Dibutyl fumarate

Reported in EPA TSCA Inventory.

The 2-Butenedioic acid(2E)-, 1,4-dibutyl ester, with the CAS registry number 105-75-9, is also known as Fumaric acid di-n-butyl ester. It belongs to the product categories of Fatty Acid Esters (Plasticizer); Functional Materials; Plasticizer. Its EINECS number is 203-327-9. This chemical's molecular formula is C₁₂H₂₀O₄ and molecular weight is 228.28. What's more, its systematic name is dibutyl (2E)-but-2-enedioate. It is used as an organic solvent and organic intermediates. When using it, you must avoid contact with eyes. 

Physical properties of 2-Butenedioic acid(2E)-, 1,4-dibutyl ester are: (1)ACD/LogP: 3.81; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.81; (4)ACD/LogD (pH 7.4): 3.81; (5)ACD/BCF (pH 5.5): 461.68; (6)ACD/BCF (pH 7.4): 461.68; (7)ACD/KOC (pH 5.5): 2810.22; (8)ACD/KOC (pH 7.4): 2810.22; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 52.6 Å²; (13)Index of Refraction: 1.451; (14)Molar Refractivity: 61.25 cm³; (15)Molar Volume: 227.1 cm³; (16)Polarizability: 24.28×10^-24cm³; (17)Surface Tension: 33.4 dyne/cm; (18)Density: 1.004 g/cm³; (19)Flash Point: 136.4 °C; (20)Enthalpy of Vaporization: 51.87 kJ/mol; (21)Boiling Point: 280 °C at 760 mmHg; (22)Vapour Pressure: 0.00388 mmHg at 25°C.

Preparation: this chemical can be prepared by acrylic acid butyl ester by heating. This reaction will need reagent ruthenium complex and solvent CH₂Cl₂ with the reaction time of 3 hours. The yield is about 87%.

Uses of 2-Butenedioic acid(2E)-, 1,4-dibutyl ester: it can be used to produce methylenesuccinic acid dibutyl ester by heating. It will need reagent CsF and solvent 1,2-dimethoxy-ethane with the reaction time of 24 hours. The yield is about 50%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCCCC)/C=C/C(=O)OCCCC
(2)Std. InChI: InChI=1S/C12H20O4/c1-3-5-9-15-11(13)7-8-12(14)16-10-6-4-2/h7-8H,3-6,9-10H2,1-2H3/b8-7+
(3)Std. InChIKey: JBSLOWBPDRZSMB-BQYQJAHWSA-N

The toxicity data is as follows: 

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	250mg/kg (250mg/kg)		National Technical Information Service. Vol. AD691-490.
rabbit	LD50	skin	15900uL/kg (15.9mL/kg)		AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.
rat	LD50	oral	8530mg/kg (8530mg/kg)		AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.