Diethyl bis(hydroxymethyl)malonate

Product Name: Diethyl bis(hydroxymethyl)malonate
CAS No.: 20605-01-0
Chemical Name: Diethyl bis(hydroxymethyl)malonate
Synonyms: Diethyl 2,2-bis(hydroxymethyl)malonate;diethyl 2,2-bis(hydroxymethyl)propanedioate;TIMTEC-BB SBB007847;Ethyl Dimethylol Malonate;bis(hydroxyMethyl)Malonate;Diethyl bis(hydroxyMethyl)Malon;bis-(Hydroxymethyl)diethylester;Diethyl bis(hydroxymethyl)malote;diethyl bis（hydroxymethyl）malonat;Diethylebis(hydroxymethyl)malonate
CBNumber: CB2777173
Molecular Formula: C9H16O6
Formula Weight: 220.22
MOL File: 20605-01-0.mol

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Diethyl bis(hydroxymethyl)malonate Property

Melting point:: 49-51 °C (lit.)
Boiling point:: 281.15°C (rough estimate)
Density: 1.2286 (rough estimate)
refractive index: 1.4390 (estimate)
Flash point:: >230 °F
storage temp.: Sealed in dry,Room Temperature
pka: 12.59±0.10(Predicted)
form: Crystalline Solid
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: Propanedioic acid, bis(hydroxymethyl)-, diethyl ester (20605-01-0)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 23-24/25-36-26
WGK Germany: 3
TSCA: Yes
HazardClass: IRRITANT
HS Code: 29181998

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 198358
Product name: Diethyl bis(hydroxymethyl)malonate
Purity: 97%
Packaging: 100g
Price: $301.15
Updated: 2025/07/31

Sigma-Aldrich

Product number: 198358
Product name: Diethyl bis(hydroxymethyl)malonate
Purity: 97%
Packaging: 25g
Price: $96.5
Updated: 2023/06/20

TRC

Product number: D445288
Product name: Diethyl bis(hydroxymethyl)malonate
Packaging: 1g
Price: $45
Updated: 2021/12/16

AK Scientific

Product number: O511
Product name: Diethyl bis(hydroxymethyl)malonate
Packaging: 1g
Price: $14
Updated: 2021/12/16

AK Scientific

Product number: J53663
Product name: Diethyl bis(hydroxymethyl)malonate
Packaging: 5g
Price: $25
Updated: 2021/12/16

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Diethyl bis(hydroxymethyl)malonate Chemical Properties,Usage,Production

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

50-00-0

105-53-3

20605-01-0

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

Diethyl bis(hydroxymethyl)malonate Preparation Products And Raw materials

Raw materials

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Diethyl bis(hydroxymethyl)malonate Suppliers

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View Lastest Price from Diethyl bis(hydroxymethyl)malonate manufacturers

PNP Biotech Co. Ltd

Product: Diethyl 2,2-bis(hydroxymethyl)propanedioate 20605-01-0
Price: US $0.00/KG
Min. Order: 25KG
Purity: ≥95%
Supply Ability: Inquiry
Release date: 2022-09-16

Career Henan Chemical Co

Product: Diethyl bis(hydroxymethyl)malonate 20605-01-0
Price: US $8.80/KG
Min. Order: 1KG
Purity: 97%-99%
Supply Ability: 100kg
Release date: 2019-08-05

20605-01-0, Diethyl bis(hydroxymethyl)malonateRelated Search:

DIETHYL DIETHYLMALONATE Diethyl methylmalonate 2-AMINODIETHYLMALONATE Diethyl phenylmalonate Diethyl phthalate Diethyl chloromalonate Diethyl dipropylmalonate Diethyl isopropylmalonate Diethyl butylmalonate Diethyl ethylmalonate Diethyl 2-ethyl-2-phenylmalonate Diethyl allylmalonate 2-Hydroxyethyl methacrylate Diethyl ketomalonate Diethyl malonate DIETHYL DIMETHYLMALONATE Disuccinimidyl glutarate Ethyl hydrogen malonate

TIMTEC-BB SBB007847

2,2-BIS(HYDROXYMETHYL)MALONIC ACID DIETHYL ESTER

Diethyl bis(hydroxymethyl)malote

Diethylebis(hydroxymethyl)malonate

diethyl 2,2-bis(hydroxymethyl)propanedioate

1,3-diethyl 2,2-bis(hydroxymethyl)propanedioate

MALONIC ACID, BIS [HYDROXYMETHYL] DIETHYL ESTER

DIETHYL BIS(HYDROXYMETHYL)MALONATE

bis(hydroxymethyl)-propanedioicacidiethylester

Diethyl 2,2-bis(hydroxymethyl)malonate

Propanedioic acid, bis(hydroxymethyl)-, diethyl ester

diethyl bis（hydroxymethyl）malonat

bis(hydroxyMethyl)Malonate

Diethyl bis(hydroxyMethyl)Malonate, 95% 25GR

Diethyl bis(hydroxyMethyl)Malon

2,2-bis(hydroxymethyl)propanedioic acid diethyl ester

2,2-dimethylolmalonic acid 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

Diethyl bis(hydroxymethyl)malonate,95%

Propanedioic acid, 2,2-bis(hydroxymethyl)-, 1,3-diethyl ester

iethyl2,2-bis(hydroxymethyl)propanedioate

2,2-bis(hydroxymethyl)-Propanedioic acid 1,3-diethyl ester

2,2-Bis(hydroxymethyl)-malonic acid 1,3-diethyl ester

20605-01-0

HOCH22CCO2CH2CH32

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C8 to C9

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