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Record W1610004497 · doi:10.1002/047084289x.rn00661

2-Fluorophenylboronic Acid

2006· reference-entry· en· W1610004497 on OpenAlexaff
Peter D. Wilson, Michael P. A. Lyle

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2006
Typereference-entry
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsSimon Fraser University
Fundersnot available
KeywordsChemistryReagentHydrochloric acidRecrystallization (geology)Nuclear chemistryHydrolysisOrganic chemistryInorganic chemistry

Abstract

fetched live from OpenAlex

[1993-03-9] C6H6BFO2 (MW 139.92) InChI = 1S/C6H6BFO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H InChIKey = QCSLIRFWJPOENV-UHFFFAOYSA-N (a reagent and substrate that is used to prepare chiral nonracemic P,N-ligands and Lewis acids, it is also commonly employed in palladium-catalyzed Suzuki coupling reactions) Physical Data: mp 101–110 °C (contains varying amounts of the anhydride). Solubility: soluble in water (sparingly) and most organic solvents. Form Supplied in: white crystalline solid. Analysis of Reagent Purity: HPLC, IR, NMR. Preparative Methods: ortho-lithiation of fluorobenzene with sec-butyllithium in tetrahydrofuran at −78 °C, treatment with trimethyl borate (−78 °C to room temperature), and subsequent hydrolysis.1 2-Fluorophenylboronic acid can also be prepared from 1-bromo-2-fluorobenzene [transmetallation with n-butyllithium at −78 °C, treatment with trimethyl borate (2 equiv, −78 °C to room temperature), and subsequent hydrolysis with 1 M hydrochloric acid] in good yield (80%) on recrystallization from boiling water.2 Purification: recrystallization from ether or water.1, 2 Handling, Storage, and Precautions: the compound should be handled with protective gloves and eyewear in a ventilated area. The compound is stable but care should be taken to avoid contact with strong oxidizing agents. Decomposition products include carbon monoxide, carbon dioxide, boron oxides, and hydrogen fluoride.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Dataset · Consensus signal: none
Teacher disagreement score0.017
Threshold uncertainty score0.058

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0010.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0170.010

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.013
GPT teacher head0.250
Teacher spread0.237 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designNot applicable
Domainnot available
GenreDataset

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

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Citations0
Published2006
Admission routes1
Has abstractyes

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