Methylene-bis(4-cyclohexylisocyanate) supplier

Name
Methylene-bis(4-cyclohexylisocyanate)
EINECS 225-863-2
CAS No. 5124-30-1
Article Data36
CAS DataBase
Density 1.07
Solubility Insoluble/Reactive
Melting Point 25 ºC
Formula C15H22 N2 O2
Boiling Point 168 °C / 1.5mmHg
Molecular Weight 262.352
Flash Point 211 ºC
Transport Information UN 3080
Appearance Clear colorless to light-yellow liquid.
Safety Poison by inhalation. Mildly toxic by ingestion. When heated to decomposition it emits very toxic fumes of NO_x and CN⁻.
Risk Codes R23;R36/37/38;R42/43
Molecular Structure
Hazard Symbols
Synonyms Isocyanicacid, methylenedi-1,4-cyclohexylene ester (6CI); Isocyanic acid,methylenedi-4,1-cyclohexylene ester (7CI,8CI); Methane,bis(4-isocyanatocyclohexyl)- (6CI); 1,1-Methylene bis(4-isocyanatocyclohexane);4,4'-Di(isocyanatocyclohexyl)methane; 4,4'-Dicyclohexylmethylene diisocyanate;4,4'-Diisocyanatodicyclohexylmethane; 4,4'-Methylenebis(cyclohexyl isocyanate);4,4'-Methylenedicyclohexyl diisocyanate; 4,4'-Methylenedicyclohexylenediisocyanate; Bis(4-isocyanatocyclohexyl)methane; Dicyclohexylmethane4,4'-diisocyanate; H12MDI; Hydrogenated MDI; Methylenebis(1,4-cyclohexylene)diisocyanate; Methylenebis(4-cyclohexyl isocyanate);Methylenebis(4-isocyanatocyclohexane); Methylenedi-1,4-cyclohexyleneisocyanate; Methylenedi-4,1-cyclohexylene isocyanate;Methylenedi-4-cyclohexylene diisocyanate;Methylenedicyclohexylene-4,4'-diisocyanate; Perhydrodiphenylmethane-4,4'-diisocyanate
PSA 58.86000
LogP 3.16570

Synthetic route

: 439680-99-6
phenyl N-[4-({4-[(phenoxycarbonyl)amino]cyclohexyl}methyl)cyclohexyl]carbamate

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
at 170℃; Temperature; Pyrolysis;	99.9%
at 170 - 220℃; under 3.75038 - 757.576 Torr; for 240h; Product distribution / selectivity;	93.2%
With DURANATE TPA-100 In 1,2-dichloro-benzene at 250℃; under 6000.6 Torr; for 200h; Inert atmosphere;	84%
In 1,2-dichloro-benzene at 160 - 250℃; under 6000.6 Torr; Inert atmosphere;	83%
at 250℃; under 9.75098 Torr; Product distribution / selectivity; Industry scale;

: 75-44-5
phosgene

: 1761-71-3
4,4'-diaminodicyclohexylmethane

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
at 360℃; under 300.03 Torr; Product distribution / selectivity; Gas phase;	97.8%
at 360℃; under 300.03 Torr; Product distribution / selectivity; Inert atmosphere;	97.8%
In 1,2-dichloro-benzene at 355 - 360℃; under 375.038 Torr; Temperature; Inert atmosphere; Large scale;	97%
at 360℃; Inert atmosphere;	97.9 %Chromat.

: 47460-66-2
dicyclohexylmethane-4,4'-diethylurethane

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
1,2-dimethyl-3-ethylimidazole nitrate at 200 - 240℃; under 48.7549 Torr; for 1.66667h;	91%

: 1761-71-3
4,4'-diaminodicyclohexylmethane

: 57-13-6
urea

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
Stage #1: 4,4'-diaminodicyclohexylmethane; urea In butan-1-ol at 135℃; under 760.051 Torr; for 8h; Stage #2: With butan-1-ol at 190 - 220℃; under 8250.83 - 10501.1 Torr; for 10.5h; Stage #3: tin(ll) chloride at 235 - 237℃; under 6.75068 - 7.50075 Torr; Product distribution / selectivity;	90%

: 99305-42-7
dibutyl (methylene-bis(cyclohexane-4,1,diyl))dicarbamate

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
1-ethyl-2,3-dimethylimidazolium hexafluorophosphate at 190 - 240℃; under 48.7549 Torr; for 1.66667h;	88%
tin(ll) chloride at 232℃; under 6.75068 Torr;
With 2.6-dimethylphenol; dibutyltin dilaurate at 220℃; under 9.75098 Torr; for 13h; Product distribution / selectivity;
at 234℃; under 6.0006 Torr; Product distribution / selectivity; falling film evaporator; Industry scale;
With tin(ll) chloride at 236℃; under 6.75068 Torr; Product distribution / selectivity;

: 63896-13-9
4,4'-methylene-di(cyclohexylcarbamate) dimethyl ester

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
zinc(II) oxide; 1-(n-butyl)-3-methylimidazolium triflate at 200 - 240℃; under 48.7549 Torr; for 1.66667h;	81%

: H12MDU

: H12MDU

: 99305-42-7
dibutyl (methylene-bis(cyclohexane-4,1,diyl))dicarbamate

A: 2,2'-methylene-dicyclohexyldiisocyanate

B: 2,4'-methylene-dicyclohexyldiisocyanate

C: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
tin(ll) chloride at 230℃; under 7.50075 Torr;

...Expand

: 99305-42-7
dibutyl (methylene-bis(cyclohexane-4,1,diyl))dicarbamate

A: 2,2'-methylene-dicyclohexyldiisocyanate

B: 2,4'-methylene-dicyclohexyldiisocyanate

C: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
tin(ll) chloride at 140 - 236℃; under 7.50075 Torr; for 8.5h;

...Expand

: 1761-71-3
4,4'-diaminodicyclohexylmethane

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: phenol / ferrous acetylacetonate / 50 °C / Industry scale 2: 240 h / 170 - 220 °C / 3.75 - 757.58 Torr View Scheme
Multi-step reaction with 3 steps 1: tert-amylphenol / 100 °C / Industry scale 2: 200 °C / 525.05 Torr / Industry scale 3: 260 °C / 9.75 Torr / Industry scale View Scheme
Multi-step reaction with 3 steps 1: tert-amylphenol / 100 °C / Industry scale 2: 200 °C / 600.06 Torr / Industry scale 3: 250 °C / 6 Torr / Industry scale View Scheme

: 1027096-18-9
bis(2,4-di-tert-amylphenyl) 4,4'-methylene-di(cyclohexylcarbamate)

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
at 210℃; under 0.975098 Torr; for 11h; Product distribution / selectivity;

: 1027096-17-8
4,4'-methylenedi(cyclohexylcarbamate) bis(3-methylbutyl) ester

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
With dibutyltin dilaurate at 270℃; under 9.75098 Torr; Product distribution / selectivity; Industry scale;

: C25H46N2O4

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
dibutyltin dilaurate at 170 - 270℃; under 9.75098 Torr;

: 4,4'-methylenebis(cyclohexyl urea)

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 200 °C / 525.05 Torr / Industry scale 2: 260 °C / 9.75 Torr / Industry scale View Scheme
Multi-step reaction with 2 steps 1: 200 °C / 600.06 Torr / Industry scale 2: 250 °C / 6 Torr / Industry scale View Scheme
Multi-step reaction with 2 steps 1: 220 °C / 450.05 Torr / Industry scale 2: 240 °C / 6 Torr / Industry scale View Scheme
Multi-step reaction with 2 steps 1: 230 °C / 262.53 Torr / Industry scale 2: 260 °C / 9.75 Torr / Industry scale View Scheme

: 1266555-02-5
N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (4-ethylphenyl) ester)

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
at 260℃; under 9.75098 Torr; Industry scale;

: N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (2-tert-amylphenyl) ester)

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
at 260℃; under 9.75098 Torr; Industry scale;

: 1266555-51-4
N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (2,4,6-trimethylphenyl) ester)

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
at 240℃; under 6.0006 Torr; Industry scale;

: N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (4-ethoxyphenyl) ester)

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
at 250℃; under 6.0006 Torr; Industry scale;

: N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (2-butyloxy)ethyl ester)

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc diacetate / 200 °C / 150.01 Torr / Industry scale 2: 250 °C / 3.75 Torr / Industry scale View Scheme

: 1266554-85-1
N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (2,6-dimethoxyphenyl) ester)

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
at 250℃; under 3.75038 Torr; Industry scale;

: 195456-49-6
trimethyl hexamethylene diisocyanate

: 822-06-0
Hexamethylene diisocyanate

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: C15H24F2N2O2

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; under 760.051 Torr; for 3h; Concentration;

: 124-38-9
carbon dioxide

: 1761-71-3
4,4'-diaminodicyclohexylmethane

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Conditions

Conditions	Yield
With phenylsilane; triethylamine; trichlorophosphate In toluene at 30℃; for 12h; Reagent/catalyst; Temperature;

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: 124-30-1
1-aminooctadecane

: C51H100N4O2

Conditions

Conditions	Yield
With Desmodur W In hexane for 1h; Reflux;	100%
In hexane for 1h; Reflux;	100%

: 2009-83-8
6-chloro-1-hexanol

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: bis(6-chlorohexyl) (methylenebis(cyclohexane-4,1-diyl))dicarbamate

Conditions

Conditions	Yield
With dibutyltin dilaurate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	91%

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: 693-57-2
12-Aminododecanoic acid

: C39H72N4O6

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; Inert atmosphere;	80%

: 41744-75-6
isostearyl Alcohol

: 7300-34-7
4,9-dioxa-1,12-dodecanediamine

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: C76H144N6O8

Conditions

Conditions	Yield
Stage #1: isostearyl Alcohol; 4,4'-bis(diisocyanato)dicyclohexylmethane; dibutyltin dilaurate In hexane at 20 - 50℃; for 1h; Stage #2: 4,9-dioxa-1,12-dodecanediamine In hexane at 20℃; for 1h;	72%

...Expand

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: 57-14-7
1,1-dimethylhydrazine

: 4,4'-bis(diimethylamino-urea)dicyclohexylmethane

Conditions

Conditions	Yield
In toluene at 20℃; for 48h;	49%

: 616-91-1
N-acetylcystein

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: 2-acetylamino-3-{4-[4-(2-acetylamino-2-carboxyethylsulfanylcarbonylamino)cyclohexylmethyl]cyclohexylcarbamoylsulfanyl}propionic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 0.25h;	29%

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: 2162-74-5
N,N'-bis(2,6-diisopropylphenyl)carbodiimide

: C65H90N6O2

Conditions

Conditions	Yield
at 110℃; for 7h; Sealed tube;	0.96%

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: C44H68N6O5

Conditions

Conditions	Yield
With water at 140℃;

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

poly(tetramethylene oxide)glycol of molecular weight 650: poly(tetramethylene oxide)glycol of molecular weight 650

4,4-methylene bis(cyclohexyl isocyanate) terminated [poly(tetramethylene oxide)glycol of molecular weight 650]: 4,4-methylene bis(cyclohexyl isocyanate) terminated [poly(tetramethylene oxide)glycol of molecular weight 650]

Conditions

Conditions	Yield
at 80℃;

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

poly(tetramethylene oxide)glycol of molecular weight 1000: poly(tetramethylene oxide)glycol of molecular weight 1000

4,4-methylene bis(cyclohexyl isocyanate) terminated [poly(tetramethylene oxide)glycol of molecular weight 1000]: 4,4-methylene bis(cyclohexyl isocyanate) terminated [poly(tetramethylene oxide)glycol of molecular weight 1000]

Conditions

Conditions	Yield
at 80℃;

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

poly(tetramethylene oxide)glycol of molecular weight 2000: poly(tetramethylene oxide)glycol of molecular weight 2000

4,4-methylene bis(cyclohexyl isocyanate) terminated [poly(tetramethylene oxide)glycol of molecular weight 2000]: 4,4-methylene bis(cyclohexyl isocyanate) terminated [poly(tetramethylene oxide)glycol of molecular weight 2000]

Conditions

Conditions	Yield
at 80℃;

: 101-14-4
4,4'-methylenebis-(2-chloroaniline)

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

copolymer; monomer(s): 4,4\-methylene-dicyclohexyl-diisocyanate; methylene-bis-ortho-chloroaniline: copolymer; monomer(s): 4,4\-methylene-dicyclohexyl-diisocyanate; methylene-bis-ortho-chloroaniline

Conditions

Conditions	Yield
In cyclohexanone; N,N-dimethyl-formamide at 80 - 90℃;

: 2,4-diamino-3,5-dimethylsulphanylchlorobenzene

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

copolymer; monomer(s): 4,4\-methylene-dicyclohexyl-diisocyanate; 2,4-diamino-3,5-dimethylsulphanylchlorobenzene: copolymer; monomer(s): 4,4\-methylene-dicyclohexyl-diisocyanate; 2,4-diamino-3,5-dimethylsulphanylchlorobenzene

Conditions

Conditions	Yield
In cyclohexanone; N,N-dimethyl-formamide at 80 - 90℃;

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: 107-15-3
ethylenediamine

copolymer; monomer(s): 4,4\-methylene-dicyclohexyl-diisocyanate; ethylene diamine: copolymer; monomer(s): 4,4\-methylene-dicyclohexyl-diisocyanate; ethylene diamine

Conditions

Conditions	Yield
dibutyltin(II) dilaurate In cyclohexanone; N,N-dimethyl-formamide at 80 - 90℃;

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: C53H92N6O8

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O / 140 °C View Scheme

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: 95848-28-5
ethyl nitroacetate potassium salt

: C23H34N4O10(2-)*2K(1+)

Conditions

Conditions	Yield
In diethylene glycol dimethyl ether at 20 - 100℃; for 16h;
In 1,2-dimethoxyethane at 20 - 85℃; for 72h;

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

Reaxys ID: 11465127: Reaxys ID: 11465127

Conditions

Conditions	Yield
Stage #1: 4,4'-bis(diisocyanato)dicyclohexylmethane; trihexyl(tetradecyl)phosphonium 1,2,4-triazolide at 30℃; for 3.5h; Stage #2: With dibutyl phosphate

: 77-99-6
1,1,1-tri(hydroxymethyl)propane

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Reaxys ID: 11465128: Reaxys ID: 11465128

Conditions

Conditions	Yield
zinc 2-ethylhexanoate at 120℃; for 6h;

...Expand

: 34454-97-2
N-methyl-1,1,2,2,3,3,4,4-nonafluoro-N-(2-hydroxyethyl)butane-1-sulphonamide

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: C22H30F9N3O5S

Conditions

Conditions	Yield
In n-heptane at 90 - 100℃;

: C46H44F34O12S2

: 5124-30-1
4,4'-bis(diisocyanato)dicyclohexylmethane

: C105H106F68N2O26S4

Conditions

Conditions	Yield
dibutyltin dilaurate In methylpentan-2-one, 4- at 55℃; for 4h; Michael Condensation; Heating / reflux;

Methylene-bis(4-cyclohexylisocyanate) Chemical Properties

Molecular Formula: C₁₅H₂₂N₂O₂
Formula Weight: 262.35
mp : 25^°C
bp : 168 ^°C / 1.5mmHg
Fp : >230 ^°F
density : 1.066 g/mL at 25 ^°C(lit.)
refractive index : n20/D 1.497(lit.)
Water Solubility of METHYLENE BIS(4-CYCLOHEXYLISO-CYANATE): Insoluble/Reactive

Methylene-bis(4-cyclohexylisocyanate) Toxicity Data With Reference

1.		orl-rat LD50:9900 mg/kg		85INA8 Documentation of the Threshold Limit Values and Biological Exposure Indices. 6 (1991),998.
2.		ihl-rbt LC50:20 ppm/5H		85INA8 Documentation of the Threshold Limit Values and Biological Exposure Indices 5 (1986),392.

Methylene-bis(4-cyclohexylisocyanate) Consensus Reports

Reported in EPA TSCA Inventory.

Methylene-bis(4-cyclohexylisocyanate) Safety Profile

Hazard Codes : T
Risk Statements : 23-36/37/38-42/43
Safety Statements : 26-28-38-45-1/2
RIDADR : UN 2206 6.1/PG 2
WGK Germany : 1
RTECS : NQ9250000
HazardClass : 6.1
PackingGroup : III

Poison by inhalation. Mildly toxic by ingestion. When heated to decomposition it emits very toxic fumes of NO_x and CN⁻.

Methylene-bis(4-cyclohexylisocyanate) Standards and Recommendations

OSHA PEL: CL 0.01
ACGIH TLV: TWA 0.005 ppm
NIOSH REL: (Dicyclohexylmethane 4,4′-diisocyanate) TWA CL 0.01 ppm

Product Name

Methylene-bis(4-cyclohexylisocyanate)

Synthetic route

Methylene-bis(4-cyclohexylisocyanate) Chemical Properties

Methylene-bis(4-cyclohexylisocyanate) Toxicity Data With Reference

Methylene-bis(4-cyclohexylisocyanate) Consensus Reports

Methylene-bis(4-cyclohexylisocyanate) Safety Profile

Methylene-bis(4-cyclohexylisocyanate) Standards and Recommendations

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