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2(1H)-Pyrazinone

2(1H)-Pyrazinone structure

CAS No:
6270-63-9
Formula:
C4H4N2O
Chemical Name:
2(1H)-Pyrazinone
Synonyms:
2(1H)-Pyrazinone;Pyrazinol;2-Hydroxypyrazine;2-Oxo-1H-pyrazine;NSC 36081;1H-Pyrazin-2-one;Pyrazin-2-ol;Pyrazin-2(1H)-one;141998-28-9;141998-27-8;20502-53-8
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

light yellow solid

2(1H)-Pyrazinone Basic Attributes

Molecular Weight：

96.09

Exact Mass：

96.09

EC Number：

228-455-2

UNII：

N5VLE8C2MU

NSC Number：

36081

DSSTox ID：

DTXSID10211781

HScode：

2933990090

Characteristics

PSA：

41.5

XLogP3：

-1.5

Density：

1.3±0.1 g/cm3

Melting Point：

187-188 °C

Flash Point：

192.6±22.3 °C

Refractive Index：

1.568

Safety Information

wgk germany：

hazard class code：

22-41

safety instructions：

26-39

Marks：

Precautionary statement(s)：

P264, P270, P280, P301+P312, P305+P351+P338, P310, P330, P501

Hazard Statements：

H302

GHS Classification：

|Danger|H302 (95.12%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P305+P351+P338, P310, P330, and P501|Aggregated GHS information provided by 41 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

1,2-dihydropyrazin-2-one

2(1H)-Pyrazinone Use and Manufacturing

Methods of Manufacturing

Sodium nitrite (3.4 g, 50 mmol, 1.3 eq.) was added in small portionsto 98percent sulfuric acid (15 mL) ice bath, and the mixture was allowed towarm up and heated to 60. When getting clear, the solution wascooled in an ice bath again. A solution of 2-amino-pyrazine (9) (4 g, 39.3 mmol, 1 eq.) in 98percent sulfuric acid (15 mL) was added dropwise.The reaction mixture was stirred at 40 for 1 h. After cooling to roomtemperature, it was slowly poured onto crushed ice and stirred until nonitrogen run out. The solution was adjusted to pH 6 with a 40percent solutionof sodium hydroxide, resulting in lots of sodium sulfate which wasfiltered off whereafter. The filtrate was extracted with EA (50 mL×3), and the combined organics were dried (Na2SO4), filtered and concentratedin vacuo to give the product as a white precipitate (6.38 g, 53percent).

Uses

Hydroxypyrazine is mainly used for the synthesis of sulfamethoxazine (SMPZ), but also for the synthesis of pharmaceutical intermediates such as 2-halopyrazine and 2-cyanopyrazine.

Computed Properties

Molecular Weight:96.09
XLogP3:-1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:96.032362755
Monoisotopic Mass:96.032362755
Topological Polar Surface Area:41.5
Heavy Atom Count:7
Complexity:137
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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