76-32-4

Basic information

• Product Name: DL-CAMPHORIC ANHYDRIDE
• Synonyms: 1,3-Cyclopentanedicarboxylic anhydride, 1,2,2-trimethyl-;3-Oxabicyclo[3.2.1]octane-2,4-dione, 1,8,8-trimethyl-;3-oxabicyclo[3.2.1]octane-2,4-dione,1,8,8-trimethyl-;3-oxabicyclo[3.2.1]octane-2,4-dione,1,8,8-trimethyl-,(±)-;DL-CAMPHOR ANHYDRIDE;DL-CAMPHORIC ANHYDRIDE;(+/-)-CAMPHORIC ACID ANHYDRIDE;(+/-)-CAMPHORIC ANHYDRIDE
• CAS NO: 76-32-4
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.22
• EINECS: 200-952-9
• Mol File: 76-32-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 222-225 °C
• Boiling Point: 269-271°C
• Flash Point: 269-271°C
• Appearance: /
• Density: 1.137 g/cm³
• Vapor Pressure: 1.56E-06mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 83114
• CAS DataBase Reference: DL-CAMPHORIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DL-CAMPHORIC ANHYDRIDE(76-32-4)
• EPA Substance Registry System: DL-CAMPHORIC ANHYDRIDE(76-32-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 76-32-4(Hazardous Substances Data)

Usage

Description

DL-CAMPHORIC ANHYDRIDE, also known as (±)-Camphoric acid anhydride or 1,8,8-Trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione, is an organic compound derived from camphor. It is characterized by its unique bicyclic structure and anhydride functional group, which makes it a versatile building block in the synthesis of various chemical compounds.

Uses

Used in Polymer Synthesis:
DL-CAMPHORIC ANHYDRIDE is used as a monomer for the synthesis of aliphatic-aromatic copolyesters. Its unique structure and anhydride functionality contribute to the formation of copolyesters with desirable properties, such as improved mechanical strength, thermal stability, and biodegradability.
Used in Pharmaceutical Industry:
DL-CAMPHORIC ANHYDRIDE is used as a key intermediate in the synthesis of camphoric acid-based acylhydrazone compounds. These compounds have potential applications in the pharmaceutical industry, particularly in the development of new drugs with diverse biological activities.

InChI:InChI=1/C20H30O3/c1-17(2)13-5-9-19(17,10-6-13)15(21)23-16(22)20-11-7-14(8-12-20)18(20,3)4/h13-14H,5-12H2,1-4H3

Upstream product

• 124-83-4 D-(+)-camphoric acid 
• 31571-14-9 (1R,E)-(+)-camphorquinone 3-oxime 
• 560-05-4 DL-camphoric acid 
• 560-08-7 (+/-)-trans-camphoric acid 
• 109342-08-7 1,2,2-trimethyl-cyclopentane-1,3-dicarboxylic acid-3-ethyl ester 
• 14487-70-8 3-diazocamphor 
• 75-05-8 acetonitrile 
• 100-47-0 benzonitrile 
• 48138-74-5 1,2,2-trimethyl-cyclopentane-1,3-dicarbonyl chloride 
• 6053-45-8 2,2-dimethyl-cyclopentane-1,1,3-tricarboxylic acid 
• 10334-26-6 (R)-camphorquinone 

Downstream Products

• 306935-15-9 α-Methylhydrogen-dl-isocamphersaeure 
• 26252-15-3 (+/-)-3-methyl hydrogen 1,2,2-trimethyl-cis-1,3-cyclopentanedicarboxylate 
• 26252-16-4 (+/-)-3-methyl hydrogen 2,2,3-trimethyl-cis-1,3-cyclopentanedicarboxylate 
• 104225-32-3 (1R,3S)-1,2,2-Trimethyl-3-(4-phenoxy-benzoyl)-cyclopentanecarboxylic acid 
• 104225-44-7 (1R,3S)-3-(Biphenyl-4-carbonyl)-1,2,2-trimethyl-cyclopentanecarboxylic acid 
• 61469-02-1 (1R,3S)-3-(3,4-Dimethyl-benzoyl)-1,2,2-trimethyl-cyclopentanecarboxylic acid 
• 104225-40-3 (1R,3S)-3-(4-Ethyl-benzoyl)-1,2,2-trimethyl-cyclopentanecarboxylic acid 
• 104225-37-8 (1R,3S)-3-(3-Chloro-4-methoxy-benzoyl)-1,2,2-trimethyl-cyclopentanecarboxylic acid 
• 6785-98-4 (+/-)-1,2,2-trimethyl-cis-3-carbamoylcyclopentanecarboxylic acid 
• 5333-17-5 (+/-)-2,2,3-trimethyl-cis-3-carbamoylcyclopentanecarboxylic acid 
• 57078-08-7 acide cis-p-anisoyl-3 trimethyl-1,2,2 cyclopentane carboxylique 
• 93740-39-7 acide cis-p-anisoyl-3 trimethyl-2,2,3 cyclopentane carboxylique 
• 104225-34-5 (1R,3R,4R)-4-(2,4-Dimethyl-phenyl)-2,2,3-trimethyl-cyclopentanecarboxylic acid 
• 61469-04-3 (1R,3S)-3-(2,4-Dimethyl-benzoyl)-1,2,2-trimethyl-cyclopentanecarboxylic acid 

Relevant articles and documents

Synthesis and antioxidant properties of α- and β-heterylamides and N-heterylimides of (±)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid

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Reactions of Pivaloin Derivatives with Lithium Tetramethylpiperidide

The reaction of lithium tetramethylpiperidide (LiTMP) with a series of derivatives of pivaloin has led to a variety of unusual transformations.The reaction of LiTMP with the triflate derivative of pivaloin (7) gave the reduced ketone 2,2,5,5-tetramethyl-3-hexanone (9), which is suggested to arise via electron transfer from LiTMP.A labeling study confirmed that α-proton abstraction from 7, giving an enolate anion, did not occur.The mesylate derivative of pivaloin (16) on treatment with LiTMP gave both isomers of 2,2,6,6-tetramethylhept-4-en-3-one (17 and 18) in which an additional carbon was incorporated into the carbon skeleton.A mechamism involving deprotonation of the methyl group of the mesyloxy function followed by intramolecular cyclization into the carbonyl function and subsequent reaction is suggested to account for this transformation.The acetate derivative of pivaloin (26) gave a cyclized product derived from proton abstraction from the methyl group of the acetoxy function, while the tosylate derivative of pivaloin (30) gave a product derived from proton abstraction from the ortho position of the aromatic ring.The α-bromo ketone 4-bromo-2,2,5,5-tetramethyl-3-hexanone (38) was reduced to ketone 9 with LiTMP.Reaction of triflate 7 and the triflate derivative of 3-hydroxycamphor (43) with potassium tert-butoxide gave the diketones 2,2,5,5-tetramethyl-3,4-hexanedione (8) and camphorquinone (44), respectively, by β elimination of trifluoromethanesulfinic acid.