4-(tert-ButoxycarbonylaMino)-1-butanol Chemical Properties

Melting point:

29 °C

Boiling point:

302.7±25.0 °C(Predicted)

Density 

1.02 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.456

Flash point:

29 °C

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

12.80±0.46(Predicted)

form 

Liquid or Low Melting Solid

color 

Colorless to yellow

BRN 

3603307

InChI

InChI=1S/C9H19NO3/c1-9(2,3)13-8(12)10-6-4-5-7-11/h11H,4-7H2,1-3H3,(H,10,12)

InChIKey

LIYMTLVBAVHPBU-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCCCO

Safety Information

WGK Germany 

3

F 

10-21

HazardClass 

IRRITANT

HS Code 

29221985

MSDS

• Language:English Provider:SigmaAldrich

4-(tert-ButoxycarbonylaMino)-1-butanol Usage And Synthesis

Chemical Properties

Light Yellow Liquid

Uses

Building block for spermidine analogues

Uses

4-(tert-ButoxycarbonylaMino)-1-butanol can be used as an intermediate for the synthesis of polymers used for in vivo delivery polyconjugate systems.

reaction suitability

reagent type: cross-linking reagent

Synthesis

GENERAL STEPS: 4-Amino-1-butanol (0.5 g, 5.61 mmol) was dissolved in acetonitrile (56 mL). The reaction system was cooled to 0 °C, followed by the sequential addition of triethylamine (Et3N, 1.56 mL, 11.22 mmol, 2 equiv) and di-tert-butyl dicarbonate (Boc2O, 1.346 g, 6.17 mmol). The reaction progression was monitored by thin layer chromatography (TLC). After 6.5 h of reaction, the reaction was quenched by the addition of water (20 mL). The reaction mixture was extracted with ethyl acetate (EtOAc, 3 × 30 mL) and saturated saline was added to facilitate phase separation. The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel fast column chromatography (eluent: dichloromethane/methanol, 95:5) to afford 4-(N-tert-butoxycarbonylamino)-1-butanol as a colorless oil (1.06 g, quantitative yield).

References

[1] Organic Letters, 2009, vol. 11, # 9, p. 2019 - 2022
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 6, p. 2536 - 2543
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1151 - 1155
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 191 - 200
[5] Inorganica Chimica Acta, 2016, vol. 452, p. 152 - 158

4-(tert-ButoxycarbonylaMino)-1-butanol(75178-87-9)Related Product Information

• N-Boc-cadaverine
• Carbamic acid, (4-amino-2-butynyl)-, 1,1-dimethylethyl ester (9CI)
• Carbamic acid, (tetrahydro-4-oxo-2H-pyran-3-yl)-, 1,1-dimethylethyl ester (9CI)
• tert-butyl N-(4,4-dimethyl-3-oxopentyl)-N-methylcarbamate
• tert-butyl N-(4-hydroxy-3-methylcyclohexyl)carbamate
• tert-butyl N-(5-aminonaphthalen-1-yl)carbamate
• tert-butyl N-(5-{[(tert-butoxy)carbonyl]amino}-3-oxopentyl)c arbamate
• BOC-GAMMA-ABU-OH
• Boc-L-glutamic acid 1-tert-butyl ester
• Boc-L-Glutamic acid 1-benzyl ester
• N-tert-Butoxycarbonyl-L-glutamic acid gamma-tert-butyl ester
• Boc-D-Glu-OBzl
• Boc-L-Glutamic acid
• 1-Butanol
• BOC-GLU(OBZL)-OH DCHA
• BOC-GLU-LYS-LYS-MCA
• BOC-STA-OH
• BOC-GLU(OSU)-OBZL