4538-37-8

Basic information

• Product Name: 1,4-DIISOCYANATOBUTANE
• Synonyms: 1,4-DIISOCYANATOBUTANE;TETRAMETHYLENE DIISOCYANATE;1,4-BUTANEDIISOCYANATE;1,4-DIISOCYANATOBUTANE 97%;1,4-Diisocyanatobutane,97%;1,4-Diisocyanatobutane 97.0%;1,4-Diisocyanatobutane technical, >=95.0% (GC);1,4-Diisocyatobutane
• CAS NO: 4538-37-8
• Molecular Formula: C₆H₈N₂O₂
• Molecular Weight: 140.14
• Mol File: 4538-37-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 0°C
• Boiling Point: 102-104 °C14 mm Hg(lit.)
• Flash Point: 224 °F
• Appearance: Clear light yellow/Liquid
• Density: 1.105 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.113mmHg at 25°C
• Refractive Index: n20/D 1.453
• Storage Temp.: 2-8°C
• BRN: 1756894
• CAS DataBase Reference: 1,4-DIISOCYANATOBUTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIISOCYANATOBUTANE(4538-37-8)
• EPA Substance Registry System: 1,4-DIISOCYANATOBUTANE(4538-37-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-27-37/39
• RIDADR: 2206
• WGK Germany: 3
• F: 10-21
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 4538-37-8(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow liquid

InChI:InChI=1/C6H8N2O2/c9-5-7-3-1-2-4-8-6-10/h1-4H2

Synthetic route

1,4-butamethylene-bis(phenyl carbamate) (102016-85-3) → 1,4-diisocyanatobutane (4538-37-8) + phenol (108-95-2)

Conditions	Yield
In diphenylether at 240℃; for 2h; Inert atmosphere;	A 58% B n/a

Adipic acid dichloride (111-50-2) → 1,4-diisocyanatobutane (4538-37-8)

Conditions	Yield
Stage #1: Adipic acid dichloride With sodium azide In water; acetone Stage #2: In cyclohexane Curtius Rearrangement; Heating; Further stages.;	57%

N,N'-diacetoxy-adipamide (24230-70-4) → 1,4-diisocyanatobutane (4538-37-8)

Conditions	Yield
at 200℃; for 0.5h; Lossen Rearrangement;	2%

adipic diazide (25021-15-2) → 1,4-diisocyanatobutane (4538-37-8)

Conditions	Yield
With benzene

phosgene (75-44-5) + 1,4-diaminobutane (110-60-1) → 1,4-diisocyanatobutane (4538-37-8)

methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + 1,4-diaminobutane (110-60-1) → 1,4-diisocyanatobutane (4538-37-8)

Conditions	Yield
With 1,2-dichloro-benzene Behandeln mit Phosgen;
With 1,2-dichloro-benzene Behandeln mit Phosgen;

NN'-diformyl-1,4-diaminobutane (50326-52-8) → 1,4-diisocyanatobutane (4538-37-8)

Conditions	Yield
With bromine In benzene

phosgene (75-44-5) + 1,4-diaminobutane (110-60-1) → 1,4-diisocyanatobutane (4538-37-8) + pyrrolidine-carboxylic acid-(1)-chloride

phosgene (75-44-5) + 1.4-diamino-butane dihydrochloride → 1,4-diisocyanatobutane (4538-37-8)

Conditions	Yield
With 1,2-dichloro-benzene at 160 - 180℃;

1,4-dichlorobutane (110-56-5) + sodium cyanate → 1,4-diisocyanatobutane (4538-37-8)

Conditions	Yield
With N,N-dimethyl-formamide

adipic acid dihydrazide (1071-93-8) → 1,4-diisocyanatobutane (4538-37-8)

Conditions	Yield
Stage #1: adipic acid dihydrazide With hydrogenchloride; sodium nitrite In water at 0 - 8℃; Curtius Rearrangement; Stage #2: In benzene at 64℃;

bis(trichloromethyl) carbonate (32315-10-9) + 1,4-diaminobutane (110-60-1) → 1,4-diisocyanatobutane (4538-37-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 30℃; for 1.5h; Inert atmosphere;

1,4-diisocyanatobutane (4538-37-8) + adamantan-2-amine hydrochloride (10523-68-9) → 1,4-(tetramthylene)bis[(adamant-2-yl)urea] (1607795-42-5)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 12h; Inert atmosphere;	99%

1,4-diisocyanatobutane (4538-37-8) + 1-Adamantanamine (768-94-5) → 1,1'-(butane-1,4-diyl)bis[3-(adamantan-1-yl)urea] (1607795-35-6)

Conditions	Yield
In N,N-dimethyl-formamide at 15 - 25℃; for 6h;	99%

1,4-diisocyanatobutane (4538-37-8) + 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2, 10034-19-2, 10034-20-5, 34948-62-4, 110253-00-4) → 1,4-bis<3-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranos-2-yl)ureido>butane

Conditions	Yield
With water; calcium carbonate In dichloromethane Ambient temperature;	98%

1,4-diisocyanatobutane (4538-37-8) + amantadine hydrochloride (665-66-7) → 1,1'-(butane-1,4-diyl)bis[3-(adamantan-1-yl)urea] (1607795-35-6)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 12h; Inert atmosphere;	98%
With triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 12h; Inert atmosphere;

1,4-diisocyanatobutane (4538-37-8) + ethyl 2-oxopyrrolidine-5-carboxylate (66183-71-9) → ethyl 1-({[4-({[2-(ethoxycarbonyl)-5-oxopyrrolidin-1-yl]carbonyl}amino)butyl]amino}carbonyl)-5-oxopyrrolidine-2-carboxylate

Conditions	Yield
With sodium hydride In diethyl ether at 20℃; for 1h;	97%

1,4-diisocyanatobutane (4538-37-8) + rimantadine (13392-28-4, 117857-51-9, 117857-52-0, 129277-01-6) → 1,1'-(butane-1,4-diyl)bis{3-[1-(adamantan-1-yl)ethyl]urea} (1607795-36-7)

Conditions	Yield
In N,N-dimethyl-formamide at 15 - 25℃; for 6h;	97%

1,4-diisocyanatobutane (4538-37-8) + 1-(adamantan-1-yl)-2-aminobutane (779989-20-7) → 1,1'-(butane-1,4-diyl)bis{-3-[1-(adamantan-1-yl)butane-2-yl]urea}

Conditions	Yield
In N,N-dimethyl-formamide at 15 - 25℃; for 6h;	97%

1,4-diisocyanatobutane (4538-37-8) + 3-(adamantan-1-yloxy)propan-1-amine (21624-07-7) → 1,1'-(butane-1,4-diyl)bis{3-[3-(adamantan-1-yloxy)propyl]urea}

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	97%

1,4-diisocyanatobutane (4538-37-8) + rimantadine hydrochloride (1501-84-4, 33122-80-4, 33122-81-5, 33298-76-9) → 1,1'-(butane-1,4-diyl)bis{3-[1-(adamantan-1-yl)ethyl]urea} (1607795-36-7)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 12h; Inert atmosphere;	96%
With triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 12h; Inert atmosphere;

1,4-diisocyanatobutane (4538-37-8) + with 1-(adamant-1-yl)butan-2-amine hydrochloride (1607795-44-7) → 1,4-(tetramethylene)bis{[(adamant-1-yl)sec-butyl-1]urea} (1607795-37-8)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 12h; Inert atmosphere;	96%

1,4-diisocyanatobutane (4538-37-8) + 3-aminophenylboronic acid pinacolate (210907-84-9) → 1,1'-(butane-1,4-diyl)bis(3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea)

Conditions	Yield
With triethylamine In tetrahydrofuran at 60℃; for 2h;	95%

1,4-diisocyanatobutane (4538-37-8) + 2-aminobicyclo[2.2.1]heptane hydrochloride → 1,1'-(butane-1,4-diyl)bis(3-(bicyclo[2.2.1]heptan-2-yl)urea)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	95%

1,4-diisocyanatobutane (4538-37-8) + Norbornylamine (822-98-0) → 1,1'-(butane-1,4-diyl)bis(3-(bicyclo[2.2.1]heptan-2-yl)urea)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 8h;	95%

1,4-diisocyanatobutane (4538-37-8) + DL-(±)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine hydrochloride → 1,1'-(butane-1,4-diyl)bis(3-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)urea)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	94%

1,4-diisocyanatobutane (4538-37-8) + bornylamine (4481-88-3) → 1,1'-(butane-1,4-diyl)bis(3-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)urea)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 8h;	94%

1,4-diisocyanatobutane (4538-37-8) + 7-diethylamino-2-imino-2H-1-benzopyran-3-carbonitrile (80860-07-7) → 1,1'-(butane-1,4-diyl)bis{3-[3-cyano-7-(diethylamino)-2H-chromen-2-ylidene]urea} (1209400-38-3)

Conditions	Yield
In chloroform at 0 - 20℃;	88%

1,4-diisocyanatobutane (4538-37-8) + 4,6-diisopropyl-1,3-bis[methylene-(N'-2-aminophenylureylene)]-m-xylene (246018-53-1) → C34H44N8O4

Conditions	Yield
In N,N-dimethyl-formamide Cycloaddition;	85%

1,6-hexanediol (629-11-8) + 1,4-diisocyanatobutane (4538-37-8) → C18H30N4O6

Conditions	Yield
With dibutyltin dilaurate In diethyl ether at 0 - 20℃; for 4h; Inert atmosphere; Schlenk technique;	85%

N-(tert-butyloxycarbonyl)-S-methylisothiourea (173998-77-1) + 1,4-diisocyanatobutane (4538-37-8) → N1,N4-bis{[(tert-butoxycarbonylamino)(methylsulfanyl)methylene]aminocarbonyl}butane-1,4-diamine

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2.5h;	83%

1,4-diisocyanatobutane (4538-37-8) + 5-Diazoimidazole-4-carboxamide (102613-59-2) → C14H14N12O4

Conditions	Yield
In dimethyl sulfoxide at 25℃; for 12h;	82%

1,4-diisocyanatobutane (4538-37-8) + N-BOC-1,2-diaminoethane (57260-73-8) → di-tert-butyl (4,11-dioxo-3,5,10,12-tetraazatetradecane-1,14-diyl)biscarbamate

Conditions	Yield
In chloroform at 20℃; for 1h;	82%

1,4-diisocyanatobutane (4538-37-8) + 2,3,4,5,6-Penta-O-acetyl-1-amino-1-deoxy-D-glucitol hydrochloride → C38H58N4O22

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 12h;	81%

1,4-diisocyanatobutane (4538-37-8) + L-alanine methyl ester hydrochloride (2491-20-5) → methyl (2S)-2-[[4-[[[(1S)-2-methoxy-1-methyl-2-oxo-ethyl]carbamoyl]amino]butylcarbamoyl]amino]propanoate (1535206-13-3)

Conditions	Yield
With triethylamine In chloroform at 70℃; for 1h;	81%

1,4-diisocyanatobutane (4538-37-8) + tert-butyl (12-aminododecyl)carbamate (109792-60-1) → C40H80N6O6

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 3h; Inert atmosphere;	80%

furan-2-ylmethanamine (617-89-0) + 1,4-diisocyanatobutane (4538-37-8) → 1,1'-(butane-1,4-diyl)bis(3-(furan-2-ylmethyl)urea)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 8h;	80%

1,4-diisocyanatobutane (4538-37-8) + 2-(2-Aminoethoxy)ethanol (929-06-6) → 1-[2-(2-hydroxy-ethoxy)-ethyl]-3-(4-{3-[2-(2-hydroxy-ethoxy)-ethyl]-ureido}-butyl)-urea

Conditions	Yield
In 1,4-dioxane Ambient temperature;	76%

1,4-diisocyanatobutane (4538-37-8) + glycine ethyl ester hydrochloride (5680-79-5) → methyl 2-[[4-[[(2-methoxy-2-oxo-ethyl)carbamoyl]amino]butylcarbamoyl]amino]acetate (1535206-12-2)

Conditions	Yield
With triethylamine In chloroform at 70℃; for 18h;	76%

1,4-diisocyanatobutane (4538-37-8) + 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethylamine (134179-38-7) → 1,1'-butane-1,4-diylbis[3-(2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}ethyl)urea]

Conditions	Yield
With triethylamine In chloroform at 20℃; for 0.166667h; Cooling with ice;	76%

hexan-1-amine (111-26-2) + 1,4-diisocyanatobutane (4538-37-8) + phenol (108-95-2) → phenyl (4-(3-hexylureido)butyl)carbamate

Conditions	Yield
Stage #1: 1,4-diisocyanatobutane; phenol With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Stage #2: hexan-1-amine In dichloromethane for 0.5h;	75%

Upstream product

• 75-44-5 phosgene 
• 110-60-1 1,4-diaminobutane 
• 13043-98-6 heptadioic acid dihydrazide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 24230-70-4 N,N'-diacetoxy-adipamide 
• 1071-93-8 adipic acid dihydrazide 
• 102016-85-3 1,4-butamethylene-bis(phenyl carbamate) 
• 111-50-2 Adipic acid dichloride 
• 110-56-5 1,4-dichlorobutane 
• 50326-52-8 NN'-diformyl-1,4-diaminobutane 
• 15719-64-9 methylammonium carbonate 
• 25021-15-2 adipic diazide 

Downstream Products

• 19055-93-7 1,3-diazepan-2-one 
• 102016-85-3 1,4-butamethylene-bis(phenyl carbamate) 
• 1571103-87-1 tert-butyl 10,17-dioxo-3,6,21,24-tetraoxa-9,11,16,18-tetraazahexacosane-1,26-diyldicarbamate 
• 1234423-95-0 tenapanor 
• 1080018-68-3 N,N'-(1,1'-(butane-1,4-diylbis(azanediyl))bis(oxomethylene)bis(piperidine-4,1-diyl))bis(azanediyl)bis((benzyloxycarbonylamino)methan-1-yl-ylidene)bis(3,5-diamino-6-chloropyrazine-2-carboxamide) 

Relevant articles and documents

FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES

The disclosure provides, inter alia, safe and environmentally-friendly methods, such as flow chemistry, to synthesize isocyanates, such as methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and tetramethylxylene diisocyanate.

ISOCYANATES, DERIVATIVES, AND PROCESSES FOR PRODUCING THE SAME

The present invention is directed to processes for producing isocyanates and isocyanate derivatives from epoxide and carbon monoxide reagents. In preferred embodiments, the processes include a step for providing carbonylation of an epoxide reagent with a carbon monoxide reagent to produce a beta-lactone intermediate. In certain preferred embodiments, further carbonylation of a beta-lactone intermediate produces a succinic anhydride intermediate. The processes of the present invention include steps for rearranging beta-lactone intermediates and/or succinic anhydride intermediates to produce isocyanate products and/or isocyanate derivatives. In certain preferred embodiments, the isocyanate products may be copolymerized with polyol oligomers to provide polyurethane products.

METHOD FOR PREPARING ALIPHATIC DIISOCYANATE

The present invention relates to a method for preparing an aliphatic diisocyanate by pyrolyzing an aliphatic dicarbamate in liquid phase, using a tin (II) or (IV) compound as a catalyst and a zwitterionic compound as a stabilizer, thereby remarkably inhibiting high-boiling by-products and providing the aliphatic diisocyanate with high yield.