N-Boc-1,3-propanediamine Chemical Properties

Melting point:

22 °C (lit.)

Boiling point:

203 °C (lit.)

Density 

0.998 g/mL at 20 °C (lit.)

refractive index 

n20/D 1.454(lit.)

Flash point:

>230 °F

storage temp. 

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

solubility 

Miscible with methanol.

pka

12.73±0.46(Predicted)

form 

Liquid

Specific Gravity

0.998

color 

Colorless

Sensitive 

Air Sensitive

BRN 

3588328

InChIKey

POHWAQLZBIMPRN-UHFFFAOYSA-N

CAS DataBase Reference

75178-96-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

22-34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3259 8/PG 3

WGK Germany 

3

F 

10-34

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

III

HS Code 

29212900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-Boc-1,3-propanediamine Usage And Synthesis

Chemical Properties

Colorless to light yellow liquid

Uses

N-Boc-1,3-diaminopropane is used in the preparation of spermidine analogues as well as in the preparation of pharmacologically active compounds. It is also used in suzuki reaction. Further, it is used in the preparation of [3-(3-cyano-propylamino)-propyl]-carbamic acid tert-butyl ester.

reaction suitability

reagent type: cross-linking reagent
reagent type: spacer

Synthesis

GENERAL PROCEDURE: To a suspension of 1,3-propanediamine (20.0 g, 172 mmol) in 50 mL of dichloromethane (DCM) cooled to 0°C, a solution of di-tert-butyl dicarbonate (Boc2O, 3.75 g, 17.2 mmol) in 24 mL of DCM was slowly added. After addition, the ice bath was removed and the reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the precipitate was removed by filtration and the filtrate was washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) (3 x 50 mL), water (2 x 50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give an oily product N-tert-butoxycarbonyl-1,3-propanediamine 3.1 g in 84% yield.

References

[1] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 411 - 416
[2] Liebigs Annales, 1996, # 6, p. 935 - 939
[3] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 4, p. 1009 - 1018
[4] Organic and Biomolecular Chemistry, 2015, vol. 14, # 2, p. 455 - 459
[5] New Journal of Chemistry, 2018, vol. 42, # 12, p. 10142 - 10147

N-Boc-1,3-propanediamine(75178-96-0)Related Product Information

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