(4R)-4-chloro-1-methylcyclohexene Physical and Chemical Properties
(4R)-4-chloro-1-methylcyclohexene
A chiral, chloro-substituted cyclohexene used as an intermediate in organic synthesis and formulation development, providing a reactive halide site for downstream functionalization.
| CAS Number | Not specified for this entry |
| Family | Chloro-substituted cycloalkenes |
| Typical Form | Colorless liquid |
| Common Grades | EP |
(4R)-4-Chloro-1-methylcyclohexene is a monosubstituted cyclohexene belonging to the class of allylic alkyl chlorides. Structurally it comprises a cyclohexene ring bearing a methyl substituent at the vinylic carbon (C-1) and a chlorine atom at the 4-position, which is a defined stereocenter with R configuration. The molecule is an unsaturated secondary allylic chloride; the conjugation and allylic stabilization around the double bond influence its reactivity by facilitating resonance-stabilized intermediates in ionic and radical pathways.
Electronically the compound is essentially nonpolar: it contains no hydrogen-bond donors or acceptors and a calculated topological polar surface area of zero. The presence of an sp2 carbon–carbon double bond confers sites for electrophilic addition and oxidation, while the allylic chloride is synthetically versatile — susceptible to nucleophilic substitution, allylic transposition, and metal-catalyzed cross-coupling. Typical physicochemical behavior for this structural class includes low aqueous solubility, moderate lipophilicity, and susceptibility of the double bond to oxidative or radical transformations under activating conditions.
Common commercial grades reported for this substance include: EP.
Basic Physical Properties
Density
No experimentally established value for this property is available in the current data context.
Melting Point
No experimentally established value for this property is available in the current data context.
Boiling Point
No experimentally established value for this property is available in the current data context.
Vapor Pressure
No experimentally established value for this property is available in the current data context.
Flash Point
No experimentally established value for this property is available in the current data context.
Chemical Properties
Solubility and Phase Behavior
As a small, nonpolar hydrocarbon with a single halogen substituent, (4R)-4-chloro-1-methylcyclohexene is expected to have limited solubility in water and good solubility in nonpolar and moderately polar organic solvents (e.g., alkanes, ethers, chlorinated solvents). The absence of polar functional groups and a TPSA of 0 are consistent with partitioning into organic phases and a preference for bulk liquid or vapor phases rather than aqueous dispersion at ambient conditions.
Reactivity and Stability
The compound is an allylic chloride: the allylic position confers enhanced reactivity relative to saturated alkyl chlorides. Typical reactions include: - Nucleophilic substitution at the allylic carbon (allylic S_N2' pathways are often kinetically accessible). - Radical substitution or abstraction at allylic sites, giving rise to allylic radicals under radical-generating conditions. - Electrophilic additions across the C=C bond (hydrohalogenation, epoxidation, dihydroxylation) and oxidative cleavage under strong oxidants (e.g., ozonolysis). - Participation in transition-metal-catalyzed transformations common to allylic halides (e.g., Pd-catalyzed allylic substitution or cross-coupling), where oxidative addition and π-allyl intermediate formation are mechanistically relevant.
Thermal and oxidative stability are representative of simple cyclohexene derivatives: stable under inert, dry conditions but prone to oxidation at the double bond on exposure to air, light, or strong oxidants. Hydrolysis of simple alkyl chlorides in neutral water is generally slow; however, allylic halides can be more reactive in polar protic media or under catalysis.
Thermodynamic Data
Standard Enthalpies and Heat Capacity
No experimentally established value for this property is available in the current data context.
Molecular Parameters
Molecular Weight and Formula
- Molecular formula: C7H11Cl
- Molecular weight: \(130.61\ \mathrm{g}\,\mathrm{mol}^{-1}\)
- Exact mass: 130.0549280
- Monoisotopic mass: 130.0549280
LogP and Polarity
- XLogP3 (estimated): 2.3
- Topological polar surface area (TPSA): 0
- Hydrogen-bond donor count: 0
- Hydrogen-bond acceptor count: 0
The estimated XLogP3 of 2.3 and TPSA of 0 quantify a predominantly lipophilic character with negligible capacity for hydrogen bonding; this is consistent with low aqueous solubility and preferential solvation in nonpolar organic solvents. The moderate positive logP indicates sufficient organic-phase partitioning for use in nonpolar reaction media and as a hydrophobic building block in synthetic sequences.
Structural Features
- SMILES: CC1=CCC@@HCl
- InChI: InChI=1S/C7H11Cl/c1-6-2-4-7(8)5-3-6/h2,7H,3-5H2,1H3/t7-/m0/s1
- InChIKey: ITSBMDIPOXKIQT-ZETCQYMHSA-N
- Defined atom stereocenter count: 1
- Rotatable bond count: 0
- Heavy atom count: 8
- Complexity: 105
The structural motif is a cyclohexene ring with a vinylic methyl substituent and a single stereogenic center at C-4 bearing chlorine. The double bond constrains rotational freedom across two ring carbons, and the molecule contains no rotatable exocyclic single bonds to peripheral substituents, reflected by a rotatable bond count of zero. The allylic chloride placement offers stereoelectronic opportunities for regioselective functionalization.
Identifiers and Synonyms
Registry Numbers and Codes
No CAS registry number is provided for this substance in the current data context.
Available machine-readable identifiers: - SMILES: CC1=CCC@@HCl - InChI: InChI=1S/C7H11Cl/c1-6-2-4-7(8)5-3-6/h2,7H,3-5H2,1H3/t7-/m0/s1 - InChIKey: ITSBMDIPOXKIQT-ZETCQYMHSA-N - Molecular formula: C7H11Cl
Synonyms and Structural Names
- IUPAC name (computed): (4R)-4-chloro-1-methylcyclohexene
- Removed synonym: ZINC71782689
Industrial and Commercial Applications
Representative Uses and Industry Sectors
No concise application summary is available in the current data context; in practice this substance is selected based on its general properties described above. More broadly, small allylic halides such as this are used as intermediates in specialty chemical and fine chemical synthesis, and as model substrates in mechanistic and catalytic studies within research and development settings.
Role in Synthesis or Formulations
Functionally this compound can serve as a building block for: - Allylic substitution reactions to introduce nucleophiles or form C–C bonds. - Transition-metal-catalyzed transformations (e.g., π-allyl chemistry, cross-coupling strategies). - Introduction of further functionality via oxidative or radical pathways at the allylic or olefinic sites.
These roles reflect class-level reactivity of allylic halides rather than documented commercial product uses.
Safety and Handling Overview
Acute and Occupational Toxicity
No experimentally established value for this property is available in the current data context.
Storage and Handling Considerations
Handle under a fume hood to avoid inhalation of vapors; employ chemical splash goggles, nitrile or chemically resistant gloves, and flame-resistant laboratory clothing when manipulating bulk quantities. Minimize sources of ignition and avoid prolonged exposure to air and light to reduce oxidative degradation of the C=C bond. Store in a cool, dry, well-ventilated area away from strong oxidizing agents and acids; containers should be tightly closed and compatible with halogenated hydrocarbons. For detailed hazard, transport and regulatory information, users should refer to the product-specific Safety Data Sheet (SDS) and local legislation.
