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

• ChemBase ID: 69721
• Molecular Formular: C5H9BrO2
• Molecular Mass: 181.02776
• Monoisotopic Mass: 179.97859153
• SMILES: O1C(OCC1)CCBr
• Canonical SMILES: BrCCC1OCCO1
• InChI: InChI=1S/C5H9BrO2/c6-2-1-5-7-3-4-8-5/h5H,1-4H2
• InChIKey: GGZQLTVZPOGLCC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-bromoethyl)-1,3-dioxolane
• IUPAC Traditional name: 2-(2-bromoethyl)-1,3-dioxolane
• Synonyms: 3-Bromopropionaldehyde ethylene acetal; 2-(2-Bromoethyl)-1,3-dioxolane; 3-Bromopropanal 1,2-ethanediol acetal; 2-(2-Bromoethyl)-1,3-dioxolane; 2-(2-溴乙基)-1,3-二噁茂烷; 2-(2-溴乙基)-1,3-二氧戊环; 2-(2-溴乙基)-1,3-二氧戊环烷

Database IDs

• CAS Number: 18742-02-4
• EC Number: 242-551-1
• MDL Number: MFCD00003216
• Beilstein Number: 103516
• PubChem SID: 24853846; 162035446; 24849942
• PubChem CID: 87776

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.3522153
• LogD (pH = 7.4): 1.3522153
• Log P: 1.3522153
• Molar Refractivity: 33.6032 cm^3
• Polarizability: 13.539787 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: brownish-yellow
• Boiling Point: 68-70 °C/8 mmHg(lit.); 68-70°C/8mm
• Flash Point: 149 °F; 65 °C; 65°C(149°F)
• Density: 1.512; 1.542 g/mL at 25 °C(lit.)
• Refractive Index: 1.4790; n20/D 1.479; n20/D 1.479(lit.)
• Hydrophobicity(logP): 0.803

Safety Information

• Storage Warning: IRRITANT; Light Sensitive
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• UN Number: 2810
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335; H315-H319-H335-H227
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A; P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 95%; 95%, stab. with silver; 95+%; 96%; 98%
• Grade: purum
• Contains: silver wool as stabilizer
• Empirical Formula (Hill Notation): C5H9BrO2

DETAILS

Sigma Aldrich - 230995

Packaging
10, 50 g in glass bottle
Application
Alkylating agent for amines,1 dithianes,2 and carboximides,3 and via the Grignard reagent, aldehydes.4
Used with eynamides and sodium azide in a "one-pot" synthesis of triazoles.

Sigma Aldrich - 16156

Other Notes
Masked 3-bromopropionaldehyde used in Grignard reactions or substitution reactions1,2,3; Reagent for annulation reactions4

REFERENCES

• For a review of 3-carbon homologating reagents, including many examples of Grignard and organocuprate reactions of these molecules, see: Chem. Rev., 84, 409 (1984).
• Masked ?-formylethyl synthon, compare preceding entry. The derived Grignard, which, unlike the dioxane analogue, is unstable above room temperature, shows similar attenuated reactivity in comparison with simple alkyl Grignard reagents, reacting with acid chlorides to give -ketoaldehydes without carbinol formation, and with enones to give, at low temperatures, predominantly the 1,4-addition product without the need for Cu catalysis:Tetrahedron Lett., 28, 3217 (1987).
• The Grignard undergoes coupling reactions (CuBr₂ + LiCl catalysis) with allylic halides: Tetrahedron Lett., 4549 (1979); J. Org. Chem., 46, 1504 (1981), allylic acetates: J. Am. Chem. Soc., 104, 2269 (1982), and primary alkyl bromides: J. Org. Chem., 48, 1767 (1983).