Basic information
- Standard SMILES
COC(=O)C(=O)Cl- InChIKey
ZXUQEPZWVQIOJE-UHFFFAOYSA-N- Molecular formula
- C3H3ClO3
- Average molar mass
- 122.51 g/mol
- Monoisotopic mass
- 121.97707164
Names & identifiers
- Preferred name
- Methyl chloroglyoxylate
- IUPAC
- methyl 2-chloro-2-oxoacetate
- English name
- METHYL OXALYL CHLORIDE
- Molecular formula
- C3H3ClO3
- Molecular weight
- 122.51
Names & synonyms
5781-53-3Methyl chlorooxoacetateMethyl chloroglyoxylateMethyl oxalyl chloridemethyl 2-chloro-2-oxoacetateAcetic acid, chlorooxo-, methyl esterChloroglyoxylic Acid Methyl Estermethoxalyl chloride42Z6XG83RQAcetic acid, 2-chloro-2-oxo-, methyl esterEINECS 227-307-4DTXSID9064003
Show more names
MONO-METHYL OXALYL CHLORIDEMethyl Oxalyl ChorideMethyl chlorooxoacetate 96%Oxalyl chloride MonoMethyl esterKelex-103orocarbonyL
RefChem:817673DTXCID3042269227-307-4Methyl (Chlorocarbonyl)formatemethyl 2-chloro-2-oxo-acetatemethyl chloro(oxo)acetateMFCD00000705Methyloxalylchloride
Database identifiers
- CAS
5781-53-3- PubChem CID
- 79846
- DTXSID
DTXSID9064003- UNII
- 42Z6XG83RQ
- EC Number
- 227-307-4
- Nikkaji
- J218.045F
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 98.4
Experimental & physicochemical properties
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
Physicochemical properties
- Boiling point
- 118 · 118-120 °C (lit.)
- Density
- 1.332 g/mL · 1.332 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.419(lit.)
- Flash point
- 116 °F · 116 °F
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- Chloroform (Slightly), Ethyl Acetate
- form
- Liquid
- color
- Clear
- Odor
- Acrid
- Water Solubility
- Miscible with water.
- Sensitive
- Moisture Sensitive
- BRN
- 1071541 · 1071541
- Stability
- Hygroscopic
- InChI
- 1S/C3H3ClO3/c1-7-3(6)2(4)5/h1H3
- InChIKey
- ZXUQEPZWVQIOJE-UHFFFAOYSA-N
- SMILES
- COC(=O)C(Cl)=O
- CAS DataBase Reference
- 5781 · 5781-53-3(CAS DataBase Reference)
- FDA UNII
- 42 Z6XG83RQ · 42Z6XG83RQ
- EPA Substance Registry System
- Acetic acid, chlorooxo-, methyl ester (5781-53-3)
- UNSPSC Code
- 12352101 · 12352101
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 226 · H226-H314-H335
- Precautionary statements
- 210 · P210-P233-P240-P280-P303+P361+P353-P305+P351+P338
- target organs
- Respiratory system
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C,F
- Risk Statements
- 34 · 34-37-10-36-14
- Safety Statements
- 26 · 26-36/37/39-45-16
- RIDADR
- 2920 · UN 2920 8/PG 2
- WGK Germany
- 3 · 3
- F
- 9 · 9-21
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29171900 · 29171900
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 1 Flam · Eye Dam. 1Flam. Liq. 3Skin Corr. 1BSTOT SE 3
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 26-11-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/22282
Chloroglyoxylic acid methyl ester: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesFlam. Liq. 3 (100%)
Safety data
- F
- 9-21
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2920 8/PG 2
- hs_code
- 29171900
- risk_code
- 34-37-10-36-14
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS07
- hazard_code
- C,F
- safety_code
- 26-36/37/39-45-16
- hazard_class
- 8
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H226-H314-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Dam. 1Flam. Liq. 3Skin Corr. 1BSTOT SE 3
- Precautionary statements
- P210-P233-P240-P280-P303+P361+P353-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationAcetic acid, 2-chloro-2-oxo-, methyl ester: ACTIVE
Applications
UsesMethyl oxalyl chloride is an important organic intermediate (building block) to synthetize substituted methyl oxalyl products. It can be used for regioselective synthesis of fused coumarins, cyclization to form substituted isoxazoles and heterocycles, intramolecular Wittig reactions, silyl enol ether acylation, and iron-mediated cleavage of C-C bonds.
UsesMethyl oxalyl chloride is used as a synthetic reagent. It serves as a reagent in the synthesis of fused coumarins, substituted isoxazoles and heterocycles. Further, it is used in intramolecular Wittig reactions, and iron-mediated cleavage of C-C bonds.
UsesReactant involved in:Regioselective synthesis of fused coumarinsCyclization to form substituted isoxazoles and heterocyclesIntramolecular Wittig reactionsSilyl enol ether acylationIron-mediated cleavage of C-C bonds
Upstream & downstream products
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Related reactions
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