Basic information
- Standard SMILES
O=C(Cl)c1ccccc1C(=O)Cl- InChIKey
FYXKZNLBZKRYSS-UHFFFAOYSA-N- Molecular formula
- C8H4Cl2O2
- Average molar mass
- 203.02 g/mol
- Monoisotopic mass
- 201.95883473
Names & identifiers
- Preferred name
- Phthaloyl chloride
- IUPAC
- benzene-1,2-dicarbonyl chloride
- English name
- Phthaloyl dichloride
- Molecular formula
- C8H4Cl2O2
- Molecular weight
- 203.02
Names & synonyms
Phthaloyl dichloridePHTHALOYL CHLORIDE88-95-9o-Phthaloyl dichloridePhthalic chloridePhthalic dichloridePhthalyl chloridePhthalyl dichloridePhthalic acid dichloride1,2-Benzenedicarbonyl dichloride1,2-Bis(chlorocarbonyl)benzene1,2-Phthaloyl dichloride
Show more names
Phthaloyl chloridthaloyl dichlorideo-Phtaloyl chlorideo-Phthalyl chloride
8S64APH24WNSC-44611DTXSID8038691RefChem:863054DTXCID6018691201-869-0benzene-1,2-dicarbonyl chloridebenzene-1,2-dicarbonyl dichloride
Database identifiers
- CAS
88-95-9- PubChem CID
- 6955
- DTXSID
DTXSID8038691- UNII
- 8S64APH24W
- EC Number
- 201-869-0
- Nikkaji
- J4.297H
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 34.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 181
Experimental & physicochemical properties
Chemical ClassesToxic Gases & Vapors -> Acid Halides
SpringerMaterials PropertiesBoiling point
Density1.409 @25 °C
Boiling Point281.1 °C @760 [mm Hg]
Vapor Pressure30 [mm Hg] @47 °C
Physical DescriptionColorless oily liquid; mp = 15-16 deg C; [Merck Index] Colorless or yellow liquid; mp = 6-12 deg C; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 6 · 6-12 °C(lit.)
- Boiling point
- 269 · 269-271 °C(lit.)
- Density
- 1.409 g/mL · 1.409 g/mL at 25 °C(lit.)
- vapor pressure
- 30 mm · 30 mm Hg ( 47 °C)
- refractive index
- 20 · n20/D 1.568(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Miscible with ether.
- form
- Liquid
- color
- Clear yellow
- Water Solubility
- decomposes
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,7375
- BRN
- 608200 · 608200
- Stability
- Moisture Sensitive
- InChI
- 1S/C8H4Cl2O2/c9-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H
- InChIKey
- FYXKZNLBZKRYSS-UHFFFAOYSA-N
- SMILES
- ClC(=O)c1ccccc1C(Cl)=O
- CAS DataBase Reference
- 88 · 88-95-9(CAS DataBase Reference)
- FDA UNII
- 8 S64APH24W · 8S64APH24W
- NIST Chemistry Reference
- 1 · 1,2-Benzenedicarbonyl dichloride(88-95-9)
- EPA Substance Registry System
- 1 · 1,2-Benzenedicarbonyl dichloride (88-95-9)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314-H290
- Precautionary statements
- 501 · P501-P234-P264-P280-P390-P301+P330+P331-P363-P405
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C
- Risk Statements
- 34 · 34
- Safety Statements
- 26 · 26-36/37/39-45
- RIDADR
- 3265 · UN 3265 8/PG 2
- WGK Germany
- 3 · 3
- F
- 21 · 21
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29173980 · 29173980
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 B · Skin Corr. 1B
- REACH Registrations
- Inactive
- Limited Quantities
- 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.4% (1 of 234) of reports.
Danger
H290 (44.9%): May be corrosive to metals [Warning Corrosive to Metals]
P233, P234, P260, P261, P264, P264+P265, P271, P272, P280, P284, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P333+P317, P342+P316, P362+P364, P363, P390, P403, P403+P233, P405, P406, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 234 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1,2-Benzenedicarbonyl dichloride
Status: Active Update: 11-12-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/5306
Phthaloyl dichloride: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryDecomposed by water; [Merck Index] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS] See Benzoyl chloride.
Hazard Classes and CategoriesMet. Corr. 1 (44.9%)
Safety & protection
Protective Action Criteria (PAC)
1.2 [mg/m3]
13 [mg/m3]
79 [mg/m3]
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 21
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 3265 8/PG 2
- hs_code
- 29173980
- risk_code
- 34
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C
- safety_code
- 26-36/37/39-45
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- H314-H290
- Limited Quantities
- 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Inactive
- Hazard Classifications
- Skin Corr. 1B
- Precautionary statements
- P501-P234-P264-P280-P390-P301+P330+P331-P363-P405
Chemistry & industry
Uses & manufacturing
General Manufacturing Information1,2-Benzenedicarbonyl dichloride: ACTIVE
Applications
UsesPhthaloyl chloride is used for the preparation of volatile acid chlorides from the acids. It acts as a trapping agent for the nitrite ion in the fluorodenitration of aromatic substrates with potassium fluoride. It serves as an additive in polymers and fibers to improve the color stability. It is used as an ingredient in ceramic mold binders, as a stabilizer for polymers and in reverse osmosis membranes.
Useso-Phthaloyl Dichloride is used in the phthaloylation of hemicelluloses as an efficient way to improve their lipophilicity and hydrophilicity. Phthaloylation of hemicelluloses is also a key precursor to preparing polysaccharide derivatives.
General Descriptionequilibrium mixture (phthaloyl chloride ~80% and pseudochloride ~10%) both components show equal chemical behaviour
Preparation methods
PreparationSynthesis of phthaloyl dichloride: Mix 148g of phthalic anhydride with 220g of phosphorus pentachloride, heat, gradually increase the temperature to 250°C, escape the phosphorus oxychloride, distill the reaction product under reduced pressure, collect the 131-133°C (1.2-1.33kPa) fraction to obtain 187g of phthaloyl dichloride.
Upstream & downstream products
Downstream products
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Related reactions
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