Production Method 1

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: (T-4)-Trihydro(tetrahydrofuran)boron Solvents: Tetrahydrofuran ;  0 °C → rt; 3 h, rt; overnight, rt; rt → 0 °C
1.2 Reagents: Water ;  cooled

Reference

Preparation of N-substituted triazolamines as inhibitors of indoleamine 2,3-dioxygenase

, World Intellectual Property Organization, , ,

Production Method 2

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  15 min, cooled
1.2 Reagents: Boron trifluoride etherate ;  15 min; 1 h, 60 °C
1.3 Reagents: Methanol ;  overnight, rt

Reference

Substitution-Controlled Selective Formation of Hexahydrobenz[e]isoindoles and 3-Benzazepines via In(OTf)3-Catalyzed Tandem Annulations

Xing, Siyang ; Gu, Nan; Wang, Xin; Liu, Jingyi; Xing, Chunyan; et al, Organic Letters, 2018, 20(18), 5680-5683

Production Method 3

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: Borane Solvents: Tetrahydrofuran ;  8 h, 40 °C
1.2 Reagents: Methanol ;  0 °C

Reference

Azolopyrimidine derivatives as selective inhibitors of protein arginine methyltransferase 5 (PRMT5) and their preparation

, World Intellectual Property Organization, , ,

Production Method 4

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: (T-4)-Trihydro(tetrahydrofuran)boron Solvents: Tetrahydrofuran ;  rt → 0 °C; 0 °C; 2 h, 0 °C → rt
1.2 Reagents: Water

Reference

Cyclic sulfonamide derivatives as monoamine reuptake inhibitors, their preparation, pharmaceutical compositions, and use in therapy

, World Intellectual Property Organization, , ,

Production Method 5

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: (T-4)-Trihydro(tetrahydrofuran)boron Solvents: Tetrahydrofuran ;  0 °C; 4 h, 25 °C
1.2 Reagents: Methanol ;  0 °C

Reference

Preparation of spiro-sulfonamide derivatives as inhibitors of myeloid cell leukemia-1 (MCL-1) protein for the treatment of cancer

, World Intellectual Property Organization, , ,

Production Method 6

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  30 min, rt; 15 min, rt
1.2 Reagents: Boron trifluoride etherate ;  30 min, 25 - 35 °C; 1 h, rt; rt → 0 °C
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Preparation of phenylalanine 4-phenylpiperidinamide derivatives as melanocortin-4 receptor modulators

, World Intellectual Property Organization, , ,

Production Method 7

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  5 min, 0 °C; 18 h, 0 °C → 25 °C

Reference

Preparation of substituted heterocyclic aryl-alkyl-aryl compounds as thrombin inhibitors

, World Intellectual Property Organization, , ,

Production Method 8

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: (T-4)-Trihydro(tetrahydrofuran)boron Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 1 h, rt
1.2 Reagents: Water ;  rt

Reference

Preparation of pyridopyrimidinyl compounds useful in the treatment of cancer

, World Intellectual Property Organization, , ,

Production Method 9

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: Borane Solvents: Tetrahydrofuran ;  8 h, 40 °C
1.2 Reagents: Methanol ;  0 °C

Reference

Preparation of nucleoside analogs as selective inhibitors of protein arginine methyltransferase 5 (PRMT5)

, World Intellectual Property Organization, , ,

Production Method 10

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: Borane Solvents: Tetrahydrofuran ;  8 h, 40 °C
1.2 Reagents: Methanol ;  0 °C

Reference

Azolopyrimidine derivatives as selective inhibitors of protein arginine methyltransferase 5 and their preparation

, World Intellectual Property Organization, , ,

Production Method 11

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  30 min, 0 °C; 1.5 h, reflux
1.2 Reagents: Sodium sulfate Solvents: Water ;  10 min

Reference

Intramolecular Aerobic Ring Expansion of Cyclic Ketone: A Mild Method for the Synthesis of Medium-Sized Lactones and Macrolactones

Liang, Qi-Ming; Zheng, Jing-Yun; Lu, Si-Yuan; Wang, Hong-Mei; Luo, Lu; et al, Advanced Synthesis & Catalysis, 2022, 364(13), 2152-2156

Production Method 12

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: Borane Solvents: Tetrahydrofuran ;  15 min, 0 °C; 0 °C → 23 °C; 3 h, 23 °C
1.2 Reagents: Methanol ,  Water ;  0 °C

Reference

Boron insertion into alkyl ether bonds via zinc/nickel tandem catalysis

Lyu, Hairong ; Kevlishvili, Ilia ; Yu, Xuan ; Liu, Peng ; Dong, Guangbin, Science (Washington, 2021, 372(6538), 175-182

Production Method 13

1342212-97-8

947614-94-0

Reaction Conditions

1.1 Reagents: 9-Borabicyclo[3.3.1]nonane Solvents: Tetrahydrofuran ;  rt; 12 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  0 °C; 1 h, 0 °C
1.3 Reagents: Hydrogen peroxide Solvents: Water ;  0 °C
1.4 Reagents: Sodium thiosulfate Solvents: Water

Reference

Enantioselective Construction of Spiro Quaternary Carbon Stereocenters via Pd-Catalyzed Intramolecular α-Arylation

Wu, Ting; Kang, Xuehua; Bai, Heng; Xiong, Wenrui; Xu, Guangqing; et al, Organic Letters, 2020, 22(12), 4602-4607

Production Method 14

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: Boron trifluoride etherate ,  Sodium borohydride Solvents: Tetrahydrofuran ;  overnight, reflux; reflux → rt
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Intramolecular Homolytic Substitution Enabled by Photoredox Catalysis: Sulfur, Phosphorus, and Silicon Heterocycle Synthesis from Aryl Halides

Garrido-Castro, Alberto F. ; Salaverri, Noelia; Maestro, M. Carmen ; Aleman, Jose, Organic Letters, 2019, 21(13), 5295-5300

Production Method 15

81682-38-4

947614-94-0

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  30 min, rt; 15 min, rt
1.2 Reagents: Boron trifluoride etherate ;  30 min, 25 - 35 °C; 1 h, rt; rt → 0 °C
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Preparation of 1-(2-amino-3-phenylpropanoyl)-4-phenylpiperidine derivatives as melanocortin-4 receptor modulators

, World Intellectual Property Organization, , ,

2-(2-bromo-5-chlorophenyl)ethan-1-ol Raw materials

• 2-(2-bromo-5-chlorophenyl)acetic acid
• 1-bromo-4-chloro-2-ethenylbenzene

2-(2-bromo-5-chlorophenyl)ethan-1-ol Preparation Products

• 2-(2-bromo-5-chlorophenyl)ethan-1-ol (947614-94-0)

• 1. An aptamer-based keypad lock system?
  Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang Wang Chem. Commun., 2012,48, 802-804
• 2. An alumina stabilized graphene oxide wrapped SnO2 hollow sphere LIB anode with improved lithium storage?
  Xiang Liu,Qian Sun,A. B. Djuri?i?,Maohai Xie,Baohu Dai,Jinyao Tang,Charles Surya,Changzhong Liao,Kaimin Shih RSC Adv., 2015,5, 100783-100789
• 3. An ion-exchange method for determining paraquat residues in food crops
  Analyst, 1965,90, 99-106
• 4. Alumina coating on 5 V lithium cobalt fluorophosphate cathode material for lithium secondary batteries – synthesis and electrochemical properties?
  S. Amaresh,K. Karthikeyan,K. J. Kim,Y. S. Lee RSC Adv., 2014,4, 23107-23115
• 5. An astrophysically-relevant mechanism for amino acid enantiomer enrichment
  Stephen P. Fletcher,Richard B. C. Jagt,Ben L. Feringa Chem. Commun., 2007, 2578-2580

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Chlorobenzenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Chlorobenzenes

2-(2-Bromo-5-Chlorophenyl)ethan-1-ol: A Comprehensive Overview

The compound CAS No. 947614-94-0, commonly referred to as 2-(2-bromo-5-chlorophenyl)ethan-1-ol, is a highly specialized organic molecule with significant applications in various fields of chemistry. This compound is characterized by its unique structure, which includes a bromine atom at the 2-position and a chlorine atom at the 5-position of the phenyl ring, along with a hydroxyl group attached to an ethane chain. The combination of these functional groups makes it a versatile compound with potential uses in pharmaceuticals, agrochemicals, and advanced materials.

Recent studies have highlighted the importance of 2-(2-bromo-5-chlorophenyl)ethan-1-ol in the development of novel therapeutic agents. Researchers have explored its ability to act as a precursor in the synthesis of bioactive compounds, particularly those with anti-inflammatory and anti-cancer properties. The bromine and chlorine substituents on the phenyl ring contribute to the molecule's reactivity, making it an ideal candidate for various substitution reactions. These reactions can lead to the formation of derivatives with enhanced pharmacological activities.

In addition to its role in drug discovery, CAS No. 947614-94-0 has also been investigated for its potential in agrochemical applications. The compound's ability to inhibit certain enzymes involved in plant growth regulation has been a focal point of recent research. By modifying the substituents on the phenyl ring, scientists have been able to create derivatives with improved selectivity and efficacy, which could be used as pesticides or growth regulators in agriculture.

The synthesis of 2-(2-bromo-5-chlorophenyl)ethan-1-ol involves a multi-step process that typically begins with the bromination and chlorination of an aromatic ring. The subsequent introduction of the hydroxyl group requires precise control over reaction conditions to ensure optimal yields and purity. Advanced techniques such as catalytic hydrogenation and nucleophilic substitution have been employed to achieve these goals, with recent advancements in catalysis further improving the efficiency of these processes.

From a structural standpoint, the compound exhibits interesting electronic properties due to the electron-withdrawing effects of both bromine and chlorine atoms. These properties make it a valuable tool in the study of electron transfer mechanisms and redox reactions. Recent experiments have demonstrated its potential as an intermediate in the synthesis of conducting polymers, which are widely used in electronics and energy storage devices.

In conclusion, CAS No. 947614-94-0, or 2-(2-bromo-5-chlorophenyl)ethan-1-ol, is a compound with diverse applications and promising research opportunities. Its unique structure and reactivity continue to attract attention from chemists across various disciplines, making it a key player in modern chemical research.

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