2-Methylene-1,3-propanediol Chemical Properties

Boiling point:

93-95 °C/2 mmHg (lit.)

Density 

1.081 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.473(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

14.14±0.10(Predicted)

form 

Viscous Liquid

color 

Clear colorless to pale yellow

BRN 

1737653

InChI

InChI=1S/C4H8O2/c1-4(2-5)3-6/h5-6H,1-3H2

InChIKey

JFFYKITVXPZLQS-UHFFFAOYSA-N

SMILES

C(O)C(=C)CO

CAS DataBase Reference

3513-81-3(CAS DataBase Reference)

EPA Substance Registry System

1,3-Propanediol, 2-methylene- (3513-81-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29053990

MSDS

• Language:English Provider:2-Methylene-1,3-propanediol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2-Methylene-1,3-propanediol Usage And Synthesis

Application

2-Methylene-1,3-propanediol, commonly known as isobutylene glycol, can be used to synthesize platelet-active factor inhibitors due to its unique methylene branched structure; it is also a crosslinking agent that can esterify with alkyd and polyester resins, effectively improving the thermal stability of polymers.

Chemical Properties

clear colorless to pale yellow viscous liquid

Synthesis

General procedure for the synthesis of 2-methylene-1,3-propanediol from 2-methylenepropane-1,3-diyl diacetate: allyl alcohol (1 eq.) was dissolved with acetic anhydride (1.2 eq.) in dichloromethane (DCM, concentration ca. 1 M) at 0 °C. Subsequently, pyridine (1 eq.) and 4-dimethylaminopyridine (DMAP, 0.1 mol%) were added to the reaction system. The reaction mixture was kept stirred at 0 °C for 30 min and then gradually warmed up to room temperature. After completion of the reaction, the reaction was quenched with 2N hydrochloric acid solution, the organic layer was separated, washed sequentially with water and brine and finally dried with anhydrous sodium sulfate. The solvent was removed by careful evaporation under reduced pressure to give pure 2-methylene propane-1,3-diyl diacetate (2d) without further purification. Subsequent processing was carried out via Method B. Specifically, purification by column chromatography (eluent ratio hexane:ethyl acetate = 20:1) afforded 2-methylene-1,3-propanediol as a colorless oil (20 g, 91% yield). The analytical data of the resulting compound were in agreement with literature reports.

References

[1] Patent: WO2018/53322, 2018, A1. Location in patent: Paragraph 0090; 00143
[2] J. Appl. Chem. USSR (Engl. Transl.), 1988, vol. 61, # 4, p. 853 - 855
[3] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1988, vol. 61, # 4, p. 934 - 937
[4] Synlett, 2008, # 15, p. 2321 - 2325

2-Methylene-1,3-propanediol(3513-81-3)Related Product Information

• 2-Phenyl-1,3-propanediol
• 1,3-Propanediol
• 1-Methoxy-2-propanol
• 2-METHYL-1,3-PROPANEDIOL
• Propylene glycol
• 1-Methoxy-2-propyl acetate
• 4,4'-Diphenylmethane diisocyanate
• Methylene Blue
• AFLATOXIN G1
• RUBRATOXIN B
• 3-CARBETHOXYUMBELIFERONE
• TETRAETHYL ETHYLENETETRACARBOXYLATE
• Coumarin-3-carboxylic acid
• diethyl [[(6-methyl-2-pyridyl)amino]methylene]malonate
• Diethyl ethoxymethylenemalonate
• PATULIN
• DIETHYL ETHYLIDENEMALONATE
• Methylene Chloride