ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Amino alcohol derivative 3-Amino-1,2-propanediol

3-Amino-1,2-propanediol

Product Name3-Amino-1,2-propanediol
CAS616-30-8
MFC3H9NO2
MW91.11
EINECS210-475-8
MOL File616-30-8.mol

Chemical Properties

Melting point	55-57 °C
Boiling point	264-265 °C739 mm Hg(lit.)
Density	1.175 g/mL at 25 °C(lit.)
vapor pressure	<1 hPa (20 °C)
refractive index	n20/D 1.492(lit.)
Flash point	>230 °F
storage temp.	Store below +30°C.
solubility	>1000g/l soluble
pka	12.11±0.35(Predicted)
form	liquid (highly viscous)
color	Clear colorless to pale yellow
Specific Gravity	1.175
PH	11 (100g/l, H2O, 20℃)
Water Solubility	soluble
Sensitive	Hygroscopic
BRN	1719121
Cosmetics Ingredients Functions	BUFFERING
InChI	1S/C3H9NO2/c4-1-3(6)2-5/h3,5-6H,1-2,4H2
InChIKey	KQIGMPWTAHJUMN-UHFFFAOYSA-N
SMILES	NCC(O)CO
LogP	-2.079 (est)
CAS DataBase Reference	616-30-8(CAS DataBase Reference)
NIST Chemistry Reference	3-Amino-1,2-propanediol(616-30-8)
EPA Substance Registry System	1,2-Propanediol, 3-amino- (616-30-8)

Safety Information

Hazard Codes	C,Xi
Risk Statements	34-36/37/38
Safety Statements	26-36/37/39-45-36
RIDADR	UN 2735 8/PG 2
WGK Germany	2
RTECS	TY2800000
F	10-21
Hazard Note	Corrosive
TSCA	TSCA listed
HazardClass	8
PackingGroup	III
HS Code	29221980
Storage Class	8A - Combustible corrosive hazardous materials
Hazard Classifications	Skin Corr. 1B
Toxicity	LD50 orally in Rabbit: 7500 mg/kg

MSDS

Provider	Language
1-Amino-2,3-propanediol	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Description

3-Amino-1,2-propanediol (APD) is a calcium metabolism regulator useful in the treatment of Paget's disease, tumor-induced hypercalcemia and other bone disorders involving increased osteoclastic activity.

Chemical Properties

3-Amino-1,2-propanediol is a very viscous transparent colorless to pale yellow liquid with a melting point of 55-57 °C and a boiling point of 264-265 °C. The density at 25 °C is 1.175 g/mL. soluble in water.

Originator

Henkel (W. Germany)

Uses

3-Amino-1,2-propanediol is used in the preparation of iohexol, which is a X-CT non-ionic contrast medium. It acts as a starting material in the production of specialty materials.

Application

3-Amino-1,2-propanediol is used as a reactant in the synthesis of lipid-like delivery molecules(lipidoids) for RNA interference (RNAi) therapeutics. It is also used in the synthesis of the bioactive template to prepare cationic α-helical polypeptides and various cationic polymers for gene delivery. It is also used in the synthesis of Decarbazolyl Carvedilol (D212720), a metabolite of Carvedilol (C184625) found in humans, rats, dogs and mice.

Uses

A chiral glycerol derivative, namely 3-amino-1,2-propanediol, was employed for as the hydrogen bond donor (HBD) in the design of a new deep eutectic solvent (DES) with choline chloride acting as the hydrogen bond acceptor (HBA). The novel mixture was characterized and unambiguously classified as a DES^[4].

Preparation

3-Amino-1,2-propanediol is synthesized by reacting 3-chloro-1,2-propanediol (CPD) with ammonia in alkaline environment by adding sodium hydroxide. Afterwards, the product undergoes a series of purification steps.

Application

3-Amino-1,2-propanediol is used as a chiral selector ligand, used subsequently for a nucleophilic substitution with the dimethoxytrityl (DMT)-protected.

brand name

Aminomux

General Description

3-Amino-1,2-propanediol is a chiral glycerol derivative. It could used as a hydrogen bond donor in the design of a new deep eutectic solvent which have emerged as a suitable alternative to VOCs (volatile organic compounds) for diverse practical applications including, among others, drug delivery, electrochemistry, material design, extractions and, of course, organic reactions, alone or together twith other sustainable reaction-media[1]. It can also used as a core present in antiviral compounds to skeleton to design a novel class of anti-adenovirus agents[2].

Hazard

3-Amino-1,2-propanediol is Danger.
H314 (93.33%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H318 (56.36%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Materials Uses

Chloromethylated polystyrene resin was modified by 3-amino-1,2-propanediol to obtain dihydroxyamine resin (KLA resin); Using trometamol as a raw material, chloromethylated polystyrene resin was modified to prepare polyhydroxyamine resin (KDN resin)^[3].

Safety Profile

Poison by intraperitoneal route.Moderately toxic by ingestion. When heated todecomposition it emits toxic fumes of NOx.

Synthesis

96-24-2

616-30-8

The synthesis of 3-amino-1,2-propanediol (APD) was carried out in a microreactor using 3-chloro-1,2-propanediol (1-CPD, 99% purity, aqueous solution, flow rate of 3.0 mL/min) as raw material. The reaction system was simultaneously injected with NaOH solution (10% concentration, flow rate 11.6 mL/min) and NH3 solution (25% concentration, flow rate 56.4 mL/min). The reaction process was divided into two phases: the first phase was carried out in the first and second reaction chambers with a residence time of 2.87 min, which mainly produced glycidol; the second phase was carried out in the fourth to tenth reaction chambers with a residence time of 21.1 min, which completed the ammonolysis reaction. The total residence time was 23.98 minutes. The reaction temperature was controlled at 42°C for the first stage and 18°C for the second stage. The products were collected in a Teflon tube collection component at ambient temperature (~22°C). Samples were taken 50 minutes from the start of the reaction, and the yield of APD was 67.4% (% area) based on the 1-CPD feed.

storage

3-Amino-1,2-propanediol absorbs moisture and needs to be kept in a container sealed. Store in cool, dry conditions in well-sealed containers.

References

[1] Antenucci A, et al. Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry. Molecules, 2022; 27.
[2] Mazzotta S, et al. Design, synthesis and in vitro biological evaluation of a novel class of anti-adenovirus agents based on 3-amino-1,2-propanediol. Bioorganic Chemistry, 2021; 114: 105095.
[3] Liao, H., Fu, Y., Hu, H., Zhu, M., Xu, M., & Zhong, S. (2022). Boron Removal from Water and Wastewater using New Polystyrene-Based Resin Grafted with Trometamol and 3-Amino-1,2-propanediol. Journal of the Chemical Society of Pakistan, 1 1. https://doi.org/10.52568/000976/jcsp/44.01.2022
[4] Antenucci, A., Bonomo, M., Ghinato, S., Blangetti, M., & Dughera, S. (2022). Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry. Molecules, 27 23. https://doi.org/10.3390/molecules27238566

3-Amino-1,2-propanediol

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