5779-93-1

Usage

Chemical Properties

Clear Colorless Oil

Uses

The major component of the umbel rays oil.

InChI:InChI=1/C9H10O/c1-7-4-3-5-9(6-10)8(7)2/h3-6H,1-2H3

Upstream product

• 50-00-0 formaldehyd 
• 100-97-0 hexamethylenetetramine 
• 13651-55-3 2,3-dimethylbenzyl chloride 
• 13651-14-4 (2,3-dimethylphenyl)methanol 
• 526-73-8 1,2,3-trimethylbenzene 
• 7664-93-9 sulfuric acid 
• 108-67-8 1,3,5-trimethyl-benzene 
• 91-22-5 quinoline 
• 56-23-5 tetrachloromethane 
• 21900-46-9 2,3-dimethylbenzoyl chloride 
• 64-19-7 acetic acid 
• 87-59-2 2,3-Dimethylaniline 
• 28162-13-2 5-tert-butyl-2,3-dimethylbenzyl chloride 
• 5724-56-1 2,3-dimethylbenzonitrile 

Downstream Products

• 108546-00-5 (5Z,10Z,14Z,19Z)-5,10,15,20-Tetrakis-(2,3-dimethyl-phenyl)-porphyrin 
• 80663-23-6 cis-2,2',3-trimethylstilbene 
• 80663-24-7 trans-2,2',3-trimethylstilbene 
• 78012-18-7 (E)-methyl 3-(2,3-dimethylstyryl)furan-2-carboxylate 
• 15914-12-2 (E)-2,2',3,3'-tetramethylstilbene 
• 68827-76-9 C₂₉H₂₄O₂ 
• 1027592-24-0 3-amino-4-(2,3-dimethyl-benzyl)-5-ethyl-6-methyl-1H-pyridin-2-one 
• 625437-38-9 cyclopropyl-(2,3-dimethyl-benzyl)-amine 
• 176721-01-0 4-<(2,3-dimethylphenyl)hydroxymethyl>-1-(triphenylmethyl)imidazole 
• 60907-90-6 1-(2,3-dimethylphenyl)ethanol 
• 1146967-27-2 C₁₇H₁₉N₃O 
• 1227460-98-1 [6-(2,3-dimethyl-benzyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl]-quinolin-3-yl-amine 
• 1021163-95-0 2-(2,3-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide 
• 1269526-54-6 7-chloro-2-methoxy-10-(4-(2',3'-dimethylbenzylidene)aminophenyl)aminobenzo[b][1,5]naphthyridine 

Relevant academic research and scientific papers

Trifluoromethylation of Allenes: An Expedient Access to α-Trifluoromethylated Enones at Room Temperature

A silver(I) catalyzed regioselective trifluoromethylation of allenes using Langlois's salt (NaOSOCF3) is demonstrated. This transformation enables direct expedient access to α-trifluoromethylated acroleins, which are valuable synthons for a number of pharmaceuticals and agrochemicals containing vinyl-CF3 moieties. Versatility of this trifluoromethylation method has been established with good yield and excellent regioselectivity. Preliminary experiments and computational studies were carried out to elucidate the mechanistic insight of this protocol.

A NOVEL ROUTE FOR PREPARATION OF L,3:2,4-BIS-(3,4- D IM ETH YLB ENZYLIDENE)SO RB ITO L

A new route for preparation of 3:2,4-bis-(3,4- dimethylbenzylidene) sorbitol [DMDBS] has been disclosed which is comprising: bromination of o-xylene to obtain a mixture of 4-bromo- o-xylene as a major product and 3-bromo-o-xylene; conversion of bromo-o-xylenes into corresponding dimethylbenzaldehyde by Grignard reaction; and reaction of 3,4-dimethylbenzaldehyde with sorbitol in presence of catalyst and solvent to obtain DMDBS. The invented route is cost-effective and it obviates the need to separate 3,4-dimethylbenzaldehyde from its 2,3-isomer.

Method for preparing 2,3-dimethyl benzaldehyde

The invention discloses a method for preparing 2,3-dimethyl benzaldehyde. The method includes the steps that firstly, under the protection of nitrogen, a Grignard reagent is prepared from 2,3-dimethyl benzene halide; secondly, the Grignard reagent and N,N-dimethyl formamide are reacted; finally, the 2,3-dimethyl benzaldehyde is prepared through hydrolyzing, purifying and separating. The method is reasonable in design, mild in reaction condition, simple in technology and easy and convenient to operate; the obtained 2,3-dimethyl benzaldehyde is a key intermediate for synthesizing dexmedetomidine hydrochloride, the sources of the raw materials are rich, and industrial applicability is achieved.

Formylation of electron-rich aromatic rings mediated by dichloromethyl methyl ether and TiCl4: Scope and limitations

Here the aromatic formylation mediated by TiCl4 and dichloromethyl methyl ether previously described by our group has been explored for a wide range of aromatic rings, including phenols, methoxy- and methylbenzenes, as an excellent way to produce aromatic aldehydes. Here we determine that the regioselectivity of this process is highly promoted by the coordination between the atoms present in the aromatic moiety and those in the metal core.

PROCESS FOR THE PREPARATION OF MEDETOMIDINE

A process of preparing Medetomidine of Formula (I) or an acid addition salt thereof, which process comprises: (i) reacting 2,3-dimethyl-methylbenzylalcohol with N-trimethylsilylimidazole, and, if desired, converting the Medetomidine to an acid addition salt thereof.

A PROCESS FOR PREPARING DIAZABICYCLO[3.3.1] NONANE COMPOUNDS

The invention is a process for preparing a diazabicyclo compound of formula (I) process for preparing a diazabicyclo compound of formula (I):where X is selected from the group consisting of hydrogen, C1-C6 alkoxycarbonyl, and carbobenzyloxy; R6 is selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, and benzyl; and R9, R 10, and R11 are independently selected from the group consisting of hydrogen, halogen, and C1-C6 alkyl. wherein the process involves cyclizing I-I, formula (II).

Oxidation of alkylarenes by nitrate catalyzed by polyoxophosphomolybdates: Synthetic applications and mechanistic insights

Alkylarenes were catalytically and selectively oxidized to the corresponding benzylic acetates and carbonyl products by nitrate salts in acetic acid in the presence of Keggin type molybdenum-based heteropolyacids, H3+xPVxMo12-xO40 (x = 0-2). H 5PV2Mo10O40 was especially effective. For methylarenes there was no over-oxidation to the carboxylic acid contrary to what was observed for nitric acid as oxidant. The conversion to the aldehyde/ketone could be increased by the addition of water to the reaction mixture. As evidenced by IR and 15N NMR spectroscopy, initially the nitrate salt reacted with H5PV2Mo10O 40 to yield a NVO2+[H 4PV2Mo10O40] intermediate. In an electron-transfer reaction, the proposed NVO2 +[H4PV2Mo10O40] complex reacts with the alkylarene substrate to yield a radical-cation-based donor-acceptor intermediate, NIVO2[H4PV 2Mo10O40]-ArCH2R+.. Concurrent proton transfer yields an alkylarene radical, ArCHR., and NO2. Alternatively, it is possible that the NVO 2+[H4PV2Mo10O 40] complex abstracts a hydrogen atom from alkylarene substrate to directly yield ArCHR. and NO2. The electron transfer-proton transfer and hydrogen abstraction scenarios are supported by the correlation of the reaction rate with the ionization potential and the bond dissociation energy at the benzylic positions of the alkylarene, respectively, the high kinetic isotope effect determined for substrates deuterated at the benzylic position, and the reaction order in the catalyst. Product selectivity in the oxidation of phenylcyclopropane tends to support the electron transfer-proton transfer pathway. The ArCHR. and NO2 radical species undergo heterocoupling to yield a benzylic nitrite, which undergoes hydrolysis or acetolysis and subsequent reactions to yield benzylic acetates and corresponding aldehydes or ketones as final products.

Benzylic biooxidation of various toluenes to aldehydes by peroxidase

A catalytic method is described for the oxidation of toluene and substituted derivatives to the corresponding benzaldehydes by hydrogen peroxide, using peroxidase. In most cases the respective benzoic acid was produced as a byproduct. The reaction proceeds under mild conditions in an aqueous medium.

Aromatic Spiranes XX [1]: Syntheses of Dimethylsubstituted 2-Carboxymethyl-indan-1-ones and Benzylchlorides as Synthones for Syntheses of di- to tetramethylsubstituted Spirobiindandiones

The isomeric dimethyl methylbenzoates 5, obtained from the bromides via Grignard reactions with dimethylcarbonate, were reduced with LiAlH4 to the hydroxymethyl derivatives 6. The latter were then transformed both to the benzylchlorides 7 (with SOCl2) and to the aldehydes 8 (with pyridinium chlorochromate). Knoevenagel-Doebner reaction of 8 afforded the acrylic acids 9 which (after hydrogenation to 11) were cyclized to the desired indanones 12 with polyphosphoric acid. On the other hand, 12c and 12e were prepared from dimethyl 3-chloropropiophenone (14) by warming with sulfuric acid. After NaH-catalyzed reaction with dimethylcarbonate, the indanones 12 gave the ketoesters 15 which then could be hydrogenated to the indanes 16. All reactions proceeded with satisfactory to excellent yields (60-90%).

Formylation of Aromatic Compounds with CO in HSO3F-SbF5 under Atmospheric Pressure

The formylation of aromatic compounds such as benzene, toluene, xylenes, mesitylene, indan, tetralin, fluorobenzene, chlorobenzene, and bromobenzene was carried out in HSO3F-SbF5 under atmospheric CO pressure at 0 deg C.In HSO3F-SbF5, both formylation and sulfonation took place to give formyl and sulfonyl compounds.In the case of alkylbenzenes, including toluene, xylenes, mesitylene, and tetralin, formylalkylbenzenesulfonyl fluorides, new compounds, were obtained by a one-pot reaction as well as alkylbenzaldehydes, alkylbenzenesulfonyl fluorides, and bis(alkylphenyl) sulfones.The direct introduction of a formyl and sulfonyl group was achieved in alkylbenzenes.The reaction path of the new compounds is a two-step reaction comprised of formylation as the first step and sulfonation as the second step.The product composition was strongly dependent on the acid strength of the HSO3F-SbF5 systems.The formyl compounds became predominant with increasing acidity of the HSO3F-SbF5 system.On the other hand, only sulfonyl compounds were produced when the acidity of the HSO3F-SbF5 system was low.