ChemicalBook--->CAS DataBase List--->24241-18-7

24241-18-7

24241-18-7 Structure

24241-18-7 Structure
IdentificationMore
[Name]

2-Amino-3,5-dibromopyrazine
[CAS]

24241-18-7
[Synonyms]

2-AMINO-3,5-DIBROMOPYRAZINE
3,5-DIBROMOPYRAZIN-2-AMINE
3,5-DIBROMOPYRAZIN-2-YLAMINE
3,5-DIBROMOPYRAZINE-2-YLAMINE
2-AMINO-3,5-DIBROMOPYRAZIN
3,5-dibromo-2-Pyrazinamine
[Molecular Formula]

C4H3Br2N3
[MDL Number]

MFCD00673150
[Molecular Weight]

252.89
[MOL File]

24241-18-7.mol
Chemical PropertiesBack Directory
[Appearance]

white to light yellow crystal powde
[Melting point ]

114-117 °C (lit.)
[Boiling point ]

294.6±35.0 °C(Predicted)
[density ]

2.287±0.06 g/cm3(Predicted)
[storage temp. ]

Refrigerator
[solubility ]

soluble in Methanol
[form ]

Powder
[pka]

0.81±0.10(Predicted)
[color ]

Yellow to brown
[InChI]

InChI=1S/C4H3Br2N3/c5-2-1-8-4(7)3(6)9-2/h1H,(H2,7,8)
[InChIKey]

DTLBKXRFWUERQN-UHFFFAOYSA-N
[SMILES]

C1(N)=NC=C(Br)N=C1Br
[CAS DataBase Reference]

24241-18-7(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Corrosion (GHS05)Skull and Crossbones (GHS06)Exclamation Mark (GHS07)
GHS05,GHS06,GHS07
[Signal word ]

Danger
[Hazard statements ]

H301-H315-H318-H335-H319
[Precautionary statements ]

P280g-P261-P280-P301+P310-P305+P351+P338-P264-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
[Hazard Codes ]

Xn,Xi
[Risk Statements ]

R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/39:Wear suitable protective clothing and eye/face protection .
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

3
[REACH Registrations]

Active
[HazardClass ]

6.1
[PackingGroup ]

III
[HS Code ]

29339900
[Storage Class]

6.1D - Non-combustible acute toxic Cat.3
toxic hazardous materials or hazardous materials causing chronic effects
[Hazard Classifications]

Acute Tox. 3 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3
Hazard InformationBack Directory
[Chemical Properties]

white to light yellow crystal powde
[Uses]

2-Amino-3,5-dibromopyrazine is used in the preparation of conjugated polymers for neurotoxin detection. 2-Amino-3,5-dibromopyrazine is an intermediate in the preparation of rho kinase (ROCK) inhibitor s.
[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.
[Synthesis]

Aminopyrazine

5049-61-6

2-Amino-3,5-dibromopyrazine

24241-18-7

The general procedure for the synthesis of 2-amino-3,5-dibromopyrazine from 2-aminopyrazine was as follows: 2-aminopyrazine (9.5 g, 100 mmol) was added to a reaction flask containing glacial acetic acid (70 mL) and heated on a steam bath until completely dissolved. Subsequently, sodium acetate trihydrate (33 g, 243 mmol) was added and constant stirring was maintained. The reaction mixture was cooled in an ice-salt bath at -5°C and bromine (16 mL) was added slowly and dropwise over a period of 4 hours (note: rapid addition of bromine may result in uncontrolled reaction and pose a safety hazard). After the dropwise addition was completed, stirring was continued in the ice bath for 2 hours, then moved to room temperature and stirred for 24 hours. Upon completion of the reaction, the mixture was poured into ice (50 g) and neutralized by adjusting to pH 8 with concentrated ammonia. The crude product was collected by filtration and recrystallized from methanol (with the addition of Norit activated charcoal) to give the final 2-amino-3,5-dibromopyrazine in colorless needles (16.8 g, 66% yield) with a melting point of 113-114 °C (literature value: 114-115 °C).

[References]

[1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 9, p. 981 - 986
[2] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1064 - 1069
[3] RSC Advances, 2015, vol. 5, # 47, p. 37887 - 37895
[4] RSC Advances, 2018, vol. 8, # 18, p. 9707 - 9717
[5] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 5, p. 1149 - 1154
Spectrum DetailBack Directory
[Spectrum Detail]

2-Amino-3,5-dibromopyrazine(24241-18-7)1HNMR
2-Amino-3,5-dibromopyrazine(24241-18-7)IR
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

2-Amino-3,5-dibromopyrazine, 99%(24241-18-7)
[TCI AMERICA]

2-Amino-3,5-dibromopyrazine,>98.0%(GC)(24241-18-7)
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