{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-170551bb44624a89b40eae81aa3c6036","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"8303b2519fe207a50a550a2eb5a92f11380e61200f4d701afe486f148bdab675","doi":"10.1021/jacs.0c05434","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-94f4664d96137ccc","route_slugs":["ord-170551bb44624a89b40eae81aa3c6036-c1490cd90426"],"reactant_slugs":["ord-compound-5b76e5a5cf0e9450159f"],"product_slugs":["ord-compound-0c3897100695e00e15fa"],"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_161"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Ni](=C1N(C=CN1C=2C(=CC(=CC2C)C)C)C=3C(=CC(=CC3C)C)C)=C4N(C=CN4C=5C(=CC(=CC5C)C)C)C=6C(=CC(=CC6C)C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"155519-31-6"}],"amount":{"moles":{"value":0.02,"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":0.3,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"FC=1C=CC=2C=CNC2C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"399-51-9"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"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":2,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":4,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"FC=1C=CC2=C(C1)NC=C2B3OC(C)(C)C(O3)(C)C"},{"type":"CAS_NUMBER","value":"1691201-28-1"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_MS","type":"YIELD","percentage":{"value":70}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (500 MHz, CDCl3): δ 8.47 (s, 1H), 7.98-7.95 (m, 1H), 7.61 (d, J = 2 Hz, 1H), 7.07-7.05 (m, 1H), 6.96-6.92 (m, 1H), 1.37 (s, 12H).; 13 C NMR 126 MHz, CDCl3): δ 160.0 (d, J = 238 Hz), 136.6 (d, J = 13 Hz), 134.2 (d, J = 3 Hz), 128.0, 123.3 (d, J = 10 Hz), 109.2 (d, J = 24 Hz), 97.2 (d, J = 26 Hz), 83.0, 24.9; 11 B NMR (160 MHz, CDCl3): δ 30.3.; 19 F NMR (471 MHz, CDCl3): δ -121.0- -121.1 (m, 1F)."}}},"product_1_MS":{"type":"MS","details":"MS"}}}],"provenance":{"doi":"10.1021/jacs.0c05434"}}},"entities":[{"slug":"ord-compound-5b76e5a5cf0e9450159f","name":"C8H6FN · ORD YYFFEPUCAKVRJX-UHFFFAOYSA-N","smiles":"Fc1ccc2cc[nH]c2c1","inchi":"InChI=1S/C8H6FN/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5,10H","formula":"C8H6FN"},{"slug":"ord-compound-0c3897100695e00e15fa","name":"C14H17BFNO2 · ORD WBMUILOQZNJVBY-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2c[nH]c3cc(F)ccc23)OC1(C)C","inchi":"InChI=1S/C14H17BFNO2/c1-13(2)14(3,4)19-15(18-13)11-8-17-12-7-9(16)5-6-10(11)12/h5-8,17H,1-4H3","formula":"C14H17BFNO2"}],"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-94f4664d96137ccc","title":"Literature experiment — 10.1021/jacs.0c05434","source_type":"paper","doi":"10.1021/jacs.0c05434","url":"https://doi.org/10.1021/jacs.0c05434","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"]}