3-Azido-1-propanamine Chemical Properties

Melting point:

47-49 °C

Boiling point:

50°C/15mmHg(lit.)

Density 

1.020 g/mL at 25 °C

refractive index 

n20/D1.471

Flash point:

60°(140°F)

storage temp. 

-20°C

solubility 

soluble in water, DMSO, DMF, DCM, THF, chloroform

form 

Liquid

color 

Pale Yellow

Appearance

Colorless or light yellow oil

Water Solubility 

Soluble in DMSO, DMF, DCM, chloroform, THF, and water.Miscible with dimethylsulfoxide, dimethyl formamide, dichloromethane, tetrahydrofuran, chloroform and water.

InChI

InChI=1S/C3H8N4/c4-2-1-3-6-7-5/h1-4H2

InChIKey

OYBOVXXFJYJYPC-UHFFFAOYSA-N

SMILES

NCCCN=[N+]=[N-]

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 1992 6.1(3) / PGIII

WGK Germany 

3

HS Code 

2929.90.5090

HazardClass 

3

PackingGroup 

III

Storage Class

3 - Flammable liquids

Hazard Classifications

Acute Tox. 3 Oral
Flam. Liq. 3

3-Azido-1-propanamine Usage And Synthesis

Description

Azidopropylamine is a water-soluble, short bifunctional crosslinker with azide and amine groups. The primary amine group possesses high reactivity towards activated ester derivatives (NHS, etc.). The azide group can be coupled with alkynes via copper-catalyzed click reaction (CuAAC). Both reactions are orthogonal and can be carried out independently.

Azidopropylamine is used to introduce an azide fragment into molecules containing carboxyl groups by activating them with carbodiimide and their further interaction with the amine group of azidopropylamine. Azidopropylamine can also be used in peptide synthesis to modify peptides with activated HBTU and HOBt carboxyl groups.

A chemically stable solid hydrochloride form of azidopropylamine is also available. It is ideal as an azidopropylamine bulk for applications when a large amount of reagent is needed.

Uses

Azido-containing reagent with carbonyl and carboxyl reactivity3-Azido-1-propylamine is used in the preparation of perylenedimides derivative by reacting with 1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxyanhydride, which is used in click chemistry.

Uses

Amine modified azide for click chemistry.

General Description

3-Azido-1-propanamine can be used to functionalize:

• Bismethylolpropionic acid (bis-MPA) monomers with azide functional group to generate high-generation dendrimers.,
• Clickable zinc tetraphenylporphyrin scaffold with an azido group through click chemistry applicable in photodynamic therapy.

reaction suitability

reaction type: click chemistry

Synthesis

3-Bromopropylamine hydrobromide (3.28 g, 15.0 mmol) was dissolved in 10 mL of water. An aqueous solution (15 mL) of sodium azide (3.25 g, 50.0 mmol) was added and the mixture was heated to reflux and stirred for 16 hours. Add ether (50 mL) and cool the mixture in an ice water bath. Slowly add KOH pellets (4 g) while keeping the temperature below 10??C. Separate the organic layer and extract the aqueous phase with ether (2 x 30 mL). The combined organic layers (K2CO3) were dried and concentrated to give 3-azidopropylamine.

3-Azido-1-propanamine (88192-19-2)Related Product Information

• AZIDOMETHYL PHENYL SULFIDE
• 11-AZIDO-3 6 9-TRIOXAUNDECAN-1-AMINE