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37519-04-3

37519-04-3 Structure

37519-04-3 Structure
IdentificationBack Directory
[Name]

3-(benzylaMino)propan-1-ol
[CAS]

37519-04-3
[Synonyms]

Benzyl 1-Methylhydrazinecarboxylate
1-(benzyloxy)carbonyl-1-Methylhydrazine
1-(benzylo×y)carbonyl-1-Methylhydrazine
Hydrazinecarboxylic acid, 1-methyl-, phenylmethyl ester
[Molecular Formula]

C9H12N2O2
[MDL Number]

MFCD21604061
[MOL File]

37519-04-3.mol
[Molecular Weight]

180.2
Chemical PropertiesBack Directory
[storage temp. ]

under inert gas (nitrogen or Argon) at 2–8 °C
[Appearance]

Colorless to light yellow Liquid
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2928009090
Spectrum DetailBack Directory
[Spectrum Detail]

3-(benzylaMino)propan-1-ol(37519-04-3)1HNMR
Hazard InformationBack Directory
[Synthesis]

Benzyl chloroformate

501-53-1

Methylhydrazine

60-34-4

3-(benzylaMino)propan-1-ol

37519-04-3

At -78 °C, methylhydrazine (5 g, 108.7 mmol) was dissolved in 15-20 mL of dichloromethane containing triethylamine (13.2 g, 130.4 mmol). Benzyl chloroformate (14.8 g, 86.9 mmol) at the same temperature was slowly added dropwise, and the reaction mixture was stirred at this temperature for 15 min before being brought to room temperature and continued to stir under nitrogen protection for 4 hr until thin-layer chromatography (TLC) analysis showed complete consumption of the feedstock. Upon completion of the reaction, the reaction was quenched by the addition of water and the product was extracted with ethyl acetate. The organic phases were combined, washed sequentially with water (50 mL x 2) and saturated saline (50 mL), and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the resulting crude product was purified by column chromatography (eluent: hexane solution of 25% ethyl acetate) to afford 8 g of the target product 1-Cbz-1-methylhydrazine (compound 20b). Liquid chromatography-mass spectrometry (LCMS) analysis result: 180.09 (M + H)+.

[References]

[1] Tetrahedron, 2006, vol. 62, # 23, p. 5454 - 5463
[2] The Journal of organic chemistry, 2002, vol. 67, # 25, p. 8962 - 8969
[3] Journal of the Chemical Society. Perkin transactions 1, 1975, # 17, p. 1712 - 1720
[4] Journal of the American Chemical Society, 1993, vol. 115, # 20, p. 8898 - 8906
[5] Journal of Medicinal Chemistry, 2008, vol. 51, # 4, p. 924 - 931
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