Diepoxybutane

Diepoxybutane (also known as butane diepoxide, butadiene diepoxide, or 1,2:3,4-diepoxybutane) is an epoxide which is a colorless liquid at room temperature. Epoxides are very reactive due to ring strain and diepoxybutane contains two of these groups, so it is highly reactive, more than other ethers.^[which?] It is hydrophilic, very flammable and easily ignited by heat or sparks.^{[citation needed]}

Diepoxybutane

Names
Preferred IUPAC name 2,2′-Bioxirane
Other names 1,1′-Bi[ethylene oxide]; 1,2:3,4-Diepoxybutane; 1,3-Butadiene diepoxide; Bioxirane; Butadiene dioxide; Butane diepoxide; Dioxybutadiene
Identifiers
CAS Number	1464-53-5 (isomeric mixture) Y 298-18-0 (D/L) Y 30419-67-1 (D) Y 30031-64-2 (L) Y 564-00-1 (meso) Y
3D model (JSmol)	Interactive image
Abbreviations	DEB
Beilstein Reference	79831
ChEBI	CHEBI:23704
ChEMBL	ChEMBL1964283
ChemSpider	21106504
ECHA InfoCard	100.014.527
EC Number	206-060-6 215-979-1
PubChem CID	11254
UNII	60OB65YNAB (isomeric mixture) Y GQK28B9ZWF (D/L) Y 4KEO88VB9L (D) Y FZ22S4GMHX (L) Y 2PFZ3Z96CY (meso) Y
UN number	3384 3082
CompTox Dashboard (EPA)	DTXSID0041307
InChI InChI=1S/C4H6O2/c1-3(5-1)4-2-6-4/h3-4H,1-2H2 Key: ZFIVKAOQEXOYFY-UHFFFAOYSA-N InChI=1/C4H6O2/c1-3(5-1)4-2-6-4/h3-4H,1-2H2 Key: ZFIVKAOQEXOYFY-UHFFFAOYAG
SMILES C1OC1C2CO2
Properties
Chemical formula	C4H6O2
Molar mass	86.090 g·mol−1
Density	1.113 g/cm3 (18 °C)[1]
Melting point	4 °C (39 °F; 277 K)[1]
Boiling point	138 °C (280 °F; 411 K)[1]
Solubility in water	Miscible[1]
Vapor pressure	0.52 kPa (at 20 °C)[2]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H310, H311, H314, H330, H340, H350
Precautionary statements	P201, P202, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P281, P284, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, P501
Flash point	46 °C (115 °F; 319 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diepoxybutane is used as a chemical intermediate, as a cross-linking agent for polymers and textiles, and as a preservative.^{[clarification needed][2][better source needed]}

Structure, reactivity, synthesis

Diepoxybutane occurs as several enantiomers and a meso form.^{[citation needed]}

Diepoxybutane polymerizes in the presence of catalysts or when heated. These polymerization reactions can be violent.^[3]

Other Uses

In research diepoxybutane is used as a chemical intermediate, and in medicine for the diepoxybutane (DEB test) to screen for Fanconi anemia (FA) among patients with bone marrow failure syndromes.^{[4][better source needed]}

Although many chemicals are capable of DNA crosslinking, the DEB test is used because it gives fewer false negatives and positives than other chemicals.^[5]

Toxicity

Effect on humans

Diepoxybutane irritates the nose, throat and lungs, causing coughing and shortness of breath. Skin exposure can cause chemical burns. Longer exposure periods can cause pulmonary edema, and damage to the liver and kidneys.^[6]

Carcinogenicity

• IARC Carcinogen - Class 1: International Agency for Research on Cancer classifies chemicals as established human carcinogens.
• NTP Carcinogen - Reasonably anticipated to be a human carcinogen.^{[citation needed]}

Effect on animals

It is experimentally shown that diepoxybutane can cause tumors in rodent species at several different tissue sites and by several different exposure routes. Dermal contact with diepoxybutane caused skin tumors in mice.^[quantify] Injection of diepoxybutane into mice and rats caused lung tumors. Furthermore, inhalation exposure to diepoxybutane caused benign Harderian-gland tumors in mice and also increased the size of benign or malignant tumors of the nasal cavity.^{[citation needed]}