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2-Amino-6-bromopyridine

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CAS:19798-81-3
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CAS:19798-81-3
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CAS:19798-81-3
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  • $1.10 / 1g
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  • CAS:19798-81-3
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  • Purity: 99.00%
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2-Amino-6-bromopyridine Basic information
Product Name:2-Amino-6-bromopyridine
Synonyms:6-Bromopyridine-2-amine;2-PyridinaMine,6-broMo-;2-AMino-6-broMopyridine, 98% 5GR;2-Amino-6-bromopyridine 98%;6-BROMO-PYRIDIN-2-YLAMINE;6-BROMO-2-PYRIDINAMINE;6-BROMO-2-AMINOPYRIDINE;Aminobromopyridine
CAS:19798-81-3
MF:C5H5BrN2
MW:173.01
EINECS:606-385-7
Product Categories:Bromopyridines;Halopyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines, Pyrimidines, Purines and Pteredines;Amines;blocks;Bromides;Pyridines;Pyridine;pharmacetical;Pyridine series;Pyridines derivates;bc0001;19798-81-3
Mol File:19798-81-3.mol
2-Amino-6-bromopyridine Structure
2-Amino-6-bromopyridine Chemical Properties
Melting point 88-91 °C (lit.)
Boiling point 273.0±20.0 °C(Predicted)
density 1.710±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Methanol (Very Slightly)
form Powder
pka2.73±0.24(Predicted)
color Slightly yellow to light brown
Water Solubility Slightly soluble in water.
InChIInChI=1S/C5H5BrN2/c6-4-2-1-3-5(7)8-4/h1-3H,(H2,7,8)
InChIKeyBKLJUYPLUWUEOQ-UHFFFAOYSA-N
SMILESC1(N)=NC(Br)=CC=C1
CAS DataBase Reference19798-81-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-20/21/22
Safety Statements 26-36-36/37/39
WGK Germany 3
HazardClass IRRITANT
HS Code 29333999
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
2-Amino-6-bromopyridine Usage And Synthesis
Chemical PropertiesSlightly yellow to light brown powder
Uses2-Amino-6-bromopyridine is a disubstituted pyridine used as a building block in the preparation of nitrogen containing bicyclic and polycylic compounds.
UsesEmployed in an efficient one-pot synthesis of 7-azaindoles. Used in the synthesis of anti-HIV agents.
Application2-Amino-6-bromopyridine is an important raw material for the synthesis of:
2-amino-6-diethylaminopyridine
2,6-di-(methylamino)-pyridine
3-(6-bromopyridin-2-yl)-2-(2,6-difluorophenyl)-1,3-thiazolidin-4-one
N-(6-bromopyridin-2-yl)dodecylamide
2-bromo-6-iodopyridine
Employed in an efficient one-pot synthesis of 7-azaindoles.
Used in the synthesis of anti-HIV agents.
General Description2-Amino- 6-bromopyridine has been synthesized from epichlorohydrin.
Synthesis
2,6-Dibromopyridine

626-05-1

2,6-Diaminopyridine

141-86-6

2-Amino-6-bromopyridine

19798-81-3

14.1 Preparation of 6-bromo-2-aminopyridine In a steel autoclave equipped with a glass liner, 10.00 g of 2,6-dibromopyridine (42.2 mmol) was suspended in 50 mL of concentrated ammonia. The autoclave was sealed and heated to 190°C using a heating jacket and maintained for 6 hours (pressure was raised to about 25 bar). After the autoclave was cooled and depressurized, the reaction mixture was mixed with 100 mL of ethyl acetate for phase separation. The aqueous phase was extracted twice with ethyl acetate, 100 mL each. the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in 250 mL of a solvent mixture of cyclohexane/ethyl acetate (1:1, v/v) to remove the by-product 2,6-diaminopyridine. Subsequently, the solution was filtered through a short silica gel column (5 x 20 cm) and washed again with 250 mL of cyclohexane/ethyl acetate (1:1, v/v) mixed solvent. After removal of the solvent under reduced pressure, the residue was sublimated at 90°C and 10-1 mbar to give 6.49 g (37.5 mmol, 88.9% yield) of 6-bromo-2-aminopyridine as a white solid.

References[1] Patent: US2004/199024, 2004, A1. Location in patent: Page 17
[2] Recueil des Travaux Chimiques des Pays-Bas, 1932, vol. 51, p. 381,386, 949
[3] Chemical Communications, 2010, vol. 46, # 6, p. 925 - 927
Tag:2-Amino-6-bromopyridine(19798-81-3) Related Product Information
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