{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-164577140edc436c99d9264e80008fb8","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"e723b176971986f0a2dfd3b9989255ee7122e69599025b0ba292ae4730bda3b7","doi":"10.1002/anie.201909786","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-deab9cf6453a0eba","route_slugs":["ord-164577140edc436c99d9264e80008fb8-d8a8b582d67d"],"reactant_slugs":["ord-compound-cf4d17f9648f6de7fe4c"],"product_slugs":["ord-compound-48a511982dc4b2069b39"],"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_926"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"OC(C)(C)C(O)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"76-09-5"}],"amount":{"moles":{"value":0.525,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"BrB(Br)Br"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"10294-33-4"}],"amount":{"moles":{"value":0.33,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(N1C=CC=2C=CC=CC21)C(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"70957-04-9"}],"amount":{"moles":{"value":0.15,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":16,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(N1C=CC=2C=CC=C(B3OC(C)(C)C(O3)(C)C)C21)C(C)(C)C"},{"type":"CAS_NUMBER","value":"2376879-92-2"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":65}}],"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 (400 MHz, CDCl3) δ 7.65 (d, J = 3.9 Hz, 1H), 7.51 (dd, J = 7.7, 1.2 Hz, 1H), 7.46 – 7.42 (m, 1H), 7.31 – 7.25 (m, 1H), 6.62 (d, J = 3.9 Hz, 1H), 1.52 (s, 9H), 1.45 (s, 12H); 13 C NMR (101 MHz, CDCl3) δ 177.4, 138.2, 129.7, 128.2, 124.7, 124.2, 121.1, 110.3, 83.1, 40.8, 28.8, 25.7.; 11 B NMR (128 MHz, CDCl3) δ 25.99."}}}}}],"provenance":{"doi":"10.1002/anie.201909786"}}},"entities":[{"slug":"ord-compound-cf4d17f9648f6de7fe4c","name":"C13H15NO · ORD DTRSVKLNWUNCQE-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)n1ccc2ccccc21","inchi":"InChI=1S/C13H15NO/c1-13(2,3)12(15)14-9-8-10-6-4-5-7-11(10)14/h4-9H,1-3H3","formula":"C13H15NO"},{"slug":"ord-compound-48a511982dc4b2069b39","name":"C19H26BNO3 · ORD DEWYSULLSQVBJV-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)n1ccc2cccc(B3OC(C)(C)C(C)(C)O3)c21","inchi":"InChI=1S/C19H26BNO3/c1-17(2,3)16(22)21-12-11-13-9-8-10-14(15(13)21)20-23-18(4,5)19(6,7)24-20/h8-12H,1-7H3","formula":"C19H26BNO3"}],"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-deab9cf6453a0eba","title":"Literature experiment — 10.1002/anie.201909786","source_type":"paper","doi":"10.1002/anie.201909786","url":"https://doi.org/10.1002/anie.201909786","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"]}