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110-17-8

Basic Information
CAS No.: 110-17-8
Name: Fumaric acid
Article Data: 509
Molecular Structure:
Molecular Structure of 110-17-8 (Fumaric acid)
Formula: C4H4O4
Molecular Weight: 116.073
Synonyms: 2-Butenedioic acid (2E)- (9CI);2-Butenedioic acid (E)-;EPA Pesticide Chemical Code 051201;trans-Butenedioic acid;Allomaleic acid;Boletic acid;(E)-2-Butenedioic acid;1,2-Ethenedicarboxylic acid, trans-;2-(E)-Butenedioic acid;trans-2-Butenedioic acid;FumaricAcid;Fumaric acid (Tech and Food grade);L-Carnitine Fumaric Acid;1, 2-Ethenedicarboxylic acid, trans-;Fumaric acid (NF);2-Butenedioic acid, (E)-;Tumaric acid;Allomalenic acid;Butenedioic acid, (E)-;2-Butenedioic acid;USAF EK-P-583;(2E)-but-2-enedioic acid;Fumaric acid (8CI);Kyselina fumarova;Fumaric acid;
EINECS: 203-743-0
Density: 1.499 g/cm3
Melting Point: 295-300 ºC
Boiling Point: 355.5°Cat760mmHg
Flash Point: 230 ºC
Solubility: 0.63 g/100 mL (25 ºC) in water
Appearance: white powder or colourless crystals
Hazard Symbols: IrritantXi
Risk Codes: 36
Safety: 26
Transport Information: UN 9126
PSA: 74.60000
LogP: -0.28820
Synthetic route
110-16-7

maleic acid

110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With (E)-4-(2-chlorostyryl)pyridine In methanol at 20℃; for 720h;100%
With maleic anhydride In water at 190℃; for 6h; Reagent/catalyst; Inert atmosphere; Autoclave; Green chemistry;99.5%
With N-Bromosuccinimide; dibenzoyl peroxide; acetic acid for 6h; Heating;90%

C13H10ClN*C4H4O4*0.5C4H4O4

A

1,3-bis(4-pyridyl)-2,4-bis(2-chlorophenyl)cyclobutane

B

110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
UV-irradiation;A 100%
B n/a
608-36-6

meso-2,3-dibromosuccinic acid

110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With aluminum oxide for 0.0166667h; microwave irradiation;98%
With sodium tetrahydroborate; nickel dichloride In tetrahydrofuran at 20℃; for 0.75h;89%
With sodium sulfide oder mit aehnlichen Thiosalzen;

(E)-But-2-enedioic acid bis-(1-phenoxy-ethyl) ester

110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0℃; for 1h;98%
In dichloromethane at 0℃; for 1h; Product distribution; 5percent CF3COOH; other reagent;98%
1114-00-7

(+-)-2,3-dibromosuccinic acid

110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With aluminum oxide for 0.0166667h; microwave irradiation;98%
With sodium tetrahydroborate; nickel dichloride In tetrahydrofuran at 20℃; for 1h;90%
617-48-1

malic acid

110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
96%
In neat (no solvent) at 200℃; for 4h; Inert atmosphere;96.6%
at 180℃; for 4h; Temperature; Inert atmosphere;88%

C22H18O10

A

110-17-8

(2E)-but-2-enedioic acid

B

4,6-dimethoxyanthracene-1,2-dicarboxylic anhydride

Conditions
ConditionsYield
In diphenylether Heating;A n/a
B 94%

C21H16O9

A

110-17-8

(2E)-but-2-enedioic acid

B

4-methoxyanthracene-1,2-dicarboxylic anhydride

Conditions
ConditionsYield
In diphenylether Heating;A n/a
B 90%
63995-70-0

trisodium tris(3-sulfophenyl)phosphine

142-45-0

Acetylenedicarboxylic acid

A

98511-67-2

tris(natrium-m-sulfonatophenyl)phosphanoxid

B

110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
In water for 5h; Ambient temperature;A n/a
B 87%
110-16-7

maleic acid

A

109-99-9

tetrahydrofuran

B

96-48-0

4-butanolide

C

110-63-4

Butane-1,4-diol

D

591-81-1

4-hydroxybutanoic acid

E

617-48-1

malic acid

F

110-15-6

succinic acid

G

100-21-0

terephthalic acid

H

64-19-7

acetic acid

I

802294-64-0

propionic acid

J

110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd/0.2percent Re on Rutile TiO2 at 110℃; for 170 - 1009h; Product distribution / selectivity;A 0.86%
B 4.34%
C 0.28%
D 1.24%
E 0%
F 85.51%
G 0%
H 0.04%
I 0%
J 0%
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  • Casno:

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    Fumaric acid [110-17-8] Product Name: Fumaric acid Synonyms: trans-2-Butenedioic acid; L-Fumaric Acid CAS RN.: 110-17-8 EINECS: 203-743-0

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History

 Fumaric acid was first prepared from Succinic acid.

Specification

The Fumaric acid, with the CAS registry number 110-17-8, is also known as (E)-2-Butenedioic acid; Butenedioic acid; (E)-1,2-Ethenedicarboxylic acid; TMEDA. It belongs to the product categories of Insect Platform;Multidrug Resistance;Phase II Enzyme Inducers;Phase II Enzyme InducersCancer Research.Its EINECS number is 203-743-0.This chemical's molecular formula is C4H4O4 and molecular weight is 116.07. What's more,Its systematic name is Fumaric acid.It is a colorless crystalline solid,stable at room temperature.Decomposes at around 230 C.Incompatible with strong oxidizing agents, bases, reducing agents. Combustible.The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses.The Fumaric acid is irritating to the eyes .In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.Inhalation of dust may cause respiratory irritation. Compound is non-toxic when ingested. Prolonged contact with eyes or skin may cause irritation.

Physical properties about Fumaric acid are:
(1)ACD/LogP: -0.008; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.73; (4)ACD/LogD (pH 7.4): -4.72; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.526; (13)Molar Refractivity: 23.767 cm3; (14)Molar Volume: 77.429 cm3; (15)Surface Tension: 67.693000793457 dyne/cm; (16)Density: 1.499 g/cm3; (17)Flash Point: 182.981 °C; (18)Enthalpy of Vaporization: 65.985 kJ/mol; (19)Boiling Point: 355.482 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:C(=C/C(=O)O)\C(=O)O;
(2)Std. InChI:InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+;
(3)Std. InChIKey:VZCYOOQTPOCHFL-OWOJBTEDSA-N;

The toxicity data of Fumaric acid as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 unreported 5gm/kg (5000mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: EXCITEMENT

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION
Toksikologicheskii Vestnik. Vol. (2), Pg. 25, 1994.
rabbit LDLo oral 5gm/kg (5000mg/kg)   Industrial and Engineering Chemistry. Vol. 15, Pg. 628, 1923.
rat LD50 oral 9300mg/kg (9300mg/kg)   Toxicology and Applied Pharmacology. Vol. 42, Pg. 417, 1977.
rat LD50 unreported 6800mg/kg (6800mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: EXCITEMENT
Toksikologicheskii Vestnik. Vol. (2), Pg. 25, 1994.
rat LDLo intraperitoneal 587mg/kg (587mg/kg) LIVER: OTHER CHANGES

GASTROINTESTINAL: OTHER CHANGES

BLOOD: HEMORRHAGE
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 35, Pg. 298, 1946.