123-34-2

Basic information

• Product Name: 3-ALLYLOXY-1,2-PROPANEDIOL
• Synonyms: 1-(prop-2-enyloxy)-propane-2,3-diol;1,2-Propanediol, 3-(2-propenyloxy)-;1,2-Propanediol, 3-(allyloxy)-;1-Allyloxy-2,3-propanediol;2-Propanediol,3-(2-propenyloxy)-1;3-(2-propenyloxy)-2-propanediol;3-(Allyloxy)propanediol;3-allyloxy-2-propanediol
• CAS NO: 123-34-2
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• EINECS: 204-620-4
• Mol File: 123-34-2.mol
• Article Data: 72

Chemical Properties

• Melting Point: -100 °C
• Boiling Point: 142 °C28 mm Hg(lit.)
• Flash Point: 132 °C
• Appearance: Clear colorless to light yellow/Viscous Liquid
• Density: 1.068 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00991mmHg at 25°C
• Refractive Index: n20/D 1.462(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Completely miscible in water
• PKA: 13.75±0.20(Predicted)
• Water Solubility: 163.2g/L at 25℃
• BRN: 1701144
• CAS DataBase Reference: 3-ALLYLOXY-1,2-PROPANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ALLYLOXY-1,2-PROPANEDIOL(123-34-2)
• EPA Substance Registry System: 3-ALLYLOXY-1,2-PROPANEDIOL(123-34-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 1
• RTECS: TY2700000
• Hazardous Substances Data: 123-34-2(Hazardous Substances Data)

Usage

Description

3-Allyloxy-1,2-propanediol, also known as allyl glycidol, is a clear colorless to light yellow viscous liquid that serves as a versatile synthetic intermediate in the chemical industry. It is characterized by its unique chemical structure, which allows for various applications in different fields.

Uses

Used in Pharmaceutical Industry:
3-Allyloxy-1,2-propanediol is used as a synthetic intermediate for the preparation of doxorubicin analogs, which are important chemotherapeutic agents used in the treatment of various types of cancer. Its unique chemical structure enables the development of novel drug candidates with improved efficacy and reduced side effects.
Used in Drug Delivery Systems:
In the field of drug delivery, 3-Allyloxy-1,2-propanediol is used to synthesize poly(ethylene glycol)-lipid conjugates. These conjugates are essential components in the development of targeted drug delivery systems, which aim to improve the bioavailability, stability, and therapeutic outcomes of various drugs. The use of 3-Allyloxy-1,2-propanediol in this application allows for the creation of more efficient and effective drug delivery platforms.
Overall, 3-Allyloxy-1,2-propanediol is a valuable compound with a wide range of applications in the pharmaceutical and drug delivery industries, contributing to the development of innovative treatments and therapies for various medical conditions.

Synthesis Reference(s)

Synthetic Communications, 24, p. 1959, 1994 DOI: 10.1080/00397919408010203

InChI:InChI=1/C6H12O3/c1-2-3-9-5-6(8)4-7/h2,6-8H,1,3-5H2/t6-/m1/s1

Upstream product

• 6806-76-4 2-allyloxy-propane-1,3-diol 
• 556-52-5 oxiranyl-methanol 
• 107-18-6 allyl alcohol 
• 96-24-2 3-monochloro-1,2-propanediol 
• 106-95-6 allyl bromide 
• 56-81-5 glycerol 
• 20907-32-8 sodium allyloxide 
• 106-92-3 Allyl glycidyl ether 
• 4421-23-2 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane 
• 3179-63-3 3-Dimethylamino-1-propanol 
• 67-56-1 methanol 
• 826-29-9 4-allyloxymethyl-1,3-dioxolan-2-one 
• 35466-83-2 allyl methyl carbonate 
• 15022-08-9 diallylcarbonate 

Downstream Products

• 59778-15-3 3-(2,3-dibromo-propoxy)-propane-1,2-diol 
• 95870-54-5 1-O-allyl-3-O-triphenylmethylglycerol 
• 71026-29-4 (S)-1-O-Trityl-3-O-allyl-glycerol 
• 95043-56-4 (-)-3-(allyloxy)-1,2-epoxypropane 
• 129257-36-9 1-Allyloxy-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-propan-2-ol 
• 95043-55-3 (+)-3-(allyloxy)-1,2-epoxypropane 
• 91324-63-9 4-Allyloxymethyl-2-((E)-styryl)-[1,3]dioxolane 
• 152752-38-0 2-hydroxy-3-allyloxypropyl 4-toluenesulfonate 
• 114719-19-6 3-allyloxy-1,2-propanediol ditosylate 
• 144685-46-1 3-(3-{[3-(2,3-Dihydroxy-propoxy)-propyl]-phenyl-phosphanyl}-propoxy)-propane-1,2-diol 
• 83016-75-5 1-O-benzyl-3-O-allyl-1,2,3-propanetriol 
• 6076-35-3 1,2-dihexadecylglycerol 
• 84812-04-4 <(Allyloxy)-methyl>-18-crown-6 
• 173950-08-8 (S)-1-(allyloxy)-3-(bis(4-methoxyphenyl)(phenyl)methoxy)propan-2-ol 

Relevant articles and documents

Synthesis of Phospholipids using an Inverse Phosphite Triester Approach

1,2-Diacylglycerols, prepared from allyl protected precursors, were transformed into glycerophosphatidylcholines through an acid catalysed coupling with a dialkyl phosphoramidite, followed by a one step deprotection-substitution reaction.

Synthesis of a plasmenylethanolamine

A concise synthesis of a plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]), known as antioxidative phospholipids commonly found in cell membranes, has been achieved from an optically active known diol through 8 steps. The key transformations for the synthesis of PlsEtn-[16:0/18:1 n-9] are (1) regio- A nd Z-selective vinyl ether formation via the alkylation of a lithioalkoxy allyl intermediate with an alkyl iodide, and (2) a one-pot phosphite esterification-oxidation sequence to construct the ethanolamine phosphonate moiety in the presence of the vinyl ether functionality. The piperidine salt of synthetic PlsEtn-[16:0/18:1 n-9] was desalinated through reversed-phase high-performance liquid chromatography purification.

Room-temperature self-healing polymers based on dynamic-covalent boronic esters

Cross-linked polymers constructed with dynamic-covalent boronic esters were synthesized via photoinitiated radical thiol-ene click chemistry. Because the reversibility of the boronic ester cross-links was readily accessible, the resulting materials were capable of undergoing bond exchange to covalently mend after failure. The reversible bonds of the boronic esters were shown to shift their exchange equilibrium at room temperature when exposed to water. Nevertheless, the materials were observed to be stable and hydrophobic and absorbed only minor amounts of water over extended periods of time when submerged in water or exposed to humid environments. The facile reversibility of the networks allowed intrinsic self-healing under ambient conditions. Highly efficient self-healing of these bulk materials was confirmed by mechanical testing, even after subjecting a single site to multiple cut-repair cycles. Several variables were considered for their effect on materials properties and healing, including cross-link density, humidity, and healing time.

Zwitterionic Quaternary Ammonium Alkoxides: Organic Strong Bases

Stable quaternary ammonium alkoxides, a new type of organic strong base, were obtained from unhindered tertiary alkanolamines and glycidol.At elevated temperatures, the 2-hydroxyethyl derivatives underwent intramolecular rearrangements and deoxyalkylation to form tertiary amine terminated 1,4-poly(3-hydroxyoxetanes).Demethylation was also observed.The 3-hydroxypropyl derivative underwent disproportionation and Hofmann elimination in addition.

Synthesis and Evaluation of New Polyurethane - Based Material for Ion Separation

The polyaddition of macrocyclic diols with diisocyanates is an easy way to prepare ionselective polymers bearing pendant crown ethers.Those polymers can be readily immobilized on silicagel, with no change of ionselective properties.

MACROCYCLIC MCL-1 INHIBITORS AND METHODS OF USE

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

MACROCYCLIC MCL-1 INHIBITORS AND METHODS OF USE

The present disclosure provides for compounds of formula (I), wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of formula (I).