| Identification | More | [Name]
2-Amino-3-benzyloxypyridine | [CAS]
24016-03-3 | [Synonyms]
2-AMINO-3-BENZYLOXYPYRIDINE
3-Benzyloxy-2-pyridylamine
3-(BENZYLOXY)PYRIDIN-2-AMINE
TIMTEC-BB SBB000394
3-Benzyloxy-2-aminopyridine
3-Benzyloxy-pyridin-2-ylamine
4-(Benzyloxy)-2-pyridinamine
Pyridine, 2-amino-3-(benzyloxy)-
2-Amino-3-benzyloxypyridine, 98+%
2-Amino-3-benzyloxypyridine, 98.50%
2-Pyridinamine, 3-(phenylmethoxy)-
3-(Phenylmethoxy)pyridin-2-amine
3-(Benzyloxy)pyridine-2-amine
3-(Phenylmethoxy)-2-pyridinamine | [EINECS(EC#)]
245-983-9 | [Molecular Formula]
C12H12N2O | [MDL Number]
MFCD00006316 | [Molecular Weight]
200.24 | [MOL File]
24016-03-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Brown crystalline powder | [Melting point ]
92-94 °C (lit.) | [Boiling point ]
337.96°C (rough estimate) | [density ]
1.1131 (rough estimate) | [refractive index ]
1.6660 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
8.40±0.10(Predicted) | [color ]
Green to brown | [BRN ]
392674 | [InChI]
InChI=1S/C12H12N2O/c13-12-11(7-4-8-14-12)15-9-10-5-2-1-3-6-10/h1-8H,9H2,(H2,13,14) | [InChIKey]
NMCBWICNRJLKKM-UHFFFAOYSA-N | [SMILES]
C1(N)=NC=CC=C1OCC1=CC=CC=C1 | [CAS DataBase Reference]
24016-03-3(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Pyridinamine, 3-(phenylmethoxy)-(24016-03-3) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [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 .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [RIDADR ]
UN2811 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Brown crystalline powder | [Uses]
2-Amino-3-benzyloxypyridine is used in preparation of pyridinyl/pyridazinyloxymethyl substituted Raf kinase inhibitors. | [General Description]
2-Amino-3-benzyloxypyridine on condensation with diethyl ethoxymethylene malonate affords 9-benzyloxy-3-ethoxycarbonylpyrido[1,2-a]pyrimidin-4-one. | [Biochem/physiol Actions]
2-Amino-3-benzyloxypyridine is an inhibitor of mitogen-activated protein kinase p38α activity. | [Synthesis]
At a temperature lower than 40°C, 48L of deionized water was added to a 300L stainless steel reactor, and 48kg of sodium hydroxide was added under slow stirring until completely dissolved. Subsequently, 16 kg of 2-amino-3-hydroxypyridine, 1.6 kg of tetrabutylammonium bromide, and 17.92 L of benzyl chloride were added sequentially to the sodium hydroxide solution. The reaction mixture was heated to 70~75°C and kept at this temperature for 6 hours. When the reaction was completed, stirring was stopped and the mixture was left to stratify. The aqueous phase was extracted with toluene (20L x 3) and the combined organic phases were washed with pure water (30L x 2). The organic phase was concentrated until a large amount of solid precipitated, followed by crystallization at 0~5°C and stirring for 2 hours. Upon completion of crystallization, centrifugation was performed and the filter cake was washed with 3.2 L of pre-cooled toluene. Finally, it was dried under vacuum at 50~55°C for 3 h to give 22.5 kg of bright yellow solid Intermediate II (2-amino-3-benzyloxypyridine) in 77.3% molar yield and 99.53% purity. | [References]
[1] Chemistry Letters, 2006, vol. 35, # 3, p. 270 - 271
[2] Synthesis, 1981, # 12, p. 971 - 973
[3] Patent: CN107311998, 2017, A. Location in patent: Paragraph 0035-0036
[4] Journal of Chemical Research, Miniprint, 1986, # 11, p. 3368 - 3390
[5] Patent: CN103570683, 2018, B. Location in patent: Paragraph 0927; 0928; 0930; 0931 |
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