2425-79-8

Usage

Chemical Properties

Clear yellow liquid

Uses

1,4-Butanediol diglycidyl ether is used for preparing amylose, xylan and hydroxyethyl-cellulose, to cross link polyethylenimine which also serves as a hole-blocking layer in organic solar cells, to cross link hyaluronic acid into hydrogels and for the activation of soluble dextran polymers. It is the most commonly used homobifunctional epoxide compound

Production Methods

The compound results from condensation of butanediol with epichlorohydrin followed by dehydrochlorination with caustic.

General Description

Clear pale yellow liquid.

Air & Water Reactions

Hygroscopic. Water soluble

Reactivity Profile

1,4-Butanediol diglycidyl ether reacts with acids.

Fire Hazard

1,4-Butanediol diglycidyl ether is combustible.

Flammability and Explosibility

Nonflammable

Contact allergens

This substance is a reactive diluent in epoxy resins

Carcinogenicity

A2 year dermal cancer bioassay was conducted in CF1 mice at doses of 0%, 0.05%, and 0.2% in acetone . Treatment did not adversely affect survival, did not increase the incidence of skin tumors, and did not result in significant skin irritation. There were no statistically significant increases in incidence of any systemic tumors, except for lymphatic tumors in females. Because there was a high background incidence of this tumor type in CF1 mice used in the testing laboratory , there was no clear evidence of 1,4-BDDGE-induced carcinogenicity.

InChI:InChI=1/C6H10O3.C4H10O2/c1(5-3-8-5)7-2-6-4-9-6;1-2-3-4(5)6/h5-6H,1-4H2;4-6H,2-3H2,1H3

Upstream product

• 110-63-4 Butane-1,4-diol 
• 106-89-8 epichlorohydrin 

Downstream Products

• 20844-43-3 3,3'-di-p-tolyl-5,5'-(2,7-dioxa-octane-1,8-diyl)-bis-oxazolidin-2-one 
• 14180-03-1 1,4-Bis-<2-hydroxy-3-chlor-propoxy-butan> 
• 29611-97-0 racemic 1,4-butanediol diglycidyl ether 
• 29611-97-0 (2'S,2''S)-1,4-butanediol diglycidyl ether 
• 868944-55-2 C₃₂H₄₉ClN₂O₁₁ 

Relevant academic research and scientific papers

Study of imidazole performance as pseudo-affinity ligand in the purification of IgG from bovine milk

The spherical sepharose CL-6B beads were activated by epichlorohydrin in different epoxy contents (80, 120 and 160 μmolepoxide/mLgel) and, L-histidine and imidazole as pseudo-affinity ligands were covalently immobilized to them. Some linkers with different length, (1,2-ethanediol diglycidyl ether and 1,4-butanediol diglycidyl ether) were synthesized for activation of sepharose and the activated sepharose beads modified with imidazole and the performance of these adsorbents in the purification of immunoglobulin G from bovine milk were evaluated. Among the L-histidine bearing adsorbents, higher adsorption of IgG (0.28 mg/mL) was obtained by adsorbent with the lower concentration of L-histidine. The highest amount of IgG adsorption (0.53 mg/mL) was obtained by imidazole bearing adsorbent with the highest amount of imidazole and Among the adsorbents with synthesized linkers, the adsorbent with 1,2-ethanediol diglycidyl ether showed better performance and was able to purify 0.25 mg/mL IgG with high purity. The synthesized pseudo-affinity adsorbents represented the abbility to purify immunoglobulin G in one-step process with high purity and efficiency.

Diol glycidyl ether-bridged cyclens: Preparation and their applications in gene delivery

Polymeric 1,4,7,10-tetraazacyclododecanes (cyclens) using diol glycidyl ether with different chain length as bridges (5a-e) were designed and synthesized from various diols, 1,7-diprotected cyclen and epichlorohydrin. The molecular weights of the title polymers were measured by GPC with good polydispersity. Agarose gel retardation and fluorescent titration using ethidium bromide showed good DNA-binding ability of 5. They could retard plasmid DNA (pDNA) at an N/P ratio of 4-6 and form polyplexes with sizes around 100-250 nm from an N/P ratio of 10 to 60 and relatively low zeta-potential values (5-22 mV). The cytotoxicity of 5 assayed by MTT is much lower than that of 20 kDa PEI. In vitro transfection against A549 and 293 cells showed that the transfection efficiency (TE) of 5c/DNA polyplexes is close to that of 20 kDa PEI at an N/P ratio of 5. Structure-activity relationship (SAR) of 5 was discussed in their DNA-binding, cytotoxicity, and transfection studies. The TE of 5c/DNA polyplexes could be improved by the introduction of 50 μM of chloroquine, the endosomolytic agents, to pretreated cells. These studies may extend the application areas of macrocyclic polyamines, especially for cyclen.

Dinuclear macrocyclic polyamine zinc(II) complexes linked with flexible spacers: Synthesis, characterization, and DNA cleavage

Dinuclear macrocyclic polyamine zinc(II) complexes, which have two cyclen groups linked by flexible spacers, have been synthesized as DNA cleavage agents. The structures of these new dinuclear complexes are consistent with the data obtained from elemental analysis, MS and 1H NMR spectroscopy. The catalytic activity of these dinuclear complexes on DNA cleavage was studied. The results showed that the dinuclear zinc(II) complexes can catalyze the cleavage of supercoiled DNA (pUC 19 plasmid DNA) (Form I) under physiological conditions to produce selectively nicked DNA (Form II).

Thiopolymers, their derivatives and methods for their preparation and use

A method for producing products for separation, ion exchange or as basic material for the preparation of various derivatives designed for separation purposes and adsorption purposes by means of a polymer being activated with a reagent containing at least two bifunctional groups so that at least one of the reactive, functional groups in each molecule is bonded to the polymer while leaving a considerable amount of remaining groups unreacted but still reactive so that the activated polymer can be caused to react with thiosulphate after surplus reagent has been eliminated. The invention also relates to the produced products or their derivatives consisting of a water-soluble hydroxyl group or amino group containing polymer substituted with organic side-chains, each containing one or more thiosulphate groups or derivatives of such groups and the use of the products for purification of water, separation, immobilization of enzymes, etc.