5-(BOC-AMINO)-1-PENTANOL

5-(BOC-AMINO)-1-PENTANOL Property

Boiling point:

318.4±25.0 °C(Predicted)

Density 

1.00 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.45

Flash point:

>109°C

storage temp. 

2-8°C

solubility 

Chloroform, Dichloromethane, Ethyl Acetate, Methanol

form 

Oil

pka

12.88±0.46(Predicted)

color 

Pale Yellow

Water Solubility 

Difficult to mix in water.

Sensitive 

Moisture Sensitive

BRN 

3603659

CAS DataBase Reference

75178-90-4(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Safety Statements 

23-24/25

WGK Germany 

3

F 

10-21

Hazard Note 

Irritant

HS Code 

2921490090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

5-(BOC-AMINO)-1-PENTANOL Chemical Properties,Usage,Production

Description

5-(Boc-amino)-1-pentanol is a linker containing a hydroxyl group and Boc-protected amino group. The hydroxyl group enables further derivatization or replacement with other reactive functional groups. The Boc group can be deprotected under mild acidic conditions to form the free amine.

Chemical Properties

Pale Yellow Oil

Uses

Linker (anthraquinone-oligopeptide)

Uses

5-(Boc-amino)-1-pentanol may also be used as non-limiting linkers.

Synthesis Reference(s)

Synthetic Communications, 20, p. 773, 1990 DOI: 10.1080/00397919008052321

reaction suitability

reagent type: cross-linking reagent

Synthesis

The general procedure for the synthesis of 5-(N-tert-butoxycarbonylamino)-1-pentanol from 5-amino-1-pentanol and di-tert-butyl dicarbonate is as follows: 1. 5-amino-1-pentanol (15.0 g, 145.4 mmol) was dissolved in water (140 mL) and saturated aqueous NaHCO3 solution (1.4 mL) in a 1.0 L single-necked round-bottomed flask. 2. To the above solution was slowly added a solution of di-tert-butyl dicarbonate (33.3 g, 152.7 mmol) in THF (280 mL). 3. The reaction mixture was stirred overnight at room temperature, keeping the flask open to the atmosphere. 4. Upon completion of the reaction, the reaction mixture was diluted with saturated aqueous NaHCO3 solution (90 mL) and extracted with EtOAc (400 mL). 5. The organic layer was separated, dried over anhydrous Na2SO4, filtered and the solvent evaporated to give 28.9 g (98% yield) of 5-(N-tert-butoxycarbonylamino)-1-pentanol as a clear colorless oil. 6. The purity of the product was confirmed by NMR analysis and no further purification was carried out. Note: 5-(N-Boc-amino)-1-pentanol is also available from TCI America (Portland, OR).

References

[1] Synthesis, 1990, p. 366 - 368
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7892 - 7901
[3] Tetrahedron Letters, 1992, vol. 33, # 20, p. 2833 - 2836
[4] Carbohydrate Research, 1999, vol. 322, # 3-4, p. 201 - 208
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1376 - 1392