Acetylpyrazine supplier | CasNO.22047-25-2

Name
Acetylpyrazine
EINECS 244-753-5
CAS No. 22047-25-2
Article Data21
CAS DataBase
Density 1.136 g/cm³
Solubility
Melting Point 75-78 °C
Formula C₆H₆N₂O
Boiling Point 212.9 °C at 760 mmHg
Molecular Weight 122.126
Flash Point 84.4 °C
Transport Information
Appearance Light yellow to yellow-brownish powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Ethanone,1-pyrazinyl- (9CI);Ketone, methyl pyrazinyl (6CI,8CI);1-(2-Pyrazinyl)-1-ethanone;1-(Pyrazin-2-yl)ethanone;2-Acetylpyrazine;NSC 72374;Pyrazine methyl ketone;
PSA 42.85000
LogP 0.67920

Synthetic route

: 290-37-9
1,4-pyrazine

: 127-17-3
2-oxo-propionic acid

: 22047-25-2
acetylpyrazine

Conditions

Conditions	Yield
With NH4S2O8; silver nitrate; trifluoroacetic acid In dichloromethane; water at 40℃; for 2.5h;	100%
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; sulfuric acid In dichloromethane; water at 40℃; Reagent/catalyst; Solvent; Minisci Aromatic Substitution;	26%

: 61892-81-7
1-(pyrazin-2-yl)butan-1-one

A: 22047-25-2
acetylpyrazine

B: 138836-01-8, 138836-02-9
2-Methyl-1-pyrazin-2-yl-cyclopropanol

Conditions

Conditions	Yield
In tert-butyl alcohol; benzene for 4h; Irradiation;	A 1% B 95%

: 120992-58-7
3-acetylpyrazine N-oxide

: 22047-25-2
acetylpyrazine

Conditions

Conditions	Yield
With Eosin Y; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 3h; Inert atmosphere; Irradiation; chemoselective reaction;	90%

: 86461-64-5
3-methyl-1-(pyrazin-2-yl)butan-1-one

A: 22047-25-2
acetylpyrazine

B: 138836-03-0
2,2-dimethyl-1-(pyrazin-2-yl)cyclopropanol

Conditions

Conditions	Yield
In tert-butyl alcohol; benzene for 4h; Irradiation;	A 2% B 86%

: 19847-12-2
2-pyrazine carbonitrile

: 74-87-3
methylene chloride

: 22047-25-2
acetylpyrazine

Conditions

Conditions	Yield
Stage #1: methylene chloride With iodine; magnesium In tetrahydrofuran at 60℃; for 2h; Inert atmosphere; Stage #2: 2-pyrazine carbonitrile With copper(l) chloride In tetrahydrofuran at 50℃; for 14h; Inert atmosphere; Stage #3: With water In tetrahydrofuran Temperature; Reagent/catalyst; Solvent; Inert atmosphere;	69%

: C6H6Cl2N2

: 22047-25-2
acetylpyrazine

Conditions

Conditions	Yield
With sodium hydrogencarbonate; dimethyl sulfoxide at 80℃; for 6h;	60%

: 290-37-9
1,4-pyrazine

: 127-17-3
2-oxo-propionic acid

A: 22047-25-2
acetylpyrazine

B: 39248-49-2
1,1′-(pyrazine-2,5-diyl)diethanone

Conditions

Conditions	Yield
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; formic acid; dimethyl sulfoxide In dichloromethane; water at 40℃; Catalytic behavior; Reagent/catalyst; Solvent; Minisci Aromatic Substitution;	A 58% B 10%
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; sulfuric acid In water at 50℃; Minisci Aromatic Substitution;	A 26% B 33%

...Expand

: 290-37-9
1,4-pyrazine

: 75-07-0
acetaldehyde

: 22047-25-2
acetylpyrazine

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; di-tert-butyl peroxide; iron(II) sulfate In dichloromethane; sulfuric acid at 5℃; for 1h;	50%

: 19847-12-2
2-pyrazine carbonitrile

: 917-64-6
methyl magnesium iodide

: 22047-25-2
acetylpyrazine

Conditions

Conditions	Yield
In diethyl ether at 20℃; for 1h; Addition;	42%
In diethyl ether at -10 - 10℃; for 1h;	40%
Stage #1: 2-pyrazine carbonitrile; methyl magnesium iodide In diethyl ether Stage #2: With water

: 138835-87-7
2-(3,3-dimethylbutyryl)pyrazine

: 22047-25-2
acetylpyrazine

Conditions

Conditions	Yield
In hexane for 20h; Irradiation;	15%
In tert-butyl alcohol; benzene for 5h; Quantum yield; Irradiation;

: 19847-12-2
2-pyrazine carbonitrile

: 75-16-1
methylmagnesium bromide

: 22047-25-2
acetylpyrazine

Conditions

Conditions	Yield
With diethyl ether

: 290-37-9
1,4-pyrazine

: 75-07-0
acetaldehyde

A: 22047-25-2
acetylpyrazine

B: 39248-49-2
1,1′-(pyrazine-2,5-diyl)diethanone

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; sulfuric acid; iron(II) sulfate In water; benzene Yields of byproduct given;	A 28 % Chromat. B n/a

...Expand

: 288-32-4
1H-imidazole

: C6H5N2O(1-)*K(1+)

A: 22047-25-2
acetylpyrazine

B: 20671-53-8
imidazole potassium salt

Conditions

Conditions	Yield
In dimethyl sulfoxide at 24.9℃; Equilibrium constant;

...Expand

: 98-96-4
pyrazinamide

: 22047-25-2
acetylpyrazine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / POCl3 / 1.5 h / 100 °C 2: 40 percent / diethyl ether / 1 h / -10 - 10 °C View Scheme

: 19847-12-2
2-pyrazine carbonitrile

: 22047-25-2
acetylpyrazine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) H+, H2O 2: 2-methyl-propan-2-ol; benzene / 5 h / Irradiation View Scheme

: 56-45-1
L-serin

: 56-87-1
L-lysine

: 50-99-7
D-glucose

A: 290-37-9
1,4-pyrazine

B: 109-08-0
2-Methylpyrazine

C: 123-32-0
2,5-dimethyl-pyrazine

D: 5910-89-4
2,3-dimethylpyrazine

E: 22047-25-2
acetylpyrazine

F: 13360-65-1
2-ethyl-3,6-dimethylpyrazine

G: 108-50-9
2,6-dimethylpyrazine

H: 14667-55-1
2,3,5-trimethylpyrazine

I: 13925-03-6
2-ethyl-6-methylpyrazine

J: 13360-64-0
2-ethyl-5-methypyrazine

Conditions

Conditions	Yield
In water at 130℃; for 2h; pH=8; Maillard reaction;

...Expand

: 56-87-1
L-lysine

: 50-99-7
D-glucose

A: 290-37-9
1,4-pyrazine

B: 109-08-0
2-Methylpyrazine

C: 123-32-0
2,5-dimethyl-pyrazine

D: 5910-89-4
2,3-dimethylpyrazine

E: 22047-25-2
acetylpyrazine

F: 13360-65-1
2-ethyl-3,6-dimethylpyrazine

G: 108-50-9
2,6-dimethylpyrazine

H: 14667-55-1
2,3,5-trimethylpyrazine

I: 13925-07-0
2-ethyl-3,5-dimethylpyrazine

J: 13360-64-0
2-ethyl-5-methypyrazine

Conditions

Conditions	Yield
In water at 130℃; for 2h; pH=8; Maillard reaction;

...Expand

: 13925-00-3
2-ethylpyrazine

: 22047-25-2
acetylpyrazine

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In water at 60℃; for 12h;	66 %Spectr.

: 22047-25-2
acetylpyrazine

: 126353-32-0
2-bromo-1-pyrazin-2-yl-ethan-1-one hydrobromide

Conditions

Conditions	Yield
With pyridinium hydrobromide perbromide; hydrogen bromide In water; acetic acid at 20℃; for 0.1h;	100%
With hydrogen bromide; bromine In water at 80 - 90℃; for 1h;	82%
With pyridinium hydrobromide perbromide; hydrogen bromide; acetic acid at 20℃; for 1h;
With hydrogen bromide; bromine; acetic acid at 23℃; for 4h; Inert atmosphere;

: 22047-25-2
acetylpyrazine

: 5-amino isophthaloyl hydrazide

: C20H19N9O2

Conditions

Conditions	Yield
With acetic acid In ethanol Reflux;	100%

: 22047-25-2
acetylpyrazine

: 1-(1-phenylethyl)-2-methyleneaziridine

: 2-pyrazin-2-yl-4-methyl-1-(1-phenylethyl)pyrrole

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) at 120℃; for 72h;	96%

: 553-90-2
Dimethyl oxalate

: 22047-25-2
acetylpyrazine

: 858599-85-6
4-(2-pyrazinyl)-2,4-dioxobutanoic acid methyl ester

Conditions

Conditions	Yield
Stage #1: acetylpyrazine With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.75h; Stage #2: Dimethyl oxalate In tetrahydrofuran for 0.166667h;	96%

: 22047-25-2
acetylpyrazine

: 14080-58-1
thieno[2,3-d]pyrimidin-4-ylhydrazine

: 4-(2-(1-(pyrazin-2-yl)ethylidene)hydrazinyl)thieno[2,3-d]pyrimidine

Conditions

Conditions	Yield
In ethanol for 24h; Reflux;	96%

: 22047-25-2
acetylpyrazine

: 94777-52-3
2-(1-hydroxyethyl)pyrazine

Conditions

Conditions	Yield
Stage #1: acetylpyrazine With C27H43AlClN3Si3; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In neat (no solvent) at 20℃; for 16h; Stage #2: With silica gel at 20℃; Catalytic behavior;	95%
With sodium tetrahydroborate In methanol Ambient temperature;
With lithium aluminium tetrahydride In diethyl ether at -78℃; for 1h;

: 22047-25-2
acetylpyrazine

: 54-85-3
isoniazid

: N’-(1-(pyrazin-2-yl)ethylidene)isonicotinohydrazide

Conditions

Conditions	Yield
With formic acid In ethanol for 4h; Reflux;	95%
With formic acid In ethanol for 5h; Reflux;	90%
In methanol for 4h; Reflux;	64%

: 22047-25-2
acetylpyrazine

: 74-85-1
ethene

: 201230-82-2
carbon monoxide

: dihydro-5-methyl-5-(2-pyradinyl)-2(3H)-furanone

Conditions

Conditions	Yield
dodecacarbonyl-triangulo-triruthenium In toluene at 140℃; for 20h;	94%

...Expand

: 22047-25-2
acetylpyrazine

: 17448-14-5
2-benzyl-3-hydroxy-2,3-dihydro-isoindol-1-one

: 2-benzyl-3-(2-oxo-2-(pyrazin-2-yl)ethyl)isoindolin-1-one

Conditions

Conditions	Yield
With Sn(4+)4C2F6NO4S2(1-)8C2H6OS In toluene at 110℃; for 24h; Inert atmosphere; Sealed tube;	94%

: 22047-25-2
acetylpyrazine

: 622-88-8
4-bromophenylhydrazine hydrochloride

: 2-acetylpyrazine 4-bromophenylhydrazone

Conditions

Conditions	Yield
With sodium acetate In ethanol; chloroform for 12h; Ambient temperature;	93.5%

: 22047-25-2
acetylpyrazine

: 615-21-4
1,3-benzothiazol-2-ylhydrazine

: N-Benzothiazol-2-yl-N'-[1-pyrazin-2-yl-eth-(E)-ylidene]-hydrazine

Conditions

Conditions	Yield
With acetic acid In methanol at 80℃;	93%

: 22047-25-2
acetylpyrazine

: 1452-63-7
picolinic acid hydrazide

: N′-(1-(pyrazin-2-yl)ethylidene)picolinohydrazide

Conditions

Conditions	Yield
With formic acid In ethanol for 5h; Reflux;	93%
In ethanol

: 22047-25-2
acetylpyrazine

: C6H8N2O

Conditions

Conditions	Yield
Stage #1: acetylpyrazine With trimethylaluminum; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; 3,3'-bis-(3,5-bis-trifluoromethyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol In toluene at 20℃; for 2h; Glovebox; Inert atmosphere; Stage #2: With methanol for 0.5h; enantioselective reaction;	93%

: pent-4-en-2-ynyl-carbamic acid tert-butyl ester

: 22047-25-2
acetylpyrazine

: [2-(1-hydroxy-1-pyrazin-2-yl-ethyl)-penta-2,4-dienyl]-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With (R)-xylyl-WALPHOS; triphenylacetic acid; hydrogen; bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate In 1,2-dichloro-ethane at 40℃; under 760 Torr;	92%

: 22047-25-2
acetylpyrazine

: C9H6F3NO2

: (S)-4,4,4-trifluoro-3-(nitromethyl)-3-phenyl-1-(pyrazin-2-yl)butan-1-one

Conditions

Conditions	Yield
Stage #1: acetylpyrazine With bis(acetylacetonate)nickel(II); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) In isopropyl alcohol at 0℃; for 0.5h; Michael Addition; Schlenk technique; Inert atmosphere; Stage #2: C9H6F3NO2 In isopropyl alcohol at 0℃; for 96h; Michael Addition; Schlenk technique; Inert atmosphere; enantioselective reaction;	92%

: 22047-25-2
acetylpyrazine

: C18H12ClF3N2O4S

: (S)-3-(5-chloro-1-tosyl-1H-indol-3-yl)-4,4,4-trifluoro-3-(nitromethyl)-1-(pyrazin-2-yl)butan-1-one

Conditions

Conditions	Yield
With C28H29N3O; cobalt(II) aceylacetonate In tert-butyl methyl ether at 20℃; Michael Addition; Schlenk technique; Inert atmosphere; enantioselective reaction;	92%

: 22047-25-2
acetylpyrazine

: 193614-92-5
5-Iodoisophthalic dihydrazide

: C20H17IN8O2

Conditions

Conditions	Yield
With acetic acid In ethanol Reflux;	92%

: 22047-25-2
acetylpyrazine

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 866000-17-1
3-(N,N-dimethylamino)-1-(pyrazin-2-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With guanidineacetic acid at 100℃; for 1h;	91%
With L-proline In neat (no solvent) at 80℃; for 1.5h;	90%
With triethylamine at 110℃; for 16h;	81%

: 22047-25-2
acetylpyrazine

: 706-08-1, 5153-69-5
trans-1-(4-fluorophenyl)-2-nitro-ethene

: 1433955-80-6
(R)-3-(4-fluorophenyl)-4-nitro-1-(pyrazin-2-yl)butan-1-one

Conditions

Conditions	Yield
With nickel(II) acetate tetrahydrate; (4R,4'R,5S,5'S)-2,2'-(propane-2,2-diyl)bis(4,5-diphenyl-4,5-dihydrooxazole) In isopropyl alcohol at 20℃; for 3h; Michael Addition; Inert atmosphere; enantioselective reaction;	91%

: 7521-41-7
2-Aminonicotinaldehyde

: 22047-25-2
acetylpyrazine

: 1338090-17-7
2-(pyrazin-2-yl)-1,8-naphthyridine

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water at 60℃;	91%
With potassium hydroxide In methanol at 60℃; Inert atmosphere; Schlenk technique; Reflux;	85%

: 22047-25-2
acetylpyrazine

: 15791-90-9
2,5-dihydroxybenzohydrazide

: N1-(2,5-dihydroxybenzoyl)-N2-[1-(2-pyrazinyl)ethylidene]hydrazine

Conditions

Conditions	Yield
With acetic acid In ethanol for 1h; Reflux;	91%

: 22047-25-2
acetylpyrazine

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 109-77-3
malononitrile

: 2-amino-4-(3,4-dimethoxyphenyl)-6-(pyrazin-2-yl)nicotinonitrile

Conditions

Conditions	Yield
With ammonium acetate In ethanol Reflux;	91%

...Expand

: 22047-25-2
acetylpyrazine

: 23341-07-3
5-methoxy isophthaloyl hydrazide

: C21H20N8O3

Conditions

Conditions	Yield
With acetic acid In ethanol Reflux;	91%

: 22047-25-2
acetylpyrazine

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 111781-53-4
3-dimethylamino-1-(3-pyrazinyl)-2-propene-1-one

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 20h; Inert atmosphere; Schlenk technique;	90.2%
In xylene Heating;	73%
In methanol for 10h; Reflux;	38%
for 19h; Heating / reflux;
Reflux;

: 22047-25-2
acetylpyrazine

: C10H5F6NO2

: (S)-4,4,4-trifluoro-3-(4-(trifluoromethyl)phenyl)-3-(nitromethyl)-1-(pyrazin-2-yl)butan-1-one

Conditions

Conditions	Yield
Stage #1: acetylpyrazine With bis(acetylacetonate)nickel(II); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) In isopropyl alcohol at 0℃; for 0.5h; Michael Addition; Schlenk technique; Inert atmosphere; Stage #2: C10H5F6NO2 In isopropyl alcohol at 0℃; Michael Addition; Schlenk technique; Inert atmosphere; enantioselective reaction;	90%

: 110-86-1
pyridine

: 22047-25-2
acetylpyrazine

: N-{1-pyrazinyl-1-oxo-2-ethyl}pyridinium iodide

Conditions

Conditions	Yield
With iodine at 110℃; for 3h;	88%
With iodine for 1h; Reflux;	82%
With iodine at 90℃; for 1.5h;	48%

: 22047-25-2
acetylpyrazine

: 4702-78-7
benzil dihydrazone

: N',N'-bis[1-(pyrazine-2-yl)ethylidene]benzil dihydrazone

Conditions

Conditions	Yield
for 5h; Heating;	87%

Acetylpyrazine Chemical Properties

Molecular Structure of 2-Acetylpyrazine (CAS NO.22047-25-2):

IUPAC Name: 1-Pyrazin-2-ylethanone
Molecular Formula: C₆H₆N₂O
Molecular Weight: 122.13
EINECS: 244-753-5
FEMA: 3126
XLogP3: 0.2
H-Bond Donor: 0
H-Bond Acceptor: 3
Melting Point: 75-78 °C
Index of Refraction: 1.498
Molar Refractivity: 33.55 cm³
Molar Volume: 114.3 cm³
Surface Tension: 32.8 dyne/cm
Density: 1.085 g/cm³
Flash Point: 121.9 °C
Enthalpy of Vaporization: 48.62 kJ/mol
Boiling Point: 249 °C at 760 mmHg
Vapour Pressure: 0.0235 mmHg at 25 °C
Appearance: Light yellow to yellow-brownish powder
Canonical SMILES: CC(=O)C1=NC=CN=C1
InChI: InChI=1S/C6H6N2O/c1-5(9)6-4-7-2-3-8-6/h2-4H,1H3
InChIKey: DBZAKQWXICEWNW-UHFFFAOYSA-N
Product Categories: Pharmaceutical Intermediates; ACETYLGROUP; Pyrazines; Pyrazine; Heterocyclic Compounds; Miscellaneous; Chloropyrazines, etc.; pyrazine Flavor; Building Blocks; Heterocyclic Building Blocks; Sulfides flavors

Acetylpyrazine Uses

2-Acetylpyrazine (CAS NO.22047-25-2) is used as a composition of flavouring especially in baked and chocolate properties.

Acetylpyrazine Safety Profile

A skin and eye irritant. When heated to decomposition emits toxic fumes of NO_x.
Safety Information of 2-Acetylpyrazine (CAS NO.22047-25-2):
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 2
Hazard Note: Irritant
TSCA: T
HazardClass: IRRITANT

Acetylpyrazine Specification

2-Acetylpyrazine (CAS NO.22047-25-2), its Synonyms are 1-Pyrazinylethanone ; Ethanone, 1-pyrazinyl- ; Acetylpyrazine ; Ketone, methyl pyrazinyl ; Methyl pyrazinyl ketone ; Ethanone, 1-(2-pyrazinyl)- ; Pyrazin-1-ylethan-1-one .

Product Name

Acetylpyrazine

Synthetic route

Acetylpyrazine Chemical Properties

Acetylpyrazine Uses

Acetylpyrazine Safety Profile

Acetylpyrazine Specification

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