Production Method 1

874-35-1

Reaction Conditions

1.1 Catalysts: Grubbs second generation catalyst Solvents: Dichloromethane ;  2 h, rt
1.2 Reagents: p-Toluenesulfonic acid ;  1 h, rt

Reference

Synthesis of substituted benzenes and phenols by ring-closing olefin metathesis

Yoshida, Kazuhiro; et al, Chemistry - A European Journal, 2008, 14(27), 8246-8261

Production Method 2

18775-42-3

874-35-1

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  20 min, 45 - 50 psi, rt

Reference

Jacobsen rearrangement. VIII. Cyclic systems; mechanism

Arnold, Richard T.; et al, Journal of the American Chemical Society, 1944, 66, 960-4

Production Method 3

1505-50-6

874-35-1

Reaction Conditions

Reference

Optically active spiranes. Part 11. Syntheses of optically active mono- to hepta-substituted 5-methyl- and 5-ethyl-2,2'-spirobiindanes and related naphthalene derivatives of known chirality and enantiomeric purity

Neudeck, Horst; et al, Monatshefte fuer Chemie, 1981, 112(6-7), 801-23

Production Method 4

874-35-1

Reaction Conditions

Reference

Product class 3: cyclic allenes

Kawase, T., Science of Synthesis, 2007, 44, 395-449

Production Method 5

874-35-1

176965-25-6

824-22-6

Reaction Conditions

Reference

Strained Cyclic Cumulene Intermediates in Diels-Alder Cycloadditions of Enynes and Diynes

Burrell, Richard C.; et al, Journal of the American Chemical Society, 1996, 118(17), 4218-19

Production Method 6

874-35-1

Reaction Conditions

1.1 Reagents: Iodine Solvents: Carbon tetrachloride

Reference

Iodination and chlorination of methyl-substituted cis-bicyclo[4.3.0]nona-3,7-dienes

Anfilogova, S. N.; et al, Neftekhimiya, 1993, 33(2), 156-63

Production Method 7

874-35-1

Reaction Conditions

1.1 Catalysts: Grubbs second generation catalyst Solvents: Dichloromethane ;  2 h, rt
1.2 Reagents: p-Toluenesulfonic acid ;  1 h, rt

Reference

Synthesis of substituted benzenes and phenols by ring-closing olefin metathesis

Yoshida, Kazuhiro; et al, Chemistry - A European Journal, 2008, 14(27), 8246-8261

Production Method 8

7480-80-0

874-35-1

Reaction Conditions

Reference

Synthesis of biological markers in fossil fuels. 2. Synthesis and carbon-13 NMR studies of substituted indans and tetralins

Adamczyk, Maciej; et al, Journal of Organic Chemistry, 1984, 49(22), 4226-37

Production Method 9

51632-06-5

874-35-1

Reaction Conditions

1.1 Reagents: Potassium hydroxide ,  Hydrazine hydrate (1:1) Solvents: Dimethyl sulfoxide ;  18 h, rt
1.2 Reagents: Water ;  rt

Reference

Light-Driven Metal-Free Direct Deoxygenation of Alcohols under Mild Conditions

Cao, Dawei; et al, iScience, 2020, 23(8),

Production Method 10

50919-77-2

874-35-1

Reaction Conditions

1.1 Reagents: Potassium hydroxide

Reference

Anodic oxidation of α-substituted p-xylenes. Electronic and stereoelectronic effects of α-substituents in the deprotonation of alkylaromatic radical cations

Baciocchi, Enrico; et al, Journal of Organic Chemistry, 1991, 56(25), 7154-60

Production Method 11

3333-13-9

874-35-1

Reaction Conditions

Reference

Bis(π-methane) rearrangements of methyl-substituted allylbenzenes

Fasel, Jean Pierre; et al, Chimia, 1981, 35(1), 9-12

Production Method 12

21969-32-4

1089664-99-2

874-35-1

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C; 30 min, rt
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Catalysts: Grubbs second generation catalyst Solvents: Dichloromethane ;  2 h, rt
2.2 Reagents: p-Toluenesulfonic acid ;  1 h, rt

Reference

Synthesis of substituted benzenes and phenols by ring-closing olefin metathesis

Yoshida, Kazuhiro; et al, Chemistry - A European Journal, 2008, 14(27), 8246-8261

Production Method 13

5674-01-1

1089664-99-2

874-35-1

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C; 30 min, rt
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Catalysts: Grubbs second generation catalyst Solvents: Dichloromethane ;  2 h, rt
2.2 Reagents: p-Toluenesulfonic acid ;  1 h, rt

Reference

Synthesis of substituted benzenes and phenols by ring-closing olefin metathesis

Yoshida, Kazuhiro; et al, Chemistry - A European Journal, 2008, 14(27), 8246-8261

Production Method 14

75476-78-7

874-35-1

Reaction Conditions

Reference

Synthesis of biological markers in fossil fuels. 2. Synthesis and carbon-13 NMR studies of substituted indans and tetralins

Adamczyk, Maciej; et al, Journal of Organic Chemistry, 1984, 49(22), 4226-37

Production Method 15

13682-77-4

874-35-1

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Triphenylphosphine ,  Palladium diacetate Solvents: Tetrahydrofuran ,  Water ;  3 h, 50 °C; 50 °C → rt
2.1 Solvents: Tetrahydrofuran ;  0 °C; 30 min, rt
2.2 Reagents: Ammonium chloride Solvents: Water
3.1 Catalysts: Grubbs second generation catalyst Solvents: Dichloromethane ;  2 h, rt
3.2 Reagents: p-Toluenesulfonic acid ;  1 h, rt

Reference

Synthesis of substituted benzenes and phenols by ring-closing olefin metathesis

Yoshida, Kazuhiro; et al, Chemistry - A European Journal, 2008, 14(27), 8246-8261

Production Method 16

6134-53-8

874-35-1

496-11-7

824-22-6

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether
1.2 -

Reference

The intermediate formation of [4]metacyclophane on flash vacuum thermolysis

Kostermans, Gerardus B. M.; et al, Journal of Organic Chemistry, 1988, 53(19), 4531-4

Production Method 17

1489-28-7

874-35-1

99304-56-0

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Diethyl ether
1.2 Solvents: Diethyl ether

Reference

Photochemical oxadi-π-methane rearrangement approach to [3.3.3]propellanes. Total synthesis of sesquiterpene hydrocarbon (±)-modhephene

Mehta, Goverdhan; et al, Journal of the Chemical Society, 1991, (2), 395-401

Production Method 18

74543-59-2

874-35-1

824-22-6

119-64-2

Reaction Conditions

Reference

The intermediate formation of [4]metacyclophane on flash vacuum thermolysis

Kostermans, Gerardus B. M.; et al, Journal of Organic Chemistry, 1988, 53(19), 4531-4

Production Method 19

496-11-7

874-35-1

496-11-7

824-22-6

Reaction Conditions

1.1 Reagents: Iron ,  Bromine Solvents: Hexane
2.1 Reagents: Butyllithium Solvents: Diethyl ether
2.2 -

Reference

The intermediate formation of [4]metacyclophane on flash vacuum thermolysis

Kostermans, Gerardus B. M.; et al, Journal of Organic Chemistry, 1988, 53(19), 4531-4

5-Methylindan Raw materials

• Potassium vinyltrifluoroborate
• Magnesium,chloro(1-methyl-2-propen-1-yl)-
• Indane
• 5-methyl-2,3-dihydro-1H-indene-1,3-dione
• Tricyclo[6.1.1.06,9]deca-2,8(10)-diene
• 4-Bromo-2,3-dihydro-1H-indene
• 3-(4-Methylphenyl)propanoic Acid
• 2-Methylprop-2-en-1-ylmagnesium chloride
• (2,3-dihydro-1H-inden-5-yl)methanol
• 5H-Inden-5-one,1,2,3,6,7,7a-hexahydro-
• 4-Allyltoluene
• 2-Ethenyl-1-cyclopentene-1-carboxaldehyde
• 5-bromo-1H-indene
• 5-(chloromethyl)-2,3-dihydro-1H-indene
• 5-methyl-1H-indene

5-Methylindan Preparation Products

• 6-Methyl-2,3,4,5-tetrahydro-1H-indene (99304-56-0)
• Indane (496-11-7)
• Cyclopentene,1-ethenyl-2-(1-propyn-1-yl)- (176965-25-6)
• 5-Methylindan (874-35-1)
• 4-Methylindan (824-22-6)
• 1,2,3,4-Tetrahydronaphthalene (119-64-2)

• 1. Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330
  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813
• 2. Exciplex emission from the mixed dimer of naphthalene and 2-cyanonaphthalene in a supersonic jet
  Aloke Das,K. K. Mahato,Chayan K. Nandi,Tapas Chakraborty,Shridhar R. Gadre,Nikhil A. Gokhale Phys. Chem. Chem. Phys., 2002,4, 2162-2168
• 3. Enabling stable MnO2 matrix for aqueous zinc-ion battery cathodes?
  Yiding Jiao,Liqun Kang,Jasper Berry-Gair,Kit McColl,Jianwei Li,Haobo Dong,Hao Jiang,Ryan Wang,Furio Corà,Dan J. L. Brett,Ivan P. Parkin J. Mater. Chem. A, 2020,8, 22075-22082
• 4. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
• 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 Indanes Indanes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Indanes
• Natural Products and Extracts Plant Extracts Plant based Ducrosia ismaelis

Introduction to 5-Methylindan (CAS No. 874-35-1)

5-Methylindan, with the chemical formula C₁₀H₁₂, is a significant compound in the realm of organic chemistry and pharmaceutical research. Its molecular structure, featuring a benzene ring substituted with a methyl group and an indane moiety, makes it a versatile intermediate in the synthesis of various pharmacologically active molecules. The compound is identified by its unique Chemical Abstracts Service (CAS) number, 874-35-1, which distinguishes it in scientific literature and databases.

The structure of 5-Methylindan lends itself to further functionalization, making it a valuable building block in medicinal chemistry. Researchers have explored its potential in developing novel therapeutic agents, particularly in the treatment of neurological disorders and pain management. The indane core is known for its ability to interact with specific biological targets, which has sparked interest in its derivatives.

In recent years, advancements in computational chemistry have allowed for more precise predictions of the pharmacokinetic properties of 5-Methylindan and its analogs. Studies have indicated that modifications to the indane ring can significantly alter binding affinities to biological receptors, offering insights into designing more effective drugs. This has led to a surge in interest among academic and industrial researchers.

The synthesis of 5-Methylindan typically involves Friedel-Crafts alkylation or acylation reactions on an indane precursor. These methods are well-documented and have been optimized for high yields and purity. The compound's stability under various reaction conditions makes it a preferred choice for multi-step synthetic routes in drug development.

One of the most compelling aspects of 5-Methylindan is its role as a precursor in the development of bioactive molecules. For instance, researchers have synthesized derivatives of this compound that exhibit potent activity against enzymes involved in inflammation pathways. These findings have opened new avenues for treating chronic inflammatory diseases without the side effects associated with traditional non-steroidal anti-inflammatory drugs (NSAIDs).

The pharmacological properties of 5-Methylindan have been extensively studied in preclinical models. Initial research suggests that it may interact with mu-opioid receptors, potentially making it useful in pain relief. However, further studies are needed to fully understand its mechanism of action and to assess its safety profile for human use.

Recent publications have highlighted the use of 5-Methylindan in combinatorial chemistry approaches. By systematically varying substituents on the indane ring, researchers can generate libraries of compounds for high-throughput screening. This strategy has led to the discovery of several lead compounds with promising therapeutic potential.

The analytical characterization of 5-Methylindan is crucial for ensuring its purity and consistency in pharmaceutical applications. Techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and high-performance liquid chromatography (HPLC) are routinely employed to confirm its identity and assess impurities.

In conclusion, 5-Methylindan (CAS No. 874-35-1) represents a fascinating compound with significant implications for drug discovery and development. Its unique structural features and potential biological activities make it a cornerstone in modern medicinal chemistry. As research continues to uncover new applications for this molecule, its importance is likely to grow even further.

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• 9004-34-6(Cellulose)
• 1074-17-5(1-Methyl-2-propylbenzene)
• 119-64-2(1,2,3,4-Tetrahydronaphthalene)
• 1610-39-5(1,2,3,4,5,6,7,8,9,10,11,12-Dodecahydrotriphenylene)
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