Description

(1R,5S)-6,6-Dimethyl-3-oxabicyclo(3.1.0)hexane-2,4-dione, also known as Caronic anhydride, is a high-purity cyclic anhydride with the molecular formula C₇H₈O₃ (CAS: 67911-21-1). This specialized compound features a bicyclic structure incorporating a cyclopropane ring fused with a lactone moiety, making it a valuable intermediate in organic synthesis and pharmaceutical research. Its stereospecific (1R,5S) configuration ensures precise reactivity for asymmetric synthesis applications. Available in crystalline form, this reagent is rigorously tested for purity (>98%) by GC/HPLC and is suitable for use in fine chemical synthesis, chiral derivatization, and material science research. Store under inert conditions at 2-8°C to maintain stability.

Properties

• CAS Number: 67911-21-1
• Complexity: 207
• IUPAC Name: 6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione
• InChI: InChI=1S/C7H8O3/c1-7(2)3-4(7)6(9)10-5(3)8/h3-4H,1-2H3
• InChI Key: QKAHKEDLPBJLFD-UHFFFAOYSA-N
• Exact Mass: 140.047344113
• Molecular Formula: C7H8O3
• Molecular Weight: 140.14
• SMILES: CC1(C2C1C(=O)OC2=O)C
• Topological: 43.4
• Monoisotopic Mass: 140.047344113
• Synonyms: 6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione, EC 614-164-1, (1R,5S)-6,6-Dimethyl-3-oxabicyclo(3.1.0)hexane-2,4-dione, (1R,5S)-6,6-Dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione, 6,6-Dimethyl-3-oxabicyclo(3.1.0)hexane-2,4-dione, 614-164-1, 67911-21-1, Caronic anhydride, 3-Oxabicyclo[3.1.0]hexane-2,4-dione, 6,6-dimethyl-, 3,3-Dimethyl-1,2-cyclopropanedicarboxylic Anhydride, 6,6-Dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione; Caronic anhydride, MFCD09751198, SCHEMBL3381973, DTXSID40438803, QKAHKEDLPBJLFD-UHFFFAOYSA-N, ALBB-007822, BBL013304, STK504828, AKOS005171679, DS-17876, SY014553, DB-011637, C2596, CS-0015906, NS00007771, EN300-82369, 6,6-dimethyl-3-oxabicyclo[3.1.0]hex-2,4-dione, 3,3-Dimethyl-1,2-cyclopropane Dicarboxylic Anhydride, 3,3-dimethyl-1,2-cyclopropanedicarboxylic acid anhydride

This compound serves as a key chiral building block in the synthesis of bioactive molecules, particularly in the development of prostaglandin analogs and other cyclopropane-containing pharmaceuticals. Researchers utilize its strained ring system for [2+1] cycloadditions and as a precursor for functionalized cyclopropanes. It also finds use in polymer chemistry as a crosslinking agent for epoxy resins and specialty coatings requiring enhanced thermal stability.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (66.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (66.7%)

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