{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-2c33c866d4e348449996e934f2708a85","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"7269bbb487fdaf6ec7ef7c8c39ce9497249a69ef08885dec742665b5f6b891c2","doi":"10.1021/ja0631652","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-3566c7a64f4eff0d","route_slugs":["ord-2c33c866d4e348449996e934f2708a85-f1dbd7fed1ad"],"reactant_slugs":["ord-compound-1e4ef582cfcb5c80c098"],"product_slugs":["ord-compound-677128261c10f5bec511"],"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_228"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"ClC=1C=CC=2NC(=CC2C1)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1075-35-0"}],"amount":{"moles":{"value":1,"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":0.015,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1BOC(C)(C)C1(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"25015-63-8"}],"amount":{"moles":{"value":1.5,"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":0.03,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"CCCCCC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"110-54-3"}],"amount":{"volume":{"value":3.000003,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":20,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"ClC1=CC=2C=C(NC2C(=C1)B3OC(C)(C)C(O3)(C)C)C"},{"type":"CAS_NUMBER","value":"919119-60-1"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":91}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (CDCl3, 500 MHz): δ 8.82 (br s, 1 H, Ha), 7.55 (d, J= 1.9 Hz, 1 H, Hc/d), 7.49 (d, J= 1.9 Hz, 1 H, Hc/d), 6.14 (m, 1 H, Hb), 2.47 (d, J =0.7 Hz, 3 H, CH3), 1.39 (br s, 12 H, CH3 of BPin); 13C NMR {1H} (CDCl3, 75 MHz): δ 139.7 (C), 136.7 (C), 129.5 (C), 127.6 (CH), 125.0 (C), 122.3 (CH), 99.6 (CH), 84.2 (2 C), 25.0 (4 CH3 of BPin), 14.0 (CH3); 11B NMR (CDCl3, 96 MHz): δ 31.0;"}}}}}],"provenance":{"doi":"10.1021/ja0631652"}}},"entities":[{"slug":"ord-compound-1e4ef582cfcb5c80c098","name":"C9H8ClN · ORD WUVWAXJXPRYUME-UHFFFAOYSA-N","smiles":"Cc1cc2cc(Cl)ccc2[nH]1","inchi":"InChI=1S/C9H8ClN/c1-6-4-7-5-8(10)2-3-9(7)11-6/h2-5,11H,1H3","formula":"C9H8ClN"},{"slug":"ord-compound-677128261c10f5bec511","name":"C15H19BClNO2 · ORD CZGYEJPYWNMRCD-UHFFFAOYSA-N","smiles":"Cc1cc2cc(Cl)cc(B3OC(C)(C)C(C)(C)O3)c2[nH]1","inchi":"InChI=1S/C15H19BClNO2/c1-9-6-10-7-11(17)8-12(13(10)18-9)16-19-14(2,3)15(4,5)20-16/h6-8,18H,1-5H3","formula":"C15H19BClNO2"}],"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-3566c7a64f4eff0d","title":"Literature experiment — 10.1021/ja0631652","source_type":"paper","doi":"10.1021/ja0631652","url":"https://doi.org/10.1021/ja0631652","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"]}