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Record W4235531869 · doi:10.1002/047084289x.rn01239

1,1′-Binaphthyl-2-[di(<i>tert</i>)-butyl]phosphine

2011· reference-entry· en· W4235531869 on OpenAlexaff
Christian Eidamshaus, Jason D. Burch

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2011
Typereference-entry
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsMerck Canada Inc. (Canada)
Fundersnot available
KeywordsPhosphineReagentChemistryRecrystallization (geology)SolubilityPalladiumMagnesiumNuclear chemistryMedicinal chemistryCatalysisOrganic chemistry

Abstract

fetched live from OpenAlex

[255836-67-0] C28H31P (MW 398.52) InChI = 1S/C28H31P/c1-27(2,3)29(28(4,5)6)25-19-18-21-13-8-10-16-23(21)26(25)24-17-11-14-20-12-7-9-15-22(20)24/h7-19H,1-6H3 InChIKey = QGBQGMHXBSLYLZ-UHFFFAOYSA-N (reagent used as ligand in palladium-catalyzed CO, CN, and CC bond forming reactions) Physical Data: mp 147–149 °C. Solubility: soluble in most organic solvents. Form Supplied in: white crystalline solid, commercially available. Analysis of Reagent Purity: 1H and 31P NMR. Purification: typically used as obtained from commercial sources. Preparative Method: 1,1′-binaphthyl-2-[di(tert)-butyl]phosphine 1 is synthesized from 2-bromo-1,1′-binaphthyl. Treatment with magnesium turnings and subsequent transmetalation with CuCl followed by phosphinylation with di-tert-butylchlorophosphine provides pure 1 after recrystallization from ethanol (eq 1).3 (1) Handling, Storage, and Precautions: moderately stable under aerobic conditions. Long-term storage under argon or nitrogen atmosphere is recommended. Irritating to skin, eyes, and mucous membrane. Long-term effects are unknown.

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 distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.003
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Research integrity, Insufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: Not applicable
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.231
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.003
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0020.001
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0020.000
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0230.001

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 head0.019
GPT teacher head0.252
Teacher spread0.233 · 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 teacher head, not a consensus.

Study designNot applicable
Domainnot available
GenreOther

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".

Quick stats

Citations0
Published2011
Admission routes1
Has abstractyes

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