161344-84-9

Basic information

• Product Name: 2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE)
• Synonyms: 2-BUTYL-N,N,N',N'-TETRAMETHYL-1,3,2-DIOXABOROLANE-(4S,5S)-DICARBOXAMIDE;2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE);(4S,5S)-2-BUTYL-N,N,N'N'-TETRAMETHYL-1,3,2-DIOXABOROLANE-4,5-DICARBOXAMIDE;Butylboronic acid N,N,N',N'-tetramethyl-D-tartaric acid diamide ester, 97%;2-Butyl-1,3,2-dioxaborolane-4S,5S-dicarboxylic;Butylboronic acid N,N,N',N'-tetrameth;2-Butyl-1;2-dioxaborolane-4S
• CAS NO: 161344-84-9
• Molecular Formula: C₁₂H₂₃BN₂O₄
• Molecular Weight: 270.13
• Mol File: 161344-84-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 305-306 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.096 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.4780(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.81±0.40(Predicted)
• CAS DataBase Reference: 2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE)(161344-84-9)
• EPA Substance Registry System: 2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE)(161344-84-9)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 161344-84-9(Hazardous Substances Data)

Usage

Description

2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE), also known as Butylboronic acid N,N,N′,N′-tetramethyl-D-tartaric acid diamide, is a dioxaborolane ligand with significant applications in the field of organic chemistry. It is characterized by its unique chemical structure, which allows it to participate in various chemical reactions and contribute to the synthesis of complex organic compounds.

Uses

Used in Chemical Synthesis:
2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE) is used as a dioxaborolane ligand for the preparation of enantiomerically enriched spiropentanes via zinc-catalyzed cyclopropanation of corresponding hydroxymethylallenes. This application is significant in the synthesis of complex organic molecules with specific stereochemistry, which is crucial for the development of pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE) is used as a key intermediate in the synthesis of 1,2,3-trisubstituted cyclopropane derivatives. These derivatives are important building blocks for the development of various drugs, as they can be incorporated into the molecular structure of pharmaceutical compounds to enhance their biological activity and selectivity.
Used in Glycolipid Synthesis:
2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE) is also used in the synthesis of glycolipids, specifically plakosides A and B, and their derivatives. This application is relevant in the field of natural product chemistry, as glycolipids are known to have various biological activities, including antimicrobial, antiviral, and anticancer properties. The synthesis of these complex molecules using the dioxaborolane ligand can lead to the development of novel therapeutic agents.
Overall, 2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE) plays a vital role in the synthesis of various organic compounds, with applications spanning across the pharmaceutical, chemical, and natural product industries. Its unique chemical properties and versatility make it a valuable tool for researchers and chemists working on the development of new drugs, materials, and other specialty chemicals.

InChI:InChI=1/C12H23BN2O4/c1-6-7-8-13-18-9(11(16)14(2)3)10(19-13)12(17)15(4)5/h9-10H,6-8H2,1-5H3/t9-,10-/m0/s1

Upstream product

• 4426-47-5 butylboronic acid 
• 63126-52-3 (S,S)-(-)-2,3-dihydroxy-N,N,N',N'-tetramethylsuccinamide 
• 92527-13-4 [^(2-)-N,O,O'[2,2'-iminobis[ethanolato]]]-2-butylboron 

Downstream Products

• 1192063-83-4 tert-butyl 4-{(1R,2S)-2-[(2R)-3-(benzyloxy)-2-hydroxy-propyl]cyclopropyl}piperidine-1-carboxylate 
• 89849-80-9 (1S,2R)-1-(tributylstannyl)-2-(hydroxymethyl)cyclopropane 

Relevant articles and documents

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