spiro<3.3>heptane-3-carboxylic acid Chemical Properties

Melting point:

25 °C

Boiling point:

256.8±8.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

liquid

pka

4.77±0.20(Predicted)

color 

Colourless

InChI

InChI=1S/C8H12O2/c9-7(10)6-4-8(5-6)2-1-3-8/h6H,1-5H2,(H,9,10)

InChIKey

FUQHLUSGMOSPRQ-UHFFFAOYSA-N

SMILES

C1C2(CCC2)CC1C(O)=O

Safety Information

HS Code 

2916200090

spiro<3.3>heptane-3-carboxylic acid Usage And Synthesis

Uses

Spiro[3.3]heptane-2-carboxylic acid is a carboxylic acid derivative that can be used as a pharmaceutical intermediate.

Synthesis

The general procedure for the synthesis of spiro[3.3]heptane-2,2-dicarboxylic acid from spiro[3.3]heptane-2,2-dicarboxylic acid was as follows: spiro[3.3]heptane-2,2-dicarboxylic acid (1.737 g, 9.43 mmol) was dissolved in pyridine (20 mL) and the reaction was heated at 115 °C overnight. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated to dryness in a rotary evaporator. The resulting residue was treated with 6 M aqueous hydrochloric acid and subsequently extracted with dichloromethane (3 x 20 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to afford spiro[3.3]heptane-2-carboxylic acid (1.21 g, 92% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 11.98 (s, 1H), 2.85 (m, 1H), 2.15-2.03 (m, 4H), 1.96 (t, J = 7.3 Hz, 2H), 1.84 (t, J = 7.3 Hz, 2H), 1.76-1.70 (m, 2H).

References

[1] Patent: US2014/275080, 2014, A1. Location in patent: Paragraph 0368
[2] Justus Liebigs Annalen der Chemie, 1961, vol. 648, p. 36 - 50

spiro<3.3>heptane-3-carboxylic acid(28114-87-6)Related Product Information

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• SPIRO[5.5]UNDECANE-2,4-DIONE
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• SPIRO[2.3]HEXANE-5-CARBOXYLIC ACID
• spiro[2.5]octan-5,7-dione
• SPIRO[3.5]NONANE-6,8-DIONE
• 2-AMINOSPIRO[3.3]HEPTANE
• Spiro[2.3]hex-5-ylamine
• spiro[3.3]heptan-2-amine hydrochloride
• Spiro[3.5]nonan-7-ol
• Spiro[2.5]octane-6-carboxylic acid
• SPIRO[2.2]PENTANE-1-CARBOXYLIC ACID
• Spiro[2.5]octane-4,6-dione
• spiro[3.5]nonan-2-one
• Spiro[3.3]?heptane-?2,?2-?dicarboxylic acid, 2,?2-?bis(1-?methylethyl) ester
• spiro[2.4]heptan-7-one