Basic information
- Standard SMILES
c1cnccn1- InChIKey
KYQCOXFCLRTKLS-UHFFFAOYSA-N- Molecular formula
- C4H4N2
- Average molar mass
- 80.09 g/mol
- Monoisotopic mass
- 80.03744813
Overview
Pyrazine is a diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms. It has a role as a Daphnia magna metabolite. It is a member of pyrazines and a diazine.
Names & identifiers
- Preferred name
- Pyrazine
- IUPAC
- pyrazine
- English name
- Pyrazine
- Molecular formula
- C4H4N2
- Molecular weight
- 80.09
Names & synonyms
PYRAZINE290-37-91,4-Diazinep-DiazineParadiazinePiazine1,4-Diazabenzenepyrazin1,4-DiazinDTXSID8049410NSC-400221FEMA NO. 4015
Show more names
PyBOFEMA 40151,4-PyrazinePyrazine>
2JKE371789CHEMBL15797CHEBI:30953RefChem:1113271206-027-6MFCD00006122pyrazine phase IVpyrazine phase III
Database identifiers
- CAS
290-37-9- PubChem CID
- 9261
- DTXSID
DTXSID8049410- ChEMBL
CHEMBL15797- ChEBI
CHEBI:30953- UNII
- 2JKE371789
- EC Number
- 206-027-6
- Nikkaji
- J2.569K
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 25.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 26.5
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Pyrazines
SpringerMaterials PropertiesSchoenflies notation
LogP
-0.26
-0.05
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
freely soluble in water, organic solvents
very soluble (in ethanol)
Boiling Point
115.00 to 116.00 °C. @ 760.00 mm Hg
115-118 °C
Melting Point54 - 56 °C
Physical Description
Solid with a strong odor like pyridine; [Merck Index] White crystalline solid with a strong odor; [Alfa Aesar MSDS]
Solid
deliquescent crystals or wax-like solid with a pungent, sweet, corn-like, nutty odour
Ionization Efficiency
Positive
0.17
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Physicochemical properties
- Melting point
- 50 · 50-56 °C (lit.)
- Boiling point
- 115 · 115-116 °C (lit.)
- Density
- 1.031 g/mL · 1.031 g/mL at 25 °C (lit.)
- refractive index
- 1.5235 · 1.5235
- FEMA
- 4015 · 4015 | PYRAZINE
- FLAVIS Number
- 14.144 · 14.144 | Pyrazine
- Flash point
- 132 °F · 132 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- SOLUBLE
- pka
- 0.65 · 0.65(at 27℃)
- form
- Crystals
- color
- White
- Specific Gravity
- 1.031 · 1.031
- Odor
- 0.1 % · at 0.10 % in propylene glycol. pungent sweet corn like roasted hazelnut barly
- Odor Type
- nutty
- biological source
- synthetic
- Water Solubility
- SOLUBLE
- Sensitive
- Hygroscopic
- Merck
- 14 · 14,7957
- JECFA Number
- 951 · 951
- BRN
- 103905 · 103905
- Dielectric constant
- 2.8 · 2.7999999999999998
- Stability
- Stable. Highly flammable. Incompatible with acids, oxidizing agents.
- InChI
- 1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H
- InChIKey
- KYQCOXFCLRTKLS-UHFFFAOYSA-N
- SMILES
- c1cnccn1
- LogP
- -0.26 · -0.26
- CAS DataBase Reference
- 290 · 290-37-9(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- PYRAZINE
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 2 JKE371789 · 2JKE371789
- NIST Chemistry Reference
- Pyrazine(290-37-9)
- EPA Substance Registry System
- Pyrazine (290-37-9)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Danger
- Hazard statements
- 228 · H228
- Precautionary statements
- 210 · P210-P240-P241-P280-P370+P378
- PPE
- 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- Xi,F
- Risk Statements
- 36 · 36/37/38-11
- Safety Statements
- 26 · 26-36-16
- RIDADR
- 1325 · UN 1325 4.1/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 2015000 · UQ2015000
- TSCA
- TSCA listed
- HazardClass
- 4.1 · 4.1
- PackingGroup
- III
- HS Code
- 29339990 · 29339990
- Storage Class
- 4.1 B · 4.1B - Flammable solid hazardous materials
- Hazard Classifications
- 1 · Flam. Sol. 1
- Limited Quantities
- 1 Kg · 1.0 Kg (2.2 lbs)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (47.9%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 165 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Pyrazine
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Pyrazine: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryIntraperitoneal LD50 (mouse) = 2,730 mg/kg; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesFlam. Liq. 2 (47.9%)
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UQ2015000
- ridadr
- UN 1325 4.1/PG 2
- hs_code
- 29339990
- risk_code
- 36/37/38-11
- Signal word
- Danger
- Symbol(GHS)
- GHS02
- hazard_code
- Xi,F
- safety_code
- 26-36-16
- hazard_class
- 4.1
- Storage Class
- 4.1B - Flammable solid hazardous materials
- packing_group
- III
- Hazard statements
- H228
- Limited Quantities
- 1.0 Kg (2.2 lbs)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Flam. Sol. 1
- Precautionary statements
- P210-P240-P241-P280-P370+P378
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationPyrazine: ACTIVE
Applications
DescriptionPyrazine is a heterocyclic aromatic organic compound and can be reacted to obtain diverse pyrazine derivatives. Pyrazines are important contributors to the flavor of various roasted, toasted, or similarly heated foods. Pyrazine derivatives exhibit a wide variety of aromas in food, e.g. 2-methoxy-3-isopropylpyrazine produces a green pea odor. Pyrazines and pyrazine derivatives are typically used as flavor agent. Pyrazines and Pyrazine derivatives are also used as fragrances.
OccurrencePyrazine has been detected in several food products including papayas, asparagus, peanuts, popcorn, soybeans, corn, French fries, bread, cheese, milk, eggs (boiled), chicken (fried), beef (cooked), shrimp, clams, beer, sherry, malt, coffee and tea (green).
UsesPyrazine is used as a flavoring agent. It serves as a component of some herbs in traditional Chinese medicine. It is employed as pharmaceutical intermediates, perfume intermediates and involved in the preparation of other chemicals. In addition to this, it is used in the production of pyrazine 1-oxide.
General DescriptionPyrazine is a 1,4-diazine and an electron-deficient N-heteroarene found in several natural products, APIs, agrochemicals, and functional materials.
Preparation methods
PreparationPrepared by cyclization of α-amino ketones, which were produced by the reduction of isonitroso ketones to yield the dihydropyrazines, which are dehydrogenated with mercury(I) oxide or copper(II) sulfate or sometimes with atmospheric oxygen.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.
DefinitionA heterocyclic aromatic compound with a six-membered ring containing four carbon atoms and two nitrogen atoms.
Definitionpyrazine: An unsaturated heterocycliccompound having two nitrogenatoms in a six-membered ring,C4H4N2; r.d. 1.03; m.p. 52°C; b.p.115°C. Pyrazine is a symmetric diazine.
Related reactions
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