{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-1b73a405c8194ffc886473eef2273b6c","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"b3df148bf2d7521cf58484cc18d92151611812cba5f07a893fded5a1bdfac5fd","doi":"10.1021/acscatal.0c00152","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-59e635a9a70cfa17","route_slugs":["ord-1b73a405c8194ffc886473eef2273b6c-ee56adf5d264"],"reactant_slugs":["tetrahydrofuran"],"product_slugs":["ord-compound-006b4ec86eb18eb8ec43"],"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_6"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"ClC1=C2C=CC=3C(Cl)=C(C=NC3C2=NC=C1C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"2222101-72-4"}],"amount":{"moles":{"value":0.008501292,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"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":0.16999921,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1CCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"109-99-9"}],"amount":{"moles":{"value":4.437,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":100,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":48,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)C2COCC2"},{"type":"CAS_NUMBER","value":"331958-90-8"}],"measurements":[{"analysis_key":"product_1_GC","type":"YIELD","percentage":{"value":23}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_GC":{"type":"GC","details":"GC"}}}],"provenance":{"doi":"10.1021/acscatal.0c00152"}}},"entities":[{"slug":"tetrahydrofuran","name":"Tetrahydrofuran","smiles":"C1CCOC1","inchi":"InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2","formula":"C4H8O"},{"slug":"ord-compound-006b4ec86eb18eb8ec43","name":"C10H19BO3 · ORD KEBDNHHRQNZXMA-UHFFFAOYSA-N","smiles":"CC1(C)OB(C2CCOC2)OC1(C)C","inchi":"InChI=1S/C10H19BO3/c1-9(2)10(3,4)14-11(13-9)8-5-6-12-7-8/h8H,5-7H2,1-4H3","formula":"C10H19BO3"}],"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-59e635a9a70cfa17","title":"Literature experiment — 10.1021/acscatal.0c00152","source_type":"paper","doi":"10.1021/acscatal.0c00152","url":"https://doi.org/10.1021/acscatal.0c00152","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"]}
