{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-04774ceac0e04925b547f57d94f715cc","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"940edb61d43b9d076a04ed10e8e396175d2df9103643d933d5491d9052f50cd6","doi":"10.1126/science.aba6146","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-5654f4c17f06289e","route_slugs":["ord-04774ceac0e04925b547f57d94f715cc-b5718e00709f"],"reactant_slugs":["ord-compound-f1608247ad5b08f04425"],"product_slugs":["ord-compound-8a77f7c4301895b320b7"],"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_741"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N1(CCCCC1)CCCCCC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7335-01-5"}],"amount":{"moles":{"value":0.25,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C[OH2+].C[OH2+].C1CC=CCCC=C1.C1CC=CCCC=C1.[Ir].[Ir]"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"12148-71-9"}],"amount":{"moles":{"value":0.00625,"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":0.75,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC=C2C=CC=3C=CC(=NC3C12)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"3002-77-5"}],"amount":{"moles":{"value":0.0125,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C1CCCCCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"292-64-8"}],"amount":{"volume":{"value":0.2,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":100,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":20,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)CCCCCCN2CCCCC2"},{"type":"CAS_NUMBER","value":"2433809-11-9"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":63}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (CDCl3, 500 MHz): δ 3.64 (t, J = 6.5 Hz, 2H), 2.43 (br s, 4H), 2.38–2.30 (m, 2H), 2.25 (brs, 1H), 1.66–1.58 (m, 4H), 1.60–1.50 (m, 4H), 1.48–1.41 (m, 2H), 1.41–1.28 (m, 4H);13C NMR (CDCl3, 150 MHz): δ 62.80, 59.11, 54.44, 32.56, 27.20, 26.36, 25.58, 25.45, 24.28."}}}}}],"provenance":{"doi":"10.1126/science.aba6146"}}},"entities":[{"slug":"ord-compound-f1608247ad5b08f04425","name":"C11H23N · ORD BBYSGWAYRRMWOW-UHFFFAOYSA-N","smiles":"CCCCCCN1CCCCC1","inchi":"InChI=1S/C11H23N/c1-2-3-4-6-9-12-10-7-5-8-11-12/h2-11H2,1H3","formula":"C11H23N"},{"slug":"ord-compound-8a77f7c4301895b320b7","name":"C17H34BNO2 · ORD OIKGNJTWNWQBLW-UHFFFAOYSA-N","smiles":"CC1(C)OB(CCCCCCN2CCCCC2)OC1(C)C","inchi":"InChI=1S/C17H34BNO2/c1-16(2)17(3,4)21-18(20-16)12-8-5-6-9-13-19-14-10-7-11-15-19/h5-15H2,1-4H3","formula":"C17H34BNO2"}],"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-5654f4c17f06289e","title":"Literature experiment — 10.1126/science.aba6146","source_type":"paper","doi":"10.1126/science.aba6146","url":"https://doi.org/10.1126/science.aba6146","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"]}