2-(2-bromoethyl)-1,3-dioxane

• ChemBase ID: 132093
• Molecular Formular: C6H11BrO2
• Molecular Mass: 195.05434
• Monoisotopic Mass: 193.99424159
• SMILES: C1COC(OC1)CCBr
• Canonical SMILES: BrCCC1OCCCO1
• InChI: InChI=1S/C6H11BrO2/c7-3-2-6-8-4-1-5-9-6/h6H,1-5H2
• InChIKey: WMDHQEHPOVOEOG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-bromoethyl)-1,3-dioxane
• IUPAC Traditional name: 2-(2-bromoethyl)-1,3-dioxane
• Synonyms: 3-Bromopropionaldehyde trimethylene acetal; 2-(2-bromoethyl)-1,3-dioxane; 2-(2-Bromoethyl)-1,3-dioxane; 2-Bromopropanal 1,3-propanediol acetal; 2-Bromopropionaldehyde trimethylene acetal; 2-(2-溴乙基)-1,3-二氧杂环己烷; 2-(2-溴乙基)-1,3-二氧六环; 2-(2-溴乙基)-1,3-二氧杂环乙烷

Database IDs

• CAS Number: 33884-43-4
• EC Number: 251-716-7
• MDL Number: MFCD00006567
• Beilstein Number: 1421628
• PubChem SID: 24849939; 162226370; 24856313
• PubChem CID: 520656

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.412175
• LogD (pH = 7.4): 1.412175
• Log P: 1.412175
• Molar Refractivity: 38.4686 cm^3
• Polarizability: 15.323789 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 67-70 °C/2.8 mmHg(lit.); 67-70°C/3mm
• Flash Point: 206.6 °F; 96°C(204°F); 97 °C
• Density: 1.431 g/mL at 25 °C(lit.); 1.434
• Refractive Index: 1.4820; n20/D 1.481; n20/D 1.481(lit.)
• Hydrophobicity(logP): 0.577

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 是
• 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: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.5% (GC); 95%; 98%
• Grade: purum
• Contains: silver wool as stabilizer
• Empirical Formula (Hill Notation): C6H11BrO2

DETAILS

Sigma Aldrich - 269131

Packaging
10, 50 g in glass bottle

Sigma Aldrich - 16154

Other Notes
Masked 3-bromopropionaldehyde used in Grignard reactions for the preparation of aldehydes1,2

REFERENCES

• Provides a useful means of introducing a masked ?-formylethyl group. In comparison with the corresponding dioxolane (following entry), the dioxane is more stable to acid, and the Grignard is thermally stable. Reaction of the Grignard with an acid chloride gives the ketone in high yield without further reaction to the tertiary alcohol. Subsequent hydrolysis of the 1,3-dioxane gives the -ketoaldehyde: J. Org. Chem., 41, 560 (1976).