Fumaryl chloride
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Basic information
- CAS
627-63-4- Standard SMILES
O=C(Cl)/C=C/C(=O)Cl- InChIKey
ZLYYJUJDFKGVKB-OWOJBTEDSA-N- Molecular formula
- C4H2Cl2O2
- Average molar mass
- 152.96 g/mol
- Monoisotopic mass
- 151.94318466
Overview
Fumaryl chloride appears as a straw colored fuming liquid with a pungent odor. Vapors irritate the eyes and mucous membranes. Corrosive to metals and tissue.
Names & identifiers
- Preferred name
- Fumaryl chloride
- IUPAC
- (E)-but-2-enedioyl dichloride
- English name
- Fumaryl chloride
- Molecular formula
- C4H2Cl2O2
- Molecular weight
- 152.96
Names & synonyms
FUMARYL CHLORIDE627-63-4Fumaroyl dichlorideFumaroyl chlorideFumarylchloridfumaryl dichlorideChlorure de fumaryle2-Butenedioyl dichloride, (E)-2-Butenedioyl dichloride, (2E)-Dichlorid kyseliny fumaroveTL 189Fumaric acid dichloride
Show more names
trans-2-Butenedioyl dichloridetl189fumarylFumarylChoridefumaroylchloride
DTXSID3033519B95L4812RGFUMARIC DICHLORIDEFUMARIC ACID CHLORIDEDTXCID1013519RefChem:607705211-005-4(E)-but-2-enedioyl dichloride
Database identifiers
- CAS
627-63-4- PubChem CID
- 5325504
- DTXSID
DTXSID3033519- ChEMBL
CHEMBL2143883- UNII
- B95L4812RG
- EC Number
- 211-005-4
- Nikkaji
- J517G、J581.481B
Properties
Computed structural propertiesFilling in
- XLogP
- 1.5
- Topological polar surface area
- 34.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 123
Experimental & physicochemical properties
Chemical Classes
Toxic Gases & Vapors -> Acid Halides
Corrosives
SpringerMaterials PropertiesSchoenflies notation
Vapor Pressure2.07 [mmHg]
Physical Description
Fumaryl chloride appears as a straw colored fuming liquid with a pungent odor. Vapors irritate the eyes and mucous membranes. Corrosive to metals and tissue.
Fuming straw-colored liquid with a pungent odor; [CAMEO] Colorless liquid with an acrid odor; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- -2 °C · -2 °C
- Boiling point
- 164 °C · 164 °C
- Density
- 1.41 · 1.41
- refractive index
- 1.5 · 1.50
- Flash point
- 77 °C · 77 °C
- storage temp.
- 2 · 2-8°C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Fumaryl chloride: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
DOT LabelCorrosive
Fire Hazards
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
· Combustible material: may burn but does not ignite readily.
Health Hazards
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.
Hazards Summary
A severe skin and eye irritant; Causes musculoskeletal changes in inhalation lethal-concentration studies of mice; [RTECS] Corrosive to tissue; Vapor causes eye and mucous membrane irritation; [CAMEO] Reacts with water; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion, inhalation, and skin absorption; [Alfa Aesar MSDS]
Chemistry & industry
Uses & manufacturing
General Manufacturing Information2-Butenedioyl dichloride, (2E)-: ACTIVE
Applications
UsesChemical intermediate for pharmaceuticals, dyestuffs, and insecticides.
UsesFumaryl chloride was used in the preparation of high molecular weight poly(propylene fumarate). The photodissociation dynamics of fumaryl chloride was studied. It is used in agrochemicals and pharmaceuticals manufacturing. Also used as an intermediate for dyes, textile auxiliaries and peroxide compounds. It is an acid halide building block.
General DescriptionFumaryl chloride appears as a straw colored fuming liquid with a pungent odor. Vapors irritate the eyes and mucous membranes. Corrosive to metals and tissue.
Preparation methods
PreparationFumaryl chloride has been prepared from fumaric acid and phthaloyl chloride, from maleic acid by the action of thionyl chloride in the presence of zinc chloride, and from maleic anhydride by the use of phthaloyl chloride in the presence of zinc chloride.Org. Synth. 1940, 20, 51DOI: 10.15227/orgsyn.020.0051
Upstream & downstream products
Upstream raw materials
Related reactions
16 records
Compound notes
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