{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-012064b8316844249cac7c9126c4a796","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"2fd5874f8e5f940b450beae46335dcb375be1403b98a92ad618ecd97989ba7e5","doi":"10.1038/nchem.2322","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-c338d03b0084d0f8","route_slugs":["ord-012064b8316844249cac7c9126c4a796-e9552181101c"],"reactant_slugs":["ord-compound-54dbf96d9d8c957125f4"],"product_slugs":["ord-compound-6210b351d632a0c492c4"],"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_598"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=P(C=1C=CC=CC1OC)(C2CCCCC2)C3CCCCC3"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1807481-17-9"}],"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":0.00375,"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":0.375,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC(=CC1C=2N=CC=C(C2)C(C)(C)C)C(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"72914-19-3"}],"amount":{"moles":{"value":0.0075,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=C(C=CC1C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"106-42-3"}],"amount":{"volume":{"value":1.499997,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":16,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=P(C1=CC(=CC=C1OC)B2OC(C)(C)C(O2)(C)C)(C3CCCCC3)C4CCCCC4"},{"type":"CAS_NUMBER","value":"1802340-18-6"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_NMR_1H","type":"YIELD","percentage":{"value":25}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (400 MHz, CDCl3)  1.14-1.19 (m, 4H), 1.21-1.42 (m, 16H), 1.44-1.51 (m, 4H), 1.64-1.68 (m, 4H), 1.80-1.84 (m, 2H), 2.03-2.17 (m, 4H), 3.86 (s, 3H), 6.87 (dd, J = 8.7, 4.7 Hz, 1H), 7.91 (d, J = 8.7 Hz, 1H), 8.36 (d, J = 11.7 Hz, 1H); 13C NMR (100 MHz, CDCl3)  24.9, 25.7 (d, JC-P = 3.8 Hz), 25.9, 26.1 (d, JC-P = 3.8 Hz), 26.6 (d, JC-P = 12.3 Hz), 26.9 (d, JC-P = 14.1 Hz), 36.9 (d, JC-P = 67.7 Hz), 55.1, 83.7, 109.3 (d, JC-P = 6.9 Hz), 118.3 (d, JC-P = 83.8 Hz), 140.1 (d, JC-P = 1.9 Hz), 142.8 (d, JC-P = 3.8 Hz), 161.5 (d, JC-P = 5.6 Hz); 11B NMR (130 MHz, CDCl3)  29.8; 31P NMR (158 MHz, CDCl3)  59.5;"}}},"product_1_NMR_1H":{"type":"NMR_1H","details":"NMR_1H"}}}],"provenance":{"doi":"10.1038/nchem.2322"}}},"entities":[{"slug":"ord-compound-54dbf96d9d8c957125f4","name":"C19H29O2P · ORD YCZKCFRODVOYJS-UHFFFAOYSA-N","smiles":"COc1ccccc1P(=O)(C1CCCCC1)C1CCCCC1","inchi":"InChI=1S/C19H29O2P/c1-21-18-14-8-9-15-19(18)22(20,16-10-4-2-5-11-16)17-12-6-3-7-13-17/h8-9,14-17H,2-7,10-13H2,1H3","formula":"C19H29O2P"},{"slug":"ord-compound-6210b351d632a0c492c4","name":"C25H40BO4P · ORD WPGGMTJJIAWJKM-UHFFFAOYSA-N","smiles":"COc1ccc(B2OC(C)(C)C(C)(C)O2)cc1P(=O)(C1CCCCC1)C1CCCCC1","inchi":"InChI=1S/C25H40BO4P/c1-24(2)25(3,4)30-26(29-24)19-16-17-22(28-5)23(18-19)31(27,20-12-8-6-9-13-20)21-14-10-7-11-15-21/h16-18,20-21H,6-15H2,1-5H3","formula":"C25H40BO4P"}],"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-c338d03b0084d0f8","title":"Literature experiment — 10.1038/nchem.2322","source_type":"paper","doi":"10.1038/nchem.2322","url":"https://doi.org/10.1038/nchem.2322","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"]}