{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0f68b60183de4d489ba1fadb5f86de76","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"46ff84cb5f9b279b7e546e2693b97bd9aac75b47474b4db3a102a2065b4286d2","doi":"10.1002/anie.201909786","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-deab9cf6453a0eba","route_slugs":["ord-0f68b60183de4d489ba1fadb5f86de76-4e6662f48b42"],"reactant_slugs":["ord-compound-2e8bc68b3c7c0e2aeec4"],"product_slugs":["ord-compound-9fe069fdf48d0716e08b"],"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_923"},{"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(Br)=CC=CC21)C(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1196981-04-0"}],"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":"BrC1=CC=C(B2OC(C)(C)C(O2)(C)C)C=3NC=CC13"},{"type":"CAS_NUMBER","value":"2376880-04-3"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":74}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz, CDCl3) δ 9.35 (s, 1H), 7.49 (d, J = 7.6 Hz, 1H), 7.34 – 7.28 (m, 2H), 6.62 – 6.58 (m, 1H), 1.40 (s, 12H). 13C{H} NMR (101 MHz, CDCl3) δ 141.3, 130. 1, 127.9, 124.8, 122.6, 119.2, 102.5, 84.2, 25.1. 11B NMR (128 MHz, CDCl3) δ 31.06."}}}}}],"provenance":{"doi":"10.1002/anie.201909786"}}},"entities":[{"slug":"ord-compound-2e8bc68b3c7c0e2aeec4","name":"C13H14BrNO · ORD TUCSLJFSOTXKRX-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)n1ccc2c(Br)cccc21","inchi":"InChI=1S/C13H14BrNO/c1-13(2,3)12(16)15-8-7-9-10(14)5-4-6-11(9)15/h4-8H,1-3H3","formula":"C13H14BrNO"},{"slug":"ord-compound-9fe069fdf48d0716e08b","name":"C14H17BBrNO2 · ORD HZJSZZRPDUPDQR-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2ccc(Br)c3cc[nH]c23)OC1(C)C","inchi":"InChI=1S/C14H17BBrNO2/c1-13(2)14(3,4)19-15(18-13)10-5-6-11(16)9-7-8-17-12(9)10/h5-8,17H,1-4H3","formula":"C14H17BBrNO2"}],"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"]}