{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-84938907c6d04c5f8d69938d452761f6","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"8cbca127445d4946c60e8f4f2f62ef8cf4fe54e9d099acbf9f442e2fa39e5c8a","doi":"10.1021/jacs.9b08920","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-4c0d645c9b328ffb","route_slugs":["ord-84938907c6d04c5f8d69938d452761f6-891f2bd6bcff"],"reactant_slugs":["ord-compound-66ae929ab6efc45f09fa"],"product_slugs":["ord-compound-7967c2b4177b681abad3"],"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_436"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=C2C3=C(C1)CCCN3CCC2"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"479-59-4"}],"amount":{"moles":{"value":0.125,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=C(C(=C2C=CC3=C(N=CC(=C3C)C)C12)C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1660-93-1"}],"amount":{"moles":{"value":0.00625,"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":0.125,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"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":0.5,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)C=2C=C3C4=C(C2)CCCN4CCC3"},{"type":"CAS_NUMBER","value":"1262331-13-4"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_NMR_1H","type":"YIELD","percentage":{"value":91}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (500 MHz, CDCl3) δ 7.25 (s, 2H), 3.19–3.16 (m, 4H), 2.74 (t, J = 6.2 Hz, 4H), 1.97–1.91 (m), 1.31 (s, 12H). 13C NMR (126 MHz, CDCl3) δ 145.52, 133.79, 120.38, 83.20, 50.06, 27.63, 24.64, 21.96. 11B NMR (193 MHz, CDCl3) δ 33.81"}}},"product_1_NMR_1H":{"type":"NMR_1H","details":"NMR_1H"}}}],"provenance":{"doi":"10.1021/jacs.9b08920"}}},"entities":[{"slug":"ord-compound-66ae929ab6efc45f09fa","name":"C12H15N · ORD DZFWNZJKBJOGFQ-UHFFFAOYSA-N","smiles":"c1cc2c3c(c1)CCCN3CCC2","inchi":"InChI=1S/C12H15N/c1-4-10-6-2-8-13-9-3-7-11(5-1)12(10)13/h1,4-5H,2-3,6-9H2","formula":"C12H15N"},{"slug":"ord-compound-7967c2b4177b681abad3","name":"C18H26BNO2 · ORD BXNYIZZTFZOUAA-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2cc3c4c(c2)CCCN4CCC3)OC1(C)C","inchi":"InChI=1S/C18H26BNO2/c1-17(2)18(3,4)22-19(21-17)15-11-13-7-5-9-20-10-6-8-14(12-15)16(13)20/h11-12H,5-10H2,1-4H3","formula":"C18H26BNO2"}],"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-4c0d645c9b328ffb","title":"Literature experiment — 10.1021/jacs.9b08920","source_type":"paper","doi":"10.1021/jacs.9b08920","url":"https://doi.org/10.1021/jacs.9b08920","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"]}