Production Method 1

87-85-4

Reaction Conditions

1.1 Reagents: Phosphorus pentachloride Solvents: Benzene

Reference

Alkyne cyclizations at reduced tantalum centers: synthesis and molecular structure of (η6-C6Me6)Ta(O-2,6-i-Pr2C6H3)2Cl

Bruck, M. A.; Copenhaver, A. S.; Wigley, D. E., Journal of the American Chemical Society, 1987, 109(21), 6525-7

Production Method 2

87-85-4

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Titanium, dichloro[3,8,14,19-tetrakis(1,1-dimethylethyl)-23,23-diphenyl-11H,17H-… Solvents: Toluene ,  Tetrahydrofuran ;  2 h, 75 °C

Reference

Synthesis, characterization, and alkyne cyclotrimerization chemistry of titanium complexes supported by calixarene-derived bis(aryloxide) ligation

Ladipo, Folami T.; Sarveswaran, Vallipuram; Kingston, Jesudoss V.; Huyck, Rebecca A.; Bylikin, Sergei Y.; et al, Journal of Organometallic Chemistry, 2004, 689(3), 502-514

Production Method 3

19405-90-4

87-85-4

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride

Reference

Synthesis and properties of polymethylbenzyl nitrites

Suzuki, Hitomi; Nakano, Kiyoshi; Mishina, Tadashi; Hanafusa, Terukiyo, Nippon Kagaku Kaishi, 1978, (7), 1049-52

Production Method 4

700-12-9

87-85-4

Reaction Conditions

1.1 Catalysts: Indium chloride tetrahydrate Solvents: 1,2-Dichloroethane ;  8 h, 110 °C; cooled

Reference

InCl3·4H2O-catalyzed trioxane as a new methylating agent for multi-methylated aromatics affording hexamethyl benzene

Chen, Song-Jie; Hua, Ruimao, Letters in Organic Chemistry, 2010, 7(1), 61-63

Production Method 5

87-85-4

Reaction Conditions

1.1 Catalysts: Tantalum chloride sulfide (TaCl3S), (T-4)- Solvents: Toluene ;  3 h, 20 °C

Reference

Reactions of vanadium(V) and tantalum(V) complexes with kinetically stabilized phosphaalkynes. A simple synthesis of 1,3,4-thia- and 1,3,4-selenadiphospholes

Peters, Christoph; Fischbeck, Uwe; Tabellion, Frank; Regitz, Manfred; Preuss, Fritz, Zeitschrift fuer Naturforschung, 2003, 58(1), 44-51

Production Method 6

87-85-4

Reaction Conditions

1.1 Catalysts: (SP-4-1)-[1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-yliden… Solvents: Diethyl ether ,  1,4-Dioxane ;  24 h, rt

Reference

Low temperature Kumada-Corriu cross-coupling of polychlorinated acene derivatives and a synthesis of sterically demanding acenes

Yagodkin, Elisey; Douglas, Christopher J., Tetrahedron Letters, 2010, 51(23), 3037-3040

Production Method 7

87-85-4

Reaction Conditions

1.1 Catalysts: Molybdenum, bis[(1,2,3,4,5,6-η)-2,6-dimethylpyridine]- Solvents: Acetonitrile

Reference

Synthesis and reactions of [Mo(2,6-lutidine)(η-allyl)] derivatives

Mehnert, Christian P.; Chernega, Alexander N.; Green, Malcolm L. H., Journal of Organometallic Chemistry, 1996, 513(1-2), 247-253

Production Method 8

87-85-4

Reaction Conditions

1.1 Catalysts: Di-μ-chlorotetrakis(η2-ethene)dirhodium Solvents: 1,2-Dichloroethane ;  3 h, 80 °C

Reference

Catalytic and Stoichiometric Reactions of the Parent Olefin Rhodium(I) Complex with Alkynes

Kolos, Andrey V.; Nelyubina, Yulia V.; Perekalin, Dmitry S., Organometallics, 2022, 41(21), 3038-3043

Production Method 9

9005-53-2

87-85-4

88-60-8

876-20-0

2219-78-5

1758-88-9

13037-79-1

15181-13-2

13632-94-5

622-96-8

1687-64-5

527-84-4

700-12-9

3698-49-5

92617-73-7

89-83-8

35946-91-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium ,  Chromium chloride (CrCl3) Solvents: Methanol ;  4 h, 2 MPa, 280 °C

Reference

Insight into the solvent, temperature and time effects on the hydrogenolysis of hydrolyzed lignin

Shu, Riyang; Zhang, Qi; Ma, Longlong; Xu, Ying; Chen, Pengru; et al, Bioresource Technology, 2016, 221, 568-575

Production Method 10

87-85-4

Reaction Conditions

1.1 Catalysts: [1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene][N-[2,6… Solvents: Benzene-d6 ;  3 h, rt

Reference

Synthesis, Characterization, and Alkyne Trimerization Catalysis of a Heteroleptic Two-Coordinate FeI Complex

Lipschutz, Michael I.; Chantarojsiri, Teera; Dong, Yuyang; Tilley, T. Don, Journal of the American Chemical Society, 2015, 137(19), 6366-6372

Production Method 11

87-85-4

Reaction Conditions

1.1 Catalysts: [(1,2,3,4,5,6-η)-1,3,5-Cycloheptatriene][(1,2,5,6-η)-1,5-cyclooctadiene]iron Solvents: Tetrahydrofuran

Reference

(η6-Cyclohepta-1,3,5-triene)(η4-cycloocta-1,5-diene)iron(0) complex as attractive precursor in catalysis

Breschi, Chiara; Piparo, Loris; Pertici, Paolo; Caporusso, Anna Maria; Vitulli, Giovanni, Journal of Organometallic Chemistry, 2000, 607(1-2), 57-63

Production Method 12

87-85-4

Reaction Conditions

1.1 Catalysts: Tantalum, μ-chloropentachloro[μ-[(1,2,3,4-η)-1,2,3,4-tetraethyl-1,3-butadiene-1,… Solvents: Benzene-d6 ;  15 min, rt

Reference

Direct evidence for [4+2] cycloaddition mechanism of alkynes to tantalacyclopentadiene on dinuclear tantalum complexes as a model of alkyne cyclotrimerization

Yamamoto, Keishi; Tsurugi, Hayato; Mashima, Kazushi, Chemistry - A European Journal, 2015, 21(32), 11369-11377

Production Method 13

87-85-4

Reaction Conditions

1.1 Reagents: Sodium amalgam Solvents: Water ;  heated

Reference

Isomerizations of carbanions. II. Rearrangements of benzyltrimethylammonium ion and related quaternary ammonium ions by sodium amide involving migration into the ring

Kantor, Simon W.; Hauser, Charles R., Journal of the American Chemical Society, 1951, 73, 4122-31

Production Method 14

87-85-4

Reaction Conditions

1.1 Catalysts: Silane, (11-azidoundecyl)trimethoxy-, homopolymer (trimethylsilyl-terminated, reaction product with tri-2-pyridylphosphine and palladium (II) chloride followed by hydrolysis) Solvents: Chloroform

Reference

Immobilization of homogeneous palladium(II) complex catalysts on novel polysiloxanes with controllable solubility: important implications for the study of heterogeneous catalysis on silica surfaces

Fu, Yaw-Shyan; Yu, Shuchun J., Angewandte Chemie, 2001, 40(2), 437-440

Production Method 15

87-85-4

Reaction Conditions

1.1 Catalysts: 2-Iodophenol ,  Indium trichloride Solvents: Chlorobenzene ;  24 h, reflux

Reference

Regioselective Synthesis of 1,3,5-Substituted Benzenes via the InCl3/2-Iodophenol-Catalyzed Cyclotrimerization of Alkynes

Xu, Yan-li; Pan, Ying-ming; Wu, Qiang; Wang, Heng-shan; Liu, Pei-zhen, Journal of Organic Chemistry, 2011, 76(20), 8472-8476

Production Method 16

87-85-4

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid monohydrate ;  3 h, 60 °C; 21 h, 140 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized

Reference

An efficient approach to the cyclotrimerisation of alkynes: solvent-free synthesis of 1,3,5-trisubstituted benzenes using p-toluenesulfonic acid monohydrate

Gao, Qi; Bao, Fang-Ping; Feng, Xiao-Jing; Pan, Ying-Ming; Wang, Heng-Shan; et al, ARKIVOC (Gainesville, 2013, (3), 49-60

Production Method 17

87-85-4

Reaction Conditions

1.1 Reagents: Titanium ,  Zirconium Solvents: Tetrahydrofuran ,  1,2-Dimethoxyethane

Reference

Cyclotrimerization of alkynes by activated metal catalyst

Choi, Kyu Sang; Park, Moon Kyeu; Han, Byung Hee, Bulletin of the Korean Chemical Society, 1998, 19(11), 1257-1261

Production Method 18

92595-29-4

87-85-4

Reaction Conditions

Reference

Ethoxycarbonylmethylthiomethylation of aromatic compounds by Friedel-Crafts reaction with ethyl α-(chloromethylthio)acetate

Tamura, Yasumitsu; Tsugoshi, Teruhisa; Annoura, Hirokazu; Ishibashi, Hiroyuki, Synthesis, 1984, (4), 326-7

Production Method 19

700-12-9

87-85-4

Reaction Conditions

1.1 Catalysts: Alumina ,  Silica

Reference

Preparation of hexamethylbenzene

, Japan, , ,

Production Method 20

87-85-4

Reaction Conditions

1.1 Catalysts: Butyllithium ,  Titanium isopropoxide Solvents: Tetrahydrofuran ,  Hexane ;  1 min, 0 °C; 5 min, 0 °C
1.2 0 °C; 15 min, 100 °C; cooled
1.3 Reagents: Hydrochloric acid Solvents: Water ;  15 min, rt

Reference

Can the Ti(OiPr)4/nBuLi combination of reagents function as a catalyst for [2+2+2] alkyne cyclotrimerisation reactions?

Siemiaszko, Gabriela; Six, Yvan, New Journal of Chemistry, 2018, 42(24), 20219-20226

Production Method 21

87-85-4

Reaction Conditions

1.1 Reagents: Aluminum oxide (Al4O6) Solvents: Methanol

Reference

Hexamethylbenzene

Cullinane, N. M.; Chard, S. J.; Dawkins, C. W. C., Organic Syntheses, 1955, 35, 73-4

Production Method 22

87-85-4

Reaction Conditions

1.1 Reagents: Magnesium ,  Nickel bromide Solvents: Tetrahydrofuran

Reference

Cyclotrimerization of alkynes catalyzed by nickel complexes formed in situ

Alphonse, P.; Moyen, F.; Mazerolles, P., Journal of Organometallic Chemistry, 1988, 345(1-2), 209-16

Production Method 23

517-60-2

87-85-4

Reaction Conditions

1.1 Catalysts: Tris(pentafluorophenyl)borane Solvents: Dichloromethane ;  10 min, rt
1.2 Reagents: Butylsilane ;  6 - 20 h, rt

Reference

A novel reduction of polycarboxylic acids into their corresponding alkanes using n-butylsilane or diethylsilane as the reducing agent

Nimmagadda, Rama D.; McRae, Christopher, Tetrahedron Letters, 2006, 47(21), 3505-3508

Hexamethylbenzene Raw materials

• Mellitic Acid
• Lignin
• 1,2,3,4,5-pentamethylbenzene
• Acetic acid, [[(pentamethylphenyl)methyl]thio]-, ethyl ester
• Benzenemethanol, 2,3,4,5,6-pentamethyl-, nitrate

Hexamethylbenzene Preparation Products

• 2-tert-butyl-5-methylphenol (88-60-8)
• Hexamethylbenzene (87-85-4)
• 2-Phenylethyl-1,1,2,2-d4-amine (876-20-0)
• Phenol,2-ethyl-4,5-dimethyl- (2219-78-5)
• 2-Ethyl-1,4-dimethylbenzene (1758-88-9)
• Phenol,2-(1,1-dimethylethyl)-3-methyl- (13037-79-1)
• Benzene,1-ethyl-3,5-bis(1-methylethyl)- (15181-13-2)
• Benzene,1,4-diethyl-2-methyl- (13632-94-5)
• 4-Ethyltoluene (622-96-8)
• 2-Ethyl-6-methylphenol (1687-64-5)
• o-Cymene (527-84-4)
• 1,2,3,4,5-pentamethylbenzene (700-12-9)
• 2,3-Dihydro-2,2,4,6-tetramethylbenzofuran (3698-49-5)
• Phenol, 2-(1,1-dimethyl-2-propen-1-yl)-3,6-dimethyl- (92617-73-7)
• Thymol (89-83-8)
• 2,5-Diisopropylphenol (35946-91-9)

• 1. Excellent peroxidase mimicking property of CuO/Pt nanocomposites and their application as an ascorbic acid sensor?
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  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 3. Enabling chloride salts for thermal energy storage: implications of salt purity?
  J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608
• 4. Fe3O4 nanosphere@microporous organic networks: enhanced anode performances in lithium ion batteries through carbonization?
  Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk Son Chem. Commun., 2014,50, 7723-7726
• 5. Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field
  XuxinCheng,XiaomingChen,PengyuanFan

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzene and substituted derivatives
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons
• Solvents and Organic Chemicals Organic Compounds

• 25619-60-7(Benzene, tetramethyl-)
• 4342-40-9(Hexamethylbenzene-d18)
• 128686-03-3(1,2-Xylene; 1,3-xylene; 1,4-xylene)
• 31176-31-5(Methyl,1,1'-phenylenebis-)
• 26204-18-2(p-Xylene-α,α,α-d3)
• 700-12-9(1,2,3,4,5-pentamethylbenzene)
• 350818-60-9(1,2,3,4-Tetramethylbenzene-d14)
• 350818-61-0(1,2,4-Trimethylbenzene-d12)
• 25319-54-4(o-Xylene-alpha,alpha,alpha,alpha',alpha',alpha'-d6)
• 2348-48-3(Methyl,(2-methylphenyl)-)