2-Amino-3-benzyloxypyridine Chemical Properties

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 Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-37/39-24/25-36/37/39-22,26-36

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29221985

MSDS

• Language:English Provider:3-Benzyloxy-2-pyridylamine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Amino-3-benzyloxypyridine Usage And Synthesis

Chemical Properties

Brown crystalline powder

Uses

2-Amino-3-benzyloxypyridine is used in preparation of pyridinyl/pyridazinyloxymethyl substituted Raf kinase inhibitors.

Uses

2-Amino-3-benzyloxypyridine was used in the synthesis of 1-acetyl-2-[2-(3-benzyloxypyridinyl)]iminoimidazolidine.

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

2-Amino-3-benzyloxypyridine(24016-03-3)Related Product Information

• 4-Dimethylaminopyridine
• 4-Methoxybenzylchloride
• 3-Aminopyridine
• Glycine
• ALTRENOGEST
• 2-Aminopyridine
• 6-Aminocaproic acid
• Iminodibenzyl
• 3-Aminophenol
• Tris(hydroxymethyl)aminomethane
• 3-AMINO-2-BENZYLOXYPYRIDINE
• Pyridine
• 3-Phenoxypyridine
• 3-[(3,4-DICHLOROBENZYL)OXY]PYRIDIN-2-AMINE
• 2-Amino-3-benzyloxypyridine
• AMINO ACIDS
• 1-(3-CHLOROPHENYL)-3-(3-(PHENYLMETHOXY)(2-PYRIDYL))UREA
• 1-(CYCLOHEXYL)-3-(3-(PHENYLMETHOXY)(2-PYRIDYL))UREA