3382-99-8

Basic information

• Product Name: 2,6-Diallylphenol
• Synonyms: Phenol, 2,6-diallyl-; 4-06-00-04087 (Beilstein Handbook Reference); BRN 2085890; NSC 59839; Phenol, 2,6-di-2-propenyl- (9CI); 2,6-di(prop-2-en-1-yl)phenol
• CAS NO: 3382-99-8
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.239
• EINECS: 222-186-4
• Mol File: 3382-99-8.mol

Chemical Properties

• Boiling Point: 261.8°C at 760 mmHg
• Flash Point: 117.6°C
• Density: 0.986g/cm³
• Vapor Pressure: 0.00697mmHg at 25°C
• Refractive Index: 1.545
• CAS DataBase Reference: 2,6-Diallylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diallylphenol(3382-99-8)
• EPA Substance Registry System: 2,6-Diallylphenol(3382-99-8)

Safety Data

• Hazardous Substances Data: 3382-99-8(Hazardous Substances Data)

Upstream product

• 100311-33-9 3,5-diallyl-4-hydroxy-benzoic acid 
• 121-69-7 N,N-dimethyl-aniline 
• 3383-05-9 allyl 2-allylphenyl ether 
• 91-66-7 N,N-diethylaniline 
• 108-95-2 phenol 
• 31456-98-1 methyl 3-allyl-salicylate 
• 1745-81-9 o-Allylphenol 
• 6969-42-2 3-allyl-2-allyloxy-benzoic acid methyl ester 
• 1746-13-0 allyl phenyl ether 
• 311806-44-7 2,6-Diallylphenol triflate 
• 84682-15-5 3-allyl-2-(allyloxy)benzaldehyde 
• 139-02-6 sodium phenoxide 
• 106-95-6 allyl bromide 
• 861530-40-7 3-allyl-2-allyloxy-benzoic acid 

Downstream Products

• 6626-32-0 2,6-di-n-propylphenol 
• 91495-56-6 2,6-Dipropenyl-phenol 
• 72490-29-0 cis-1.3-dipropyl-cyclohexanone-⁽²⁾ 
• 72490-29-0 (+/-)-trans-1.3-dipropyl-cyclohexanone-⁽²⁾ 
• 55980-23-9 2,6-diallylanisole 
• 94573-55-4 N-(β-Brom-propionyl)-carbamidsaeure-(2,6-diallyl-phenylester) 
• 80227-78-7 2,6-diallyl-6-benzylcyclohexa-2,4-dien-1-one 
• 74663-50-6 2,4,6-tri-n-Propylphenol 
• 20490-22-6 2,4,6-tris(2-propenyl)phenol 
• 97029-34-0 2t,6t-dipropyl-cyclohexan-r-ol 
• 97029-34-0 2c,6c-dipropyl-cyclohexan-r-ol 
• 92031-39-5 (+/-)-cis-1.3-dipropyl-cyclohexanone-⁽²⁾-semicarbazone 
• 94439-23-3 phenylcarbamic acid-(2t.6t-dipropyl-cyclohexyl-(r)-ester) 
• 94439-23-3 phenylcarbamic acid-(2c.6c-dipropyl-cyclohexyl-(r)-ester) 

Relevant articles and documents

Sequential Two-Fold Claisen Rearrangement, One-Pot Ring-Closing Metathesis and Cross-Metathesis as a Route to Substituted Benzo[b]azepine-2-one, Benzo[b]azepine and Benzo[b]oxepine Derivatives

A synthetic protocol involving sequential use of three atom-economic processes viz. Claisen rearrangement, ring-closing metathesis and cross metathesis has been developed to access 7-substituted benzo[b]azepine and benzo[b]oxepine derivatives starting from appropriate aniline or phenol in good overall yield. A one-pot RCM-CM protocol has also been developed for the synthesis of benzazepine and benzoxepine derivatives.

Allylphenols as a new class of human 15-lipoxygenase-1 inhibitors

In this study, a series of mono- and diallylphenol derivative were designed, synthesized, and evaluated as potential human 15-lipoxygenase-1 (15-hLOX-1) inhibitors. Radical scavenging potency of the synthetic allylphenol derivatives was assessed and the results were in accordance with lipoxygenase (LOX) inhibition potency. It was found that the electronic natures of allyl moiety and para substituents play the main role in radical scavenging activity and subsequently LOX inhibition potency of the synthetic inhibitors. Among the synthetic compounds, 2,6-diallyl-4-(hexyloxy)phenol (42) and 2,6-diallyl-4-aminophenol (47) showed the best results for LOX inhibition (IC50 = 0.88 and 0.80 μM, respectively).

Cobalt-Nitrenoid Insertion-Mediated Amidative Carbon Rearrangement via Alkyl-Walking on Arenes

We herein disclose the Cp*Co(III)(LX)-catalyzed amidative alkyl migration using 2,6-disubstituted phenyl azidoformates. Upon the cobalt-nitrenoid insertion toward the substituted ortho carbon, an arenium cationic species bearing a quaternary carbon is generated, and a subsequent alkyl migration process is suggested to occur through an unforeseen alkyl-walking mechanism. A quinolinol ligand of the cobalt catalyst system is proposed to facilitate the final product-releasing rearomatization process by serving as an internal base. This new mechanistic mode enabled both [1,2]- and [1,4]-alkyl rearrangements to allow the structural variation of N-heterocyclic compounds.

Synthesis of novel H-shaped chromophores

A series of H-shaped chromophores with two parallel and non-conjugated D-π-A units have been synthesized, in which a 9,10-dihydroanthracene was employed as molecular backbone. The synthesis of these H-shaped chromophores 9a-11a was accomplished via an eight-step reaction, including double Claisen rearrangement, hydroboration-oxidation, Rieche formylation reaction, Knoevenagel condensation and Corey-Fuchs reaction, with a total yield about 12.5%. The corresponding mono-D-π-A unit compounds 9b-11b were also prepared in a similar procedure for the purpose of comparison. Crystal structures of three intermediates 5a, 7a and 8a were measured, which demonstrate that the two D-π-A units in a single H-shaped chromophore molecule are nearly arranged at the same direction. The studies of UV-vis spectra and the solvatochromic method indicate that the molecular second-order polarizabilities values (μβ) of H-shaped chromophores are remarkably increased compared with the corresponding mono-D-π-A unit reference compounds, without causing a large shift of the absorption band to longer wavelength.

Novel diepoxide derivatives of diallyl phenolics

The present invention relates to the preparation of ethers and esters of diallylphenols and the epoxidation of the diallyl moiety to provide bis-epoxide ether and ester intermediates useful in the preparation of epoxy resins.

Synthesis of 1,1,6,6-tetramethylphosphajulolidine

The synthesis of fused tricyclic dialkyl(phenyl)phosphine was studied to verify the ligand influence upon the catalytic alkoxycarbonylation of propyne. The quantum mechanical calculations were performed to determine the ligand-derived influences upon catalytic activity. The results showed that the ellipticity of the bond was maximized by tethering the alkyl substituents to the ortho carbons of the aromatic ring.