

PROBLEM TO BE SOLVED: To provide a novel production method of 3-ethoxy-2-tert-butyl alkyl propionate used for the production of an olefin polymerization solid catalyst. SOLUTION: A 2-ethoxy methyl malonic acid diester derivative represented by formula (1) (where R1 and R2 represent a 1-4C alkyl group) is reacted in the presence of a base. COPYRIGHT: (C)2015,JPO&INPIT

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