{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-e6314e92965a4736956197783bb8498a","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"485bb746a505786fb67c3d9cd1e4a32b9d869aa1f0ad5f6c288be510ca431f20","doi":"10.1021/jacs.5b02052","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-a35bcbac4ad4cb0a","route_slugs":["ord-e6314e92965a4736956197783bb8498a-70d4f3bd76f9"],"reactant_slugs":["ord-compound-e247ef8f79fe4a293ccf"],"product_slugs":["ord-compound-595778aa51f6b4ca32d2"],"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_167"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"ClC=1C=CC=CC1Cl"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"95-50-1"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Ir+]1234([O-][Ir+]567([O-]1)C1=C7CCC5=C6CC1)C1=C4CCC2=C3CC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"118657-60-6"}],"amount":{"moles":{"value":0.0075,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O(C1=CC=CC(=C1C=2C(OC)=CC=CC2P(C=3C=C(C=C(C3)C)C)C=4C=C(C=C(C4)C)C)P(C=5C=C(C=C(C5)C)C)C=6C=C(C=C(C6)C)C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1000172-57-5"}],"amount":{"moles":{"value":0.015,"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":0.5,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"CCCCCC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"110-54-3"}],"amount":{"volume":{"value":1,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":85,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":20,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"ClC1=CC=C(C=C1Cl)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"401797-02-2"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":87}}],"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 (600 MHz, CDC13) δ 7.87 (d,J =1.8 Hz, 1H), 7.60 (dd,J =7.8, 1.2 Hz, 1H), 7.44 (d,J =7.8 Hz, 1H), 13.4 (s, 12H); 13 C NMR (150 MHz, CDC13) δ 136.5, 135.4, 133.7,132.1, 130.0, 129.1, 84.3, 24.8;"}}}}}],"provenance":{"doi":"10.1021/jacs.5b02052"}}},"entities":[{"slug":"ord-compound-e247ef8f79fe4a293ccf","name":"C6H4Cl2 · ORD RFFLAFLAYFXFSW-UHFFFAOYSA-N","smiles":"Clc1ccccc1Cl","inchi":"InChI=1S/C6H4Cl2/c7-5-3-1-2-4-6(5)8/h1-4H","formula":"C6H4Cl2"},{"slug":"ord-compound-595778aa51f6b4ca32d2","name":"C12H15BCl2O2 · ORD DTAZBCNEXKOLPE-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2ccc(Cl)c(Cl)c2)OC1(C)C","inchi":"InChI=1S/C12H15BCl2O2/c1-11(2)12(3,4)17-13(16-11)8-5-6-9(14)10(15)7-8/h5-7H,1-4H3","formula":"C12H15BCl2O2"}],"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-a35bcbac4ad4cb0a","title":"Literature experiment — 10.1021/jacs.5b02052","source_type":"paper","doi":"10.1021/jacs.5b02052","url":"https://doi.org/10.1021/jacs.5b02052","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"]}