| Identification | More | [Name]
5-Amino-2-methoxypyridine | [CAS]
6628-77-9 | [Synonyms]
2-METHOXY-5-AMINOPYRIDINE
3-PYRIDINAMINE, 6-METHOXY-
5-AMINO-2-METHOXYPYRIDINE
6-Methoxy-3-pyridylamine
6-METHOXY-PYRIDIN-3-YLAMINE
OTAVA-BB BB7020410079
3-Amino-6-methoxypyridine
5-amino-2-methoxy-pyridin
6-methoxy-3-pyridinamin
6-Methoxy-3-pyridinamine
Pyridine,5-amino-2-methoxy-
5-Amino-2-Methoxy Pyridine 2-Methoxy-5-Amino Pyridine
5-Amino-2-Methoxypyridine95%
6-METHOXYPYRIDIN-3-AMINE
5-Amino-2-methoxypyridine, tech., 90%
5-Amino-2-methoxy
5-AMINO-2-METHOXYPYRIDIN (HAZARDOUS)
5-AMINO-2-METHOXYPYRIDIN (NON-HAZARDOUS)
2-METHOXY-5-AMINOPYRIDINE 6-METHOXY-PYRIDIN-3-YLAMINE
6-METHOXY-3-PYRIDINYLAMINE | [EINECS(EC#)]
229-612-8 | [Molecular Formula]
C6H8N2O | [MDL Number]
MFCD00006264 | [Molecular Weight]
124.14 | [MOL File]
6628-77-9.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow-brown or red to very dark red liquid | [Melting point ]
29-31 °C (lit.) | [Boiling point ]
85-90 °C/1 mmHg (lit.) | [density ]
1.575
| [refractive index ]
n20/D 1.575(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C | [solubility ]
Chloroform, Methanol (Slightly) | [form ]
Liquid | [pka]
4.33±0.10(Predicted) | [color ]
Yellow-brown or red to very dark red | [Water Solubility ]
Slightly soluble | [Detection Methods]
HPLC,NMR | [InChI]
1S/C6H8N2O/c1-9-6-3-2-5(7)4-8-6/h2-4H,7H2,1H3 | [InChIKey]
UUVDJIWRSIJEBS-UHFFFAOYSA-N | [SMILES]
COc1ccc(N)cn1 | [CAS DataBase Reference]
6628-77-9(CAS DataBase Reference) | [NIST Chemistry Reference]
5-Amino-2-methoxypyridine(6628-77-9) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
US1836000
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow-brown or red to very dark red liquid | [Uses]
5-Amino-2-methoxypyridine is used as a reagent in the synthesis of a novel series of thienopyrimidines as highly potent and selective PI3K inhibitors. 5-Amino-2-methoxypyridine is also used to synthesize EMPA (E521550); a novel high-affinity selective antagonist for the OX2 receptor. | [Application]
5-Amino-2-methoxypyridine is widely used in drug synthesis, organic synthesis and materials science due to its unique chemical properties and diverse reaction pathways. | [Definition]
ChEBI: 6-Methoxypyridin-3-amine is an aminopyridine. | [Chemical Reactivity]
The amino unit in 5-Amino-2-methoxypyridine structure has significant nucleophilicity. It can undergo condensation reactions with acyl chlorides under alkaline conditions to give the corresponding amide derivatives, and it can also undergo condensation reactions with organic carboxylic acids in the presence of condensing agents. | [Synthesis]
The general procedure for the synthesis of 5-amino-2-methoxypyridine from 5-nitro-2-methoxypyridine was as follows: 67.28 g of 2-methoxy-5-nitropyridine (0.1 mol), 0.50 g of 10% Pd/C were sequentially added to methanol, hydrogen was passed to a pressure of 0.01 MPa, and the reaction was carried out for 62±1.5 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature and filtered to recover the 10% Pd/C catalyst. The filtrate was concentrated under reduced pressure to recover solvent. The residue was extracted twice with 75 g of dichloroethane and the combined extracts were washed once with purified water. Subsequently, the extract was evaporated under reduced pressure to afford a slightly yellow oily liquid 5-amino-2-methoxypyridine 11.69 g. The purity was determined by HPLC to be 97.63% and the yield was 92.03%. | [References]
[1] Synthesis, 2006, # 19, p. 3316 - 3340
[2] Tetrahedron Letters, 2010, vol. 51, # 5, p. 786 - 789
[3] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 1, p. 302 - 318
[4] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 1, p. 302 - 318
[5] Journal of Heterocyclic Chemistry, 1983, vol. 20, # 1, p. 199 - 203 |
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