TETRAMETHYLPYRAZINE supplier

Name
Tetramethylpyrazine
EINECS 214-391-2
CAS No. 1124-11-4
Article Data58
CAS DataBase
Density 1.08 g/cm³
Solubility Soluble in water (4 g/L at 20°C).
Melting Point 82-86 °C
Formula C₈H₁₂N₂
Boiling Point 192.7 °C at 760 mmHg
Molecular Weight 136.197
Flash Point 71.6 °C
Transport Information
Appearance white crystals or powder
Safety 26-39-24/25-37/39-36
Risk Codes 22-37/38-41-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms BS factor;Chuanxingzine;Pyrazine,tetramethyl- (6CI,7CI,8CI,9CI);Ligustrazine;NSC 36080;NSC 46451;Tetramethylpyrazine;Tetrapyrazine;Ligustrazin;
PSA 25.78000
LogP 1.71020

Synthetic route

: 2,3,5,6-tetramethylpyrazine hydrochloride

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With sodium hydroxide In water	96%

: 27023-19-4
2,5-dichloro-3,6-dimethylpyrazine

: 75-24-1
trimethylaluminum

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; hexane for 4h; Heating;	90%

: 52648-79-0
3-amino-butan-2-one

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
Stage #1: 3-amino-butan-2-one With acetic acid for 1.3h; Stage #2: With potassium bromate; sodium hydrogensulfite Time;	87.2%

: 513-85-9
2.3-butanediol

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With carbonylchlorohydrido(4,5-bis((diisopropylphosphino)methyl)acridine)ruthenium(II); ammonia In toluene at 150℃; under 5250.53 Torr; for 36h; Inert atmosphere; Glovebox;	85%
With aluminium oxide catalysts; ammonia at 400℃;

: 135636-66-7
butane-2,3-dione mono-oxime

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With palladium on activated charcoal; ammonium formate In water at 80 - 90℃; for 4h; Solvent; Temperature;	84.6%
With hydrogenchloride; tin Behandlung des entstandenen Methyl-<α-amino-aethyl>-ketons mit Alkalien;
With hydrogenchloride; tin(ll) chloride Behandlung des entstandenen Methyl-<α-amino-aethyl>-ketons mit Alkalien;

: Tetramethylpyrazine hydrochloride

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With sodium hydroxide In water	76.1%

: 21419-24-9
3-Amino-2-butanone hydrochloride

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With air; sodium acetate In methanol at 60℃;	73%

: ligustrazine hydrochloride

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With sodium hydroxide In water pH=3 - ~ 8;	61.1%

: diammonium hydrogenphosphate

: 513-86-0, 52217-02-4
3-hydroxy-2-butanon

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
In water	55.5%

: 431-03-8
dimethylglyoxal

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With hydrogenchloride; pyridoxal 5'-phosphate; (S)-1,2,3,4-tetrahydronapht-1-yl-amine; amine transaminase-113 In water; dimethyl sulfoxide at 30℃; for 72h; pH=7.4; Reagent/catalyst; Enzymatic reaction; chemoselective reaction;	50%

: 75-05-8
acetonitrile

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran for 144h; Heating;	44%
With titanium tetrachloride; zinc In tetrahydrofuran for 144h; Heating; other nitriles;	44%

: 110-86-1
pyridine

: 56-84-8
L-Aspartic acid

: 108-24-7
acetic anhydride

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
und Einw. von Ammoniak;

...Expand

: 6628-81-5
2-acetamido-3-butanone

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With hydrogenchloride Destillieren des Reaktionsprodukts mit Quecksilber(II)-chlorid und Kaliumcarbonat;

: 17117-97-4
dimethyl glyoxime

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With ethanol; nickel at 70 - 90℃; Hydrogenation;

: 4091-39-8
3-chloro-2-butanone

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With ammonia

: 56-84-8
L-Aspartic acid

: 108-24-7
acetic anhydride

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With pyridine Einw. von Ammoniak auf das Reaktionsprodukt;

: 88234-17-7
N-methyl-2,5-dimethylpyrazinium bromide

A: 1124-11-4
Tetramethylpyrazine

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

Conditions

Conditions	Yield
at 275 - 280℃;

: 95-45-4
butane-2,3-dione dioxime

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With sodium hydroxide; zinc

: 72725-72-5
2-<2-Hydroxy-2-(p-methylphenyl)ethyl>-3,5,6-trimethylpyrazine

A: 1124-11-4
Tetramethylpyrazine

B: 104-87-0
4-methyl-benzaldehyde

Conditions

Conditions	Yield
In diethylene glycol dimethyl ether at 160℃; Kinetics; Thermodynamic data; other temperature (170 deg C) investigated; ΔH(excit.) and ΔS(excit.) given;
In various solvent(s) at 171.5℃; Kinetics; in diglyme-d14; isotopic effect;

: 72725-77-0
2-<2-Hydroxy-2-(p-chlorophenyl)ethyl>-3,5,6-trimethylpyrazine

A: 1124-11-4
Tetramethylpyrazine

B: 104-88-1
4-chlorobenzaldehyde

Conditions

Conditions	Yield
In diethylene glycol dimethyl ether at 160℃; Kinetics; Thermodynamic data; other temperature (170 deg C) and other solvent (DMF) investigated; ΔH(excit.) and ΔS(excit.) given;

: 72725-74-7
2-<2-Hydroxy-2-(p-methoxyphenyl)ethyl>-3,5,6-trimethylpyrazine

A: 1124-11-4
Tetramethylpyrazine

B: 123-11-5
4-methoxy-benzaldehyde

Conditions

Conditions	Yield
In various solvent(s) at 171.5℃; Kinetics; in diglyme-d14; isotopic effect;
In diethylene glycol dimethyl ether at 160℃; Kinetics; Thermodynamic data; other temperature (170 deg C) and other solvent (DMF) investigated; ΔH(excit.) and ΔS(excit.) given;

: 72725-76-9
2-<2-Hydroxy-2-ethyl>-3,5,6-trimethylpyrazine

A: 1124-11-4
Tetramethylpyrazine

B: 100-10-7
4-dimethylamino-benzaldehyde

Conditions

Conditions	Yield
In various solvent(s) at 171.5℃; Kinetics; in diglyme-d14; isotopic effect;

: 72725-78-1
2-<2-Hydroxy-2-(p-nitrophenyl)ethyl>-3,5,6-trimethylpyrazine

A: 1124-11-4
Tetramethylpyrazine

B: 555-16-8
4-nitrobenzaldehdye

Conditions

Conditions	Yield
In diethylene glycol dimethyl ether at 160℃; Kinetics; Thermodynamic data; other temperature (170 deg C) investigated; ΔH(excit.) and ΔS(excit.) given;

: 10130-14-0
2-(2-Hydroxy-2-phenylethyl)-3,5,6-trimethylpyrazine

A: 1124-11-4
Tetramethylpyrazine

B: 100-52-7
benzaldehyde

Conditions

Conditions	Yield
In diethylene glycol dimethyl ether at 160℃; Kinetics; Thermodynamic data; other temperature (170 deg C) investigated; ΔH(excit.) and ΔS(excit.) given;

: 98022-59-4
3-azido-butan-2-one

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With sodium hydrogen telluride 1.) ethanol; 2.) Celite; Yield given. Multistep reaction;

: 513-86-0, 52217-02-4
3-hydroxy-2-butanon

: 1124-11-4
Tetramethylpyrazine

Conditions

Conditions	Yield
With diammonium phosphate In water for 24h; Ambient temperature;	42.6 % Chromat.
With ammonium acetate at 85℃; for 4h;
With ammonium acetate In water at 25℃; under 735.5 Torr; Rate constant; Thermodynamic data; Mechanism; Ea; other ammonium salts; var. solvents, temperature and pressure; effect of high pressure; effect of propylene glycol; effect of nicotinamide adenine dinucleotide and flavin adenine dinucleotide as hydrogen acceptors;
With sodium hydroxide; ammonium phosphate; ammonium citrate In water at 85℃; for 5h; phosphate buffer, pH 7.2; reaction in acetate buffer, pH 7.2; addition of MeOH and EtOH; effects of a buffer and solvent on tetramethylpyrazine formation in a 3-hydroxy-2-butanone-ammonium hydroxide system;
With ammonium acetate In water

: 513-86-0, 52217-02-4
3-hydroxy-2-butanon

A: 1124-11-4
Tetramethylpyrazine

B: 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline

Conditions

Conditions	Yield
With diammonium phosphate In water for 24h; Product distribution; Mechanism; Ambient temperature; other acetols, other ammonia precursors, var. reaction time;	A 5.6 % Chromat. B 51.0 % Chromat.
With diammonium phosphate In water for 24h; Ambient temperature;	A 5.6 % Chromat. B 51.0 % Chromat.

: 513-86-0, 52217-02-4
3-hydroxy-2-butanon

A: 20662-84-4
2,4,5-trimethyloxazole

B: 22694-96-8
2,4,5-trimethyl-2,5-dihydro-1,3-oxazole

C: 1124-11-4
Tetramethylpyrazine

D: 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline

E: (E)-5-Hydroxy-3,4-dimethyl-hex-3-en-2-one

F: 3-[2-Hydroxy-1-methyl-prop-(E)-ylideneamino]-butan-2-one

Conditions

Conditions	Yield
With ammonium acetate In water at 25℃; Rate constant; Thermodynamic data; Mechanism; E(a); other solvents, var. temp.;

...Expand

: 513-86-0, 52217-02-4
3-hydroxy-2-butanon

A: 13623-11-5
2,4,5-trimethylthiazole

B: 1124-11-4
Tetramethylpyrazine

C: 84310-28-1
2-(1-mercaptoethyl)-2,4,5-trimethyl-3-thiazoline

D: 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline

E: 2-(1-mercaptoethyl)-2,4,5-trimethyl-3-oxazoline

F: 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-thiazoline

Conditions

Conditions	Yield
With hydrogenchloride; ammonium sulfide at 50℃; for 2h; Product distribution; var. temp.;

...Expand

: 1124-11-4
Tetramethylpyrazine

: cyclobis[[cis-Pt(R(-)-DIPO)(4-ethynylpyridine)2][cis-Pt(R(+)-BINAP)(CF3SO3)2]]*2AgCF3SO3*4H2O

: cyclobis[[cis-Pt(R(-)-DIOP)(4-ethynylpyridine)2][cis-Pt(R(+)-BINAP)(OSO2CF3)2]]*2AgOTf*tetramethylpyrazine*4H2O

Conditions

Conditions	Yield
In dichloromethane-d2 shaking (25°C); solvent removal (N2, vac.); elem. anal.;	100%

: 1124-11-4
Tetramethylpyrazine

: cycylobis[[cis-Pt(S(+)-DIOP)(4-ethynylpyridine)2][cis-Pd(R(+)-BINAP)(OSO2CF3)2]]*2AgOTf*4H2O

: cyclobis[[cis-Pt(S(+)-DIOP)(4-ethynylpyridine)2][cis-Pd(R(+)-BINAP)(OSO2CF3)2]]*2AgOTf*tetramethylpyrazine*4H2O

Conditions

Conditions	Yield
In dichloromethane-d2 shaking (25°C); solvent removal (N2, vac.); elem. anal.;	100%

: 1124-11-4
Tetramethylpyrazine

: 124-38-9
carbon dioxide

: 107209-20-1
3,5,6-trimethyl-2-pyrazinylacetic acid lithium salt

Conditions

Conditions	Yield
With lithium diisopropyl amide In hexane 1) hexane, 0 deg C, 30 min, 2) 0 deg C, 30 min;	99%

: 1124-11-4
Tetramethylpyrazine

: cyclobis[[cis-Pt(R(+)-DIOP)(4-ethynylpyridine)2][cis-Pd(PEt3)2-(OSO2CF3)2]]*2AgOTf

: cycylobis[[cis-Pt(R(+)-DIOP)(4-ethynylpyridine)2][cis-Pd(PEt3)2(OSO2CF3)2]]*2AgOTf*tetramethylpyrazine*3H2O

Conditions

Conditions	Yield
In acetone shaking (room temp., 5 min), NMR monitoring; solvent removal (dry N2), drying (vac.); elem. anal.;	99%

: 1124-11-4
Tetramethylpyrazine

: dichloro-bis(triethylphosphine)-di-μ-chloro-diplatinum(II)

: 118515-87-0
trans-{PtCl2(triethylphosphine)}2(2,3,5,6-tetamethylpyrazine)

Conditions

Conditions	Yield
In chloroform-d1 ligand and Pt complex (1:2 mol) in CDCl3 (or CD2Cl2) were stirred for 5 min; floating layer of hexane over soln.; elem. anal.;	94%

: 1124-11-4
Tetramethylpyrazine

: 79074-45-6
2-(bromomethyl)-3,5,6-trimethylpyrazine

Conditions

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 30℃; Reflux;	92%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane	75%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 75℃; for 10h; Incandescent irradiation;	72.8%

: 1124-11-4
Tetramethylpyrazine

: 16633-87-7
{Pt2Cl2(μ-Cl)2(PMePh2)2}

: 118515-91-6
trans-{PtCl2(diphenylmethylphosphine)}2(2,3,5,6-tetramethylpyrazine)

Conditions

Conditions	Yield
In chloroform-d1 ligand and Pt complex (1:2 mol) in CDCl3 (or CD2Cl2) were stirred for 5 min; floating layer of hexane over soln.; elem. anal.;	91%

: 1124-11-4
Tetramethylpyrazine

: 5736-94-7
4-(hexyloxy)benzaldehyde

: (E,E,E,E)-2,3,5,6-tetrakis[2-(4-hexyloxyphenyl)ethenyl]pyrazine

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 23℃; for 4h; Inert atmosphere;	91%
Multi-step reaction with 2 steps 1: potassium tert-butylate / N,N-dimethyl-formamide 2: potassium tert-butylate / N,N-dimethyl-formamide View Scheme

: 1124-11-4
Tetramethylpyrazine

: 1271-55-2
acetylferrocene

: C20H22FeN2

Conditions

Conditions	Yield
Stage #1: Tetramethylpyrazine With n-butyllithium In tetrahydrofuran; hexane at -25 - 20℃; Inert atmosphere; Stage #2: acetylferrocene With acetic anhydride; acetic acid In tetrahydrofuran; hexane at 120℃; for 2h; Inert atmosphere;	90%

: 1124-11-4
Tetramethylpyrazine

: 22978-83-2
2,3,5,6-tetramethylpyrazine mono N-oxide

Conditions

Conditions	Yield
With dihydrogen peroxide; acetic acid at 70℃;	88.2%
With dihydrogen peroxide; acetic acid at 0 - 60℃;	82%
With dihydrogen peroxide; acetic acid at 94℃; for 12h;	78.8%

: 1124-11-4
Tetramethylpyrazine

: 636-46-4
4-hydroxyisophthalic acid

: 2C8H6O5*C8H12N2

Conditions

Conditions	Yield
In methanol at 20℃; for 336h;	88%

TETRAMETHYLPYRAZINE Chemical Properties

IUPAC Name:2,3,5,6-tetramethylpyrazine
Molecular Formula:C₈H₁₂N₂
Molecular Weight:136.194280 g/mol
Appearance:White crystals
Melting Point:77-80 °C(lit.)
Boiling Point:190 °C(lit.)
Flash Point:128-130°C/200mm
density:1.08
FEMA:3237
BRN:113100
Synonyms of TETRAMETHYLPYRAZINE(1124-11-4):
BS Factor;Ligustrazine;Pyrazine,tetramethyl-;Tetramethylpyrazin;tetramethyl-pyrazin;2,3,5,6-TETRAMETHYLPYRAZINE;2,3,5,6-TETRAMETHYLPYRAZINES;2,3,5,6-TETRAMETHYL-1,4-PYRAZINE
Categories of TETRAMETHYLPYRAZINE(1124-11-4):
Pyrazine;Heterocyclic Compounds;Pyrazines;Mono- & Polyalkylpyrazines;pyrazine Flavor;Alphabetical Listings;Flavors and Fragrances;Q-Z;Certified Natural ProductsFlavors and Fragrances;Building Blocks;Heterocyclic Building Blocks

TETRAMETHYLPYRAZINE Uses

TETRAMETHYLPYRAZINE(1124-11-4) is used for the production of drug.
TETRAMETHYLPYRAZINE(1124-11-4) is used as a flavoring agent, sweetness enhancer of alcohol, corrective and supplements of cigarettes.

TETRAMETHYLPYRAZINE Toxicity Data With Reference

1.	orl-rat LD50:1910 mg/kg	DCTODJ Drug and Chemical Toxicology. 3 (1980),249.
2.	ipr-mus LD50:800 µg/kg	IJCREE International Journal of Crude Drug Research. 23 (1985),119.
3.	ivn-mus LD50:239 mg/kg	CMJODS Chinese Medical Journal (Beijing, English Edition). New Series. (Guozi Shudian, Beijing, People’s Republic of China) V.1- 1975- 4 (1978),319.

TETRAMETHYLPYRAZINE Consensus Reports

Reported in EPA TSCA Inventory.

TETRAMETHYLPYRAZINE Safety Profile

Safety Information of TETRAMETHYLPYRAZINE(1124-11-4):
Hazard Codes:Xn,Xi

Risk Statements:22-37/38-41-36/37/38
22:Harmful if swallowed
37/38:Irritating to respiratory system and skin
41:Risk of serious damage to eyes
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:26-39-24/25-37/39-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
39:Wear eye/face protection
24/25:Avoid contact with skin and eyes
37/39:Wear suitable gloves and eye/face protection
36:Wear suitable protective clothing
WGK Germany:3
RTECS:UQ3905000
HS Code:29339990
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NO_x.

TETRAMETHYLPYRAZINE Specification

First Aid Measures of TETRAMETHYLPYRAZINE(1124-11-4):
Ingestion:Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Skin:Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Eyes:Flush eyes with

Storage of TETRAMETHYLPYRAZINE(1124-11-4):
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Product Name

Tetramethylpyrazine

Synthetic route

TETRAMETHYLPYRAZINE Chemical Properties

TETRAMETHYLPYRAZINE Uses

TETRAMETHYLPYRAZINE Toxicity Data With Reference

TETRAMETHYLPYRAZINE Consensus Reports

TETRAMETHYLPYRAZINE Safety Profile

TETRAMETHYLPYRAZINE Specification

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