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Sigma-Aldrich

1,4-Diisocyanatobutane

97.0%

Synonym(s):

Tetramethylene diisocyanate

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About This Item

Linear Formula:
OCN(CH2)4NCO
CAS Number:
4538-37-8
Molecular Weight:
140.14
Beilstein:
1756894
MDL number:
MFCD00075559
UNSPSC Code:
12162002
PubChem Substance ID:
24863093
NACRES:
NA.23

Quality Level

200

Assay

97.0%

form

liquid

bp

102-104 °C/14 mmHg (lit.)

density

1.105 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

O=C=NCCCCN=C=O

InChI

1S/C6H8N2O2/c9-5-7-3-1-2-4-8-6-10/h1-4H2

InChI key

OVBFMUAFNIIQAL-UHFFFAOYSA-N

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General description

1,4-Diisocyanatobutane is a highly reactive compound with two isocyanate (-NCO) groups separated by a butane chain. It can undergo reactions such as urethane formation, crosslinking, and chain extension. It is widely used as a building block to synthesize polyurethane-based materials with excellent flexibility, impact resistance, and mechanical properties, making them useful in tissue engineering, contact lenses, biocompatible coatings, adhesives, foams, elastomers, and sealants.

Application

1,4-Diisocyanatobutanecan be used in the following fields:

Tissue engineering -As a precursor to synthesize polyurethane composites which can be used as 3D scaffolds for tissue engineering,

Contact lenses- As a cross-linking agent to prepare inorganic-organic hydrogel contact lenses for high refractive index ocular refractive correction biomaterial,

Controlled drug delivery- As a chain extender to synthesize segmented polyurethanes for redox-sensitive controlled drug release systems.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

222.8 °F

Flash Point(C)

106 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis and characterization of redox-sensitive polyurethanes based on l-glutathione oxidized and poly(ether ester) triblock copolymers
Fabio S. Palumbo, et al.
Reactive and Functional Polymers, 126, 104986-104986 (2021)
Polymerizable-group capped ZnS nanoparticle for high refractive index inorganic-organic hydrogel contact lens
Peili Zhao, et al.
Materials Science and Engineering, C, 90, 485-493 (2018)
Vladimir Burmistrov et al.
Bioorganic & medicinal chemistry letters, 24(9), 2193-2197 (2014-04-02)
A series of inhibitors of the soluble epoxide hydrolase (sEH) containing two urea groups has been developed. Inhibition potency of the described compounds ranges from 2.0 μM to 0.4 nM. 1,6-(Hexamethylene)bis[(adamant-1-yl)urea] (3b) was found to be a potent slow tight
3D-composite scaffolds from radiation-induced chitosan grafted poly(3-hydroxybutyrate) polyurethane
Maykel Gonzalez Torres
Materials Today Communications, 23, 100902-100902 (2020)

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