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3268-49-3

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3268-49-3 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 3268-49-3 differently. You can refer to the following data:
1. CLEAR COLOURLESS LIQUID
2. 3-(Methylthio) propionaldehyde has a powerful, onion, meat-like odor. It has a pleasant, warm, meat and soup-like flavor at low levels

Occurrence

Reported found in potato, potato chips, asparagus, tomato, tomato paste, wheat and rye bread, many cheeses, boiled egg, meats, hop oil, beer, malt whiskey, cocoa, coffee, roasted filberts and peanuts, popcorn, baked potato, cooked chicken, oatmeal, passion fruit, beans, mushroom, macadamia nut, tamarind, parsnip root, jackfruit, pumpkin, sweet corn, dried bonito, krill, shrimps, crayfish and scallops

Uses

Different sources of media describe the Uses of 3268-49-3 differently. You can refer to the following data:
1. 3-Methylthiopropionaldehyde is a synthetic flavoring agent that is a colorless to light yellow liquid with an intense meat odor. it polymerizes with age and is stable in a 50% alcohol solution. it should be stored in glass containers. it is used at low concentrations for meat and broth flavors for applications in meats and condiments at 3 ppm and in baked goods and beverages at 0.5 ppm.
2. 3-(Methylthio)propionaldehyde, is used as food flavour ,for making Baked food, spices, soft drinks, candy. It is also used as an intermediate. It has wide applications in organic synthesis as solvents as well as reagents. They are used in the synthesis of specific compound classes include agricultural chemical, property-enhancing additives, pharmacological drugs, chemical resistant polymers, detergents, and rubber antioxidants. Some examples of aliphatic and aromatic thioethers found in flavouring agents

Preparation

By transamination and decarboxylation of various amino acids; by oxidation of the alcohol

Aroma threshold values

Aroma characteristics at 0.1%: vegetable oil, creamy tomato, potato skin and French fry, yeasty, bready, limburger cheese with a savory meaty brothy nuance

Taste threshold values

Taste characteristics at 5 ppb to 5 ppm: potato, musty, tomato, mold ripened cheeses, onion, beefy brothy, egg, seafood and vegetative nuances.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 1450, 1948 DOI: 10.1021/ja01184a044

General Description

A colorless to amber liquid with an extremely foul and persistent odor. Slightly soluble in water and denser than water. Contact may slightly irritate skin, eyes and mucous membranes. Moderately toxic. Used as a food additive.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Organosulfides, such as 3-(Methylthio)propionaldehyde, are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.

Health Hazard

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

Taste at 0.5-1ppm

Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of SOx.

Check Digit Verification of cas no

The CAS Registry Mumber 3268-49-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,6 and 8 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 3268-49:
(6*3)+(5*2)+(4*6)+(3*8)+(2*4)+(1*9)=93
93 % 10 = 3
So 3268-49-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H8OS/c1-4(3-5)6-2/h3-4H,1-2H3

3268-49-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A14774)  3-(Methylthio)propionaldehyde, 98%   

  • 3268-49-3

  • 10g

  • 336.0CNY

  • Detail
  • Alfa Aesar

  • (A14774)  3-(Methylthio)propionaldehyde, 98%   

  • 3268-49-3

  • 50g

  • 716.0CNY

  • Detail
  • Alfa Aesar

  • (A14774)  3-(Methylthio)propionaldehyde, 98%   

  • 3268-49-3

  • 250g

  • 2936.0CNY

  • Detail

3268-49-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-methylthiopropanal

1.2 Other means of identification

Product number -
Other names 3-Methylthiopropana

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:3268-49-3 SDS

3268-49-3Synthetic route

3-(methylthio)-1-propanol
505-10-2

3-(methylthio)-1-propanol

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
With (NH4)4[CuMo6O18(OH)6]·5H2O; oxygen; sodium sulfite In water; acetonitrile at 60℃; under 760.051 Torr; for 12h;96%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate In acetonitrile at 20℃; for 24h;25%
With 5H3N*5H(1+)*IMo6O24(5-); oxygen; sodium acetate In water; acetonitrile at 70℃; under 760.051 Torr; for 15h; Green chemistry;97 %Chromat.
With 1-methyl-1H-imidazole; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C22H16BrCuF2N2O2 In acetonitrile at 20℃; for 24h; Reagent/catalyst;78 %Chromat.
3-methanesulfinyl-propionaldehyde

3-methanesulfinyl-propionaldehyde

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; triphenylphosphine In dichloromethane at 20℃; for 0.0166667h;90%
methylthiol
74-93-1

methylthiol

acrolein
107-02-8

acrolein

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
With hydroquinone88.5%
Fructose-methionine Amadori intermediate
87251-88-5

Fructose-methionine Amadori intermediate

A

2,4-Dimethyltetrahydrofuran
64265-26-5

2,4-Dimethyltetrahydrofuran

B

N-Methylpyrrole
96-54-8

N-Methylpyrrole

C

2-Methylpyrazine
109-08-0

2-Methylpyrazine

D

2-acetylpyridine
1122-62-9

2-acetylpyridine

E

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

F

3,4-dihydro-6-methyl-2H-pyran-2-one
3740-59-8

3,4-dihydro-6-methyl-2H-pyran-2-one

Conditions
ConditionsYield
at 260℃; for 0.0833333h; Thermal degradation;A n/a
B n/a
C n/a
D n/a
E 70%
F n/a
methylthiol
74-93-1

methylthiol

acrolein
107-02-8

acrolein

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
at 0℃;41%
With copper diacetate
With pyridine; copper diacetate
3-(methylthio)propionitrile
54974-63-9

3-(methylthio)propionitrile

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride
1,1-diethoxy-3-methylsulfanyl-propane
16630-61-8

1,1-diethoxy-3-methylsulfanyl-propane

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
With hydrogenchloride; water
methylthiol
74-93-1

methylthiol

triethylamine
121-44-8

triethylamine

acrolein
107-02-8

acrolein

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
reagiert analog mit Thioessigsaeure;
reagiert analog mit Thioessigsaeure;
methylthiol
74-93-1

methylthiol

sodium methylate
124-41-4

sodium methylate

acrolein
107-02-8

acrolein

benzene
71-43-2

benzene

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

chloro-methylsulfanyl-methane
2373-51-5

chloro-methylsulfanyl-methane

chloroethylene
75-01-4

chloroethylene

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
With sulfuric acid
indan-1,2,3-trione hydrate
485-47-2

indan-1,2,3-trione hydrate

DL-methionine
59-51-8

DL-methionine

NaCl

NaCl

aqueous KH2PO4

aqueous KH2PO4

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
(+-)-2-amino-4-methylsulfanyl-butyric acid;
methylthiol
74-93-1

methylthiol

ethene
74-85-1

ethene

carbon monoxide

carbon monoxide

A

Ethyl methyl sulfide
624-89-5

Ethyl methyl sulfide

B

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
With di-tert-butyl peroxide at 130℃; under 2206520 Torr;
With di-tert-butyl peroxide at 130℃; under 2206520 Torr;
methylthiol
74-93-1

methylthiol

ethene
74-85-1

ethene

di-tert-butyl peroxide
110-05-4

di-tert-butyl peroxide

carbon monoxide

carbon monoxide

A

Ethyl methyl sulfide
624-89-5

Ethyl methyl sulfide

B

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
at 130℃; under 2206520 Torr;
DL-methionine
59-51-8

DL-methionine

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
With perchloric acid; cerium(IV) ammonium sulphate; sulfuric acid at 31℃; for 1h; Kinetics; Further Variations:; Temperatures; pH-values;
acetic acid 1-(4,5-dimethoxy-2-nitrobenzyloxy)-3-methylsulfanylpropyl ester
863608-03-1

acetic acid 1-(4,5-dimethoxy-2-nitrobenzyloxy)-3-methylsulfanylpropyl ester

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
In [D3]acetonitrile for 4h; Irradiation;
4-methylthio-2-oxobutanoic acid
583-92-6

4-methylthio-2-oxobutanoic acid

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
With 1,4-dihydronicotinamide adenine dinucleotide; horse liver alcohol dehydrogenase In phosphate buffer at 30℃; pH=6.0; Enzyme kinetics;
methylthiol
74-93-1

methylthiol

acrolein
107-02-8

acrolein

A

3-hydroxy-2-methylthiomethyl-4-pentenal

3-hydroxy-2-methylthiomethyl-4-pentenal

B

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

C

5-methylsulfanyl-2-methylsulfanylmethyl-pent-2-enal
59902-01-1

5-methylsulfanyl-2-methylsulfanylmethyl-pent-2-enal

Conditions
ConditionsYield
With pyridine; acetic acid at 70℃; for 0.75 - 0.833333h;A 0.23 - 0.73 %Chromat.
B 87.79 - 89.26 %Chromat.
C 0.06 - 0.12 %Chromat.
1,1,3-tris-methylsulfanyl-propane
81382-04-9

1,1,3-tris-methylsulfanyl-propane

acrolein
107-02-8

acrolein

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
dimethylaminomethylpolystyrene at 0℃; for 2h;
methylthiol
74-93-1

methylthiol

glycerol
56-81-5

glycerol

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
zeolith HZSM-5 (Modul 28, H0 <-8.2) In methanol at 300℃; under 45754.6 Torr; for 1h; Product distribution / selectivity;
zeolith ammonium β CP 814E (H0 <-3.0) In methanol at 100 - 300℃; under 2250.23 - 30003 Torr; for 4.5h; Product distribution / selectivity;
DL-methionine
59-51-8

DL-methionine

A

DL-Homoserine
1927-25-9

DL-Homoserine

B

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

C

methionine S-oxide
3226-65-1

methionine S-oxide

Conditions
ConditionsYield
With water; oxygen pH=7; Mechanism; Quantum yield; γ-irradiation;
With water; oxygen; dinitrogen monoxide pH=7; Mechanism; Quantum yield; γ-irradiation;
DL-methionine
59-51-8

DL-methionine

A

3-methylthio-1-propanamine
4104-45-4

3-methylthio-1-propanamine

B

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

C

methionine S-oxide
3226-65-1

methionine S-oxide

D

2-aminobutanoic acid
2835-81-6

2-aminobutanoic acid

Conditions
ConditionsYield
With water; dinitrogen monoxide Mechanism; Quantum yield; γ-irradiation;
L-methionine
63-68-3

L-methionine

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

Conditions
ConditionsYield
With potassium permanganate; sodium perchlorate; sodium hydroxide In water at 35℃; Kinetics; Concentration; Reagent/catalyst; Temperature;
methylthiol
74-93-1

methylthiol

acrolein
107-02-8

acrolein

A

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

B

3-(methylthio)propanal hydrate

3-(methylthio)propanal hydrate

Conditions
ConditionsYield
In aq. phosphate buffer; water-d2 for 0.333333h; pH=7;
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

3-(methylthio)-1-propanol
505-10-2

3-(methylthio)-1-propanol

Conditions
ConditionsYield
With hydrogen; phosphotungstic acid 44-hydrate; [Fe(C5H4P(i-Pr)2)2Rh(C8H12)]BF4 In water; isopropyl alcohol at 20℃; under 5171.62 Torr; for 16h;100%
With sodium tetrahydroborate at 0 - 20℃;99%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

3-methanesulfinyl-propionaldehyde

3-methanesulfinyl-propionaldehyde

Conditions
ConditionsYield
With Mn(III) Schiff-base; dihydrogen peroxide In water; acetic acid at 20℃; for 0.116667h;100%
With C44H55ClMnN4O2(2+)*2I(1-); dihydrogen peroxide In water at 20℃; for 0.416667h; chemoselective reaction;100%
With dihydrogen peroxide; Amberlyst 15 In methanol at 20℃; for 0.1h;98%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

tert-butyl glyoxylate
7633-32-1

tert-butyl glyoxylate

Phenyl vinyl ketone
768-03-6

Phenyl vinyl ketone

tert-butyl 3-methyl-2-(3-methylsulfanylpropionyloxy)-4-oxo-4-phenylbutanoate

tert-butyl 3-methyl-2-(3-methylsulfanylpropionyloxy)-4-oxo-4-phenylbutanoate

Conditions
ConditionsYield
[Rh(bis(diphenylphosphanyl)ethane)]ClO4 In 1,2-dichloro-ethane at 70℃; for 16h;99%
With (bicyclo[2.2.1]hepta-2,5-diene)(1,2-bis(diphenylphosphanyl)ethane)rhodium(I) perchlorate; hydrogen In 1,2-dichloro-ethane at 70℃; for 18h; Inert atmosphere; optical yield given as %de;83%
hydrogen cyanide
74-90-8

hydrogen cyanide

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

2-hydroxy-4-(methylthio)butyronitrile
17773-41-0

2-hydroxy-4-(methylthio)butyronitrile

Conditions
ConditionsYield
With ammonia In water at 35 - 40℃; Temperature; Large scale;98.8%
With ammonia at 55℃; Reagent/catalyst; Inert atmosphere;96.1%
With potassium cyanide
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

hex-1-yne
693-02-7

hex-1-yne

(E)-1-methylsulfanyl-non-4-en-3-one

(E)-1-methylsulfanyl-non-4-en-3-one

Conditions
ConditionsYield
[Rh(bis(diphenylphosphanyl)ethane)]ClO4 In acetone at 55℃; for 1h;98%
With bis(norbornadiene)rhodium(l)tetrafluoroborate; 1,2-bis-(diphenylphosphino)ethane In 1,2-propylene cyclic carbonate at 70℃; for 1h; Inert atmosphere;91%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

hydrocyanic acid

hydrocyanic acid

2-hydroxy-4-(methylthio)butyronitrile
17773-41-0

2-hydroxy-4-(methylthio)butyronitrile

Conditions
ConditionsYield
With pyridine at 45℃;98%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

(E)-4-methyl-1-(methylthio)-6-phenylhex-5-en-3-one
1173936-70-3

(E)-4-methyl-1-(methylthio)-6-phenylhex-5-en-3-one

Conditions
ConditionsYield
With [Rh(dppe)]ClO4 In acetone at 55℃; Inert atmosphere; regioselective reaction;97%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

2-hydroxy-4-(methylthio)butyronitrile
17773-41-0

2-hydroxy-4-(methylthio)butyronitrile

Conditions
ConditionsYield
With sodium hydroxide; hydrogen isocyanide; sulfuric acid In methanol96.1%
With hydrogen cyanide; dimethylaminomethylpolystyrene at 35 - 40℃; for 0.5h;
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

isopropyl vinyl ketone
1606-47-9

isopropyl vinyl ketone

tert-butyl glyoxylate
7633-32-1

tert-butyl glyoxylate

tert-butyl 3,5-dimethyl-2-(3-(methylthio)propanoyloxy)-4-oxohexanoate
1097736-14-5

tert-butyl 3,5-dimethyl-2-(3-(methylthio)propanoyloxy)-4-oxohexanoate

Conditions
ConditionsYield
With (bicyclo[2.2.1]hepta-2,5-diene)(1,2-bis(diphenylphosphanyl)ethane)rhodium(I) perchlorate; hydrogen In 1,2-dichloro-ethane at 70℃; for 18h; Inert atmosphere; optical yield given as %de;96%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

ethyl 2,3-pentadienecarboxylate
74268-51-2

ethyl 2,3-pentadienecarboxylate

ethyl (E)-4-methyl-7-(methylthio)-5-oxohept-3-enoate
1173936-79-2

ethyl (E)-4-methyl-7-(methylthio)-5-oxohept-3-enoate

Conditions
ConditionsYield
With [Rh(dppe)]ClO4 In acetone at 55℃; Inert atmosphere; regioselective reaction;96%
pent-1-yn-5-ol
5390-04-5

pent-1-yn-5-ol

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

(E)-8-hydroxy-1-methylsulfanyl-oct-4-en-3-one

(E)-8-hydroxy-1-methylsulfanyl-oct-4-en-3-one

Conditions
ConditionsYield
[Rh(bis(diphenylphosphanyl)ethane)]ClO4 In acetone at 55℃; for 1h;95%
tetraethylammonium petntacarbonylcyanotungstate

tetraethylammonium petntacarbonylcyanotungstate

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

aniline hydrochloride
142-04-1

aniline hydrochloride

pentacarbonyltungsten(Δ4-(CNHC(HN(t-Bu))C(CH2CH2SMe)N(Ph)))

pentacarbonyltungsten(Δ4-(CNHC(HN(t-Bu))C(CH2CH2SMe)N(Ph)))

Conditions
ConditionsYield
In methanol to a stirred soln. of Cr-compd. the aldehyde is added via syringe followed by isocyanide at ice-bath temp., to this soln. a soln. of amine hydrochloride is added (Ar); mixt. is allowed to warm to room temp. overnight, silica gel is added and mixt. is evapd., ppt. is chromd. (silica gel; n-pentane/diethyl ether), recrystd. from CH2Cl2/pentane, elem. anal.;95%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

C12H10N2O2

C12H10N2O2

methyl (1-((methylthio)methyl)-3H-benzo[e]indol-3-yl)carbamate

methyl (1-((methylthio)methyl)-3H-benzo[e]indol-3-yl)carbamate

Conditions
ConditionsYield
With pyrrolidine; acetic acid In dichloromethane at 20℃; for 24h;95%
With pyrrolidine; acetic acid In dichloromethane at 20℃; for 48h;95%
4-penten-3-one
1629-58-9

4-penten-3-one

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

tert-butyl glyoxylate
7633-32-1

tert-butyl glyoxylate

tert-butyl 3-methyl-2-(3-(methylthio)propanoyloxy)-4-oxohexanoate
1097736-12-3

tert-butyl 3-methyl-2-(3-(methylthio)propanoyloxy)-4-oxohexanoate

Conditions
ConditionsYield
With (bicyclo[2.2.1]hepta-2,5-diene)(1,2-bis(diphenylphosphanyl)ethane)rhodium(I) perchlorate; hydrogen In 1,2-dichloro-ethane at 70℃; for 18h; Inert atmosphere; optical yield given as %de;94%
1-(tetrahydropyranyloxy)-4-pentyn
62992-46-5

1-(tetrahydropyranyloxy)-4-pentyn

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

(E)-1-methylsulfanyl-8-(tetrahydro-pyran-2-yloxy)-oct-4-en-3-one

(E)-1-methylsulfanyl-8-(tetrahydro-pyran-2-yloxy)-oct-4-en-3-one

Conditions
ConditionsYield
[Rh(bis(diphenylphosphanyl)ethane)]ClO4 In acetone at 55℃; for 1h;93%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

acetylenemagnesium bromide
4301-14-8

acetylenemagnesium bromide

5-(methylsulfanyl)pent-1-yn-3-ol
1227268-10-1

5-(methylsulfanyl)pent-1-yn-3-ol

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 2h;93%
Stage #1: 3-(methylsulfenyl)propanal; acetylenemagnesium bromide In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: With water; ammonium chloride In tetrahydrofuran
acetamide
60-35-5

acetamide

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

carbon monoxide
201230-82-2

carbon monoxide

A

N-acetyl-DL-methionine
1115-47-5

N-acetyl-DL-methionine

B

1,3-bis(methylthio)propane
24949-35-7

1,3-bis(methylthio)propane

Conditions
ConditionsYield
With hydrogen; dicobalt octacarbonyl In acetic acid butyl ester at 70℃; under 97509.8 Torr; for 8h; Product distribution / selectivity;A 92.2%
B 5%
With hydrogen; dicobalt octacarbonyl In acetic acid butyl ester at 70℃; under 97509.8 Torr; for 8h; Product distribution / selectivity;A 92.2%
B n/a
oct-1-ene
111-66-0

oct-1-ene

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

1-(methylsulfanyl)undecan-3-one

1-(methylsulfanyl)undecan-3-one

Conditions
ConditionsYield
With C21H44N2P2Rh*C32H12BF24 In acetone at 55℃; for 3h; Inert atmosphere;92%
With silver perchlorate; chloro(1,5-cyclooctadiene)rhodium(I) dimer In acetone at 55℃; for 24h;70%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; silver perchlorate; bis[2-(diphenylphosphino)phenyl] ether In acetone at 55℃; for 24h; Inert atmosphere;67%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

tert-butyl glyoxylate
7633-32-1

tert-butyl glyoxylate

(E)-1-phenylpenta-1,4-dien-3-one
73291-51-7

(E)-1-phenylpenta-1,4-dien-3-one

(E)-tert-butyl 3-methyl-2-(3-(methylthio)propanoyloxy)-4-oxo-6-phenylhex-5-enoate
1097736-16-7

(E)-tert-butyl 3-methyl-2-(3-(methylthio)propanoyloxy)-4-oxo-6-phenylhex-5-enoate

Conditions
ConditionsYield
With (bicyclo[2.2.1]hepta-2,5-diene)(1,2-bis(diphenylphosphanyl)ethane)rhodium(I) perchlorate; hydrogen In 1,2-dichloro-ethane at 70℃; for 18h; Inert atmosphere; optical yield given as %de;92%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

tert-butyl glyoxylate
7633-32-1

tert-butyl glyoxylate

methyl vinyl ketone
78-94-4

methyl vinyl ketone

tert-butyl 3-methyl-2-(3-(methylthio)propanoyloxy)-4-oxopentanoate
1097736-11-2

tert-butyl 3-methyl-2-(3-(methylthio)propanoyloxy)-4-oxopentanoate

Conditions
ConditionsYield
With (bicyclo[2.2.1]hepta-2,5-diene)(1,2-bis(diphenylphosphanyl)ethane)rhodium(I) perchlorate; hydrogen In 1,2-dichloro-ethane at 70℃; for 18h; Inert atmosphere; optical yield given as %de;92%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

(E)-4-((3-methylbut-1-enyl)-1-methylthio)nonan-3-one
1173936-68-9

(E)-4-((3-methylbut-1-enyl)-1-methylthio)nonan-3-one

Conditions
ConditionsYield
With [Rh(dppe)]ClO4 In acetone at 55℃; Inert atmosphere; regioselective reaction;92%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

N,N-diphenylhydrazine hydrochloride
530-47-2

N,N-diphenylhydrazine hydrochloride

(E)-2-(3-(methylthio)propylidene)-1,1-diphenylhydrazine

(E)-2-(3-(methylthio)propylidene)-1,1-diphenylhydrazine

Conditions
ConditionsYield
With sodium acetate; magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;92%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

thienyl vinyl ketone
13191-29-2

thienyl vinyl ketone

tert-butyl glyoxylate
7633-32-1

tert-butyl glyoxylate

tert-butyl-3-methyl-2-(3-(methylthio)propanoyloxy)-4-oxo-4-(thiophen-2-yl)butanoate
1097736-17-8

tert-butyl-3-methyl-2-(3-(methylthio)propanoyloxy)-4-oxo-4-(thiophen-2-yl)butanoate

Conditions
ConditionsYield
With (bicyclo[2.2.1]hepta-2,5-diene)(1,2-bis(diphenylphosphanyl)ethane)rhodium(I) perchlorate; hydrogen In 1,2-dichloro-ethane at 70℃; for 18h; Inert atmosphere; optical yield given as %de;91%
n-octyne
629-05-0

n-octyne

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

(E)-1-(methylthio)undec-4-en-3-one
1321899-91-5

(E)-1-(methylthio)undec-4-en-3-one

Conditions
ConditionsYield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; 1,2-bis-(diphenylphosphino)ethane In 1,2-propylene cyclic carbonate at 70℃; for 1h; Inert atmosphere;91%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

2-(2-(methylthio)ethyl)-1,3-dithiane
73401-96-4

2-(2-(methylthio)ethyl)-1,3-dithiane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;91%
acetamide
60-35-5

acetamide

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

carbon monoxide
201230-82-2

carbon monoxide

A

cobalt acetylmethionate

cobalt acetylmethionate

B

N-acetyl-DL-methionine
1115-47-5

N-acetyl-DL-methionine

Conditions
ConditionsYield
Stage #1: acetamide; 3-(methylsulfenyl)propanal; carbon monoxide With hydrogen; dicobalt octacarbonyl In ethyl acetate at 80℃; under 97509.8 Torr; for 5h;
Stage #2: With oxygen at 20 - 80℃; under 7500.75 Torr;
A 90%
B 80.7%
3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

phenylacetylene
536-74-3

phenylacetylene

(E)-5-(methylthio)-1-phenylpent-1-en-3-one
84175-29-1

(E)-5-(methylthio)-1-phenylpent-1-en-3-one

Conditions
ConditionsYield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; 1,2-bis-(diphenylphosphino)ethane In 1,2-propylene cyclic carbonate at 70℃; for 1h; Inert atmosphere;90%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

3-(methylsulfenyl)propanal
3268-49-3

3-(methylsulfenyl)propanal

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

N-cyclohexyl-3-(2-(methylthio)ethyl)quinoxaline-2-amine
1523157-59-6

N-cyclohexyl-3-(2-(methylthio)ethyl)quinoxaline-2-amine

Conditions
ConditionsYield
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide In ethanol at 20℃; for 1.3h; Ugi Condensation;90%

3268-49-3Relevant articles and documents

Comparison of pyrazines formation in methionine/glucose and corresponding Amadori rearrangement product model

Cui, Heping,Deng, Shibin,Hayat, Khizar,Ho, Chi-Tang,Zhai, Yun,Zhang, Qiang,Zhang, Xiaoming

, (2022/03/07)

The generation of pyrazines in a binary methionine/glucose (Met/Glc) mixture and corresponding methionine/glucose-derived Amadori rearrangement product (MG-ARP) was studied. Quantitative analyses of pyrazines and methional revealed that MG-ARP generated more methional compared to Met/Glc, whereas lower content and fewer species of pyrazines were observed in the MG-ARP model. Comparing the availability of α-dicarbonyl compounds generated from the Met/Glc model, methylglyoxal (MGO) was a considerably effective α-dicarbonyl compound for the formation of pyrazines during MG-ARP degradation, but glyoxal (GO) produced from MG-ARP did not effectively participate in the corresponding formation of pyrazines due to the asynchrony on the formation of GO and recovered Met. Diacetyl (DA) content was not high enough to form corresponding pyrazines in the MG-ARP model. The insufficient interaction of precursors and rapid drops in pH limited the formation of pyrazines during MG-ARP degradation. Increasing reaction temperature could reduce the negative inhibitory effect by promoting the content of precursors.

Highly efficient and practical aerobic oxidation of alcohols by inorganic-ligand supported copper catalysis

Wei, Zheyu,Ru, Shi,Zhao, Qixin,Yu, Han,Zhang, Gang,Wei, Yongge

supporting information, p. 4069 - 4075 (2019/08/07)

The oxidation of alcohols to aldehydes or ketones is a highly relevant conversion for the pharmaceutical and fine-chemical industries, and for biomass conversion, and is commonly performed using stoichiometric amounts of highly hazardous oxidants. The aerobic oxidation of alcohols with transition metal complex catalysts previously required complicated organic ligands and/or nitroxyl radicals as co-catalysts. Herein, we report an efficient and eco-friendly method to promote the aerobic oxidation of alcohols using an inorganic-ligand supported copper catalyst 1, (NH4)4[CuMo6O18(OH)6], with O2 (1 atm) as the sole oxidant. Catalyst 1 is synthesized directly from cheap and commonly available (NH4)6Mo7O24·4H2O and CuSO4, which consists of a pure inorganic framework built from a central CuII core supported by six MoVIO6 inorganic scaffolds. The copper catalyst 1 exhibits excellent selectivity and activity towards a wide range of substrates in the catalytic oxidation of alcohols, and can avoid the use of toxic oxidants, nitroxyl radicals, and potentially air/moisture sensitive and complicated organic ligands that are not commercially available. Owing to its robust inorganic framework, catalyst 1 shows good stability and reusability, and the catalytic oxidation of alcohols with catalyst 1 could be readily scaled up to gram scale with little loss of catalytic activity, demonstrating great potential of the inorganic-ligand supported Cu catalysts in catalytic chemical transformations.

Highly practical and efficient preparation of aldehydes and ketones from aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst

Zhang, Mengqi,Zhai, Yongyan,Ru, Shi,Zang, Dejin,Han, Sheng,Yu, Han,Wei, Yongge

supporting information, p. 10164 - 10167 (2018/09/13)

Herein, we divulge an efficient protocol for aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst, (NH4)5[IMo6O24]. The catalyst system is compatible with a wide range of groups and exhibits high selectivity, and shows excellent stability and reusability, thus serving as a potentially greener alternative to the classical transformations.

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