{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-569e06f9c9914e7fa68d69361f4213d5","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"fdf043eb95f2fb33cacfd9731e9032ad1fdff73ee45b4cef8351db2646155399","doi":"10.1021/jacs.6b06144","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-3ce10f8854c66bd4","route_slugs":["ord-569e06f9c9914e7fa68d69361f4213d5-80662ea2171d"],"reactant_slugs":["toluene"],"product_slugs":["ord-compound-c57d6b6b57a5cbd43cea"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lit_pub_bo_311"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Co+3]12(P(C(C)C)(C(C)C)CC3=N2C(=CC(=C3)C)CP1(C(C)C)C(C)C)[BH-]1OC(C(O1)(C)C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1978314-72-5"}],"amount":{"moles":{"value":0.0275,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"73183-34-3"}],"amount":{"moles":{"value":0.55,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=CC(=CC1)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"108-88-3"}],"amount":{"moles":{"value":0.55,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1CCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"109-99-9"}],"amount":{"volume":{"value":1,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":43,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)C2=CC=CC(=C2)C"},{"type":"CAS_NUMBER","value":"253342-48-2"}],"measurements":[{"analysis_key":"product_1_GC","type":"YIELD","percentage":{"value":27}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_GC":{"type":"GC","details":"GC"}}}],"provenance":{"doi":"10.1021/jacs.6b06144"}}},"entities":[{"slug":"toluene","name":"Toluene","smiles":"CC1=CC=CC=C1","inchi":"InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3","formula":"C7H8"},{"slug":"ord-compound-c57d6b6b57a5cbd43cea","name":"C13H19BO2 · ORD XDKYCZBGHPGKEP-UHFFFAOYSA-N","smiles":"Cc1cccc(B2OC(C)(C)C(C)(C)O2)c1","inchi":"InChI=1S/C13H19BO2/c1-10-7-6-8-11(9-10)14-15-12(2,3)13(4,5)16-14/h6-9H,1-5H3","formula":"C13H19BO2"}],"dataset":{"dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","name":"Borylation dataset from Roche","description":"Borylation reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":1111,"path":"data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","sha256":"e01a389cac3e6cce5746ef54dbe6b8d3040d764f987b1fc13790f5aeff5598fa","bytes":210626,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet"},"publication":{"slug":"ord-publication-3ce10f8854c66bd4","title":"Literature experiment — 10.1021/jacs.6b06144","source_type":"paper","doi":"10.1021/jacs.6b06144","url":"https://doi.org/10.1021/jacs.6b06144","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}