(3R)-4,4-dimethyl-2-oxooxolan-3-yl prop-2-enoate

• ChemBase ID: 146367
• Molecular Formular: C9H12O4
• Molecular Mass: 184.18918
• Monoisotopic Mass: 184.07355886
• SMILES: CC1(COC(=O)[C@@H]1OC(=O)C=C)C
• Canonical SMILES: C=CC(=O)O[C@H]1C(=O)OCC1(C)C
• InChI: InChI=1S/C9H12O4/c1-4-6(10)13-7-8(11)12-5-9(7,2)3/h4,7H,1,5H2,2-3H3/t7-/m0/s1
• InChIKey: ICMBTQSRUNSRKI-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-4,4-dimethyl-2-oxooxolan-3-yl prop-2-enoate
• IUPAC Traditional name: (3R)-4,4-dimethyl-2-oxooxolan-3-yl prop-2-enoate
• Synonyms: (R)-α-Acryloyloxy-β,β-dimethyl-γ-butyrolactone; (R)-α-丙烯酰基氧基-β,β-二甲基-γ-丁内酯

Database IDs

• CAS Number: 102096-60-6
• MDL Number: MFCD00043403
• Beilstein Number: 4668587
• PubChem SID: 24863437; 162240565
• PubChem CID: 2794997

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.6081183
• LogD (pH = 7.4): 1.6081183
• Log P: 1.6081183
• Molar Refractivity: 44.3152 cm^3
• Polarizability: 17.934916 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 7-8 °C(lit.)
• Boiling Point: 84 °C/0.1 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 1.125 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.46(lit.); n20/D 1.461
• Optical Rotation: [α]20/D +6.0±0.4°, c = 17% in methylene chloride; [α]20/D +6.0°, c = 17 in methylene chloride

Safety Information

• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3082
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 36/37/38-51/53
• Safety Statements: 26-28-61; 26-61
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3082 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (sum of enantiomers, GC); 95%
• Grade: purum
• Optical Purity: enantiomeric ratio: ≥97:3 (GC)
• Contains: ~0.2% hydroquinone as stabilizer; 0.1% monomethyl ether hydroquinone as stabilizer
• Empirical Formula (Hill Notation): C9H12O4

DETAILS

Sigma Aldrich - 376361

Packaging
5 g in glass bottle

Sigma Aldrich - 01728

Other Notes
Chiral acrylate used for titanium tetrachloride catalyzed Diels-Alder reactions. The cycloaddition with dienes proceeds with a very high diastereofacial selectivity.; Chiral bridged esters are formed with cyclic dienes and 3-cyclohexene-carboxylic esters with acyclic dienes. The high diastereomeric purity of the products (~97%) can be further increased by 2 or 3 crystallizations to give esters of de ≥99%1,2