Basic information
- Standard SMILES
O=C(Cl)C(=O)Cl- InChIKey
CTSLXHKWHWQRSH-UHFFFAOYSA-N- Molecular formula
- C2Cl2O2
- Average molar mass
- 126.92 g/mol
- Monoisotopic mass
- 125.9275346
Names & identifiers
- Preferred name
- Oxalyl chloride
- IUPAC
- oxalyl dichloride
- English name
- Oxalyl chloride
- Molecular formula
- C2Cl2O2
- Molecular weight
- 126.93
Names & synonyms
Oxalyl chlorideOxalyl dichloride79-37-8Ethanedioyl dichlorideOxalic dichlorideOxaloyl chlorideOxalic acid dichlorideOxalic acid chlorideEthanedioyl chlorideR4Y96317DWDTXSID3058822RefChem:6088
Show more names
Oxalylformyl chlorideOCCOXOxalic chlorideOCN
DTXCID0048137201-200-2oxalylchlorideFaropenem Impurity 9MFCD00000704(COCl)2EINECS 201-200-2C2Cl2O2
Database identifiers
- CAS
79-37-8- PubChem CID
- 65578
- DTXSID
DTXSID3058822- UNII
- R4Y96317DW
- EC Number
- 201-200-2
- Nikkaji
- J3.842C
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 34.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 75.5
Experimental & physicochemical properties
Chemical ClassesToxic Gases & Vapors -> Acid Halides
SpringerMaterials PropertiesSchoenflies notation
Density1.4785 @ 20°C
Boiling Point63.5 °C @760 [mm Hg]
Melting Point-16 °C
Vapor Pressure150.0 [mmHg]
Physical Description
Liquid
Colorless fuming liquid with a penetrating odor; [Merck Index]
Physicochemical properties
- Melting point
- -10 · -10--8 °C (lit.)
- Boiling point
- 62 · 62-65 °C (lit.)
- Density
- 1.5 g/mL · 1.5 g/mL at 20 °C (lit.)
- vapor density
- 4.4 · 4.4 (vs air)
- vapor pressure
- 150 mm · 150 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.429(lit.)
- Flash point
- 176 · 176-178°C
- storage temp.
- Store Cold
- solubility
- Chloroform (Soluble), Ethyl Acetate
- form
- Liquid
- color
- 0 · APHA: 0-150
- Odor
- penetrating odor
- Water Solubility
- reacts
- Decomposition
- 176 · 176-178 ºC
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,6914
- BRN
- 1361988 · 1361988
- Dielectric constant
- 3.5 · 3.5(21℃)
- Stability
- Stable. Incompatible with bases, alcohols, steel, oxidizing agents, alkali metals. Moisture sensitive. Reacts violently with water, liberating toxic gas.
- InChI
- 1S/C2Cl2O2/c3-1(5)2(4)6
- InChIKey
- CTSLXHKWHWQRSH-UHFFFAOYSA-N
- SMILES
- ClC(=O)C(Cl)=O
- CAS DataBase Reference
- 79 · 79-37-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 Y96317DW · R4Y96317DW
- NIST Chemistry Reference
- Oxalyl chloride(79-37-8)
- EPA Substance Registry System
- Ethanedioyl dichloride (79-37-8)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 331 · H331-H314
- Precautionary statements
- 501 · P501-P261-P271-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P233-P405
- PPE
- Faceshields, Gloves, Goggles
- Hazard Codes
- C,T
- Risk Statements
- 14 · 14-20-29-34-40-23/24/25-37-35-23
- Safety Statements
- 26 · 26-36/37/39-43-45-8-24/25-23-27
- RIDADR
- 2927 · UN 2927 6.1/PG 2
- WGK Germany
- 2 · 2
- RTECS
- 2950000 · KI2950000
- F
- 9 · 9-19-21
- Hazard Note
- Toxic/Corrosive/Store Cold/Lacrymatory
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29171990 · 29171990
- Storage Class
- 4.3 · 4.3 - Hazardous materials which set free flammable gases upon contact with water
- Hazard Classifications
- 3 InhalationAcute · Acute Tox. 3 InhalationAcute Tox. 3 OralEye Dam. 1Skin Corr. 1BWater-react 1
- REACH Registrations
- Active
- Excepted Quantities
- Not Permitted as Excepted Quantity
Safety & regulation
GHS classification
GHS Classification
Danger
H260 (60%): In contact with water releases flammable gases which may ignite spontaneously [Danger Substances and mixtures which in contact with water, emit flammable gases]
P223, P231+P232, P260, P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P330+P331, P302+P335+P334, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P363, P370+P378, P402+P404, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 300 reports by companies from 34 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Ethanedioyl dichloride
Ethanedioyl dichloride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanedioyl dichloride are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 04-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/12537
Oxalyl chloride: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes corneal damage and dyspnea in inhalation lethal-concentration studies of rats; [RTECS] Decomposed violently by water; A severe skin, eye, and respiratory tract irritant; Toxic; [Merck Index] Reacts violently with water evolving toxic gas; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Toxic by inhalation; [Sigma-Aldrich MSDS] See Oxalic acid.
Hazard Classes and CategoriesWater-react. 1 (60%)
CSL Reaction Information
CSL00032
N,N-DIMETHYLFORMAMIDE + OXALYL CHLORIDE
Health Hazard
Harmful,Toxic
Chlorination
Generation of dimethylcarbamoyl chloride (carcinogen). DMCC is also toxic and a severe irritant.
Safety & protection
Protective Action Criteria (PAC)
0.77 [ppm]
8.5 [ppm]
51 [ppm]
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Toxicity DataLC50 (rat) = 1,840 ppm/1hr
Safety data
- F
- 9-19-21
- PPE
- Faceshields, Gloves, Goggles
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- KI2950000
- ridadr
- UN 2927 6.1/PG 2
- hs_code
- 29171990
- risk_code
- 14-20-29-34-40-23/24/25-37-35-23
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06
- hazard_code
- C,T
- hazard_note
- Toxic/Corrosive/Store Cold/Lacrymatory
- safety_code
- 26-36/37/39-43-45-8-24/25-23-27
- hazard_class
- 8
- Storage Class
- 4.3 - Hazardous materials which set free flammable gases upon contact with water
- packing_group
- II
- Hazard statements
- H331-H314
- Excepted Quantities
- Not Permitted as Excepted Quantity
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 InhalationAcute Tox. 3 OralEye Dam. 1Skin Corr. 1BWater-react 1
- Precautionary statements
- P501-P261-P271-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P233-P405
Chemistry & industry
Uses & manufacturing
UsesUsed as a chlorinating reagent; [Merck Index]
U.S. Production2022: 22,046 lb
Industry UsesIntermediate
General Manufacturing Information
Pharmaceutical and Medicine Manufacturing
Ethanedioyl dichloride: ACTIVE
Applications
UsesOxalyl Chloride is used in the preparation of cardiolipin analogs which induce peroxidase activity by Cytochrome C. It is also used in the preparation of fluorescent indicators for cytosolic calcium.
General DescriptionOxalyl chloride is a commonly used chlorinating reagent that can be prepared by the reaction of oxalic acid and phosphorus pentachloride.
Preparation methods
PreparationOxalyl chloride was first prepared in 1892 by the French chemist Adrien Fauconnier, who reacted diethyl oxalate with phosphorus pentachloride. Oxalyl chloride is also produced commercially from ethylene carbonate. Photochlorination gives the tetrachloride, which is subsequently degraded:C2H4O2CO + 4 Cl2 → C2Cl4O2CO + 4 HClC2Cl4O2CO → C2O2Cl2 + COCl2
Upstream & downstream products
Upstream raw materials
Downstream products
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