{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0337d2f5f87247f795d864efbda2616b","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"fc632a170dd3dcc5dc22d6169de3948f6365244dcb286d1da3f50167da4558a9","doi":"10.1038/nchem.2322","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-c338d03b0084d0f8","route_slugs":["ord-0337d2f5f87247f795d864efbda2616b-8f6aa1cc047b","ord-0337d2f5f87247f795d864efbda2616b-8e4349aec7e4"],"reactant_slugs":["ord-compound-904116342bf822866a9d"],"product_slugs":["ord-compound-1e2f9d3f06120835fad1","ord-compound-fc35c704f58f3deafe53"],"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_536"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(C=1C=CC=CC1Cl)N(CCCCCC)CCCCCC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"544690-16-6"}],"amount":{"moles":{"value":0.25,"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":0.00375,"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":0.0075,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"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":0.375,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=C(C=CC1C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"106-42-3"}],"amount":{"volume":{"value":1.499997,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":16,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(C1=CC(=CC=C1Cl)B2OC(C)(C)C(O2)(C)C)N(CCCCCC)CCCCCC"},{"type":"CAS_NUMBER","value":"1802339-76-9"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_NMR_1H","type":"YIELD","percentage":{"value":38}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"O=C(C1=CC=C(C=C1Cl)B2OC(C)(C)C(O2)(C)C)N(CCCCCC)CCCCCC"},{"type":"CAS_NUMBER","value":"1802339-77-0"}],"measurements":[{"analysis_key":"product_2_UNKNOWN","type":"YIELD","percentage":{"value":61}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (400 MHz, CDCl3)  (meta isomer) 0.80 (t, J = 7.2 Hz, 3H), 0.91 (t, J = 6.7 Hz, 3H), 1.08-1.19 (m, 6H), 1.25-1.61 (m, 20H), 1.63-1.69 (m, 2H), 2.98-3.12 (m, 2H), 3.28-3.34 (m, 1H), 3.64-3.70 (m, 1H), 7.36 (d, J = 8.5 Hz, 1H), 7.69 (s, 1H), 7.70 (d, J = 8.5 Hz, 1H), (para isomer) 0.81 (t, J = 7.2 Hz, 3H), 0.90 (t, J = 6.5 Hz, 3H), 1.07-1.20 (m, 6H), 1.25-1.51 (m, 20H), 1.65-1.67 (m, 2H), 2.98-3.12 (m, 2H), 3.19-3.26 (m, 1H), 3.71-3.79 (m, 1H), 7.25 (d, J = 7.6 Hz, 1H), 7.69 (d, J = 7.6 Hz, 1H), 7.80 (s, 1H); 13C NMR (100 MHz, CDCl3)  (meta isomer) 14.1, 14.2, 22.5, 22.8, 24.8, 26.3, 26.9, 27.4, 28.4, 31.3, 31.8, 44.7, 48.5, 84.3, 129.0, 133.5, 134.3, 136.0, 136.4, 168.2, (para isomer) 14.1, 14.2, 22.5, 22.8, 25.0, 26.4, 26.9, 27.3, 28.4, 31.4, 31.8, 44.6, 48.5, 84.3, 127.4, 132.2, 133.1, 135.7, 139.3, 168.1; 11B NMR (130 MHz, CDCl3)  (meta isomer) 32.1, (para isomer) 30.2"}}},"product_2_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"product_1_NMR_1H":{"type":"NMR_1H","details":"NMR_1H"}}}],"provenance":{"doi":"10.1038/nchem.2322"}}},"entities":[{"slug":"ord-compound-904116342bf822866a9d","name":"C19H30ClNO · ORD YLXJZILDBRLBMT-UHFFFAOYSA-N","smiles":"CCCCCCN(CCCCCC)C(=O)c1ccccc1Cl","inchi":"InChI=1S/C19H30ClNO/c1-3-5-7-11-15-21(16-12-8-6-4-2)19(22)17-13-9-10-14-18(17)20/h9-10,13-14H,3-8,11-12,15-16H2,1-2H3","formula":"C19H30ClNO"},{"slug":"ord-compound-1e2f9d3f06120835fad1","name":"C25H41BClNO3 · ORD PHYXVXPMWYMQNW-UHFFFAOYSA-N","smiles":"CCCCCCN(CCCCCC)C(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccc1Cl","inchi":"InChI=1S/C25H41BClNO3/c1-7-9-11-13-17-28(18-14-12-10-8-2)23(29)21-19-20(15-16-22(21)27)26-30-24(3,4)25(5,6)31-26/h15-16,19H,7-14,17-18H2,1-6H3","formula":"C25H41BClNO3"},{"slug":"ord-compound-fc35c704f58f3deafe53","name":"C25H41BClNO3 · ORD CSRGKUUWZMFRCJ-UHFFFAOYSA-N","smiles":"CCCCCCN(CCCCCC)C(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1Cl","inchi":"InChI=1S/C25H41BClNO3/c1-7-9-11-13-17-28(18-14-12-10-8-2)23(29)21-16-15-20(19-22(21)27)26-30-24(3,4)25(5,6)31-26/h15-16,19H,7-14,17-18H2,1-6H3","formula":"C25H41BClNO3"}],"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-c338d03b0084d0f8","title":"Literature experiment — 10.1038/nchem.2322","source_type":"paper","doi":"10.1038/nchem.2322","url":"https://doi.org/10.1038/nchem.2322","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"]}