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600-22-6

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  • High Quality 99% 600-22-6 Methyl pyruvate,(Pyruvic acid methyl ester); Pyruvic acid methyl ester; 3-Chlorophenylacetone; Brenztraubensaeure-methylester Manufacturer

    Cas No: 600-22-6

  • USD $ 0.1-0.1 / Gram

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  • 100 Metric Ton/Year

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600-22-6 Usage

Chemical Properties

Methyl pyruvate is a clear, light yellow, and flammable liquid.

Uses

Different sources of media describe the Uses of 600-22-6 differently. You can refer to the following data:
1. Methyl Pyruvate acts as a potent secretagogue used in the study of stimulus-secretion coupling. Also used in the preparation of quinoxalines as dual phoosphodiesterase 2/10 (PDE2/10) inhibitors. It increases free calcium ion concentration in the cytosol of pancreatic cells. It is used in the preparation of dimethyl 2,3-dimethylenebutanedioate.
2. Methyl pyruvate may be used to investigate the adsorption and reactivity of methyl pyruvate on Pt{111}. It may be used in the preparation of dimethyl 2,3-dimethylenebutanedioate.

Definition

ChEBI: Methyl pyruvate is a pyruvate ester resultinf grom the formal condensation of the carboxy group of pyruvic acid with the hydroxy group of methanol. It is a pyruvate ester and a methyl ester. It derives from a pyruvic acid.

Preparation

Methyl pyruvate has been prepared from the silver salt of pyruvic acid and methyl iodide; from the free acid, by the ethanol-vapor method without a catalyst, by azeotropic removal of the water produced by the reaction of methanol in the presence of p-toluenesulfonic acid (the present method), and by refluxing with methanol in ethylene dichloride using ethanesulfonic acid as a catalyst (73% yield). Pyruvic esters have also been prepared by the catalytic dehydrogenation of lactic acid esters and by the oxidation of ethyl lactate with potassium permanganate. DOI: 10.15227/orgsyn.024.0072

General Description

Methyl pyruvate is a pyruvic ester. Surface conditions during Pt/silica EUROPT-1 modified by cinchonidine catalyzed by enantioselective hydrogenation of methyl pyruvate to R-(+)-methyl lactate were investigated. Enantioselective hydrogenation of methyl pyruvate over finely dispersed polyvinylpyrrolidone-stabilized and the corresponding alumina-supported iridium clusters modified with cinchonidine was studied. The molecular orientation and conformation of methyl pyruvate on Ni(111) surface has been investigated in the temperature range 105-220K. Methyl pyruvate is reported to stimulate insulin secretion in vitro and in vivo.

Check Digit Verification of cas no

The CAS Registry Mumber 600-22-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 0 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 600-22:
(5*6)+(4*0)+(3*0)+(2*2)+(1*2)=36
36 % 10 = 6
So 600-22-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O3/c1-3(5)4(6)7-2/h1-2H3

600-22-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A13966)  Methyl pyruvate, 98%   

  • 600-22-6

  • 25g

  • 278.0CNY

  • Detail
  • Alfa Aesar

  • (A13966)  Methyl pyruvate, 98%   

  • 600-22-6

  • 100g

  • 748.0CNY

  • Detail
  • Alfa Aesar

  • (A13966)  Methyl pyruvate, 98%   

  • 600-22-6

  • 500g

  • 3166.0CNY

  • Detail

600-22-6SDS

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 methyl pyruvate

1.2 Other means of identification

Product number -
Other names Methyl pyruvate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:600-22-6 SDS

600-22-6Synthetic route

methyl lactate
547-64-8

methyl lactate

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride; zinc(II) nitrate; hydroxylamine hydrochloride; oxygen; copper(II) nitrate; sodium hydroxide at 100℃; under 75.0075 Torr; for 8h; Molecular sieve; Autoclave; Green chemistry;98.9%
With p-methoxybenzenetellurinic acid anhydride In neat (no solvent) at 130℃; for 1h;90%
With hydrogenchloride; sodium hypobromide In dichloromethane; water at 25℃; for 5h;90%
methanol
67-56-1

methanol

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 83℃; Temperature;76.38%
With ethanesulfonic acid; 1,2-dichloro-ethane
methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

A

formaldehyd
50-00-0

formaldehyd

B

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid at 24.84℃; under 760.051 Torr; Kinetics; Mechanism; UV-irradiation;A n/a
B 76%
With ozone at 20.84℃; under 760 Torr; Kinetics; Darkness;A 55%
B 69%
benzofurazan oxide
480-96-6

benzofurazan oxide

methyl 2-(triphenylphosphoranylidene)propionate
2605-68-7

methyl 2-(triphenylphosphoranylidene)propionate

A

benzofurazan
273-09-6

benzofurazan

B

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
In benzene for 6h; Heating;A 45%
B n/a
methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With dihydrogen peroxide; triethylamine; chromium(VI) oxide In acetonitrile at 40℃; for 20h; Product distribution; variation of catalyst, reagent, temperature, time;41%
With dihydrogen peroxide; triethylamine; chromium(VI) oxide In acetonitrile at 40℃; for 20h;41%
Stage #1: methacrylic acid methyl ester With cis-[Ru(2,9-Me2phen)2(OH2)2](PF6)2 In acetonitrile at 55℃; for 0.5h;
Stage #2: With dihydrogen peroxide In acetonitrile for 8h;
methanol
67-56-1

methanol

2-oxopropanal
78-98-8

2-oxopropanal

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With carbon dioxide; 1,3-bis[2,6-di(propan-2-yl)phenyl]-2-methoxyimidazolidine In tetrahydrofuran at 20℃; for 8h; Inert atmosphere; Sealed tube;10%
methanol
67-56-1

methanol

acrolein
107-02-8

acrolein

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With selenium(IV) oxide
Methyl 2-acetamidoacrylate
35356-70-8

Methyl 2-acetamidoacrylate

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With hydrogen bromide In chloroform
1,4-Bis-methoxycarbonyl-1,2,3,4-tetramethyl-butadien-1,3
91765-79-6

1,4-Bis-methoxycarbonyl-1,2,3,4-tetramethyl-butadien-1,3

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
(i) O3, MeOH, (ii) H2, Pd-C; Multistep reaction;
silver pyruvate
62163-16-0

silver pyruvate

methyl iodide
74-88-4

methyl iodide

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

methanol
67-56-1

methanol

2-chloro-3-methylbutadiene
1809-02-5

2-chloro-3-methylbutadiene

A

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

B

Dimethoxymethane
109-87-5

Dimethoxymethane

C

acetic acid methyl ester
79-20-9

acetic acid methyl ester

D

methyl 2,2-dimethoxypropionate
10076-48-9

methyl 2,2-dimethoxypropionate

E

methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

F

2-Chlor-3,3-dimethoxy-1-buten
108365-85-1

2-Chlor-3,3-dimethoxy-1-buten

Conditions
ConditionsYield
With ozone at -78℃; Product distribution; mono- and diozonolysies; with and without work up with DMS;A n/a
B n/a
C 35 % Spectr.
D 47 % Spectr.
E 7 % Spectr.
F 93 % Spectr.
methanol
67-56-1

methanol

(2-Chlor-1-methoxy-1-methyl-2-propenyl)hydroperoxide
108365-81-7

(2-Chlor-1-methoxy-1-methyl-2-propenyl)hydroperoxide

A

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

B

Dimethoxymethane
109-87-5

Dimethoxymethane

C

acetic acid methyl ester
79-20-9

acetic acid methyl ester

D

methoxymethyl hydroperoxide
10027-72-2

methoxymethyl hydroperoxide

E

acetic acid
64-19-7

acetic acid

F

methyl α-hydroperoxy-α-methoxypropionate
108365-82-8

methyl α-hydroperoxy-α-methoxypropionate

Conditions
ConditionsYield
With ozone In 1,1,2,2-tetrachloroethylene at -50℃; Product distribution; ozonolysis;
Methyl 2-bromopropionate
5445-17-0

Methyl 2-bromopropionate

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With 4-(dimethylamino)pyridine N-oxide In acetonitrile for 0.333333h; Heating;90 % Chromat.
3-chloro-DL-alanine methyl ester
56410-68-5

3-chloro-DL-alanine methyl ester

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With H2O In water at 25℃; Rate constant; Thermodynamic data; Kinetics; E(act.), ΔH(act.), ΔS(act.); with or without pyridoxal methochloride;
methyl 2-methoxyacrylate
7001-18-5

methyl 2-methoxyacrylate

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With perchloric acid at 25℃; Rate constant;
C10H14O10
96204-70-5

C10H14O10

A

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

B

methyl lactate
547-64-8

methyl lactate

C

carbon dioxide
124-38-9

carbon dioxide

Conditions
ConditionsYield
In benzene at 55℃; Rate constant; Product distribution; oth. temperature. oth. solvent;
3-carbomethoxy-3-methyl-1,2,4-trioxolane
105949-86-8

3-carbomethoxy-3-methyl-1,2,4-trioxolane

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With dimethylsulfide In chloroform-d1 Yield given;
dimethylglyoxal
431-03-8

dimethylglyoxal

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With (η5-C5H4SiMe3)2NbH(O)C=CPh2 at 25℃;
methanol
67-56-1

methanol

methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

A

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

B

methoxymethanol
4461-52-3

methoxymethanol

C

methoxymethyl hydroperoxide
10027-72-2

methoxymethyl hydroperoxide

D

3-carbomethoxy-3-methyl-1,2,4-trioxolane
105949-86-8

3-carbomethoxy-3-methyl-1,2,4-trioxolane

E

methyl α-hydroperoxy-α-methoxypropionate
108365-82-8

methyl α-hydroperoxy-α-methoxypropionate

Conditions
ConditionsYield
With ozone at -78℃; Product distribution; ozonolysis;
Oxalacetic acid
328-42-7

Oxalacetic acid

methyl iodide
74-88-4

methyl iodide

A

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

B

3-methyl-2-oxo-butane-1,4-dioic acid dimethyl ester
63921-06-2

3-methyl-2-oxo-butane-1,4-dioic acid dimethyl ester

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given;
methanol
67-56-1

methanol

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

A

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

B

methyl 2,2-dimethoxypropionate
10076-48-9

methyl 2,2-dimethoxypropionate

Conditions
ConditionsYield
With chloro-trimethyl-silane; 2,2-dimethoxy-propane for 24h; Ambient temperature;A 71 % Chromat.
B 29 % Chromat.
Methyl isobutyrate
547-63-7

Methyl isobutyrate

A

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

B

acetone
67-64-1

acetone

Conditions
ConditionsYield
With hydroxide at 23.85℃; under 760 Torr; Kinetics; Oxidation;
methyl iodide
74-88-4

methyl iodide

silver salt of/the/ pyruvic acid

silver salt of/the/ pyruvic acid

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

cis-form of γ-methyl-glutaconic acid dimethyl ester
53358-15-9

cis-form of γ-methyl-glutaconic acid dimethyl ester

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

methyl lactate
547-64-8

methyl lactate

air

air

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
in der Waerme am Licht;
methyl lactate
547-64-8

methyl lactate

oxygen

oxygen

vanadium pentoxide

vanadium pentoxide

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

propanoic acid methyl ester
554-12-1

propanoic acid methyl ester

A

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

B

Methyl glyoxylate
922-68-9

Methyl glyoxylate

C

Propionic formic anhydride
10500-31-9

Propionic formic anhydride

D

propionic acid
802294-64-0

propionic acid

Conditions
ConditionsYield
With air; Propanil at 22.85℃; under 740 Torr; Kinetics; Oxidation;A 0.289 mol
B 0.111 mol
C 0.099 mol
D 0.139 mol
methyl pyruvate oxime
5634-53-7

methyl pyruvate oxime

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With hydroxylamine In 1,4-dioxane; water at 30℃; pH=6.75; Equilibrium constant;
methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

A

methyl 2-methyl-2-oxiranecarboxylate
58653-97-7

methyl 2-methyl-2-oxiranecarboxylate

B

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Conditions
ConditionsYield
With Nitrogen dioxide; ozone at 250℃; for 4.44444E-06h; gas phase;A 88 % Spectr.
B n/a
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

methyl lactate
547-64-8

methyl lactate

Conditions
ConditionsYield
With magnesium(II) perchlorate; polymer-bound NADH (2a) In acetonitrile; benzene at 80℃; for 120h; Further byproducts given;100%
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); hydrogen; sodium hydrogencarbonate In methanol at 25℃; under 7500.75 Torr; for 12h; Glovebox; Autoclave; chemoselective reaction;98%
With hydrogen; Et4N91%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

1-ethylthio-1-(trimethylsiloxy)ethene
63584-41-8

1-ethylthio-1-(trimethylsiloxy)ethene

(S)-ethyl 3-hydroxy-3-methoxycarbonylbutanethioate
127658-10-0

(S)-ethyl 3-hydroxy-3-methoxycarbonylbutanethioate

Conditions
ConditionsYield
With hydrogenchloride; (S,S)-Cu(II) complex from bis(oxazolinyl) ligand and Cu(OTf)2 In tetrahydrofuran at -78℃;100%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

(R)-Methyl lactate
17392-83-5

(R)-Methyl lactate

Conditions
ConditionsYield
With hydrogen; Cinchonidin; polyvinylpyrrolidone-stabilized platinum clusters In acetic acid at 25℃; under 30002.4 Torr; for 0.5h;100%
With hydrogen; butan-1-ol; PVP-Pt; Cinchonidin In acetic acid at 24.85℃; under 30002.4 Torr; for 0.5h;
Stage #1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (R)-N-diphenylphosphino-N-methyl-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine In tetrahydrofuran at 25℃; for 0.25h;
Stage #2: pyruvic acid methyl ester With hydrogen In tetrahydrofuran under 1277.21 - 1794.37 Torr; for 6h; Product distribution / selectivity;
n/a
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

4,4-bis(benzyloxycarbonyl)-1,7-dimethylhepta-1,6-diyne
507989-55-1

4,4-bis(benzyloxycarbonyl)-1,7-dimethylhepta-1,6-diyne

C29H30O7

C29H30O7

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In dichloromethane at 20℃; for 0.166667h;100%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

(2-chloro-5-methyl-phenyl)-hydrazine

(2-chloro-5-methyl-phenyl)-hydrazine

methyl pyruvate 2-chloro-5-methylphenylhydrazone
187607-97-2

methyl pyruvate 2-chloro-5-methylphenylhydrazone

Conditions
ConditionsYield
In benzene100%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

(S)-Methyl lactate
27871-49-4

(S)-Methyl lactate

Conditions
ConditionsYield
With hydrogen; Cinchonin In acetic acid at 25℃; under 7500.75 Torr; for 12h; enantioselective reaction;99.8%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

2-methoxy-4-nitrophenylhydrazine
41978-94-3

2-methoxy-4-nitrophenylhydrazine

(E)-2-[(2-methoxy-4-nitrophenyl)hydrazono]propionic acid methyl ester

(E)-2-[(2-methoxy-4-nitrophenyl)hydrazono]propionic acid methyl ester

Conditions
ConditionsYield
With sodium acetate In methanol at 20℃; for 18h;99%
1-methylindole
603-76-9

1-methylindole

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

methyl 2,2-bis(1-methyl-1H-indol-3-yl)propanoate

methyl 2,2-bis(1-methyl-1H-indol-3-yl)propanoate

Conditions
ConditionsYield
With (S)-[1,1']-binaphthalenyl-2,2'-diol; titanium(IV) isopropylate In diethyl ether; toluene at -20℃; for 60h; Friedel-Crafts reaction;99%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

2-(1-allyl-2-oxoindolin-3-ylidene)malononitrile
519168-62-8

2-(1-allyl-2-oxoindolin-3-ylidene)malononitrile

(R)-methyl 1-allyl-2'-amino-3'-cyano-2-oxospiro[indoline-3,4'-pyran]-6'-carboxylate
1370462-66-0

(R)-methyl 1-allyl-2'-amino-3'-cyano-2-oxospiro[indoline-3,4'-pyran]-6'-carboxylate

Conditions
ConditionsYield
With 1-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-3-((1R)-(6-methoxyquinolin-4-yl)(8-vinylquinuclidin-2-yl)-methyl)thiourea In diethyl ether at 20℃; for 0.5h; asymmetric Michael cyclization; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

2-(2-oxo-1-phenylindolin-3-ylidene)malononitrile
1370462-98-8

2-(2-oxo-1-phenylindolin-3-ylidene)malononitrile

(R)-methyl 2'-amino-3'-cyano-2-oxo-1-phenylspiro[indoline-3,4'-pyran]-6'-carboxylate
1370462-64-8

(R)-methyl 2'-amino-3'-cyano-2-oxo-1-phenylspiro[indoline-3,4'-pyran]-6'-carboxylate

Conditions
ConditionsYield
With 1-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-3-((1R)-(6-methoxyquinolin-4-yl)(8-vinylquinuclidin-2-yl)-methyl)thiourea In diethyl ether at 20℃; for 3h; asymmetric Michael cyclization; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

2-oxo-2,3-dihydroindolylidenemalononitrile
6623-89-8

2-oxo-2,3-dihydroindolylidenemalononitrile

(R)-methyl 2'-amino-3'-cyano-2-oxospiro[indoline-3,4'-pyran]-6'-carboxylate
1370462-61-5

(R)-methyl 2'-amino-3'-cyano-2-oxospiro[indoline-3,4'-pyran]-6'-carboxylate

Conditions
ConditionsYield
With 1-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-3-((1R)-(6-methoxyquinolin-4-yl)(8-vinylquinuclidin-2-yl)-methyl)thiourea In diethyl ether at 20℃; for 12h; asymmetric Michael cyclization; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
2-Aminonicotinaldehyde
7521-41-7

2-Aminonicotinaldehyde

pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

1,8-naphthyridine-2-carboxylic acid
215523-34-5

1,8-naphthyridine-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 20℃; for 16h; Cooling;99%
With water; sodium hydroxide In ethanol at 0 - 20℃; for 18h;
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

Benzoic acid (2S,3R,4R,4aS,10aR)-3-acetylamino-2-benzyloxy-6,6,8,8-tetraisopropyl-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocycloocten-4-yl ester
145259-91-2

Benzoic acid (2S,3R,4R,4aS,10aR)-3-acetylamino-2-benzyloxy-6,6,8,8-tetraisopropyl-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocycloocten-4-yl ester

Benzyl 2-acetamido-3-O-benzoyl-2-deoxy-4,6-O-<1-(methoxycarbonyl)ethylidene>-α-D-glucopyranoside
143836-21-9

Benzyl 2-acetamido-3-O-benzoyl-2-deoxy-4,6-O-<1-(methoxycarbonyl)ethylidene>-α-D-glucopyranoside

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane for 15h; Ambient temperature;98%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

aniline
62-53-3

aniline

methyl 2-methyl-5-oxo-1-phenyl-4-(phenylamino)-2,5-dihydro-1H-pyrrole-2-carboxylate
26458-36-6

methyl 2-methyl-5-oxo-1-phenyl-4-(phenylamino)-2,5-dihydro-1H-pyrrole-2-carboxylate

Conditions
ConditionsYield
In dichloromethane at 20 - 25℃; for 1h; Irradiation;98%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

[1-(4-methoxyphenyl)vinyloxy]trimethylsilane
55991-65-6

[1-(4-methoxyphenyl)vinyloxy]trimethylsilane

(R)-methyl 2-hydroxy-2-methyl-4-oxo-4-(4-methoxy-phenyl)butanoate
1010691-58-3

(R)-methyl 2-hydroxy-2-methyl-4-oxo-4-(4-methoxy-phenyl)butanoate

Conditions
ConditionsYield
With (S)-N-[2-[(4S,5R)-4-methyl-5-phenyl-4,5-dihydro-2-oxazolyl]phenyl]-S-methyl-S-phenylsulfoximine; copper(II) bis(trifluoromethanesulfonate) In 2,2,2-trifluoroethanol; toluene at -20℃; for 16h; Mukaiyama reaction; optical yield given as %ee; enantioselective reaction;98%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

p-toluidine
106-49-0

p-toluidine

dimethyl 2,6‐dimethyl‐1,2‐dihydroquinoline‐2,4‐dicarboxylate
1333149-53-3

dimethyl 2,6‐dimethyl‐1,2‐dihydroquinoline‐2,4‐dicarboxylate

Conditions
ConditionsYield
With TiO2 nanoparticles In neat (no solvent) at 80℃; for 1h; Green chemistry;98%
With iodine In acetonitrile at 50℃; for 12h;94%
With N-chloro-succinimide; O,O-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) hydrazine-1,2-bis(carbothioate) In acetonitrile at 60℃; Green chemistry;92%
With lithium carbonate; magnesium bromide In neat (no solvent) at 60℃; for 1h; regioselective reaction;78%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

trimethyl orthoformate
149-73-5

trimethyl orthoformate

methyl 2,2-dimethoxypropionate
10076-48-9

methyl 2,2-dimethoxypropionate

Conditions
ConditionsYield
With sulfuric acid In methanol for 5h; Heating;97%
With sulfuric acid In methanol for 4h; Reflux;77%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

p-toluidine
106-49-0

p-toluidine

2-methyl-4-(4-methyl-anilino)-5-oxo-1-p-tolyl-2,5-dihydro-pyrrole-2-carboxylic acid methyl ester
26458-39-9

2-methyl-4-(4-methyl-anilino)-5-oxo-1-p-tolyl-2,5-dihydro-pyrrole-2-carboxylic acid methyl ester

Conditions
ConditionsYield
In dichloromethane at 20 - 25℃; for 1h; Irradiation;97%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

4-chloro-aniline
106-47-8

4-chloro-aniline

methyl 3-(4-chloroanilino)-1-(4-chlorophenyl)-5-methyl-2-oxo-3-pyrroline-5-carboxylate
141214-22-4

methyl 3-(4-chloroanilino)-1-(4-chlorophenyl)-5-methyl-2-oxo-3-pyrroline-5-carboxylate

Conditions
ConditionsYield
In dichloromethane at 20 - 25℃; for 1h; Irradiation;97%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

(4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone
188120-44-7

(4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone

zinc(II) chloride
7646-85-7

zinc(II) chloride

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

(4R,6R,7R,8S)-8-t-Butyldimethylsilyloxy-4-(1'-hydroxy-1'-methoxycarbonyl)ethyl-6,7-dimethylbicyclo[4,4,0]deca-1-en-3-one
194789-70-3

(4R,6R,7R,8S)-8-t-Butyldimethylsilyloxy-4-(1'-hydroxy-1'-methoxycarbonyl)ethyl-6,7-dimethylbicyclo[4,4,0]deca-1-en-3-one

Conditions
ConditionsYield
In tetrahydrofuran; hexane97%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

(furan-2-yloxy)-trimethylsilane
61550-02-5

(furan-2-yloxy)-trimethylsilane

(1'R,4S)-4-(1'-hydroxy-1'-methoxycarbonylethyl)-5-oxacyclopent-2-enone

(1'R,4S)-4-(1'-hydroxy-1'-methoxycarbonylethyl)-5-oxacyclopent-2-enone

Conditions
ConditionsYield
With 2,2,2-trifluoroethanol; (R)-N-[2-(2,4,6-trimethylbenzyl)aminophenyl]-S-(4-biphenyl)-S-methylsulfoximine; copper(II) bis(trifluoromethanesulfonate) In diethyl ether at 20℃; Vinylogous Mukaiyama-type aldol reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;97%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

aniline
62-53-3

aniline

dimethyl 2‐methyl‐1,2‐dihydroquinoline‐2,4‐dicarboxylate
120453-92-1

dimethyl 2‐methyl‐1,2‐dihydroquinoline‐2,4‐dicarboxylate

Conditions
ConditionsYield
With iodine In acetonitrile at 50℃; for 13h;97%
With TiO2 nanoparticles In neat (no solvent) at 80℃; for 1.5h; Green chemistry;97%
With nitric acid In water; acetonitrile at 80℃; Inert atmosphere;95%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

dimethyl 6-cyano-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate
1403657-23-7

dimethyl 6-cyano-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 100℃; under 7500.75 Torr; for 10h; Temperature; Time; Microwave irradiation;97%
With lithium carbonate; magnesium bromide In neat (no solvent) at 90℃; for 5h; regioselective reaction;94%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

(2E, 2'E)-dimethyl 2,2'-(hydrazine-1,2-diylidene)dipropanoate

(2E, 2'E)-dimethyl 2,2'-(hydrazine-1,2-diylidene)dipropanoate

Conditions
ConditionsYield
With carbazic acid In neat (no solvent) at 70℃; for 0.5h; Green chemistry;97%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

C15H30O2Si

C15H30O2Si

C19H36O5Si

C19H36O5Si

Conditions
ConditionsYield
Stage #1: C15H30O2Si With lithium hexamethyldisilazane In tetrahydrofuran at -78 - -45℃; for 2h; Inert atmosphere;
Stage #2: pyruvic acid methyl ester In tetrahydrofuran at -45℃; for 1h; Inert atmosphere;
97%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

methyl 2-methyl-2-(dimethylphenylsilyl)-3-butenoate
106046-48-4

methyl 2-methyl-2-(dimethylphenylsilyl)-3-butenoate

dimethyl 5-hydroxy-2,5-dimethyl-2-hexedioate

dimethyl 5-hydroxy-2,5-dimethyl-2-hexedioate

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane for 3h; from -78 deg C to RT;96%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

methyl-2-dimethoxyphosphoryl-2-dichlorophosphinoxypropanoate

methyl-2-dimethoxyphosphoryl-2-dichlorophosphinoxypropanoate

Conditions
ConditionsYield
With phosphorus trichloride at 20℃; for 1h;96%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

(Z)-1-(tert-butylthio)-1-trimethylsilyloxyprop-1-ene
76943-94-7

(Z)-1-(tert-butylthio)-1-trimethylsilyloxyprop-1-ene

(2S,3S)-tert-butyl 3-hydroxy-3-methoxycarbonyl-2-methylbutanethioate

(2S,3S)-tert-butyl 3-hydroxy-3-methoxycarbonyl-2-methylbutanethioate

Conditions
ConditionsYield
With hydrogenchloride; (S,S)-Cu(II) complex from bis(oxazolinyl) ligand and Cu(OTf)2 In dichloromethane at -78℃;96%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

1-methoxy-2-methyl-1-trimethylsiloxy-1-propene
31469-15-5

1-methoxy-2-methyl-1-trimethylsiloxy-1-propene

dimethyl 3-hydroxy-2,2,3-trimethylbutanedioate

dimethyl 3-hydroxy-2,2,3-trimethylbutanedioate

Conditions
ConditionsYield
[bis(diphenylphosphino)methane]bis(propenyl)Ru(II) In tetrahydrofuran at 65℃; for 20h; Condensation; aldol addition;96%
Stage #1: pyruvic acid methyl ester; 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene With pentafluorophenylammonium trifluoromethanesulfonimide In toluene at -50 - -45℃; for 1h; Mukaiyama reaction; Inert atmosphere;
Stage #2: With hydrogenchloride In methanol; water at 20 - 25℃; for 1h; Mukaiyama reaction; Inert atmosphere;
68%

600-22-6Relevant articles and documents

The electron stimulated chemistry of methyl lactate on Cu(1 1 1)

Fleming,Kadodwala

, p. 409 - 414 (2010)

The electron stimulated chemistry of monolayers of (R)/(S)-methyl lactate ((S)/(R)-MLAc) adsorbed on Cu(1 1 1) has been investigated. Monolayers of MLAc undergo highly efficient electron stimulated processes predominately desorption, but also a significant fraction is converted to an adsorbed alkoxide moiety through the selective cleavage of the O-H bond. The efficiency of the depletion of the adsorbed MLAc state and the absence of significant non-selective fragmentation contrasts with previous studies of the electron beam irradiation of monolayers of oxygen containing organic molecules.

-

Simon,Piaux

, (1924)

-

Metal-Free Synthesis of Polysubstituted Imidazolinone Through Cyclization of Amidines with 2-Substituted Acrylates

Liu, Zhen,Zhang, Yan-Shun,Wei, Yin,Shi, Min

supporting information, p. 1093 - 1099 (2020/02/27)

Polysubstituted imidazolinones were synthesized in a facile metal-free cascade nucleophilic cyclization of easily available amidines and 2-substituted acrylates. This protocol is distinguished by simple, mild, and catalyst-free reaction conditions with a broad substrate scope, affording the desired products in moderate to good yields and providing an efficient strategy for synthesis of polysubstituted imidazolinone.

Base-free conversion of glycerol to methyl lactate using a multifunctional catalytic system consisting of Au-Pd nanoparticles on carbon nanotubes and Sn-MCM-41-XS

Tang, Zhenchen,Boer, Dina G.,Syariati, Ali,Enache, Mihaela,Rudolf, Petra,Heeres, Hero J.,Pescarmona, Paolo P.

, p. 4115 - 4126 (2019/08/12)

Multifunctional catalytic systems consisting of physical mixtures of (i) bimetallic Au-Pd nanoparticles (average size of 3-5 nm) supported on functionalised carbon nanotubes (CNTs) and (ii) Sn-MCM-41 nanoparticles (50-120 nm), were synthesised and investigated for the base-free, selective conversion of glycerol to methyl lactate in a batch reactor. The catalysts were characterised by means of transmission electron microscopy, N2-physisorption, energy-dispersive X-ray spectroscopy, X-ray photoelectron spectroscopy and by Boehm titration. The catalyst based on bimetallic AuPd/CNTs showed much higher activity than the monometallic Au or Pd counterparts, thus indicating synergetic effects. Functionalisation of the CNTs by oxidative treatments had a positive effect on catalyst performance, which was correlated to the observed increase in surface acidity and hydrophilicity. The highest yield of methyl lactate achieved in this work was 85% at 96% glycerol conversion (140 °C, 10 h at 30 bar air), which is the highest yield ever reported in the literature so far. Insights in the reaction pathway were obtained by monitoring the conversion-time profiles for intermediates and their possible role as inhibitors. Batch recycling experiments demonstrated the excellent reusability of the catalyst.

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