13199-54-7

Usage

Physical state

Colorless liquid

Odor

Sweet, floral

Uses

Fragrance ingredient in perfumes and personal care products
Solvent
Intermediate in the synthesis of other organic compounds

Toxicity

Relatively non-toxic

Acute toxicity

Low potential

Skin irritation

Low potential

Skin sensitization

Low potential

Precautions

Prolonged or repeated exposure to high concentrations may cause harmful effects

Safety procedures

Handle with caution and in accordance with proper safety procedures

Upstream product

• 527-18-4 Durohydroquinone 
• 77-78-1 dimethyl sulfate 
• 527-17-3 Duroquinone 
• 60-29-7 diethyl ether 
• 54757-17-4 1-chloromethyl-2,5-dimethoxy-3,4,6-trimethyl-benzene 
• 205862-10-8 2,3-bis(bromomethyl)-1,4-dimethoxy-5,6-dimethylbenzene 

Downstream Products

• 527-17-3 Duroquinone 
• 104157-20-2 1,2,4,5-tetrakis(bromomethyl)-3,6-dimethoxybenzene 
• 99622-28-3 2,2'-pentamethylenebis(3,5,6-trimethyl-1,4-benzoquinone) 
• 1132810-78-6 (S)-1-benzyloxy-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-butan-2-ol 
• 1132810-77-5 (R)-1-benzyloxy-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-butan-2-ol 
• 85148-25-0 (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-butanediol 
• 59-02-9 Tocopherol 
• 96203-94-0 (S)-4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1-(4-tolylsulfonyloxy)butan-2-ol 
• 96203-95-1 (S)-4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-1,2-epoxy-2-methylbutan 
• 91418-95-0 (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol 
• 7559-04-8 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione 

Relevant academic research and scientific papers

Enantiocomplementary chemoenzymatic asymmetric synthesis of (R)- And (S)-chromanemethanol

A non-lipase-based, enantiocomplementary chemoenzymatic route towards enantiopure (R)- and (S)-chromane-methanol (12), which are the key building blocks for the synthesis of stereoisomerically pure α-tocopherols, has been achieved by the biocatalytic reso

Reaction of trialkyl(dibromomethyl)silanes or 1,2-bis(dibromomethyl)benzene with triorganomanganates. A facile and selective synthesis of alkenylsilanes and 1,2-diaryl-1,2-dihydrobenzocyclobutenes

Treatment of trialkyl(dibromomethyl)silanes with trialkylmanganates, derived from manganese(II) chloride and three molar amounts of Grignard reagents or alkyllithiums, provided (E)-1-trialkylsilyl-1-alkenes with high stereoselectivity in good yields. The reaction of trialkyl(dibromomethyl)silanes with alkylmagnesium halides proceeded in the presence of a catalytic amount of manganese(II) chloride. Treatment of 1,2-bis(dibromomethyl)benzene with triphenylmanganate gave 1,2-diphenyl-1,2-dihydrobenzocyclobutene.

Oxidative Dealkylation of Hydroquinone Ethers with Nitrogen Dioxide in the Convenient Preparation of Quinones

Various Hydroquinone dialkyl ethers (R2Q) are effectively converted by nitrogen dioxide into the corresponding quinone (Q) and alkyl nitrite (RONO) in dichloromethane at room temperature or below.The preparative procedure for the isolation of crystalline quinones in quantitative yield merely involves the convenient removal of the low boiling solvent in vacuo.Isotopic labelling studies demonstrate that the oxidative dealkylation proceeds via alkoxy scission of the labile cation radical (R2Q-cation radical) formed via the oxidation of the hydroquinone ether by nitrogen dioxide ( as the disproportionated ion pair NO+NO3-).The electron-transfer mechanism is confirmed by the spectral observation of R2Q-cation radical (identified by the isolation of the crystalline salt R2Q-cation radical-SbCl6-) and its rapid conversion into quinone and alkyl nitrite by combination with nitrate (NO3-) and nitric oxide (NO).

Total synthesis of naturally occurring α-tocopherol. Assymetric alkylation and asymmetric epoxidation as means to introduce (R)-configuration at C(2) of the chroman moiety

Based on the reductive, stereospecific ring closure of (2R,4'R,8'R)-α-'Tocopherylquinone' or corresponding analogues with a short, functionalized side chain (B, Scheme 1) to 1 resp. the chroman system of 1 (C), two different approaches for the introduction of the required tertiary methyl-substituted alcohol structure in the side chain of the aromatic precursors (A, Scheme 1) were developed. The first approach uses asymmetric alkylation in three different versions featuring a) diastereoselective steering with chiral auxiliaries I-IV (Scheme 2) attached as esters to α-keto acids, b) intermediate transfer of chirality in an ester enolate (from 18, Scheme 4) derived from an optically active α-hydroxyacid, c) enantioselective alkylation of phytenal (20) and subsequent ring closure with chirality transfer (Schemes 5-7). The second approach is based on the asymmetric epoxidation of β-metallylalcohol (Sharpless epoxidation), the corresponding epoxyalcohol being converted in situ to the (S)- or (R)-chlorodiol (S)- and (R)-29, respectively, for isolation (Schemes 8 and 9). Nucleophilic epoxide opening with a (3R,7R)-3,7,11-trimethyldodecyl (C15**) and an ArCH2 unit in appropriate sequence is used to assemble the C-framework of the target molecule via corresponding epoxide intermediates from either chlorodiol. Combined with the use of the methoxymethyl-ether function for protection of the hydroquinone system, the epoxide approach provides a short route to 1 (Scheme 10).

Repetitive Diels-Alder Reactions for the Growth of Linear Polyacenequinoid Derivatives

Starting from 2,3,5,6-tetramethylidene-7-oxanorbornane, repetitive quinone Diels-Alder/oxidation reactions produced a series of epoxypolyacenequinones with up to eleven linearly annulated rings.Epoxide ring opening-oxidation gave polyacenequinones with se