Description

(+)-Pinanediol, also known as (1S,2S,3R,5S)-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol, is a high-purity chiral diol widely used in asymmetric synthesis and pharmaceutical research. This bicyclic compound features a rigid pinane skeleton with two hydroxyl groups at the 2 and 3 positions, offering excellent stereochemical control in reactions. With a molecular formula of C₁₀H₁₈O₂ and CAS number 18680-27-8, it is supplied as a white crystalline solid with ≥99% purity (HPLC). Its enantiomeric excess (>98% ee) makes it invaluable for preparing chiral auxiliaries, ligands, and resolving agents. (+)-Pinanediol is stable under standard conditions but should be stored in a cool, dry place away from strong oxidizers.

Properties

• CAS Number: 18680-27-8
• Complexity: 212
• IUPAC Name: (1S,2S,3R,5S)-2,6,6-trimethylnorpinane-2,3-diol
• InChI: InChI=1S/C10H18O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,11-12H,4-5H2,1-3H3/t6-,7-,8+,10-/m0/s1
• InChI Key: MOILFCKRQFQVFS-OORONAJNSA-N
• Exact Mass: 170.130679813
• Molecular Formula: C10H18O2
• Molecular Weight: 170.25
• SMILES: C[C@@]1([C@H]2C[C@H](C2(C)C)C[C@H]1O)O
• Topological: 40.5
• Monoisotopic Mass: 170.130679813
• Synonyms: 18680-27-8, (+)-Pinanediol, (1S,2S,3R,5S)-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol, Pinanediol, (+)-, Y6ZCV4AVRA, 2alpha,3alpha-Pinanediol, (1S,2S,3R,5S)-(+)-pinane-2,3-diol, 2,3-Pinanediol, (1S,2S,3R,5S)-(+)-, DTXSID00171941, (1S,2S,3R,5S)-(+)-2,6,6-trimethylbicyclo(3.1.1)heptane-2,3-diol, Bicyclo(3.1.1)heptane-2,3-diol, 2,6,6-trimethyl-, (1S,2S,3R,5S)-, Bicyclo[3.1.1]heptane-2,3-diol, 2,6,6-trimethyl-, (1S,2S,3R,5S)-, 2.ALPHA.,3.ALPHA.-PINANEDIOL, Bicyclo(3.1.1)heptane-2,3-diol, 2,6,6-trimethyl-, (1S-(1alpha,2alpha,3alpha,5alpha))-, (1s,2s,3r,5s)-(+)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol, BICYCLO(3.1.1)HEPTANE-2,3-DIOL, 2,6,6-TRIMETHYL-, (1S-(1.ALPHA.,2.ALPHA.,3.ALPHA.,5.ALPHA.))-, (1S,2S,3R,5S)-2,6,6-trimethylbicyclo(3.1.1)heptane-2,3-diol, DTXCID1094432, 606-096-6, (1S,2S,3R,5S)-(+)-2,3-pinanediol, (1S,2S,3R,5S)-(+)-Pinanediol, MFCD00077851, (+)-2-Hydroxyisopinocampheol, (1S,2S,3R,5S)-2,3-Pinanediol, 2,3-cis/exo-pinanediol, UNII-Y6ZCV4AVRA, (1S,2S,3R,5S)-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol;, SCHEMBL621468, CHEMBL4303429, GLXC-06698, BCP27431, CS-D1770, CX1160, AKOS005256255, FP15403, AS-13984, BP-30024, HY-20074, PD132360, NS00026108, P1934, (1S,2S,3R,5S)-(+)-Pinanediol, 99%, EN300-303828, Q27294324, Z1255402889, (1 S,2S,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol, (1S,2S,3R,55)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol

(+)-Pinanediol serves as a versatile chiral building block in organic synthesis, particularly for asymmetric reductions and stereoselective transformations. Researchers employ it to synthesize enantiomerically pure pharmaceuticals, agrochemicals, and specialty chemicals. Its rigid structure makes it ideal for designing chiral catalysts and ligands in transition-metal catalysis. The compound also finds use in derivatization reactions for analytical method development, such as chiral chromatography.

Safety and Hazards

GHS Hazard Statements

• H302 (10%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (10%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (10%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (10%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
• H412 (60%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (10%)
• Skin Irrit. 2 (10%)
• Eye Irrit. 2 (10%)
• STOT SE 3 (10%)
• Aquatic Chronic 3 (60%)

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