| Identification | More | [Name]
1,1-Bis(hydroxymethyl)cyclopropane | [CAS]
39590-81-3 | [Synonyms]
1,1-BIS(HYDROXYMETHYL)CYCLOPROPANE
1,1-CYCLOPROPANEDIMETHANOL
1,1-DIMETHYLCYCLOPROPANE
(1-HYDROXYMETHYLCYCLOPROPYL)METHANOL
CYCLOPROPANE DIMETHANOL
CYCLOPROPYLIDENEDIMETHANOL
1,1-Cyclopropane dimethanlol
1,1-Cyclopropyldimethanol
cyclopropyl dimethanol
1,1-DIMETHOLCYCLOPROPANE
1,1-BIS(HYDROMETHYL)CYCLOPROPANE
CYCLOPROPANE-1,1-DIYLDIMETHANOL
1,1-Cyclopropane
1,1-Bis(hydroxymethyl)cyclopropane 97%
1,1-BIS(HYDROXYMETHYLCYCLOPROPANE) 98+% | [EINECS(EC#)]
212-146-4 | [Molecular Formula]
C5H10O2 | [MDL Number]
MFCD00053258 | [Molecular Weight]
102.13 | [MOL File]
39590-81-3.mol |
| Chemical Properties | Back Directory | [Boiling point ]
235-236 °C(lit.)
| [density ]
1.065 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.4700(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform, Ethyl Acetate (Slightly) | [form ]
Colourless to Off-White Oil to Semi-Solid | [pka]
14.80±0.10(Predicted) | [color ]
Colorless to Light yellow to Light orange | [Specific Gravity]
1.065 | [Detection Methods]
GC,NMR | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29021990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2 |
| Hazard Information | Back Directory | [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 |
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