1,1-Bis(hydroxymethyl)cyclopropane Chemical Properties

Boiling point:

235-236 °C(lit.)

Density 

1.065 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4700(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Ethyl Acetate (Slightly)

pka

14.80±0.10(Predicted)

form 

Colourless to Off-White Oil to Semi-Solid

Specific Gravity

1.065

color 

Colorless to Light yellow to Light orange

InChI

InChI=1S/C5H10O2/c6-3-5(4-7)1-2-5/h6-7H,1-4H2

InChIKey

YAINYZJQSQEGND-UHFFFAOYSA-N

SMILES

C1(CO)(CO)CC1

CAS DataBase Reference

39590-81-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29021990

MSDS

• Language:English Provider:SigmaAldrich

1,1-Bis(hydroxymethyl)cyclopropane Usage And Synthesis

Chemical Properties

Colorless to yellow liquid

Uses

1,1-Bis(hydroxymethyl)cyclopropane is used in the synthesis of morphine alkaloids. It also serves as an inhibitor of 5-lipoxygenase.

Synthesis

The general procedure for the synthesis of 1,1-cyclopropanedimethanol from dimethyl 1,1-cyclopropanedicarboxylate was as follows: lithium aluminum hydride (LiAlH4, 569 mg, 15.0 mmol) was added batchwise to a solution of dimethyl-1,1-cyclopropanedicarboxylate (791 mg, 5.01 mmol) in ether (Et2O, 20 mL) at 0 °C. The reaction mixture was stirred at room temperature for 4 h. The reaction was subsequently quenched with saturated sodium sulfate (Na2SO4) solution at 0 °C. The precipitated solid was filtered and washed with tetrahydrofuran (THF). The filtrate was concentrated and purified by column chromatography (eluent: ethyl acetate, EtOAc) to afford 440 mg (86% yield) of the target product 1,1-cyclopropanedimethanol. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 4.02 (s, 2H), 3.56 (s, 4H), 0.48 (s, 4H); mass spectrum (electrospray ionization, ES) m/z: 125 ([M + Na]+).

References

[1] Patent: WO2005/30694, 2005, A1. Location in patent: Page/Page column 84-85
[2] Patent: WO2005/12324, 2005, A2. Location in patent: Page/Page column 106-107
[3] Patent: WO2014/209034, 2014, A1. Location in patent: Paragraph 580; 581; 582

1,1-Bis(hydroxymethyl)cyclopropane(39590-81-3)Related Product Information

• Malononitrile
• Tris(hydroxymethyl)nitromethane
• Benzhydrol
• Cyclopropane
• Diethyl malonate
• Dimethyl malonate
• Malonic acid
• propanedial
• Cyclopropyl carbinol
• 1,3-Diaminopropane
• Cyclopropanecarboxylic acid
• Bromoacetaldehyde dimethyl acetal
• Aminoacetaldehyde dimethyl acetal
• 1,1-Cyclopropanedicarboxylic acid
• 6,6-DIMETHYL-5,7-DIOXASPIRO[2.5]OCTANE-4,8-DIONE
• 1,1-CYCLOPROPANEDICARBOXYLIC ACID MONOETHYL ESTER
• 1,1-Cyclopropanedicarboxylic acid monomethyl ester
• Diethyl 1,1-cyclopropanedicarboxylate