| Identification | More | [Name]
Diethyl bis(hydroxymethyl)malonate | [CAS]
20605-01-0 | [Synonyms]
2,2-BIS(HYDROXYMETHYL)MALONIC ACID DIETHYL ESTER
DIETHYL BIS(HYDROXYMETHYL)MALONATE
MALONIC ACID, BIS [HYDROXYMETHYL] DIETHYL ESTER
TIMTEC-BB SBB007847
bis(hydroxymethyl)-propanedioicacidiethylester
Diethyl 2,2-bis(hydroxymethyl)malonate
Propanedioic acid, bis(hydroxymethyl)-, diethyl ester
Ethyl Dimethylol Malonate
bis-(Hydroxymethyl)diethylester
BIS-(HYDROXYMETHYL)-DIETHYLMALONATE
Diethyl bis(hydroxymethyl)malonate, 98+%
Bis(1-hydroxypropan-2-yl) propanedioate
2,2-Di(hydroxymethyl)malonic acid diethyl ester | [EINECS(EC#)]
243-916-8 | [Molecular Formula]
C9H16O6 | [MDL Number]
MFCD00009130 | [Molecular Weight]
220.22 | [MOL File]
20605-01-0.mol |
| Chemical Properties | Back Directory | [Appearance]
white to almost white crystalline solid | [Melting point ]
49-51 °C (lit.) | [Boiling point ]
281.15°C (rough estimate) | [density ]
1.2286 (rough estimate) | [refractive index ]
1.4390 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Crystalline Solid | [pka]
12.59±0.10(Predicted) | [color ]
White to almost white | [Water Solubility ]
Slightly soluble in water. | [BRN ]
1788515 | [InChI]
InChI=1S/C9H16O6/c1-3-14-7(12)9(5-10,6-11)8(13)15-4-2/h10-11H,3-6H2,1-2H3 | [InChIKey]
WIOHBOKEUIHYIC-UHFFFAOYSA-N | [SMILES]
C(OCC)(=O)C(CO)(CO)C(OCC)=O | [CAS DataBase Reference]
20605-01-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Diethyl bis(hydroxymethyl)malonate(20605-01-0) | [EPA Substance Registry System]
20605-01-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29181998 |
| Hazard Information | Back Directory | [Chemical Properties]
white to almost white crystalline solid | [Uses]
Diethyl bis(hydroxymethyl)malonate is used as a reagent for preparing 1,3-dioxanes from acetals, aldehydes and ketones. It is also used as an intermediate for the preparation of substituted malonic, acrylic and isobutyric esters, for conversion to the useful dienophiles, ?-bromomethylacrylic acid and its ethyl ester and to bis(bromomethyl)acetic acid and its methyl ester. | [Synthesis]
A 35% aqueous formaldehyde solution (16.07 mL, 187.3 mmol, 3.0 eq.) was mixed with potassium bicarbonate (0.53 g, 5.27 mmol, 0.08 eq.) in a 20 °C water bath. Diethyl malonate (10.00 g, 62.43 mmol, 1.0 eq.) was added slowly and the reaction mixture was stirred overnight. After completion of the reaction, saturated sodium sulfate solution was added and the product was extracted with ether. The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product diethyl 2,2-bis(hydroxymethyl)malonate (13.79 g, 100%) as a clear colorless oil. The product could be used in the next reaction without further purification. Thin layer chromatography (TLC) Rf value was 0.31 (unfolding agent: 50% ethyl acetate/hexane). IR spectrum (neat, cm-1): 3433 (O-H), 2982 (C-H), 1790 (C=O), 1209, 1028. 1H NMR (300 MHz, CDCl3): δ 4.22 (q, 4H, J = 6.7 Hz, 2 × OCH2CH3), 4.09-4.04 (m, 4H, 2 × CH2OH), and 2.99 (s, 2H, 2 × OH), 1.25 (t, 3H, J = 7.1 Hz, OCH2CH3), 1.24 (t, 3H, J = 7.1 Hz, OCH2CH3).13C NMR (75 MHz, CDCl3): δ 169.58, 63.54, 61.97, 61.21, 14.04. | [References]
[1] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 671 - 690
[2] Synthesis, 1997, # 11, p. 1281 - 1284
[3] Patent: WO2014/110388, 2014, A1. Location in patent: Page/Page column 21; 22
[4] Tetrahedron, 1991, vol. 47, # 6, p. 1001 - 1012
[5] Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1675 - 1692 |
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