Production Method 1

593-71-5

83622-42-8

Reaction Conditions

1.1 Reagents: Butyllithium
1.2 Reagents: Hydrochloric acid Solvents: Diethyl ether

Reference

Pinacol (chloromethyl)boronate

Matteson, Donald S., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-2

Production Method 2

76-09-5

83622-42-8

Reaction Conditions

1.1 Reagents: Butyllithium ,  Triisopropyl borate Solvents: Tetrahydrofuran ,  Hexane ;  < -80 °C; 2 h, < -80 °C; 1 h, -80 °C; 30 min, -80 °C → rt; 2 min, rt; rt → 0 °C
1.2 Reagents: Methanesulfonic acid ;  10 min, 0 °C; 0 °C → rt; 1 min, rt
1.3 overnight, rt

Reference

Pd-Catalyzed Organometallic-Free Homologation of Arylboronic Acids Enabled by Chemoselective Transmetalation

Bastick, Kane A. C.; et al, ACS Catalysis, 2023, 13(10), 7013-7018

Production Method 3

76-09-5

83622-42-8

Reaction Conditions

1.1 Reagents: Butyllithium ,  Triisopropyl borate Solvents: Tetrahydrofuran ,  Hexane ;  < -80 °C; 2 h, < -80 °C; 1 h, -80 °C; 30 min, -80 °C → rt; 2 h, rt; rt → 0 °C
1.2 Reagents: Methanesulfonic acid ;  10 min, 0 °C; 0 °C → rt; 1 h, rt
1.3 overnight, rt

Reference

A Pd-catalyzed organometallic-free homologation of arylboronic acids enabled by chemoselective transmetalation

Bastick, Kane A. C.; et al, ChemRxiv, 2023, 1, 1-6

Production Method 4

486402-87-3

83622-42-8

Reaction Conditions

1.1 Reagents: Bromochloromethane ,  Butyllithium Solvents: Dimethylformamide

Reference

Glutathione-like tripeptides as inhibitors of glutathionylspermidine synthetase. Part 1: Substitution of the glycine carboxylic acid group

Amssoms, Katie; et al, Bioorganic & Medicinal Chemistry Letters, 2002, 12(18), 2553-2556

Production Method 5

83622-42-8

Reaction Conditions

1.1 Reagents: Butyllithium ;  cooled
1.2 Reagents: Chlorotrimethylsilane Solvents: Tetrahydrofuran
2.1 -

Reference

Pinacol (chloromethyl)boronate

Matteson, Donald S., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-2

Production Method 6

593-71-5

61676-62-8

83622-42-8

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 30 min, -78 °C
1.2 Reagents: Chlorotrimethylsilane ;  -78 °C; 10 min, -78 °C; -78 °C → rt; 24 h, rt
1.3 Reagents: Water ;  rt

Reference

Regioselective Cross-Coupling of Allylboronic Acid Pinacol Ester Derivatives with Aryl Halides via Pd-PEPPSI-IPent

Farmer, Jennifer L.; et al, Journal of the American Chemical Society, 2012, 134(42), 17470-17473

Production Method 7

593-71-5

61676-62-8

83622-42-8

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  rt → -78 °C; -78 °C; 30 min, -78 °C
1.2 Reagents: Chlorotrimethylsilane ;  -78 °C; 10 min, -78 °C; 24 h, rt

Reference

Stereocontrolled Synthesis of Carbon Chains Bearing Contiguous Methyl Groups by Iterative Boronic Ester Homologations: Application to the Total Synthesis of (+)-Faranal

Dutheuil, Guillaume; et al, Angewandte Chemie, 2009, 48(34), 6317-6319

Production Method 8

76-09-5

83622-42-8

Reaction Conditions

Reference

Pinacol (chloromethyl)boronate

Matteson, Donald S., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-2

Production Method 9

74-95-3

83622-42-8

Reaction Conditions

1.1 Reagents: Butyllithium
1.2 Reagents: Hydrochloric acid Solvents: Diethyl ether

Reference

Pinacol (chloromethyl)boronate

Matteson, Donald S., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-2

Production Method 10

76-09-5

83622-42-8

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether ,  Tetrahydrofuran

Reference

Design and Evaluation of a New Lewis Acid-Assisted Lewis Acid Catalyst System and Further Applications of a Double-Allylation Reagent (MSc Thesis)

Sivasubramaniam, Umakanthan, 2009, , ,

Production Method 11

593-71-5

497165-15-8

83622-42-8

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether ;  1 h, -78 °C; 30 min, 10 °C
1.2 16 h, rt

Reference

Characterization of D-boroAla as a novel broad-spectrum antibacterial agent targeting D-Ala-D-Ala ligase

Putty, Sandeep; et al, Chemical Biology & Drug Design, 2011, 78(5), 757-763

Production Method 12

83622-41-7

83622-42-8

Reaction Conditions

1.1 Catalysts: Tributylstannane

Reference

Preparation of halomethaneboronates

Wuts, Peter G. M.; et al, Journal of Organometallic Chemistry, 1982, 234(2), 137-41

Production Method 13

917-54-4

18680-27-8

83622-42-8

Reaction Conditions

1.1 Reagents: Triisopropyl borate ,  Hydrochloric acid Solvents: Diethyl ether ;  16 h, -72 °C; 0 °C
1.2 -
1.3 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  30 min, -100 °C
1.4 Reagents: Zinc chloride ;  16 h
1.5 Reagents: Butyllithium ,  Hexamethyldisilazane Solvents: Tetrahydrofuran ;  16 h, -78 °C
1.6 Reagents: Hydrochloric acid Solvents: Diethyl ether ,  Water ;  1 h, 0 °C
2.1 Reagents: Butyllithium Solvents: Diethyl ether ;  1 h, -78 °C; 30 min, 10 °C
2.2 16 h, rt

Reference

Characterization of D-boroAla as a novel broad-spectrum antibacterial agent targeting D-Ala-D-Ala ligase

Putty, Sandeep; et al, Chemical Biology & Drug Design, 2011, 78(5), 757-763

Production Method 14

76-09-5

62260-98-4

83622-42-8

Reaction Conditions

1.1 -
2.1 Catalysts: Tributylstannane

Reference

Preparation of halomethaneboronates

Wuts, Peter G. M.; et al, Journal of Organometallic Chemistry, 1982, 234(2), 137-41

2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Raw materials

• Chloroiodomethane
• 2,3-Dimethylbutane-2,3-diol
• 4,6-Methano-1,3,2-benzodioxaborole-2-methanamine,hexahydro-a,3a,8,8-tetramethyl-, (aR,3aS,4S,6S,7aR)-
• (4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)methanol
• Methyllithium (1.6M in Diethyl Ether)
• Dibromomethane
• Dichloromethyl pinacolboronate
• 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• (+)-Pinanediol
• (dichloromethyl)boronic acid

2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Preparation Products

• 2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (83622-42-8)

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• 4. An insight into the role of side chains in the microstructure and carrier mobility of high-performance conjugated polymers?
  Jianyao Huang,Dong Gao,Zhihui Chen,Weifeng Zhang Polym. Chem., 2021,12, 2471-2480
• 5. An air-stable organometallic polymer containing titanafluorene moieties obtained by the Sonogashira–Hagihara cross-coupling polycondensation?
  Alvin Tanudjaja,Shinsuke Inagi,Fusao Kitamura,Toshikazu Takata,Ikuyoshi Tomita Dalton Trans., 2021,50, 3037-3043

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Boronic acid derivatives Boronic acid esters
• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Professional Introduction to 2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 83622-42-8)

2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a highly specialized organoboron compound that has garnered significant attention in the field of chemical and pharmaceutical research. This compound, identified by its CAS number 83622-42-8, is a key intermediate in the synthesis of various boronic acid derivatives and has demonstrated remarkable utility in cross-coupling reactions. Its unique structural features, particularly the presence of a chloromethyl substituent and a tetramethyl-substituted dioxaborolane core, make it an invaluable tool for organic chemists and pharmaceutical researchers.

The compound's structure is characterized by a borylated dioxolane ring system, which is highly stable and reactive under controlled conditions. The tetramethyl substitution at the 4-position enhances the steric environment around the boron center, influencing its reactivity and selectivity in various chemical transformations. This makes 2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane particularly useful in the synthesis of complex molecular architectures.

In recent years, there has been a surge in research focusing on the development of novel boronic acid derivatives for pharmaceutical applications. These derivatives are widely used as key intermediates in the synthesis of active pharmaceutical ingredients (APIs) due to their ability to participate in efficient and high-yielding cross-coupling reactions. The chloromethyl group in 2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a versatile handle for further functionalization, allowing chemists to introduce additional substituents and tailor the properties of the resulting compounds.

One of the most notable applications of this compound is in the Suzuki-Miyaura cross-coupling reaction. This reaction is a cornerstone of modern organic synthesis and has been extensively used to construct carbon-carbon bonds in a wide range of molecular frameworks. The boronic acid derivatives derived from 2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane have shown exceptional reactivity with various aryl halides and alkyl halides under palladium catalysis. This property has made it a preferred choice for researchers aiming to synthesize biaryl compounds and other complex organic molecules.

The compound's stability under ambient conditions also makes it an attractive candidate for industrial applications. Unlike some other boronic acid derivatives that require stringent storage conditions or specialized handling procedures, 2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be stored and handled relatively easily. This ease of use translates into cost savings and improved efficiency for pharmaceutical companies and research institutions.

Recent advancements in synthetic methodologies have further expanded the utility of this compound. For instance， researchers have developed novel protocols for the direct functionalization of the tetramethyl-substituted dioxaborolane ring system using transition metal catalysts. These protocols have enabled the synthesis of highly substituted boronic acids that were previously inaccessible through traditional methods. Such innovations are crucial for developing next-generation pharmaceuticals with improved pharmacokinetic properties.

The role of 2-(Chloromethyl)-4,4，5，5-tetramethyl-1，3，2-dioxaborolane extends beyond small-molecule drug synthesis. It has also found applications in materials science， particularly in the development of advanced polymers and coatings. The ability to incorporate boron-containing units into polymer backbones can lead to materials with enhanced thermal stability， mechanical strength， and chemical resistance. These properties are highly desirable for applications ranging from aerospace components to medical implants.

The growing interest in green chemistry has also influenced the use of this compound。 Researchers are increasingly seeking sustainable alternatives to traditional synthetic routes， and organoboron compounds like 2-(Chloromethyl)-4，4，5，5-tetramethyl-1，3，2-dioxaborolane offer several advantages in this context。 They typically participate in high-yielding reactions with minimal waste generation， making them environmentally friendly choices for industrial processes。

In conclusion， 2-(Chloromethyl)-4，4，5，5-tetramethyl-1，3，2-dioxaborolane (CAS No. 83622-42-8) is a multifaceted compound with significant potential in both academic research and industrial applications。 Its unique structural features make it an excellent intermediate for cross-coupling reactions， while its stability and ease of handling make it a practical choice for pharmaceutical synthesis。 As research continues to evolve? it is likely that this compound will play an even greater role in shaping the future of chemical biology and medicinal chemistry。

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