(1R,4R)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid

Basic Information

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CAS Number

67111-66-4

Molecular Formula

C10H14O4

Molecular Weight

198.22 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Basic Physical Properties

Physical State

Solid

Melting Point

200-202 °C(Lit)

Boiling Point

355.5 °C at 760 mmHg

Density

1.296

Flash Point

142.1 °C

Refractive Index

1.532

SMILES

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CC1(C2(CCC1(OC2=O)C(=O)O)C)C

InChI

InChI=1S/C10H14O4/c1-8(2)9(3)4-5-10(8,6(11)12)14-7(9)13/h4-5H2,1-3H3,(H,11,12)/t9-,10-/m0/s1

InChIKey

KPWKPGFLZGMMFX-UWVGGRQHSA-N

LogP

1.1929

Topological Polar Surface Area

63.6 Å²

Hydrogen Bond Donor/Acceptor

1 / 4

Complexity

333

Safety Information

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Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

AS-36060
(1r,4s)-4,7,7-Trimethyl-3-Oxo-2-Oxabicyclo[2.2.1]heptane-1-Carboxylic Acid
J-800437
(1R)-3-Oxo-4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid
(1R)-(+)-Camphanic acid
CS-0172030
(+)-Camphanic acid, purum, >=98.0% (T)
D-(1S,3R)-(-)-Camphoric acid
(+)-Camphanic acid
(1S,4R)-1,7,7-Trimethyl-2-oxo-3-oxabicyclo(2.2.1)heptane-4-carboxylic acid
Q27452446
1U5
SCHEMBL5575317
(1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylicacid
(1R)-(+)-Camphanic acid, 98%
2-Oxabicyclo[2.2.1]heptane-1-carboxylicacid,4,7,7-trimethyl-3-oxo-,(1R,4S)-
4kz7
MFCD00005535
67111-66-4
AKOS006281832
(1R)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid
(1R)-(+)-CAMPHANIC ACID
1R)-(+)-CAMPHANIC ACID
2-Oxabicyclo[2.2.1]heptane-1-carboxylicacid, 4,7,7-trimethyl-3-oxo-, (1R,4S)-

MDL Number

MFCD00005535

FAQ

What are the physical and chemical properties of (1R,4R)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid (CAS: 67111-66-4)?

(1R,4R)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid (CAS: 67111-66-4) is a white, crystalline solid with a molecular weight of approximately 218.34 g/mol. It is slightly soluble in water but more soluble in organic solvents like methanol and ethanol. Chemically, it exhibits moderate reactivity, particularly in esterification and amidation reactions. It is stable under normal conditions but should be stored at room temperature, protected from moisture and light.

How is (1R,4R)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid (CAS: 67111-66-4) typically synthesized?

(1R,4R)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid is commonly synthesized via a Wittig reaction followed by acidification. The synthesis involves the reaction of a suitable ketone with methylene tribromide in the presence of a phosphonium salt as a base. The product is then isolated and purified by recrystallization. The reaction typically yields a high purity product with good selectivity and moderate to high yield.

What industries use (1R,4R)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid (CAS: 67111-66-4)?

(1R,4R)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid is primarily used in the pharmaceutical industry as a precursor in the synthesis of certain drugs. It also finds applications in the polymer industry, where it can be used in the synthesis of certain polymers with specific properties. Additionally, it is used in the production of sensors and in semiconductor manufacturing as a precursor in the formation of certain organic films.

What precautions should be taken when handling (1R,4R)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid (CAS: 67111-66-4)?

When handling (1R,4R)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid (CAS: 67111-66-4), it is important to use appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. The compound should be handled in a fume hood to minimize inhalation exposure. If a spill occurs, it should be cleaned up using appropriate absorbent materials, and the area should be well-ventilated. Always consult the safety data sheet (SDS) for detailed handling and storage information.