1,3-Diamino-2-propanol Property

Melting point:

40-44 °C(lit.)

Boiling point:

235°C

Density 

1.0352 (rough estimate)

refractive index 

1.4610 (estimate)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

water: soluble1g/10 mL

form 

Low Melting Solid

pka

9.69, 7.93(at 20℃)

color 

White to yellow

Water Solubility 

Very soluble in water.

BRN 

741859

InChI

InChI=1S/C3H10N2O/c4-1-3(6)2-5/h3,6H,1-2,4-5H2

InChIKey

UYBWIEGTWASWSR-UHFFFAOYSA-N

SMILES

C(N)C(O)CN

CAS DataBase Reference

616-29-5(CAS DataBase Reference)

EPA Substance Registry System

2-Propanol, 1,3-diamino- (616-29-5)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

RIDADR 

3259

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29221990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1,3-Diamino-2-propanol Chemical Properties,Usage,Production

Description

1,3-Diamino-2-propanol (DAP), also known as 2-hydroxy-1,3-diaminopropane, is a white to yellowish low melting solid. Keep in a cool, well-ventilated place. Avoid prolonged storage periods. Store under inert gas, in a tightly sealed container and at ambient temperatures. 1,3-Diamino-2-propanol is incompatible with acids and strong oxidizing agents and should not be stored or handled in their vicinity.

Chemical Properties

white to yellowish low melting solid

Uses

• 1,3-Diamino-2-propanol is a versatile bidentate diamine ligand which is used in the synthesis of a variety of organometallic compounds.
• It is a precursor to synthesize the fluorogenic dsDNA binder, N¹,N³-bis(4-amidinophenyl)propane-1,3-diamine (BAPPA).
• It can also be used as a branching unit in the synthesis of peptide dendrimers.

Application

1,3-diamino-2-propanol (DAPL), a close analog of 1,3-diaminopropane, is an indirect inhibitor of ornithine decarboxylase (ODC). It is administered orally and inhibits ODC activity in the livers of partially hepatectomized rats[1]. It contains amine and hydroxyl groups. Therefore, it can be crosslinked with the carboxyl group via covalent and hydrogen bonds and has been investigated as a diamine monomer in the aqueous phase to fabricate the high-performance RO membrane[2].

Preparation

1,3-Diamino-2-propanol is synthesized by reacting Epichlorohydrin with ammonia in alkaline environment by adding sodium hydroxide. Afterwards, the product undergoes a series of purification steps.

Hazard

1,3-Diamino-2-propanoli is a hazardous chemical.
H302 (66.17%): Harmful if swallowed [Warning Acute toxicity, oral]. H314 (66.92%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]. H315 (33.08%): Causes skin irritation [Warning Skin corrosion/irritation]. H317 (66.17%): May cause an allergic skin reaction [Warning Sensitization, Skin]. H318 (66.17%): Causes serious eye damage [Danger Serious eye damage/eye irritation]. H319 (33.08%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]. H335 (34.59%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation.

Purification Methods

Dissolve it in an equal amount of water, shake it with charcoal and distil it at 68o/0.1mm. The distillate solidifies. It is too viscous to be distilled through a packed column. [Beilstein 4 IV 1694.]

References

[1] Raunio H, et al. The inhibition of induction of microsomal monooxygenase activity by 1,3-diamino-2-propanol, an inhibitor of ornithine decarboxylase. Biochemical and Biophysical Research Communications, 1979; 9: 285–290.
[2] Su T, et al. A novel polyamide thin-film nanocomposite reverse osmosis membrane constructed by a 3D multi-layer graphene oxide assembled with 1,3-diamino-2-propanol. Journal of Membrane Science, 2023; 681: 121773.