2-Methylenepropane-1,3-diol

Base Information

• Chemical Name: 2-Methylenepropane-1,3-diol
• CAS No.: 3513-81-3
• Molecular Formula: C4H8O2
• Molecular Weight: 88.1063
• Hs Code.: 29053990
• European Community (EC) Number: 222-516-7
• UNII: YVG2NNQ7K2
• DSSTox Substance ID: DTXSID7063055
• Nikkaji Number: J216.163J
• Wikidata: Q72490495
• Mol file: 3513-81-3.mol

Synonyms:2-Methylene-1,3-propanediol;3513-81-3;2-Methylenepropane-1,3-diol;2-methylidenepropane-1,3-diol;1,3-Propanediol, 2-methylene-;MFCD00075162;EINECS 222-516-7;1,3-Dihydroxy-2-methylenepropane;Dimethylol Ethylene;YVG2NNQ7K2;2-methylene1,3-propanediol;2-methylenepropan-1,3-diol;2-methylene-propane-1,3-diol;1,3-Hydroxy-2-methylenepropane;DTXSID7063055;2-hydroxymethyl-2-propene-1-ol;BBL102282;STL556081;2-Methylene-1,3-propanediol, 97%;AKOS015840476;CS-W009247;GS-3611;PB20901;SY009429;AM20090550;FT-0634884;M2473;EN300-124426;A874748;J-510049

Chemical Property of 2-Methylenepropane-1,3-diol

Chemical Property:

• Appearance/Colour: clear colorless to pale yellow viscous liquid
• Vapor Pressure: 0.00867mmHg at 25°C
• Refractive Index: n20/D 1.473(lit.)
• Boiling Point: 236.203 °C at 760 mmHg
• PKA: 14.14±0.10(Predicted)
• Flash Point: 98.573 °C
• PSA: 40.46000
• Density: 1.043 g/cm³
• LogP: -0.47280
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 88.052429494
• Heavy Atom Count: 6
• Complexity: 43.5

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=C(CO)CO

Technology Process of 2-Methylenepropane-1,3-diol

There total 15 articles about 2-Methylenepropane-1,3-diol 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: 98.0%

1,3-diacetoxy-2-methylenepropane (3775-29-9) → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 - 20 ℃; for 0.5h;

Reference yield: 98.0%

2-methylene-1,3-propane-[bis-(tert-butyl)carbonate] (620161-75-3) → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Guidance literature:

With dmap; In tetrahydrofuran; Heating;

Reference yield: 70.0%

2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol (19184-65-7) → 3,3-bis(hydroxymethyl)oxetane (2754-18-9) + 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Guidance literature:

With base;

DOI:10.1023/A:1022112124741

upstream raw materials:

2-chloromethyl-3-chloroprop-1-ene

2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol

1,3-diacetoxy-2-methylenepropane

2,2-di-hydroxymethylnorborn-5-ene

Downstream raw materials:

2-methylpropenal

2-chloromethyl-3-chloroprop-1-ene

1,3-diacetoxy-2-methylenepropane

3,9-dimethylidene-1,5,7,11-tetraoxaspiro[5.5]undecane

Refernces

Convenient synthesis of pyrrolidines by amphiphilic allylation of imines with 2-methylenepropane-1,3-diols

10.1002/anie.200801252

The research focuses on the development of a convenient synthesis method for pyrrolidines through amphiphilic allylation of imines with 2-methylenepropane-1,3-diols, utilizing a Pd catalyst and Et3B system. The study explores the reactivity of various aldimines, prepared from a wide range of amines and aldehydes, with 2-methylenepropane-1,3-diols to form pyrrolidines, marking the first example of such a synthesis using nonactivated 2-methylenepropane-1,3-diols as a zwitterionic carbon framework. The experiments involved in situ aldimine formation, followed by the addition of 2-methylenepropane-1,3-diol, Pd(OAc)2, nBu3P, and Et3B, and the reactions were conducted under a nitrogen atmosphere at 50°C. The reactants included aromatic and aliphatic aldehydes and amines, with the addition of halogens or acidic OH groups in some cases. The analyses used to characterize the products included techniques such as IR spectroscopy, 1H and 13C NMR spectroscopy, and HRMS, with the structure of one product confirmed by X-ray single-crystal analysis.