{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-18a75699f8fc40179e3bebc6eaa44775","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"5f0824b0bd3ce7491133a0f277164e2b6f2880f319d8edcc484f605094d5a6a8","doi":"10.1039/c2sc20776a","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-78c7181f4410dadf","route_slugs":["ord-18a75699f8fc40179e3bebc6eaa44775-6b71edcbc66c","ord-18a75699f8fc40179e3bebc6eaa44775-51c4da492a9d"],"reactant_slugs":["ord-compound-2082267ad403fbfa6f3c"],"product_slugs":["ord-compound-466c3dbf87e6d6bea818","ord-compound-0ab13611f93ba338f522"],"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_682"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(C=1C=CC=CC1Cl)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"2142-68-9"}],"amount":{"moles":{"value":4,"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":0.06,"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":0.12,"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":4.8,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O(C)C(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1634-04-4"}],"amount":{"volume":{"value":3.0000007,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"notes":{"procedure_details":"General  procedure  C  was  applied  to  2-(2-chlorophenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane15k(96 mg,  0.4  mmol).  The  reaction  mixture was  stirredat  room  temperature for  16hours giving  a  conversion  of >99%  (GCMS)  and  monoborylated  products  (16k+zzarising  from  trace  chlorobenzene  impurity  in  the reaction mixture)and 17k in a84:16mixture (1H NMR spectrum)."},"outcomes":[{"reaction_time":{"value":16,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(C1=CC=C(C=C1Cl)B2OC(C)(C)C(O2)(C)C)C"},{"type":"CAS_NUMBER","value":"1417036-32-8"}],"measurements":[{"analysis_key":"product_1_NMR_1H","type":"YIELD","percentage":{"value":84}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"O=C(C1=CC(=CC=C1Cl)B2OC(C)(C)C(O2)(C)C)C"},{"type":"CAS_NUMBER","value":"1417036-33-9"}],"measurements":[{"analysis_key":"product_2_UNKNOWN","type":"YIELD","percentage":{"value":16}}],"reaction_role":"PRODUCT"}],"analyses":{"product_2_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"product_1_NMR_1H":{"type":"NMR_1H","details":"NMR_1H"}}}],"provenance":{"doi":"10.1039/c2sc20776a"}}},"entities":[{"slug":"ord-compound-2082267ad403fbfa6f3c","name":"C8H7ClO · ORD ZDOYHCIRUPHUHN-UHFFFAOYSA-N","smiles":"CC(=O)c1ccccc1Cl","inchi":"InChI=1S/C8H7ClO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,1H3","formula":"C8H7ClO"},{"slug":"ord-compound-466c3dbf87e6d6bea818","name":"C14H18BClO3 · ORD OJZIJXVVLUQHKL-UHFFFAOYSA-N","smiles":"CC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1Cl","inchi":"InChI=1S/C14H18BClO3/c1-9(17)11-7-6-10(8-12(11)16)15-18-13(2,3)14(4,5)19-15/h6-8H,1-5H3","formula":"C14H18BClO3"},{"slug":"ord-compound-0ab13611f93ba338f522","name":"C14H18BClO3 · ORD URNQTFVMOQZYIA-UHFFFAOYSA-N","smiles":"CC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccc1Cl","inchi":"InChI=1S/C14H18BClO3/c1-9(17)11-8-10(6-7-12(11)16)15-18-13(2,3)14(4,5)19-15/h6-8H,1-5H3","formula":"C14H18BClO3"}],"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-78c7181f4410dadf","title":"Literature experiment — 10.1039/c2sc20776a","source_type":"paper","doi":"10.1039/c2sc20776a","url":"https://doi.org/10.1039/c2sc20776a","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"]}