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ChemicalBook--->CAS DataBase List--->24016-03-3

24016-03-3

24016-03-3 Structure

24016-03-3 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack 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
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

3-Benzyloxy-2-pyridylamine(24016-03-3).msds
Hazard InformationBack 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]

2-Amino-3-hydroxypyridine

16867-03-1

Benzyl chloride

100-44-7

2-Amino-3-benzyloxypyridine

24016-03-3

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
Spectrum DetailBack Directory
[Spectrum Detail]

2-Amino-3-benzyloxypyridine(24016-03-3)MS
2-Amino-3-benzyloxypyridine(24016-03-3)1HNMR
2-Amino-3-benzyloxypyridine(24016-03-3)13CNMR
2-Amino-3-benzyloxypyridine(24016-03-3)IR1
2-Amino-3-benzyloxypyridine(24016-03-3)IR2
2-Amino-3-benzyloxypyridine(24016-03-3)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

2-Amino-3-benzyloxypyridine, 98.50%(24016-03-3)
[Alfa Aesar]

2-Amino-3-benzyloxypyridine, 98+%(24016-03-3)
[Sigma Aldrich]

24016-03-3(sigmaaldrich)
[TCI AMERICA]

2-Amino-3-benzyloxypyridine,>98.0%(T)(24016-03-3)
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