111905-36-3

Basic information

• Product Name: 1,4-Cyclohexadiene, 1,2-dimethyl-4-nitro-
• Synonyms: 1,4-Cyclohexadiene, 1,2-dimethyl-4-nitro-
• CAS NO: 111905-36-3
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.18
• Mol File: 111905-36-3.mol

Chemical Properties

• Boiling Point: 244.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.08±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1,4-Cyclohexadiene, 1,2-dimethyl-4-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Cyclohexadiene, 1,2-dimethyl-4-nitro-(111905-36-3)
• EPA Substance Registry System: 1,4-Cyclohexadiene, 1,2-dimethyl-4-nitro-(111905-36-3)

Safety Data

• Hazardous Substances Data: 111905-36-3(Hazardous Substances Data)

Usage

Appearance

Bright yellow solid

Solubility

Insoluble in water, soluble in organic solvents

Usage

Laboratory research as a precursor in the synthesis of various organic compounds

Reactivity

Highly reactive due to the presence of the nitro group

Applications

Production of pharmaceuticals, agrochemicals, and specialty chemicals

Role in organic synthesis

Reagent and radical acceptor in various chemical reactions

Safety precautions

Should be handled and stored with proper care due to its potentially hazardous nature

Upstream product

• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 101933-28-2 (E)-1-nitro-2-(phenylsulfinyl)ethylene 

Relevant articles and documents

A new strategy for the construction of polycycles bearing a nitrogen atom on the ring fusion

Nitroethylenes bearing either a phenylthio or a selenoether group in β-position are efficient synthetic equivalents of nitroacetylene. A [4+2] cycloaddition/carbenoid-mediated elimination of PhS(e)CH3/[4+2] cycloaddition sequence of reactions is shown to produce formal biscycloadducts or nitroacetylene in high yields. The cycloaddition reactions are activated by high-pressure and proceed with high regioselectivities and stereoselectivities.

Regioselective Preparation of Cyclohexadienes or Aromatic Nitro Compounds by Diels-Alder Reactions of β-Sulfonylnitroolefins or β-Sulfinylnitroethylene

β-Sulfonylnitroolefins react with various dienes to give 4-nitro-5-(phenylsulfonyl)cyclohexenes under mild conditions, where the nitro group controls the direction of the addition more effectively than the sulfonyl group.Subsequent treatment of the adducts with Bu3SnH results in the reductive elimination of the nitro and sulfonyl groups to give 1,4-cyclohexadienes.The Diels-Alder reaction of β-sulfinylnitroethylene with dienes and subsequent thermal elimination of sulfenic acid give 1-nitro-1,4-cyclohexadienes, which are readily aromatized to give nitrobenzene derivatives.Thus, β-sulfonylnitroolefins or β-sulfinylnitroethylene is regarded as alkynes or nitroacetylene equivalents for the Diels-Alder reaction, respectively.