Basic information
- 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 properties
- 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
- 161 · 161-164 °C(lit.)
- Density
- 1.415 g/mL · 1.415 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.499(lit.)
- Flash point
- 165 °F · 165 °F
- storage temp.
- 2 · 2-8°C
- form
- Liquid
- Specific Gravity
- 1.415 · 1.415 (20/4℃)
- color
- Clear yellow
- Water Solubility
- decomposes
- Sensitive
- Moisture Sensitive
- BRN
- 1721342 · 1721342
- InChI
- 1S/C4H2Cl2O2/c5-3(7)1-2-4(6)8/h1-2H/b2-1+
- InChIKey
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N
- SMILES
- ClC(=O)\C=C\C(Cl)=O
- CAS DataBase Reference
- 627 · 627-63-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 95 L4812RG · B95L4812RG
- NIST Chemistry Reference
- Fumaryl chloride(627-63-4)
- EPA Substance Registry System
- 2 · 2-Butenedioyl dichloride, (2E)- (627-63-4)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302+H312-H314-H227-H290
- Precautionary statements
- 501 · P501-P270-P210-P234-P264-P280-P370+P378-P390-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P235-P406-P405
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C
- Risk Statements
- 20 · 20/21/22-34-37-29-36/37-14
- Safety Statements
- 26 · 26-36/37/39-45-8-27
- RIDADR
- 1780 · UN 1780
- WGK Germany
- 3 · 3
- RTECS
- 2800000 · LT2800000
- F
- 21 · 21
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29171990 · 29171990
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 OralSkin Corr. 1B
- 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
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]
DOT ID and Guide1780 156
Reactive GroupHydrocarbons, Aliphatic Unsaturated
Reactivity AlertsAir-Reactive
Reactivity Profile
FUMARYL CHLORIDE is incompatible with strong oxidizing agents, alcohols, amines and other bases. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
DOT Hazard Classification
Fumaryl chloride
UN1780
Class 8 Corrosive material (49 eCFR § 173.136)
PG II: the degree of danger presented by the material is medium
Air and Water ReactionsFumes in moist air. The liquid very slowly reacts exothermically with water to form hydrogen chloride.
Hazard Classes and Categories
Acute Tox. 4 (100%)
Corrosives, Flammable agents - 2nd degree, Reactive agents - 2nd degree
Safety & protection
Fire FightingExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
General First Aid:
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Nonfire Spill ResponseExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Isolation and Evacuation
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Immediate precautionary measure
Personal Protective Equipment (PPE)Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Emergency Response Planning Guidelines· Note: Most foams will react with the material and release corrosive/toxic gases.
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Toxicity DataLCLo (rat) = 500 ppm/4hr
Safety data
- F
- 21
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- LT2800000
- ridadr
- UN 1780
- hs_code
- 29171990
- risk_code
- 20/21/22-34-37-29-36/37-14
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- C
- safety_code
- 26-36/37/39-45-8-27
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- H302+H312-H314-H227-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)
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 OralSkin Corr. 1B
- Precautionary statements
- P501-P270-P210-P234-P264-P280-P370+P378-P390-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P235-P406-P405
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
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Upstream raw materials
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