{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-08ddf5ec2e6a40b3acf143be724c313b","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"69b7f3647684d74ebfaf0701be84686226e0b17a85c4be53fe1913b0a1f4b221","doi":"10.1021/jacs.6b13346","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-361e4a9249924ae7","route_slugs":["ord-08ddf5ec2e6a40b3acf143be724c313b-49e5d8fca829"],"reactant_slugs":["ord-compound-7cb210f74436aafabf5d"],"product_slugs":["ord-compound-cfe141bf5e1fac6ee666"],"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_358"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(OCC)C=1C=CC=C(F)C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"451-02-5"}],"amount":{"moles":{"value":0.17,"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":0.0017,"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":0.17,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC=CC1OC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1628-89-3"}],"amount":{"moles":{"value":0.0034,"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":1,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":16,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OCC)C1=CC=C(B2OC(C)(C)C(O2)(C)C)C(F)=C1"},{"type":"CAS_NUMBER","value":"851334-92-4"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_NMR_1H","type":"YIELD","percentage":{"value":8}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (500 MHz, CDCl3, 23 °C): δ 7.78-7.76 (m, 2H), 7.64 (d, J = 9.84 Hz, 1H), 4.35 (q, J = 7.36 Hz, 2H), 1.36 (t, J = 7.46 Hz, 3H), 1.33 (s, 12H).; 13 C NMR (126 MHz, CDCl3, 23 °C): δ 166.85 (d, J = 251.81 Hz), 165.47 (d, J = 2.93 Hz), 136.87 (d, J = 7.96 Hz), 135.19 (d, J = 8.24 Hz), 124.45 (d, J = 3.37 Hz), 116.16 (d, J = 26.74 Hz), 84.32, 61.45, 24.85, 14.29.; 11 B NMR (96 MHz, CDCl3, 23 °C): δ 29.82 (br s).; 19 F NMR (282 MHz, CDCl3, 23 °C): δ -102.37."}}},"product_1_NMR_1H":{"type":"NMR_1H","details":"NMR_1H"}}}],"provenance":{"doi":"10.1021/jacs.6b13346"}}},"entities":[{"slug":"ord-compound-7cb210f74436aafabf5d","name":"C9H9FO2 · ORD SMMIKBXLEWTSJD-UHFFFAOYSA-N","smiles":"CCOC(=O)c1cccc(F)c1","inchi":"InChI=1S/C9H9FO2/c1-2-12-9(11)7-4-3-5-8(10)6-7/h3-6H,2H2,1H3","formula":"C9H9FO2"},{"slug":"ord-compound-cfe141bf5e1fac6ee666","name":"C15H20BFO4 · ORD ZXSGWPHDXQZIAF-UHFFFAOYSA-N","smiles":"CCOC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)c(F)c1","inchi":"InChI=1S/C15H20BFO4/c1-6-19-13(18)10-7-8-11(12(17)9-10)16-20-14(2,3)15(4,5)21-16/h7-9H,6H2,1-5H3","formula":"C15H20BFO4"}],"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-361e4a9249924ae7","title":"Literature experiment — 10.1021/jacs.6b13346","source_type":"paper","doi":"10.1021/jacs.6b13346","url":"https://doi.org/10.1021/jacs.6b13346","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"]}