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494364

Sigma-Aldrich

2-Amino-3,5-dibromopyrazine

97%

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About This Item

Empirical Formula (Hill Notation):
C4H3Br2N3
CAS Number:
24241-18-7
Molecular Weight:
252.89
MDL number:
MFCD00673150
UNSPSC Code:
12352100
PubChem Substance ID:
24872896

Assay

97%

mp

114-117 °C (lit.)

functional group

bromo

SMILES string

Nc1ncc(Br)nc1Br

InChI

1S/C4H3Br2N3/c5-2-1-8-4(7)3(6)9-2/h1H,(H2,7,8)

InChI key

DTLBKXRFWUERQN-UHFFFAOYSA-N

General description

2-Amino-3,5-dibromopyrazine can be synthesized from 2-aminopyrazine via bromination using N-bromosuccinimide (NBS). It reacts with sodium dicyanocuprate to form a mixture of mono and dicyanation products. The formation of 2-aminothiazolopyrazines by reacting 2-amino-3,5-dibromopyrazine with isothiocyanates has been reported.

Application

2-Amino-3,5-dibromopyrazine may be used in the synthesis of:
  • 2-amino-5-bromopyrazin-3-thiol
  • 2-amino-3,5-bis(p-methoxyphenyl)-1,4-pyrazine
  • 3,7-dihydroimidazo[1,2a]pyrazine-3-ones

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H315,H318,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
00818HH
15217AH
01115PE
08225DE
11604DE

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Synthesis of N-Substituted-2-Aminothiazolo [4,5-b] pyrazines by Tandem Reaction of o-Aminohalopyrazines with Isothiocyanates.
Kwak SH, et al.
Bull. Korean Chem. Soc., 33, 4271-4274 (2012)
Synthesis of Tetraaza Derivatives of Benzoxazinophenothiazine.
Ezema BE, et al.
Orient. J. Chem., 31(1), 133-139 (2015)
Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties.
Adamczyk M, et al.
Tetrahedron, 59(41), 8129-8142 (2003)
Studies on pyrazines. XX, A simple synthesis of 5-substituted 2-amino-3-cyanopyrazines: useful intermediates for pteridine synthesis.
Synthesis 8 (1990): 659-660.
Sato N and Takeuchi R.
Synthesis, 8, 659-660 (1990)
2,6-Diamino-3,5-diaryl-1,4-pyrazine derivatives as novel antioxidants.
Rees JF and Marchand-Brynaert J
Synthesis, 5, 768-772 (2001)
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