{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-5e7f3eae47f147d3b723e00940fd0e6d","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"7addc60409ccf2254bdb8937c818009bcfe94109811a5abc7ef0acf0cd41286e","doi":"10.1021/ja0428309","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-365ae2bd8446aa8c","route_slugs":["ord-5e7f3eae47f147d3b723e00940fd0e6d-2ad08dab8575","ord-5e7f3eae47f147d3b723e00940fd0e6d-e63d902c1f1f"],"reactant_slugs":["ord-compound-f380d2bb65f4a1d1065e"],"product_slugs":["ord-compound-d2485a682d9385282dbf","ord-compound-7ecbcf1ef6b1d8ecf301"],"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_1259"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N#CC1=CC=C(Br)C=C1F"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"105942-08-3"}],"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":"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"}]},"reagent_2":{"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":2,"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":3.000003,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":9,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N#CC=1C(F)=CC(Br)=CC1B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"863868-38-6"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":81}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"N#CC=1C=C(B2OC(C)(C)C(O2)(C)C)C(Br)=CC1F"},{"type":"CAS_NUMBER","value":"863868-55-7"}],"measurements":[{"analysis_key":"product_2_UNKNOWN","type":"YIELD","percentage":{"value":4}}],"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 (major isomer) 7.77 (d, J = 1.7 Hz, 1H), 7.44 (dd, 2 J H-F = 8.3 Hz, J = 1.7 Hz, 1H), 1.35 (br s, 12H), (minor isomer) 7.90 (d, 3 J H-F = 7.5 Hz, 1H), 7.42 (d, 2 J H-F = 8.5 Hz, 1H), 1.35 (br s, 12H); 13C NMR {1H} (CDCl3, 75 MHz): δ (major isomer) 163.3 (d, 1 J C-F =262.8 Hz, C3), 134.6 (d, 4 J C-F = 4 Hz, C6), 127.8 (d, 3 J C-F = 8 Hz, C5), 122 (d, 2 J C-F =23 Hz, C4), 112.9 (nitrile, C1), 104.6 (d, 2 J C-F = 14.1 Hz, C2), 85.4, 24.7; 11B NMR (CDCl3, 96 MHz): δ 29.94; 19F NMR (CDCl3, 282 MHz): δ (major isomer) -103.9 (d, J = 7.9 Hz);"}}},"product_2_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"}}}],"provenance":{"doi":"10.1021/ja0428309"}}},"entities":[{"slug":"ord-compound-f380d2bb65f4a1d1065e","name":"1-bromo,3-fluoro,4-cyanobenzene","smiles":"N#Cc1ccc(Br)cc1F","inchi":"InChI=1S/C7H3BrFN/c8-6-2-1-5(4-10)7(9)3-6/h1-3H","formula":"C7H3BrFN"},{"slug":"ord-compound-d2485a682d9385282dbf","name":"C13H14BBrFNO2 · ORD CVVZEHHIEWRAAA-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2cc(Br)cc(F)c2C#N)OC1(C)C","inchi":"InChI=1S/C13H14BBrFNO2/c1-12(2)13(3,4)19-14(18-12)10-5-8(15)6-11(16)9(10)7-17/h5-6H,1-4H3","formula":"C13H14BBrFNO2"},{"slug":"ord-compound-7ecbcf1ef6b1d8ecf301","name":"C13H14BBrFNO2 · ORD FAGYMAOSACMWSQ-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2cc(C#N)c(F)cc2Br)OC1(C)C","inchi":"InChI=1S/C13H14BBrFNO2/c1-12(2)13(3,4)19-14(18-12)9-5-8(7-17)11(16)6-10(9)15/h5-6H,1-4H3","formula":"C13H14BBrFNO2"}],"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-365ae2bd8446aa8c","title":"Literature experiment — 10.1021/ja0428309","source_type":"paper","doi":"10.1021/ja0428309","url":"https://doi.org/10.1021/ja0428309","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"]}