2,5-bis(hydroxymethyl)-1,4-dioxane-2,5-diol

• ChemBase ID: 141931
• Molecular Formular: C6H12O6
• Molecular Mass: 180.15588
• Monoisotopic Mass: 180.0633881
• SMILES: C1C(OCC(O1)(CO)O)(CO)O
• Canonical SMILES: OCC1(O)OCC(OC1)(O)CO
• InChI: InChI=1S/C6H12O6/c7-1-5(9)3-12-6(10,2-8)4-11-5/h7-10H,1-4H2
• InChIKey: KEQUNHIAUQQPAC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-bis(hydroxymethyl)-1,4-dioxane-2,5-diol
• IUPAC Traditional name: 2,5-bis(hydroxymethyl)-1,4-dioxane-2,5-diol
• Synonyms: 2,5-Dihydroxydioxane-2,5-dimethanol; 1,3-Dihydroxyacetone dimer; 2,5-Dihydroxy-1,4-dioxane-2,5-dimethanol; 2,5-二羟基二噁烷-2,5-二甲醇; 1,3-二羟基丙酮二聚体

Database IDs

• CAS Number: 26776-70-5; 62147-49-3
• EC Number: 202-494-5
• MDL Number: MFCD00051019
• Beilstein Number: 112910
• Merck Index: 143182
• PubChem SID: 24863297; 24893342; 162236163; 24863288
• PubChem CID: 4180364
• Flavis Number: 13.11

CALCULATED PROPERTIES

• Acid pKa: 10.237295
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.733997
• LogD (pH = 7.4): -1.7346197
• Log P: -1.733989
• Molar Refractivity: 36.9466 cm^3
• Polarizability: 15.219522 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white to off-white powder
• Melting Point: 75-80 °C; 75-80 °C(lit.); ca 75-82°C

Safety Information

• Storage Warning: Hygroscopic
• RTECS: UC1645000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%
• Grade: puriss.; purum
• Ignition Residue: ≤1%
• Empirical Formula (Hill Notation): C6H12O6

DETAILS

Sigma Aldrich - W403326

Application
Component of tanning products

Sigma Aldrich - D107204

Packaging
100, 500 g in poly bottle
5 g in glass bottle
Application
Substrate for galactose oxidase.1

Sigma Aldrich - 37430

General description
can still contain monomer

REFERENCES

• In solid state, exists predominantly as trans-2,5-dihydroxy-1,4-dioxane-2,5-dimethanol (structure and CAS registry number as shown). On melting or in solution, mainly dissociates to monomeric 1,3-dihydroxyacetone [96-26-4]: J. Mol. Struct., 35, 85 (1976).
• For a review of the dihydroxyacetone unit as a verstaile 3-carbon building block in organic synthesis, see: Angew. Chem. Int. Ed., 44, 1305 (2005).