7517-76-2

Basic information

• Product Name: TRANS-1,4-CYCLOHEXANE DIISOCYANATE
• Synonyms: 1,4-cyclohexyleneester,trans-isocyanicaci;1,4-diisocyanato-,trans-Cyclohexane;4-diisocyanato-trans-cyclohexan;h-19218;trans-1,4-cyclohexyleneisocyanate;trans-1,4-Diisocyanatocyclohexane;TRANS-1,4-CYCLOHEXYLENE DIISOCYANATE;TRANS-1,4-CYCLOHEXANE DIISOCYANATE
• CAS NO: 7517-76-2
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• EINECS: -0
• Product Categories: Isocyanate Monomers;Monomers;Polymer Science
• Mol File: 7517-76-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 59-62 °C(lit.)
• Boiling Point: 145-146°C 32mm
• Flash Point: 145-146°C/32mm
• Appearance: /
• Density: 1.2265 (rough estimate)
• Vapor Pressure: <0.02 mm Hg ( 20 °C)
• Refractive Index: 1.6180 (estimate)
• Water Solubility: Hydrolyzes in water.
• Sensitive: Moisture Sensitive
• BRN: 2804862
• CAS DataBase Reference: TRANS-1,4-CYCLOHEXANE DIISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-1,4-CYCLOHEXANE DIISOCYANATE(7517-76-2)
• EPA Substance Registry System: TRANS-1,4-CYCLOHEXANE DIISOCYANATE(7517-76-2)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-34-42/43
• Safety Statements: 22-26-36/37/39-45
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• RTECS: GU9642500
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 7517-76-2(Hazardous Substances Data)

Usage

Uses

Mixed aromatic/alicyclic polyimides were prepared by polycondensation reactions of trans-1,4-cyclohexane diisocyanate CHDI with PMDA, BTDA, and 6FDA. The intermediate reactivity observed for CHDI, allows preparation of polyurethanes.

InChI:InChI=1/C8H10N2O2/c11-5-9-7-1-2-8(4-3-7)10-6-12/h7-8H,1-4H2/t7-,8-

Synthetic route

carbon dioxide (124-38-9) + trans-1,4-cyclohexyldiamine (2615-25-0) → trans-1,4-cyclohexane diisocyanate (7517-76-2)

Conditions	Yield
With triethylamine; trichlorophosphate 1.) acetonitrile, 1 atm., 2.) acetonitrile; Yield given. Multistep reaction;

trans-1,4-diaminocyclohexane (3114-70-3) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) → trans-1,4-cyclohexane diisocyanate (7517-76-2) + cis-1.4-diisocyanato-cyclohexane

Conditions	Yield
With 1,2-dichloro-benzene at 95℃; und Einleiten von Phosgen in eine Suspension der erhaltenen Carbamidsaeure,zuletzt bei 160grad;

4-tritylphenol (978-86-9) + trans-1,4-cyclohexane diisocyanate (7517-76-2) + 11'-(tert-butyl)-5',17',23',35',38',40'43',45'-octamethyldispiro[cyclohexane-1,2'-[7,15,25,33]tetraazaheptacyclo[32.2.2.2.2(3,6).2(16,19).2(21,24).1(3,13).1(27,31)]hexatetraconta[3,5,9,11,13(44),16,18,21,23,27,29,31(39),34,36,37,40,42,45]octadecaene..]. (169179-44-6) → C64H72N4O4*C58H50N2O4

Conditions	Yield
With triethylamine In dichloromethane Addition; Heating;	23%

pyridin-3-ylamine (462-08-8) + trans-1,4-cyclohexane diisocyanate (7517-76-2) → 1-pyridin-3-yl-3-[4-(3-pyridin-3-yl-ureido)-cyclohexyl]-urea

trans-1,4-cyclohexane diisocyanate (7517-76-2) + 2-(4-aminophenoxy)-2-methyl propionic acid (117011-70-8) → C28H36N4O8

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water Reflux;

C32H43N5O5 + trans-1,4-cyclohexane diisocyanate (7517-76-2) → C72H96N12O12

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 20℃;

histamine (51-45-6) + trans-1,4-cyclohexane diisocyanate (7517-76-2) → 1,1'-((1r,4r)-cyclohexane-1,4-diyl)bis(3-(2-(1H-imidazol-4-yl)ethyl)urea)

Conditions	Yield
In tetrahydrofuran; N,N-dimethyl acetamide; ethyl acetate at 120℃; for 0.25h; Temperature;

Upstream product

• 124-38-9 carbon dioxide 
• 2615-25-0 trans-1,4-cyclohexyldiamine 
• 3114-70-3 trans-1,4-diaminocyclohexane 
• 15719-64-9 methylammonium carbonate 

Relevant articles and documents

Isocyanates From Primary Amines and Carbon Dioxide: 'Dehydration' of Carbamate Anions

Carbamate anions, derived from primary amines CO2 and an added base (e.g.NEt3), undergo rapid reaction with electrophilic 'dehydrating agents' (e.g.POCl3, P4O10) to give the corresponding isocyanates in excellent yields.

Process for the preparation of organic mono- and polyisocyanates

A process for the preparation of organic mono- and polyisocyanates is described, in which a hydrogen chloride adduct of a trisubstituted urea is thermally decomposed to form the isocyanate. The hydrogen chloride adduct at minimum contains the stoichiometric amount of HCl, and at maximum a 10 mole-% excess. The process is carried out in a closed system at a temperature between about 80° and 180° C.; the reaction is effected either in a melt or in the presence of an inert organic solvent.