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2-(Trimethylsilyl)ethanethiol

2010· reference-entry· en· W4238134259 on OpenAlexaff
Adrian L. Schwan, Bruno Bernet

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2010
Typereference-entry
Languageen
FieldChemistry
TopicAnalytical Chemistry and Chromatography
Canadian institutionsUniversity of Guelph
Fundersnot available
KeywordsChemistryEthanethiolReagentTrimethylsilylAcetic acidThiolOrganic chemistrySolubility

Abstract

fetched live from OpenAlex

[18143-30-1] C5H14SSi (MW 134.32) InChI = 1S/C5H14SSi/c1-7(2,3)5-4-6/h6H,4-5H2,1-3H3 InChIKey = BCOLNMGFOWHFNI-UHFFFAOYSA-N (reagent used as a monoprotected sulfide dianion equivalent for the two-step installation of a divalent sulfur atom into organic molecules) Physical Data: bp 144–146 °C [52–54 °C (25 Torr)]; d 0.850. Solubility: soluble in MeOH, CH2Cl2, THF, and most organic solvents. Form Supplied in: liquid from major research chemical suppliers at a cost of ca. US$60/g (7.4 mmol) of 97% pure material. Analysis of Reagent Purity: GC. Preparative Methods: the high commercial cost of 2-(trimethylsilyl)ethanethiol necessitates methods for its lab scale synthesis. The radical addition of thiolacetic acid to vinyltrimethylsilane occurs thermally to afford a 9:1 ratio of regioisomers, the 1- and 2-(trimethylsilyl)ethyl thiolesters of acetic acid (eq 1).2, 3 Photochemical initiation may improve the ratio of regioisomers obtained.4 Purification of the thiolacetate by careful fractional distillation should be performed prior to conversion to the thiol in order to ensure high purity. The conversion to thiol is best performed with LAH3 or methanolic K2CO3,2 but ammonolysis may also be suitable.5 Saponification with KOH in water/ethanol is slightly less efficient.4 Direct radical addition of liquid H2S to vinyl trimethylsilane has been demonstrated, but the procedure is low-yielding and inconvenient.4 (1) Purification: distillation. Handling, Storage, and Precautions: the thiol possesses a strong unpleasant aroma that combines the characteristic olfactory features of thiol and low molecular weight silane. As a thiol, the reagent is incompatible with oxygen, base, and common oxidants. Distillation should be carried out with care since uncontrollable frothing may occur under reduced pressure, even with vigorous stirring.

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 score0.279
Threshold uncertainty score0.999

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 science0.0010.000
Research integrity0.0030.001
Insufficient payload (model declined to judge)0.0350.000

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 head0.246
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".

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Citations0
Published2010
Admission routes1
Has abstractyes

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