Basic information
- Standard SMILES
Cc1cnc(C)cn1- InChIKey
LCZUOKDVTBMCMX-UHFFFAOYSA-N- Molecular formula
- C6H8N2
- Average molar mass
- 108.14 g/mol
- Monoisotopic mass
- 108.06874826
Overview
2,5-Dimethylpyrazine is a member of pyrazines.
Names & identifiers
- Preferred name
- 2,5-Dimethylpyrazine
- IUPAC
- 2,5-dimethylpyrazine
- English name
- 2,5-Dimethyl pyrazine
- Molecular formula
- C6H8N2
- Molecular weight
- 108.14
Names & synonyms
2,5-DIMETHYLPYRAZINE123-32-0Pyrazine, 2,5-dimethyl-2,5-Dimethyl-1,4-diazineKetineFEMA No. 3272V99Y0MUY1QNSC-49139DTXSID6047652RefChem:82971DTXCID4027652204-618-3
Show more names
Pyrazine,2,5-dimethyl-2,5-Dimethylprazin2,5-DimethylStructural formula2,5-dimethyl-pyrazintomfor
2,5-Dimethyl pyrazineNSC 491392,5-Dimethylpiazine2,5-DimethylparadiazineMFCD000061472,5-Dimethyl-pyrazinePYRAZINE,2,5-DIMETHYLFEMA 3272
Database identifiers
- CAS
123-32-0- PubChem CID
- 31252
- DTXSID
DTXSID6047652- ChEMBL
CHEMBL94709- ChEBI
CHEBI:89762- UNII
- V99Y0MUY1Q
- EC Number
- 204-618-3
- Nikkaji
- J2.009E
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 25.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 62.9
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Pyrazines
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (2,5-Dimethylpyrazine) -> IFRA transparency List
LogP0.63
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.982-1.000
Flavoring AgentsEU Flavoring substances
Solubility
soluble in water, organic solvents, oils
miscible at room temperature (in ethanol)
Boiling Point
154.00 to 156.00 °C. @ 760.00 mm Hg
155 °C
Melting Point15 °C
Vapor Pressure1.5 [mmHg]
Refractive Index1.497-1.503
Physicochemical properties
- Melting point
- 15 °C · 15°C
- Boiling point
- 155 °C · 155 °C (lit.)
- Density
- 0.99 g/mL · 0.99 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.502(lit.)
- FEMA
- 3272 · 3272 | 2,5-DIMETHYLPYRAZINE
- FLAVIS Number
- 14.02 · 14.020 | 2,5-Dimethylpyrazine
- Flash point
- 147 °F · 147 °F
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- 2.21 · 2.21±0.10(Predicted)
- form
- Liquid
- Specific Gravity
- 0.99 · 0.990
- color
- Clear colorless to pale yellow
- PH
- 7 · 7 (H2O)
- Odor
- 0.1 % · at 0.10 % in dipropylene glycol. nutty roasted baked potato
- Odor Type
- chocolate
- biological source
- synthetic
- Sensitive
- Hygroscopic
- JECFA Number
- 766 · 766
- BRN
- 107052 · 107052
- Henry's Law Constant
- 7.1 · 7.1×100 mol/(m3Pa) at 25℃, Marin et al. (1999)
- Dielectric constant
- 2.44 · 2.4399999999999999
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C6H8N2/c1-5-3-8-6(2)4-7-5/h3-4H,1-2H3
- InChIKey
- LCZUOKDVTBMCMX-UHFFFAOYSA-N
- SMILES
- Cc1cnc(C)cn1
- LogP
- 0.64 · 0.64
- CAS DataBase Reference
- 123 · 123-32-0(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 2 · 2,5-DIMETHYLPYRAZINE
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 99 Y0MUY1Q · V99Y0MUY1Q
- NIST Chemistry Reference
- 2 · Pyrazine, 2,5-dimethyl-(123-32-0)
- EPA Substance Registry System
- 2 · Pyrazine, 2,5-dimethyl- (123-32-0)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 301 · P301+P312+P330
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38-R22
- Safety Statements
- 26 · 26-36
- RIDADR
- 1993 · NA 1993 / PGIII
- WGK Germany
- 3 · 3
- RTECS
- 2800000 · UQ2800000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29339990 · 29339990
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1762 reports by companies from 9 notifications to the ECHA C&L Inventory.
Warning
H226: Flammable liquid and vapor [Warning Flammable liquids]
Hazard information
Regulatory Information
Chemical: Pyrazine, 2,5-dimethyl-
Regulation (EC) No 1831/2003 (amended)
2,5-Dimethylpyrazine: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses convulsions in acute intraperitoneal studies of mice; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; Harmful by ingestion; [Alfa Aesar MSDS]
Hazard Classes and Categories
Acute Tox. 4 (100%)
Flammable liquids - Category 3
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UQ2800000
- ridadr
- NA 1993 / PGIII
- hs_code
- 29339990
- risk_code
- 22-36/37/38-R22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-36
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as flavoring agent or adjuvant; [FDA]
Use Classification
Fragrance Ingredients
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, 2,5-dimethyl-: ACTIVE
Applications
OccurrenceReported to be present in bakery products, roasted barley, cocoa products, roasted coffee, dairy products, pork, peanuts, pecans, filberts, popcorn, potato products, rum and whiskey, soy products; a volatile component in roasted filberts and in potato chips; reportedly identified in the fat of cooked beef; also reported found in toasted off-flavors. Also reported in cheeses, butter, boiled eggs, grilled beef, tea, barley, oats, oatmeal, soybeans, heated beans, kohlrabi, shrimp and mushrooms. Also reported found in coffee, potato chips and shrimp
Uses2,5-Dimethylpyrazine is used as a reagent in the synthesis of bone-targeted proteasome inhibitors for multiple myeloma (MM). 2,5-Dimethylpyrazine is also used in the preparation of 3-Methyl-2,5-bis-(2-hydroxyethyl)pyrazine (M295340); a degredation product of Clavulanic Acid (C563750) which is a β-lactamase inhibitor, typically added to amoxicillin to increase its effectiveness.
Uses2,5-Dimethyl pyrazine is used for blending food, nuts and beverage flavors.
General Description2,5-Dimethylpyrazine is a pyrazine compound that is mainly formed in food products such as cooked rice or roasted peanuts due to the Maillard reaction between sugars and proteins during cooking or roasting process.
Preparation methods
PreparationBy the interaction of acrolein and ammonia when heated in glycerol in the presence of ammonium salts; by self-condensation of aminoacetone, followed by oxidation with mercury chloride.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: 2,5-Dimethylpyrazine is a member of pyrazines.
Related reactions
11 records
Linked notes
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