{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-7e7df91f5c16474cbf653dc44bbbf6e2","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"ab71b3fcf0055e4c7f0bf7ff7f9d924d9c66103d47e56233ed0543d54d40de29","doi":"10.1021/jacs.7b02232","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-a17f83d783de9635","route_slugs":["ord-7e7df91f5c16474cbf653dc44bbbf6e2-3a7c1c2ca70e"],"reactant_slugs":["4-methylphenol"],"product_slugs":["ord-compound-c1b3b4ad781237175a62"],"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_374"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C1CCCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"110-82-7"}],"amount":{"volume":{"value":3.000003,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"OC1=CC=C(C=C1)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"106-44-5"}],"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":0.03,"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":0.7,"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":1.1,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_3":{"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":0.06,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"OC1=CC=C(C=C1B2OC(C)(C)C(O2)(C)C)C"},{"type":"CAS_NUMBER","value":"1398414-30-6"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":85}}],"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 (500 MHz, CDCl3): δH 7.66 (s, 1H), 7.42 (d, J = 1.5 Hz, 1H), 7.20 (dd, J = 8.5, 2.0 Hz, 1H), 6.81 (d, J = 8.5 Hz, 1H), 2.27 (s, 3H), 1.38 (s, 12H).; 13 C NMR (125 MHz, CDCl3): δC 161.5, 135.6, 134.6, 128.5, 115.3, 84.4, 24.8, 20.3.; 11 B NMR (160 MHz, CDCl3): δB 31.0 (br. s)."}}}}}],"provenance":{"doi":"10.1021/jacs.7b02232"}}},"entities":[{"slug":"4-methylphenol","name":"4-Methylphenol","smiles":"CC1=CC=C(C=C1)O","inchi":"InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3","formula":"C7H8O"},{"slug":"ord-compound-c1b3b4ad781237175a62","name":"C13H19BO3 · ORD QUYCGOSWQMOXCJ-UHFFFAOYSA-N","smiles":"Cc1ccc(O)c(B2OC(C)(C)C(C)(C)O2)c1","inchi":"InChI=1S/C13H19BO3/c1-9-6-7-11(15)10(8-9)14-16-12(2,3)13(4,5)17-14/h6-8,15H,1-5H3","formula":"C13H19BO3"}],"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-a17f83d783de9635","title":"Literature experiment — 10.1021/jacs.7b02232","source_type":"paper","doi":"10.1021/jacs.7b02232","url":"https://doi.org/10.1021/jacs.7b02232","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"]}