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

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

Uses

Used in Pharmaceutical Industry:
Fumaryl chloride is used as a chemical intermediate for the synthesis of pharmaceuticals. It plays a crucial role in the production of high molecular weight poly(propylene fumarate), which has potential applications in drug delivery systems and tissue engineering.
Used in Agrochemical Industry:
Fumaryl chloride is used in the manufacturing of agrochemicals, specifically as an intermediate for the production of insecticides. Its use in this industry helps in the development of effective pest control solutions.
Used in Dye Industry:
Fumaryl chloride serves as an intermediate for the production of dyes, particularly in the dyestuff industry. Its presence in the synthesis process contributes to the development of various colorants used in different applications.
Used in Textile Industry:
In the textile industry, fumaryl chloride is used as an intermediate for the production of textile auxiliaries. These auxiliaries are essential in the processing and finishing of textiles, enhancing their quality and performance.
Used in Peroxide Compounds Production:
Fumaryl chloride is also used as an intermediate in the synthesis of peroxide compounds. These compounds have various applications, including as initiators in polymerization reactions and as bleaching agents in the paper and pulp industry.

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

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

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 
• 6270-21-9 fumaric acid bis-(2,2,2-trichloro-ethyl ester) 
• 7511-97-9 Bis-<2,2,2-tribromoethyl>-fumarat 
• 112652-58-1 optically inactive fumaric acid bis-(1-ethoxycarbonyl-ethyl ester) 
• 6332-09-8 (E)-1,4-bis(4-bromophenyl)but-2-ene-1,4-dione 
• 98362-45-9 di-p-nitrophenyl fumarate 
• 53164-47-9 bis(4-methylphenyl) fumarate 
• 59344-89-7 1,4-bis-(4-phenoxy-phenyl)-but-2-ene-1,4-dione 
• 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 
• 131240-32-9 fumaric acid bis-(4-bromo-phenyl ester) 
• 26367-48-6 fumaric acid ethyl ester mono chloride 
• 623-91-6 diethyl Fumarate 

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 of a Thiophene Analogue of Isoindigo by C–H Activation/Oxidative Cyclization and Application of Its Copolymeric Materials to Organic Transistors

A novel method for the synthesis of a thiophene analogue of isoindigo (TIIG) is described. The reaction involves a palladium-catalyzed C–H activation/oxidative cyclization sequence. This new methodology has potential for diversifying the isoindigo family. The thin-film transistors (TFTs) prepared from a TIIG-based copolymer (PIDTT-TIIG) with indacenodithieno[3,2-b]thiophene (IDTT) exhibit unipolar charge-transport properties with hole mobilities of 0.17 cm2 V–1 s–1.

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.

ADENYLYL CYCLASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND METHOD OF USE THEREOF

The present invention relates to novel adenine based inhibitors of adenylyl cyclase of the formula: wherein X, L, R1, R2, R5 are those defined herein. Compounds of the present invention are useful to treat cardiovascular diseases. The present invention also relates to a method of preventing heart failure by administering an effective amount of compound according to the invention following vascular injury and reperfusion therapy.

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.

Sixteen-core manganese cluster as well as synthetic method and application thereof

The invention discloses a sixteen-core manganese cluster as well as a synthetic method and application thereof. The chemical formula of the cluster is [MnII4MnIII12(L)6([Mu]3-O)4H2O)12].7DMF.H2O, L indicates N,N'-di(salicyloyl)-(E)-butylene hydrazide taking off six hydrogen atoms with six units of negative charges. The coordination compound belongs to a triclinic system, P-1 space group. The synthetic method of the cluster comprises the following steps: taking N,N'-di(salicyloyl)-(E)-butylene hydrazide and Mn(OAc)2.4H2O to be dissolved with a mixed solvent, adjusting the pH of an obtained solution to be 5.1 to 5.6, putting the mixed solution into a hydrothermal reaction kettle, reacting in a heating condition, cooling the reaction product, and standing for crystallization to obtain the cluster. Antiferromagnetic exchange exists among manganese ions in molecules of the cluster disclosed by the invention, and the cluster has good adsorption effect for carbon dioxide gas.

Preparation method of acyl chloride

The invention relates to a preparation method of acyl chloride. The method comprises the following steps that 1, carboxylic acid is added into a reactor, or carboxylic acid is dissolved in organic solvent, a device is connected, and the temperature is raised to 100 DGE C-250 DEG C; 2, phosgene is introduced into the reactor for a reaction, and then the temperature is decreased to room temperature; 3, nitrogen is introduced, residual phosgene and hydrogen chloride are cleaned away, reaction liquid which is reacted without solvent is subjected to decompression distillation and purification directly, and needed acyl chloride is obtained; reaction liquid which is reacted with the solvent is subjected to decompression distillation to remove the solvent, and needed acyl chloride is obtained. According to the preparation method of acyl chloride, no catalyst is added, the risks that in the synthesizing process, due to the fact that the catalyst is dissolved, color of the finial product of acyl chloride is increased, and the catalyst is remained in late products are avoided, after the reaction is finished, high-quality acyl chloride can be obtained through decompression distillation, and the technological process is simple; due to the fact that in the whole technological process, except for absorbable and available phosgene, hydrogen chloride and carbon dioxide, no other three waste is discharged, the preparation method of acyl chloride is environmentally friendly, and the good implement value is achieved.

Studies on the synthesis of bis-quaternary ammonium salts of geometrical isomers and its potential as bioregulators

Tertiary amine N,N-dimethyl-2-nitrophenylmethanamine 4 prepared from 2-nitrobenzaldehyde 3 by Leuckart's reaction and (3-N,N-diethylamino-2- hydroxypropyl)-3-(3-nitrophenyl) prop-2-en-oate 9 and 3-(diethylamino)-2- hydroxypropyl 2-(4-chloro-3-methylphenoxy)acetate 14 prepared through the formation of glycidyl ester have been reacted with dichlorides of maleic acid and fumaric acid, which in turn have been prepared by reacting these acids with thionyl chloride to get bis-quaternary ammonium salts 1a-c and 2a-c. The synthesized salts 1a-c and 2a-c are tested on rice (Oryza sativa, PR-114) for their biological activity. All the tested compounds are found to possess good plant growth retardant activity. Compound 2c is found to be the best plant growth retardant among the six newly synthesized compounds.

Lewis acid-catalyzed one-pot, three-component route to chiral 3,3′-bipyrroles

(Chemical Equation Presented) 3,3′-Bipyrroles 3 could be synthesized using a double Michael addition reaction involving diaroyl acetylene 1 and the appropriate 1,3-dicarbonyls 2 using ammonium acetate as a nitrogen source. The axial chirality of bipyrrole was anticipated from the X-ray crystal structure and DFT calculations and confirmed by separating the racemates on a chiral column and subsequent CD spectra of the enantiomers. The absolute configuration of the enantiomers was achieved by theoretical CD spectra calculation using the ZINDO method.

Synthesis and characterization of 2-phenyl-4-benzoyl-6,7-dihydro-5H-cyclopenta[b]pyridine and its derivatives

Amination-cyclization of triketones derived from variously substituted dibenzoyl ethylene and cyclopentanone furnished 2-phenyl-4-benzoyl-6,7-dihydro-5H-cyclopenta[b]pyridine and its derivatives.