3-Allyloxy-1,2-propanediol

Base Information

• Chemical Name: 3-Allyloxy-1,2-propanediol
• CAS No.: 123-34-2
• Deprecated CAS: 90940-93-5
• Molecular Formula: C6H12 O3
• Molecular Weight: 132.159
• Hs Code.: 2909 49 80
• European Community (EC) Number: 204-620-4
• NSC Number: 59722
• UNII: 085RW4Y3PU
• DSSTox Substance ID: DTXSID4044375
• Nikkaji Number: J36.836I
• Wikidata: Q27236374
• ChEMBL ID: CHEMBL3182656
• Mol file: 123-34-2.mol

Synonyms:3-Allyloxy-1,2-propanediol;123-34-2;3-(Allyloxy)propane-1,2-diol;Glycerol 1-allylether;Ether, allyl glyceryl;Glycerin 1-allyl ether;3-(Allyloxy)propanediol;Glycerol alpha-monoallyl ether;glyceryl allyl ether;3-prop-2-enoxypropane-1,2-diol;1-Allyloxy-2,3-propanediol;3-(2-Propenyloxy)-1,2-propanediol;3-(Allyloxy)-1,2-propanediol;Glycerol alpha-allyl ether;1,2-Propanediol, 3-(2-propenyloxy)-;Glycerol 1-allyl ether;alpha-Allyl glycerol ether;1,2-Propanediol, 3-(2-propen-1-yloxy)-;NSC 59722;Glycerol .alpha.-monoallyl ether;Glycerol-1-allyl ether;EINECS 204-620-4;Glycerol 1-monoallyl ether;BRN 1701144;UNII-085RW4Y3PU;3-Allyloxy-1,2 propanediol;AI3-26697;085RW4Y3PU;1,2-Propanediol, 3-allyloxy-;DTXSID4044375;1,2-Propanediol, 3-(allyloxy)-;NSC-59722;4-01-00-02759 (Beilstein Handbook Reference);1-allylglycerin;1-O-Allylglycerol;1-Glyceryl Allyl Ether;1, 3-(allyloxy)-;Allyl-alpha-glyceryl ether;Glycerol a-monoallyl ether;3-allyloxy-1,2propanediol;1, 3-(2-propenyloxy)-;3-allyloxypropane-1,2-diol;SCHEMBL30534;.alpha.-Allyl glycerol ether;Allyl-.alpha.-glyceryl ether;Glycerol .alpha.-allyl ether;Glycerol-.alpha.-allyl ether;WLN: Q1YQ1O2U1;CHEMBL3182656;DTXCID2024375;3-allyloxy-1,2-dihydroxypropane;PAKCOSURAUIXFG-UHFFFAOYSA-;ALLYL OXY-1,2-PROPANEDIOL;GLYCERYL ALLYL ETHER [INCI];NSC59722;Tox21_302125;(+/-)-GLYCERYL ALLYL ETHER;3-Allyloxy-1,2-propanediol, 99%;MFCD00004721;AKOS015916380;GLYCERYL-.ALPHA.-MONOALLYLETHER;SB44822;SB83910;1-(ALLYLOXY)-2,3-PROPANEDIOL;GLYCERYL ALLYL ETHER, (+/-)-;1-ALLYLOXY-2,3-DIHYDROXYPROPANE;NCGC00255725-01;PROPANE-1,2-DIOL, 3-ALLYLOXY-;1394949-67-7;AS-63581;CAS-123-34-2;3-(prop-2-en-1-yloxy)propane-1,2-diol;LS-120125;CS-0130745;FT-0694570;G0189;E78805;A890791;W-109459;Q27236374

Chemical Property of 3-Allyloxy-1,2-propanediol

Chemical Property:

• Appearance/Colour: clear, colorless liquid.
• Vapor Pressure: 0.00991mmHg at 25°C
• Melting Point: -100 °C
• Refractive Index: n20/D 1.462(lit.)
• Boiling Point: 142 °C28 mm Hg(lit.)
• PKA: 13.75±0.20(Predicted)
• Flash Point: 132 °C
• PSA: 49.69000
• Density: 1.068 g/mL at 25 °C(lit.)
• LogP: -0.45780
• Storage Temp.: Store below +30°C.
• Solubility.: Completely miscible in water
• Water Solubility.: 163.2g/L at 25℃
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 72.7

Purity/Quality:

98% ^*data from raw suppliers

3-Allyloxy-1,2-propanediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCOCC(CO)O
• Uses: 3-Allyloxy-1,2-propanediol is a useful synthetic intermediate. It is used to prepare doxorubicin analogs. It is also used to synhesize poly(ethylene glycol)-lipid conjugates suitable for use in drug delivery.

Technology Process of 3-Allyloxy-1,2-propanediol

There total 44 articles about 3-Allyloxy-1,2-propanediol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

Allyl glycidyl ether (106-92-3,25639-25-2,90907-93-0) → 3-allyloxy-1,2-propanediol (123-34-2)

Guidance literature:

With tin(IV)tetraphenylporphyrinato trifluoromethanesulfonate; water; In acetonitrile; for 1.66667h; Heating;

DOI:10.1016/j.tet.2004.05.069

Reference yield: 92.0%

4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane (4421-23-2,18657-14-2,56083-15-9) → 3-allyloxy-1,2-propanediol (123-34-2)

Guidance literature:

With sulfuric acid; at 60 ℃; for 4h;

DOI:10.1134/S1070427215100079

Reference yield: 85.0%

Allyl glycidyl ether (106-92-3,25639-25-2,90907-93-0) + carbon dioxide (124-38-9,18923-20-1) + aniline (62-53-3) → 3-allyloxy-1,2-propanediol (123-34-2) + 5-<(allyloxy)methyl>-3-phenyl-1,3-oxazolidin-2-one (100372-80-3)

Guidance literature:

With C₂₄H₂₅N₄O₃⁽¹⁺⁾*I^(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; at 110 ℃; for 25h; under 3750.38 Torr; Autoclave;

DOI:10.1039/c9ob00224c

upstream raw materials:

2-allyloxy-propane-1,3-diol

oxiranyl-methanol

allyl alcohol

3-monochloro-1,2-propanediol

Downstream raw materials:

(-)-3-(allyloxy)-1,2-epoxypropane

<(Allyloxy)-methyl>-18-crown-6

4-oxa-1,6-heptadien-2-ol tosylate

2-(allyloxy)acetaldehyde

Refernces

• 1、 Tharun, Jose,Kathalikkattil, Amal Cherian,Roshan, Roshith,Kang, Dong-Heon,Woo, Hee-Chul,Park, Dae-Won. "Microwave-assisted, rapid cycloaddition of allyl glycidyl ether and CO 2 by employing pyridinium-based ionic liquid catalysts". . p. 31 - 34. Retrieved 2014.
• 2、 Timmer, Mattie S. M.,Sauvageau, Janelle,Foster, Amy J.,Ryan, Jason,Lagutin, Kirill,Shaw, Odette,Harper, Jacquie L.,Sims, Ian M.,Stocker, Bridget L.. "Discovery of lipids from B. longum subsp. infantis using whole cell MALDI analysis". . p. 7332 - 7341. Retrieved 2014.
• 3、 Ding, Xiong,Devalankar, Dattatray A.,Wang, Pengfei. "Structurally Simple Benzylidene-Type Photolabile Diol Protecting Groups". . p. 5396 - 5399. Retrieved 2016.
• 4、 Kathalikkattil, Amal Cherian,Kim, Dong-Woo,Tharun, Jose,Soek, Han-Geul,Roshan, Roshith,Park, Dae-Won. "Aqueous-microwave synthesized carboxyl functional molecular ribbon coordination framework catalyst for the synthesis of cyclic carbonates from epoxides and CO2". . p. 1607 - 1616. Retrieved 2014.
• 5、 Milani, Jorge L. S.,Meireles, Alexandre M.,Bezerra, Werberson A.,Martins, Dayse. C. S.,Cangussu, Danielle,das Chagas, Rafael P.. "MnIII Porphyrins: Catalytic Coupling of Epoxides with CO2 under Mild Conditions and Mechanistic Considerations". . p. 4393 - 4402. Retrieved 2019/08/01.
• 6、 Xie, Ya-Fei,Guo, Cheng,Shi, Lei,Peng, Bang-Hua,Liu, Ning. "Bifunctional organocatalysts for the conversion of CO2, epoxides and aryl amines to 3-aryl-2-oxazolidinones". supporting information. p. 3497 - 3506. Retrieved 2019/04/14.