Terebic acid

Base Information

• Chemical Name: Terebic acid
• CAS No.: 79-91-4
• Molecular Formula: C7H10 O4
• Molecular Weight: 158.154
• Hs Code.: 2932190090
• European Community (EC) Number: 201-233-2
• UNII: 5LZG478K6E
• DSSTox Substance ID: DTXSID201000184
• Nikkaji Number: J4.243I
• Wikidata: Q27262538
• Mol file: 79-91-4.mol

Synonyms:2,2-dimethyl-5-oxotetrahydrofuran-3-carboxylic acid;terebic acid

Chemical Property of Terebic acid

Chemical Property:

• Vapor Pressure: 9.29E-06mmHg at 25°C
• Melting Point: 175 °C
• Refractive Index: 1.4610 (estimate)
• Boiling Point: 347.6°C at 760 mmHg
• PKA: 3.87±0.40(Predicted)
• Flash Point: 148.6°C
• PSA: 63.60000
• Density: 0.815
• LogP: 0.41270
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 207

Purity/Quality:

97% ^*data from raw suppliers

2,2-dimethyl-5-oxotetrahydrofuran-3-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C(CC(=O)O1)C(=O)O)C

Technology Process of Terebic acid

There total 94 articles about Terebic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → terpenylic acid (116-51-8,26754-48-3) + terebic acid (79-91-4,97416-85-8)

Guidance literature:

With chromic acid; inactive terpenylic acid;

Reference yield:

→ terpenylic acid (116-51-8,26754-48-3) + terebic acid (79-91-4,97416-85-8)

Guidance literature:

With potassium permanganate; Ansaeuern der Reaktionsfluessigkeit;

Reference yield:

→ terpenylic acid (116-51-8,26754-48-3) + terebic acid (79-91-4,97416-85-8)

Guidance literature:

With nitric acid;

upstream raw materials:

methyl magnesium iodide

diethyl acetylsuccinate

2-isopropylsuccinic acid

2-isopropylidenesuccinic acid

Downstream raw materials:

dihydro-5,5-dimethyl-2(3H)-furanone

4-methyl-pent-3-enoic acid

2-isopropylidenesuccinic acid

2,2-dimethyl-5-oxo-tetrahydro-furan-3-carboxylic acid anilide

Refernces

Synthesis of endo-4-bromo-6-thiabicyclo[3.2.1]octane and 6-thiabicyclo[3.2.1]oct-3-ene

10.1021/jo00805a031

The study investigates the synthesis and properties of certain cyclic and bicyclic sulfur compounds. Key chemicals involved include 3-cyclohexenylmethyl p-bromobenzenesulfonate (1), which serves as a starting material. Through a series of reactions, it is converted to 3-cyclohexenylmethyl thioacetate (2). The critical step involves bromination of 2 to yield 3,4-dibromocyclohexenylmethyl thioacetate (3), which upon further reaction with potassium hydroxide in methanol, leads to the formation of endo-4-bromo-6-thiabicyclo[3.2.1]octane (5). Compound 5 is then used to synthesize other derivatives like 6-thiabicyclo[3.2.1]octane (6) via reduction with triphenyltin hydride and azobisisobutyronitrile, and 6-thiabicyclo[3.2.1]oct-3-ene (4) through dehydrobromination with potassium hydroxide in ethylene glycol. The study also examines the dipole moment of 5 and explores its reactivity, noting its unreactiveness in common elimination, displacement, and solvolytic reactions, likely due to steric hindrance from the proximity of sulfur to the bromide.