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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.

Novel effect of zinc nitrate/vanadyl oxalate for selective catalytic oxidation of α-hydroxy esters to α-keto esters with molecular oxygen: An in situ ATR-IR study

Ju, Yongwei,Du, Zhongtian,Xiao, Chuhong,Li, Xingfei,Li, Shuang

supporting information, (2019/04/05)

Selective oxidation of α-hydroxy esters is one of the most important methods to prepare high value-added α-keto esters. An efficient catalytic system consisting of Zn(NO3)2/VOC2O4 is reported for catalytic oxidation of α-hydroxy esters with molecular oxygen. Up to 99% conversion of methyl DL-mandelate or methyl lactate could be facilely obtained with high selectivity for its corresponding α-keto ester under mild reaction conditions. Zn(NO3)2 exhibited higher catalytic activity in combination with VOC2O4 compared with Fe(NO3)3 and different nitric oxidative gases were detected by situ attenuated total reflection infrared (ATR-IR) spectroscopy. UV-vis and ATR-IR results indicated that coordination complex formed in Zn(NO3)2 in CH3CN solution was quite different from Fe(NO3)3; it is proposed that the charge-transfer from Zn2+ to coordinated nitrate groups might account for the generation of different nitric oxidative gases. The XPS result indicate that nitric oxidative gas derived from the interaction of Zn(NO3)2 with VOC2O4 could be in favor of oxidizing VOC2O4 to generate active vanadium (V) species. It might account for different catalytic activity of Zn(NO3)2 or Fe(NO3)3 combined with VOC2O4. This work contributes to further development of efficient aerobic oxidation under mild reaction conditions.

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