627-63-4

Basic information

• Product Name: Fumaryl chloride
• Synonyms: dichloridkyselinyfumarove;Fumaroyl chloride;fumaroylchloride;fumaryl;Fumarylchlorid;TL 189;tl189;(2E)-2-Butenedioyl dichloride
• CAS NO: 627-63-4
• Molecular Formula: C₄H₂Cl₂O₂
• Molecular Weight: 152.96
• EINECS: 211-005-4
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 627-63-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: -2 °C
• Boiling Point: 161-164 °C(lit.)
• Flash Point: 165 °F
• Appearance: Clear yellow/Liquid
• Density: 1.415 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.16mmHg at 25°C
• Refractive Index: n20/D 1.499(lit.)
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• BRN: 1721342
• CAS DataBase Reference: Fumaryl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Fumaryl chloride(627-63-4)
• EPA Substance Registry System: Fumaryl chloride(627-63-4)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34-37-29-36/37-14
• Safety Statements: 26-36/37/39-45-8-27
• RIDADR: UN 1780 8/PG 2
• WGK Germany: 3
• RTECS: LT2800000
• F: 21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 627-63-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear yellow liquid

Uses

Different sources of media describe the Uses of 627-63-4 differently. You can refer to the following data:
1. Chemical intermediate for pharmaceuticals, dyestuffs, and insecticides.
2. Fumaryl 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.

Preparation

Fumaryl 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

General 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.

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].

Hazard

Corrosive to eyes and skin.

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Safety Profile

Moderately toxic by ingestion, inhalation, and skin contact. A skin, eye, and mucous membrane irritant. A corrosive agent. Will react with water or steam to produce toxic and corrosive fumes. When heated to decomposition it emits highly toxic fumes of phosgene and HCl.

InChI:InChI=1/C4H2Cl2O2/c5-3(7)1-2-4(6)8/h1-2H/b2-1-

Upstream product

• 108-31-6 maleic anhydride 
• 10026-13-8 phosphorus pentachloride 
• 98-07-7 Benzotrichlorid 
• 7530-87-2 L-malic acid ; barium-L malate 
• 7782-50-5 chlorine 
• 543-20-4 succinoyl dichloride 
• 110-17-8 (2E)-but-2-enedioic acid 
• 88-95-9 Phthaloyl dichloride 

Downstream Products

• 105788-09-8 (+/-)-4,4-dimethoxy-cyclohexane-1r,2t-dicarboxylic acid dimethyl ester 
• 13990-96-0 rac-(1S,2S)-dimethyl 4-oxocyclohexane-1,2-dicarboxylate 
• 59344-86-4 1,4-bis-biphenyl-4-yl-but-2-ene-1,4-dione 
• 59344-86-4 1,4-bis-biphenyl-4-yl-but-2t-ene-1,4-dione 
• 5240-51-7 N,N'-di-p-tolyl-fumaramide 
• 6852-88-6 divinyl fumarate 
• 28871-80-9 bicyclo<2.2.2>oct-5-ene 2,3-endo,exo-dicarboxylic acid 
• 97299-34-8 bis(4-(chloro)phenyl) fumarate 
• 36342-10-6 4-(4-nitrophenylamino)-4-oxobut-2-enoic acid 
• 88-98-2 trans-cyclohex-4-ene-1,2-dicarboxylic acid 
• 2807-54-7 diallyl fumarate 
• 108-31-6 maleic anhydride 
• 685543-77-5 trans-3-(benzylcarbamoyl)acrylic acid 
• 17233-65-7 1,2-bis(5-methylbenzoxazol-2-yl)ethylene 

Relevant articles and documents

Kinetic studies of pepsin active site model compound and porcine pepsin

The kinetic parameters for the hydrolysis of the heptapeptide Pro-Thr-Glu-Phe-(4-NO2)Phe-Arg-Leu by the pepsin model compound tetrabutylammonium monosalt of m-aminobenzoic acid diamide of fumaric acid (TBA m-FUM) and porcine pepsin were determined using a spectrophotometric technique. According to the AS* values obtained, in the transition state the inner motion in the TBA m-FUM-heptapeptide complex is more restricted than that in the pepsin-heptapeptide complex. The model compound TBA m-FUM can cause a cleavage of the Phe -(4-NO2)Phe bond in the substrate molecules following a mechanism similar as that suggested for pepsin. but its catalytic activity is much lower. Copyright

Synthesis and characterization of ferrocenyl esters: Their anti-oxidant activity and DNA-binding ability

In continuation to our work on biologically active material, some new ferrocenyl esters were prepared by condensation of 4-ferrocenyl phenol (ROH) with ferrocenyl dicarboxylic acid chlorides (DCC) at low temperature. The synthesized compounds (E1-E9) were characterized by analyzing their physical properties, FT-IR, 1H-NMR, UV-visible spectroscopic and cyclic voltammetric studies. The DPPH free radical scavenging assay was performed to explore their potential as antioxidant which showed that the E1 had maximum scavenging ability (77.11%) whereas E3 showed minimum (52%) compared with the standard. Cyclic voltammetric studies indicated that these compounds were electroactive in potential window of 2.0-0.0V. Binding mode found in these esters was an electrostatic interaction which is considered as strongest amongst all. Therefore, these compounds are considered to have DNA-binding capability and are potential DNA binders.

Undeca-nuclear-iron cluster compound as well as synthesis method and application thereof

The invention discloses an undeca-nuclear-iron cluster compound as well as a synthesis method and application thereof. The chemical formula of the cluster compound is [Fe11(L)6(DMF)5(H2O)].4DMF.H2O.3C2H8N.0.5Py, wherein L represents N,N'-dis(salicylic acyl)-(E)-butenyl hydrazine; the ligand is subjected to six-hydrogen-atom removal and is charged with six negative charges, and three non-coordinated dimethylamine cations still exist outside. The synthesis method of the cluster compound comprises the following steps: dissolving the N,N'-dis(salicylic acyl)-(E)-butenyl hydrazine and FeCl3.6H2O with a mixed solvent, then adjusting the pH value of the obtained solution to be 5.3 to 5.9 with pyridine, putting the obtained mixed solution into a hydrothermal reaction kettle, performing reaction under a heating condition, cooling a reactant, and leaving to stand and crystallizing the reactant, namely obtaining the cluster compound. The anti-ferromagnetic exchange interaction exists among intramolecular iron ions of the cluster compound, so that the whole compound shows paramagnetism and can be used for preparing a magnetic material.