25506-13-2

Basic information

• Product Name: CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2- DIOL
• Synonyms: CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2- DIOL;CIS-1,2-DIHYDRO-3-METHYLCATECHOL;CIS-1,2-DIHYDROXY-3-METHYLCYCLOHEXA-3,5-DIENE;20w/v%solutioninethylacetate,stab.with0.2%ea;cis-3-methyl-3,5-cyclohexadiene-1,2-diol;cis-1,2-Dihydro-3-methylcatechol,20 w/v% sol.in ethyl acetate, stab. with 0.2%;cis-1,2-Dihydro-3-methylcatecholcis-1,2-Dihydroxy-3-methylcyclohexa-3,5-diene
• CAS NO: 25506-13-2
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.15
• Mol File: 25506-13-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 234.3°Cat760mmHg
• Flash Point: -4 °C
• Appearance: /
• Density: 0.94
• Vapor Pressure: 0.00978mmHg at 25°C
• Refractive Index: 1.4052
• Storage Temp.: 0-6°C
• PKA: 13.43±0.60(Predicted)
• CAS DataBase Reference: CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2- DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2- DIOL(25506-13-2)
• EPA Substance Registry System: CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2- DIOL(25506-13-2)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 33-29-23-16
• Hazardous Substances Data: 25506-13-2(Hazardous Substances Data)

Usage

Description

CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2-DIOL is an organic chemical compound characterized by its molecular formula C7H10O2. It features a cyclohexadiene ring with two hydroxyl groups, making it a diol. CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2DIOL is in the cis conformation, with both methyl groups positioned on the same side of the ring. Its unique structure and properties may offer potential applications in various industries, including pharmaceuticals and agrochemicals.

Uses

Used in Organic Synthesis:
CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2-DIOL is utilized as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for the formation of new chemical bonds and the synthesis of complex molecules.
Used in Pharmaceutical Industry:
CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2-DIOL is used as a building block in the development of pharmaceutical compounds. Its specific conformation and functional groups may contribute to the creation of novel drugs with unique therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2-DIOL may be employed as a precursor for the synthesis of agrochemicals, such as pesticides and herbicides. Its unique structure could potentially enhance the effectiveness of these products.
Used in Natural Products:
CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2-DIOL can also be found in some natural products, where it may contribute to their biological activities or serve as a starting point for the synthesis of bioactive compounds.

InChI:InChI=1/C7H10O2/c1-5-3-2-4-6(8)7(5)9/h2-4,6-9H,1H3/t6-,7-/m1/s1

Upstream product

• 108-88-3 toluene 

Downstream Products

• 95-48-7 ortho-cresol 

Relevant articles and documents

Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used in the synthesis of ampelomins and deoxy-carbasugars

Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used as important intermediates for the preparation of ampelomins and deoxy-carbasugars was studied. These olefins were obtained in few steps from a chiral cis-diol resulting from microbial oxidation of toluene. Although the stereoselective hydrogenation of this type of substrates is difficult, high yields were obtained for heterogeneous hydrogenation using Adam's catalyst, where steric hindrance controlled the stereochemical outcome of the process. On the other hand, for homogeneous hydrogenation of similar olefins using Crabtree's catalyst, coordination with the allylic alcohols allowed for a controlled hydrogen addition from the more hindered face. In this manner two protocols for the hydrogenation of these types of substrates resulting in complementary stereoselectivities are described.