{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-502144bb24ec47d5a8090f4ed0dbd46e","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"f6925f29a85deeb58c8aac843e8677fdeb5a467f9146c8ff396927df17b54408","doi":"10.1021/ja0428309","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-365ae2bd8446aa8c","route_slugs":["ord-502144bb24ec47d5a8090f4ed0dbd46e-c44c182cf4b2","ord-502144bb24ec47d5a8090f4ed0dbd46e-270c6cd7e352"],"reactant_slugs":["ord-compound-e94d6fd8fffd1a9b8b0c"],"product_slugs":["ord-compound-ea274f313b70a3dd96f3","ord-compound-f971af7d86e254e2c36d"],"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_1260"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N#CC1=CC=C(Cl)C(Cl)=C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"6574-99-8"}],"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":"O1BOC(C)(C)C1(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"25015-63-8"}],"amount":{"moles":{"value":1.5,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"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"}]},"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":18,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N#CC1=CC(Cl)=C(Cl)C=C1B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"863868-39-7"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":72}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"N#CC1=CC(Cl)=C(Cl)C(=C1)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"863868-40-0"}],"measurements":[{"analysis_key":"product_2_UNKNOWN","type":"YIELD","percentage":{"value":17}}],"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) 7.92 (s, 1H), 7.73 (s, 1H), 1.35 (br s, 12H), (minor isomer) 7.84 (d, J = 2 Hz, 1H), 7.74 (d, J = 2 Hz, 1H), 1.35 (br s, 12H); 13C NMR {1H} (CDCl3, 125 MHz): δ (major isomer) 137.7, 137.1, 135.8, 134.8, 116.9, 111.3, 85.3, 24.7, (minor isomer) 142.7, 137.6, 135, 134.3, 116.8, 111.3, 85, 24.7; 11B NMR (CDCl3, 96 MHz): δ 29.9;"}}},"product_2_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"}}}],"provenance":{"doi":"10.1021/ja0428309"}}},"entities":[{"slug":"ord-compound-e94d6fd8fffd1a9b8b0c","name":"C7H3Cl2N · ORD KUWBYWUSERRVQP-UHFFFAOYSA-N","smiles":"N#Cc1ccc(Cl)c(Cl)c1","inchi":"InChI=1S/C7H3Cl2N/c8-6-2-1-5(4-10)3-7(6)9/h1-3H","formula":"C7H3Cl2N"},{"slug":"ord-compound-ea274f313b70a3dd96f3","name":"C13H14BCl2NO2 · ORD USJOSEVEPCTAMO-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2cc(Cl)c(Cl)cc2C#N)OC1(C)C","inchi":"InChI=1S/C13H14BCl2NO2/c1-12(2)13(3,4)19-14(18-12)9-6-11(16)10(15)5-8(9)7-17/h5-6H,1-4H3","formula":"C13H14BCl2NO2"},{"slug":"ord-compound-f971af7d86e254e2c36d","name":"C13H14BCl2NO2 · ORD IJUABOWVAKKDPN-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2cc(C#N)cc(Cl)c2Cl)OC1(C)C","inchi":"InChI=1S/C13H14BCl2NO2/c1-12(2)13(3,4)19-14(18-12)9-5-8(7-17)6-10(15)11(9)16/h5-6H,1-4H3","formula":"C13H14BCl2NO2"}],"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"]}