Basic information
- CAS
134-81-6- Standard SMILES
O=C(C(=O)c1ccccc1)c1ccccc1- InChIKey
WURBFLDFSFBTLW-UHFFFAOYSA-N- Molecular formula
- C14H10O2
- Average molar mass
- 210.23 g/mol
- Monoisotopic mass
- 210.06807956
Overview
Benzil is an alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively. It is an alpha-diketone and an aromatic ketone.
Names & identifiers
- Preferred name
- Benzil
- IUPAC
- 1,2-diphenylethane-1,2-dione
- English name
- Benzil
- Molecular formula
- C14H10O2
- Molecular weight
- 210.23
Names & synonyms
BENZIL134-81-6DibenzoylDiphenylethanedioneDiphenylglyoxal1,2-Diphenylethane-1,2-dioneBibenzoyl1,2-Diphenylethanedionediphenylethane-1,2-dioneDiphenyldiketon1,2-ethanedione, 1,2-diphenyl-DTXSID3044380
Show more names
β-diketone DiphenylethanedioneBenzilForSynthesisCHC-12Wy 20910
Diphenyl-alpha,beta-diketoneEsacure KBOWY-20910NSC-4041NSC-220315S85X61172JDTXCID1024380CHEBI:51507
Database identifiers
- CAS
134-81-6- PubChem CID
- 8651
- DTXSID
DTXSID3044380- ChEMBL
CHEMBL189886- ChEBI
CHEBI:51507- UNII
- S85X61172J
- EC Number
- 205-157-0
- Nikkaji
- J5.599I
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 34.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 230
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Aromatic Ketones
Industrial compound
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP3.38
Physical DescriptionYellow solid; [Merck Index] Yellow crystalline solid; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 94 · 94-95 °C(lit.)
- Boiling point
- 346 °C · 346 °C
- Density
- 1 · 1,521 g/cm3
- vapor pressure
- 1 mm · 1 mm Hg ( 128.4 °C)
- refractive index
- 1.5681 · 1.5681 (estimate)
- Flash point
- 346 · 346-348°C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 0.5 g/l · <0.5g/l
- form
- Crystalline Powder
- color
- White
- Water Solubility
- 0.5 g/L · 0.5 g/L (20 ºC)
- Merck
- 14 · 14,1078
- BRN
- 608047 · 608047
- Henry's Law Constant
- 3 · 3.0×101 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
- Dielectric constant
- 13 · 13.0(94℃)
- Stability
- Stable. Combustible. Incompatible with strong oxidizing agents.
- InChI
- 1S/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H
- InChIKey
- WURBFLDFSFBTLW-UHFFFAOYSA-N
- SMILES
- O=C(c1ccccc1)C(=O)c2ccccc2
- CAS DataBase Reference
- 134 · 134-81-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 85 X61172J · S85X61172J
- NIST Chemistry Reference
- Ethanedione, diphenyl-(134-81-6)
- EPA Substance Registry System
- Benzil (134-81-6)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 2 · 2
- RTECS
- 1925000 · DD1925000
- F
- 10 · 10
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29143900 · 29143900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2
- Toxicity
- 50 orally · LD50 orally in Rabbit: 2710 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.2% (1 of 593) of reports.
Warning
H315 (99.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 593 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Ethanedione, diphenyl-
Status: Active Update: 20-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/28193
Benzil: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA moderate eye irritant; Causes somnolence in oral lethal-dose studies of mice; [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS] See Acetophenone.
Hazard Classes and CategoriesSkin Irrit. 2 (99.7%)
Safety data
- F
- 10
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- DD1925000
- hs_code
- 29143900
- Toxicity
- LD50 orally in Rabbit: 2710 mg/kg
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
Chemistry & industry
Uses & manufacturing
UsesUsed in organic syntheses; [Merck Index]
General Manufacturing Information1,2-Ethanedione, 1,2-diphenyl-: ACTIVE
Applications
DescriptionBenzil (134-81-6) also known as 1,2-diphenylethane-1,2-dione is an organic compound with the molecular formula (C6H5CO)2. The compound belongs to the group of organic compounds known as stilbenes which contains a 1,2-diphenylethylene moiety. Benzyl is yellow in color and is one of the most common diketones.
UsesBenzil is used as a pharmaceutical intermediate and uv curing resin photosensitizer. In polymer chemistry, it is used as a photoinitiator. Further, it serves as a potent inhibitor of human carboxylesterases. It is used in the preparation of diketimines by reacting with amines. It is also involved in the famous benil-benzilic acid rearrangement. In addition this, it reacts with 1,3-diphenylacetone to get tetraphenylcyclopentadienone.
Preparation methods
PreparationBenzyl is synthesized from benzoin, for instance with copper (II) acetate. PhC(O)CH(OH)Ph + 2 Cu2+ → PhC(O)C(O)Ph + 2 H+ + 2 Cu+
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
55 records
Compound notes
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