Basic information
- CAS
3282-32-4- Standard SMILES
[N-]=[N+]=CC(=O)c1ccccc1- InChIKey
ZSTBZBURMWJKSQ-UHFFFAOYSA-N- Molecular formula
- C8H6N2O
- Average molar mass
- 146.15 g/mol
Names & identifiers
- Preferred name
- Diazoacetophenone
- IUPAC
- 2-diazo-1-phenylethanone
- English name
- Diazoacetylbenzene
- Molecular formula
- C8H6N2O
- Molecular weight
- 146.15
Names & synonyms
Diazoacetophenone2-Diazo-1-phenylethanone3282-32-4Phenyl diazomethyl ketone2-DiazoacetophenoneDiazomethyl phenyl ketoneEthanone, 2-diazo-1-phenyl-ACETOPHENONE, 2-DIAZO-NSC 25280BRN 16361224-07-00-02133 (Beilstein Handbook Reference)RefChem:132758
Show more names
α-DiazoacetophenoneNsc25280Benzoyldiazomethanea-Diazoacetophenone
Ethanone, 2-diazo-1-phenyl-(9CI)ZSTBZBURMWJKSQ-UHFFFAOYSA-NDiazoacetylbenzene2-Diazo-1-phenylethan-1-onealpha-Diazoacetophenone.alpha.-Diazoacetophenone.omega.-Diazoacetophenone2-diazo-1-phenyl-ethanone
Database identifiers
- CAS
3282-32-4- PubChem CID
- 18667
- DTXSID
DTXSID80954476- Nikkaji
- J2.294.264F、J80.679J
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 19.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 188
Experimental & physicochemical properties
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Physicochemical properties
- Melting point
- 49 °C · 49 °C
- Boiling point
- 265.75 °C · 265.75°C (rough estimate)
- Density
- 1.2312 · 1.2312 (rough estimate)
- refractive index
- 1.49 · 1.4900 (estimate)
- solubility
- sol ether, THF; slightly sol pentane.
- form
- rods
- color
- pale yellow
- EWG's Food Scores
- 1 · 1
Chemistry & industry
Applications
Usesα-Diazoacetophenone is used as a precursor to carbenes and carbenoids; reagent for preparation of sulfonium, oxonium, and pyridinium ylides; 1,3 dipole for heterocycle synthesis; reagent for Lewis acid or transition metal-mediated insertion reactions; reagent for cyclopropanation of alkenes and for aromatic annulation.
Preparation methods
PreparationPreparative Methods of α-Diazoacetophenone: an improved method of synthesis of diazo ketones has been recently published, via acylation of the lithium enolate of the ketone with 2,2,2-Trifluoroethyl Trifluoroacetate and subsequent reaction with Methanesulfonyl Azide. [1] Alternatively, acylation of diazomethane with aroyl chlorides in the presence of triethylamine provides a general method for the synthesis of aromatic diazo ketones.[2]
Upstream & downstream products
Downstream products
Suppliers2 total
上海凯米莱铂生物科技有限公司18116465878 · [email protected]
烟台盛凯伦化学科技有限公司开发区第一分公司13356901049 · [email protected]
Related reactions
13 records
Compound notes
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