538-75-0

Basic information

• Product Name: Dicyclohexylcarbodiimide
• Synonyms: N,N'-DICYLOHEXYLCARBODIIMIDE;N,N-DICYCHOHEXYLCARBODIIMIDE;N,N-DICYCLOHEXYL CARBODIIMIDE;N,N'-DICYCLOHEXYLCARBODIIMIDE;1,3-DICYCLOHEXYLCARBODIIMIDE;Bis(cyclohexyl)carbodiimide;DCCI;DCC
• CAS NO: 538-75-0
• Molecular Formula: C₁₃H₂₂N₂
• Molecular Weight: 206.33
• EINECS: 208-704-1
• Product Categories: Pharmaceutical Intermediates;Amino Acid Derivatives;Starting Raw Materials & Intermediates;Miscellaneous;Organics;Coupling Reagent;Peptide Coupling Reagents;Condensing Agents (DNA / RNA Synthesis);Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Nucleosides, Nucleotides & Related Reagents;Peptide Synthesis;Protecting Agents, Phosphorylating Agents & Condensing Agents;Reagents for Oligosaccharide Synthesis;Synthetic Organic Chemistry;Peptide;Protected Amino Acids;Synthetic Reagents;CarbodiimidesSynthetic Reagents;Carbodiimides;Coupling;Peptide Synthesis;peptides;Zero-Length Crosslinker
• Mol File: 538-75-0.mol
• Article Data: 52

Chemical Properties

• Melting Point: 34-35 °C(lit.)
• Boiling Point: 122-124 °C6 mm Hg(lit.)
• Flash Point: 190 °F
• Appearance: White to pale yellow/Waxy Solid or Crystalline Mass
• Density: 1.247 g/mL at 25 °C
• Vapor Pressure: 1.044-1.15Pa at 20-25℃
• Refractive Index: n20/D 1.48
• Storage Temp.: Store at RT.
• Solubility: methylene chloride: 0.1 g/mL, clear, colorless
• Water Solubility: Reaction
• Sensitive: Moisture Sensitive
• Stability: Stable, but moisture sensitive. Combustible. Incompatible with strong oxidizing agents. Avoid exposure to air or moisture.
• Merck: 14,3096
• BRN: 610662
• CAS DataBase Reference: Dicyclohexylcarbodiimide(CAS DataBase Reference)
• NIST Chemistry Reference: Dicyclohexylcarbodiimide(538-75-0)
• EPA Substance Registry System: Dicyclohexylcarbodiimide(538-75-0)

Safety Data

• Hazard Codes: T,Xn,T+
• Statements: 23/24/25-34-40-43-41-36/38-21-24-22-62-37/38-10-61-26-38-20/22
• Safety Statements: 26-36/37/39-45-41-24-37/39-24/25-36-16-53-28
• RIDADR: UN 2922 8/PG 2
• WGK Germany: 3
• RTECS: FF2160000
• F: 3-8-10-21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 538-75-0(Hazardous Substances Data)

Usage

Chemical Description

Dicyclohexylcarbodiimide is a coupling reagent used in organic synthesis.

Chemical Description

Dicyclohexylcarbodiimide is a coupling agent that is used to activate the carboxylic acid group of the amino acid.

Chemical Description

Dicyclohexylcarbodiimide is a coupling reagent used in the synthesis of p-Nitrophenyl benzyloxycarbonyl-D-asparaginate.

Synthetic route

1,3-Dicyclohexylurea (2387-23-7) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With dichloromethylenedimethyliminium chloride; triethylamine In dichloromethane at 0℃;	100%
With bis(trichloromethyl) carbonate In 1-methyl-pyrrolidin-2-one at 30 - 40℃; for 6h; Autoclave;	99.5%
With pyridine; chloroacetyl chloride In dichloromethane at 0 - 60℃; for 10h; Solvent; Temperature; Reagent/catalyst;	97.3%

1,3-dicyclohexylthiourea (1212-29-9) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With dicarbonyl(cyclopentadienyl)methyliron(II) In tetrahydrofuran at 60℃; for 24h; Reagent/catalyst; Inert atmosphere;	99%
With dicarbonyl(cyclopentadienyl)methyliron(II); Triethoxysilane In tetrahydrofuran at 60℃; for 24h; Schlenk technique; Inert atmosphere;	95%
With 1,1'-Thiocarbonyldi-2(1H)-pyridone In toluene for 8h; Heating;	94%

N,N'-Dicyclohexyl-C-chlor-formamidinium (114316-64-2) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With sodium hydroxide In water	92.4%

Cyclohexyl isocyanate (3173-53-3) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
O=P(MeNCH2CH2)3N at 200 - 230℃; for 91h;	92%
at 20 - 230℃; for 4h; Product distribution / selectivity; Molecular sieve;	30.8%
[C5H5Fe(CO)2]2 In xylene for 24h; Heating;	27%

1,3-dicyclohexylthiourea (1212-29-9) → 2-hydroxypyridin (142-08-5) + dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With di-2-pyridyl thionocarbonate; dmap In acetonitrile at 80℃; for 15h;	A n/a B 84%

1,3-Dicyclohexylurea (2387-23-7) + triphenylphosphine (603-35-0) → dicyclohexyl-carbodiimide (538-75-0) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
With aluminum oxide; LutClO4 constant current electrolysis;	A 72% B n/a
With aluminum oxide; LutClO4 In dichloromethane constant current electrolysis;	A 72% B n/a

1,3-dicyclohexylthiourea (1212-29-9) + triphenylphosphine (603-35-0) → dicyclohexyl-carbodiimide (538-75-0) + triphenylphosphine sulfide (3878-45-3)

Conditions	Yield
With aluminum oxide; LutClO4 In dichloromethane constant current electrolysis;	A 56% B n/a

1,3-dicyclohexylthiourea (1212-29-9) + triphenylphosphine (603-35-0) → dicyclohexyl-carbodiimide (538-75-0) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
With aluminum oxide; LutClO4 In dichloromethane constant current electrolysis;	A 56% B n/a

1,3-Dicyclohexylurea (2387-23-7) → Cyclohexyl isocyanide (931-53-3) + N-cyclohexylimidocarbonyl dichloride (2666-80-0) + dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With sodium hydroxide; triethylamine In chloroform for 4h; Heating;	A 21% B 38% C 18%

Cyclohexyl isocyanide (931-53-3) + cyclohexylamine (108-91-8) → 1,3-Dicyclohexylurea (2387-23-7) + dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With oxygen; sodium carbonate; palladium diacetate In acetonitrile at 100℃; under 2068.6 Torr; for 3h;	A 10 % Chromat. B 35%

Cyclohexyl isocyanide (931-53-3) + cyclohexylamine (108-91-8) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In acetonitrile at 50℃; for 12h; Inert atmosphere; Electrochemical reaction;	26%
With iodine; oxygen; sodium carbonate; palladium diacetate In acetonitrile at 100℃; under 2068.6 Torr; for 3h;	67 % Chromat.
With air; gold In hexane at 20℃; for 0.166667h; Kinetics;
With Cumene hydroperoxide; iodine In tert-butyl methyl ether at 55℃; for 6h;	51 %Chromat.

Cyclohexyl isocyanate (3173-53-3) + 3-methyl-1-phenylphospholane (24901-29-9, 32721-26-9, 32721-27-0, 54932-28-4, 57664-94-5) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With xylene

1,3-Dicyclohexylurea (2387-23-7) + p-toluenesulfonyl chloride (98-59-9) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With pyridine

N-ethylmorpholine; (100-74-3) + C29H41N2O2PS2 (83599-89-7) → Dithiophosphoric acid O,O'-bis-(2,6-dimethyl-phenyl) ester; compound with 4-ethyl-morpholine + dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
In dichloromethane

C29H41N2O2PS2 (83599-89-7) → C16H18O2PS2(1-) + dicyclohexyl-carbodiimide (538-75-0) + C29H41N2O2PS2*BF4(1-)*H(1+)

Conditions	Yield
In dichloromethane at 20℃; Rate constant; Product distribution; equilibrium studies, effect of addition of excess base or acid on the rate constants, effect of addition of triethylamine in various concentrations on the rate constants;

C29H41N2O2PS2 (83599-89-7) + triethylamine (121-44-8) → Dithiophosphoric acid O,O'-bis-(2,6-dimethyl-phenyl) ester; compound with triethyl-amine + dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
In dichloromethane Mechanism;
In dichloromethane

C25H33N2O2PS2 (92366-10-4) → O,O-diphenyl dithiophosphate (55979-88-9) + dicyclohexyl-carbodiimide (538-75-0) + C25H33N2O2PS2*BF4(1-)*H(1+)

Conditions	Yield
In dichloromethane at 20℃; Rate constant; Product distribution; equilibrium studies, effect of addition of excess base or acid on the rate constants;

C37H57N2O2PS2 (92366-11-5) → C24H34O2PS2(1-) + dicyclohexyl-carbodiimide (538-75-0) + C37H57N2O2PS2*BF4(1-)*H(1+)

Conditions	Yield
In dichloromethane at 20℃; Rate constant; Product distribution; equilibrium studies, effect of addition of excess base or acid on the rate constants, effect of the initial substrate concentration on the rate constants;

C29H41N2O2PS2*BF4(1-)*H(1+) → C29H41N2O2PS2 (83599-89-7) + C16H18O2PS2(1-) + dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Product distribution; Rate constant; further amines, effect of base:substrate ratio on the product formation;

isothiocyanatocyclohexane (1122-82-3) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With silica gel 1.) CH2Cl2, controlled potential electrolysis, 2.) petroleum ether, ether, 200 deg C; Yield given. Multistep reaction;

N,N'-dicyclohexylselenourea (34656-93-4) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 5h; Heating; Yield given;

Cyclohexyl isocyanide (931-53-3) → dicyclohexyl-carbodiimide (538-75-0) + N-benzyloxycarbonyl-alanine

Conditions	Yield
Multi-step reaction with 2 steps 1: Se, DBU / tetrahydrofuran / 1 h / Heating 2: DBU, O2 / tetrahydrofuran / 5 h / Heating View Scheme

cyclohexylamine (108-91-8) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-methyl-butan-1-ol 2: pyridine View Scheme

C37H37N2O5PW + diisopropyl-carbodiimide (693-13-0) → C31H29N2O5PW + dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;

C13H23ClN2*Cl2HO2P → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With triethylamine In tetrahydrofuran

Cyclohexyl isocyanate (3173-53-3) + cyclohexyl azide (19573-22-9) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
With triphenylphosphine In acetonitrile at 20℃;

carbon disulfide (75-15-0) + cyclohexylamine (108-91-8) → dicyclohexyl-carbodiimide (538-75-0)

Conditions	Yield
In water at 30℃;

O,O-dimethyl S-hydrogen phosphorothioate (1112-38-5) + dicyclohexyl-carbodiimide (538-75-0) → N-Dimethylphosphoryl-N,N'-dicyclohexylthiourea (87763-29-9)

Conditions	Yield
In diethyl ether Product distribution; Ambient temperature; other phosphoro acids investigated;	100%
In diethyl ether Ambient temperature;

bis(trifluoromethyl)trichlorophosphorane (353-77-5) + dicyclohexyl-carbodiimide (538-75-0) → C15H22Cl3F6N2P

Conditions	Yield
In tetrachloromethane Heating;	100%

tris(trifluoromethyl)phosphine dichloride (420-72-4) + dicyclohexyl-carbodiimide (538-75-0) → C16H22Cl2F9N2P

Conditions	Yield
In tetrachloromethane Heating;	100%

Trifluormethyl-phosphor-tetrachlorid (1066-48-4) + dicyclohexyl-carbodiimide (538-75-0) → C14H22Cl4F3N2P

Conditions	Yield
In tetrachloromethane Heating;	100%

2-hydroxy-2-thiono-5,5-dimethyl-1,3,2-dioxaphosphorinane (45734-11-0) + dicyclohexyl-carbodiimide (538-75-0) → 5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl 5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl-oxide (15762-04-6) + 1,3-dicyclohexylthiourea (1212-29-9)

Conditions	Yield
In acetonitrile Mechanism; Product distribution; Ambient temperature;	A 100% B 98%

3-(acetoxymethyl)-7α-chloro-Δ3-cephem-4-carboxylic acid 1,1-dioxide (126621-87-2) + dicyclohexyl-carbodiimide (538-75-0) → 3-acetoxymethyl-7α-chloro-4-spiro-<3'-(1'-cyclohexyl-4'-cyclohexylimino-2'-oxoazetidinyl)>-2-cephem 1,1-dioxide (129441-69-6, 129519-60-4, 148153-25-7)

Conditions	Yield
In dichloromethane for 0.0833333h; Product distribution; Mechanism; various cephalosporanic acid sulphones;	100%
In dichloromethane for 0.0833333h;	100%

dicyclohexyl-carbodiimide (538-75-0) → C13H22Cl5N2P

Conditions	Yield
With phosphorus pentachloride In tetrachloromethane Heating;	100%

dicyclohexyl-carbodiimide (538-75-0) + p-chlorobenzoic p-nitrophenyldiazoacetic anhydride (627892-65-3) → 4-Chloro-benzoic acid 1-cyclohexyl-4-[(Z)-cyclohexylimino]-2-(4-nitro-phenyl)-3-oxo-azetidin-2-yl ester

Conditions	Yield
dirhodium tetraacetate In benzene	100%

trans-4-oxo-2-pentenoic acid (2833-28-5) + dicyclohexyl-carbodiimide (538-75-0) → 1,3-dicyclohexyl-5-(2,2,2-trifluoro-1-trifluoromethylethyl)imidazolidine-2,4-dione

Conditions	Yield
With 2,4,6-trimethyl-pyridine In acetonitrile at 20℃;	100%

dicyclohexyl-carbodiimide (538-75-0) → (C6H11NH)2CN2C(C6H11NH)2 (53959-22-1)

Conditions	Yield
With hydrazine hydrate In tetrahydrofuran at 20℃; for 48h;	100%

morpholine (110-91-8) + dicyclohexyl-carbodiimide (538-75-0) + 4-nitrophenyl phosphate monoester bis(cyclohexylammonium) salt → 4-morpholinyl-N,N'-dicyclohexylcarboxamidinium p-nitrophenyl phosphomorpholidate

Conditions	Yield
In 2-methyl-propan-1-ol; water for 15h; Heating;	100%

Cp2Zr(N(2,6-Me2C6H3)C=N(SiMe3)N(SiMe3)) + dicyclohexyl-carbodiimide (538-75-0) → [(C5H5)2ZrN(C6H3(CH3)2)C(NC6H11)N(C6H11)]

Conditions	Yield
In benzene-d6 byproducts: Me3SiN=C=NSiMe3; (inert gas); an NMR tube charged with complex, 1,4-dimethoxybenzene and C6D6; carbodiimide added; not isolated, detected by NMR;	100%

2-bromophenylacetic acid (4870-65-9) + dicyclohexyl-carbodiimide (538-75-0) → 1,3-dicyclohexyl-5-phenylimidazolidine-2,4-dione

Conditions	Yield
With thymidine 5'-phosphate In dichloromethane at 20℃;	100%
With 2,4,6-trimethyl-pyridine In dichloromethane at 20℃;	98%

Trifluoromethanesulfonamide (421-85-2) + dicyclohexyl-carbodiimide (538-75-0) → N-[bis(cyclohexylamino)methylidene]-1,1,1-trifluoromethanesulfonamide (1338440-24-6)

Conditions	Yield
In dichloromethane at 20℃; for 6h;	100%
In dichloromethane for 6h;	100%
With nitromethane; copper dichloride for 2h; Milling; Green chemistry;	98%

1-benzylindole-3-carboxylic acid (27018-76-4) + dicyclohexyl-carbodiimide (538-75-0) → 2-(1-benzyl-1H-indole-3-carbonyl)-1,3-dicyclohexylisourea (1363386-89-3)

Conditions	Yield
With dmap In dichloromethane at 20℃; for 1.5h;	100%

cis-Octadecenoic acid (112-80-1) + N3,N6-di(tert-butoxycarbonyl)-3,6-diazaoctane-1,8-diol (167407-91-2) + dicyclohexyl-carbodiimide (538-75-0) → N,N'-di-tert-butylcarbonyl-N,N'-bis(2-hydroxyethyl)ethylenediamine dioleate (167951-93-1) + 1,3-Dicyclohexylurea (2387-23-7)

Conditions	Yield
dmap In n-heptane at 20 - 40℃; Product distribution / selectivity;	A n/a B 99.6%

2-Chloroaniline (95-51-2) + dicyclohexyl-carbodiimide (538-75-0) → N-o-chlorophenyl-N', N"-dicyclohexylguanidine (96405-47-9)

Conditions	Yield
With Sm[N(TMS)2]2(THF)3 at 20℃; for 0.25h; Inert atmosphere;	99.3%
Stage #1: o-chloroaniline With C76H124N6Nd2O6Si4 In neat (no solvent) for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: dicyclohexyl-carbodiimide In neat (no solvent) at 60℃; for 0.25h; Schlenk technique; Inert atmosphere;	98%
With C114H132N6O6Yb3*2C7H8 at 60℃; for 0.25h; Schlenk technique; Inert atmosphere;	98%

dicyclohexyl-carbodiimide (538-75-0) → N,N'-di-cyclohexylformamidine (2303-89-1)

Conditions	Yield
Stage #1: dicyclohexyl-carbodiimide With iron(II) tetrafluoroborate hexahydrate; phenylsilane; tris(2-diphenylphosphinoethyl)phosphine In tetrahydrofuran at 100℃; for 20h; Stage #2: With water Reagent/catalyst;	99%
With water; 5-methoxy-1,3,4-triphenyl-4,5-dihydro-1H-1,2-4-triazoline In 1,2-dimethoxyethane at 150℃; under 760.051 Torr; Inert atmosphere; Sealed tube; Microwave irradiation;	75%
With sodium tetrahydroborate In isopropyl alcohol
With hydrogen; palladium dihydroxide; barium sulfate In ethanol

carboxymethyltriphenylphosphoniumm chloride (7343-26-2) + dicyclohexyl-carbodiimide (538-75-0) → (1,3-dicyclohexylureidocarbonylmethyl)triphenylphosphonium chloride (80304-21-8)

Conditions	Yield
In dichloromethane for 0.0833333h;	99%

cyclohexylamine (108-91-8) + dicyclohexyl-carbodiimide (538-75-0) → N,N',N''-tricyclohexylguanidine (4833-41-4)

Conditions	Yield
With C24H50N5Si2Y In neat (no solvent) at 20℃; for 2h; Inert atmosphere; Schlenk technique;	99%
With zinc(II) oxide In toluene at 80℃; for 8h;	95%
In tert-butyl alcohol at 100℃; for 24h;	74%
With Zn-Al hydrotalcite In toluene at 110℃; for 12h; Sealed tube;	52%
In hexane at 90℃; for 48h; Inert atmosphere; Pressure tube;

dicyclohexyl-carbodiimide (538-75-0) + diphenylphosphane (829-85-6) → (Z)-N,N'-dicyclohexyl(diphenylphosphino)formamidine (643014-87-3, 810692-09-2)

Conditions	Yield
potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 0.0833333h;	99%
With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃;	71%

cyclohexyl isoselenocyanate (4426-69-1) + dicyclohexyl-carbodiimide (538-75-0) → cyclohexyl-N-[3-cyclohexyl-4-(cyclohexylimino)-1,3-selenazetidin-2-ylidene]benzenamine

Conditions	Yield
In hexane for 12h; Heating;	99%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + dicyclohexyl-carbodiimide (538-75-0) → (E)-N,N'-dicyclohexyl-3,4-dihydro-1H-isoquinoline-2-carboxamidine

Conditions	Yield
[Y((CH3)4C5Si(CH3)2N(phenyl))(trimethylsilylmethyl)(tetrahydrofuran)2] In benzene at 80℃; for 0.5h;	99%
[{Me2Si(C5Me4)(NPh)}Y(CH2SiMe3)(thf)2] In benzene at 80℃; for 0.5h;

2,6-diisopropylbenzenamine (24544-04-5) + dicyclohexyl-carbodiimide (538-75-0) → N,N"-dicyclohexyl-N'-2,6-diisopropylphenylguanidine

Conditions	Yield
[(Me3Si)2N]3Yb(μ-Cl)Li(THF)3 In tetrahydrofuran at 60℃; for 24h;	99%
With (C9H6CMe2CH2C5H4N-α)Y[N(SiHMe2)2]2 In toluene at 80℃; for 24h; Temperature; Schlenk technique; Glovebox; Inert atmosphere;	90%
With [Ph2B(tBuIm)2FeNDipp][K(18-C-6)THF2] In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	83%
With bis(tetrahydrofuran)calcium-bis[bis(trimethylsilyl)amide] In hexane at 80℃; for 2h;	55%
With [Cp*2(Me)Zr(μ-O)Zr(NMe2)2(μ-O)Zr(Me)Cp*2] In benzene-d6 at 80℃; for 7.3h; Temperature; Reagent/catalyst; Time; Inert atmosphere;

dicyclohexyl-carbodiimide (538-75-0) + 1,4-phenylenediamine (106-50-3) → 2',2'-(1,4-phenylene)bis(1,3-dicyclohexylguanidine) (5012-73-7)

Conditions	Yield
With diethylzinc In toluene at 50℃; for 2h;	99%
[(Me3Si)2N]3Yb(μ-Cl)Li(THF)3 In tetrahydrofuran at 60℃; for 4h;	96%
With [Li(THF)(DME)]3La[μ-η2η1(iPrN)2C(NC6H4p-Cl)]3 at 50℃; for 5h; Inert atmosphere;	95%

4-Isopropylaniline (99-88-7) + dicyclohexyl-carbodiimide (538-75-0) → N-(p-isopropylphenyl)-N',N''-dicyclohexylguanidine

Conditions	Yield
[(Me3Si)2N]3Yb(μ-Cl)Li(THF)3 In dichloromethane at 40℃; for 4h;	99%
With C23H40AlN In toluene at 25℃; for 1h; Inert atmosphere; Schlenk technique;	92%
With [Cp*2(Me)Zr(μ-O)Zr(NMe2)2(μ-O)Zr(Me)Cp*2] In benzene-d6 at 110℃; for 12h; Temperature; Reagent/catalyst; Time; Inert atmosphere;

1-amino-naphthalene (134-32-7) + dicyclohexyl-carbodiimide (538-75-0) → N',N''-dicyclohexyl-N-(1-naphthyl)guanidine

Conditions	Yield
With C24H34Al2N4 In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;	99%
With C36H52N5O4Si2Yb In neat at 60℃; for 6h; Inert atmosphere;	97%
With [(1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene)Ga—Ga(1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene)] In benzene-d6 at 60℃; for 1.3h; Temperature; Schlenk technique; Sealed tube;	97%
[(Me3Si)2N]3Yb(μ-Cl)Li(THF)3 In tetrahydrofuran at 60℃; for 12h;	96%
Stage #1: dicyclohexyl-carbodiimide In neat (no solvent) at 80℃; for 0.166667h; Stage #2: 1-amino-naphthalene In neat (no solvent) at 80℃;	61%

aniline (62-53-3) + dicyclohexyl-carbodiimide (538-75-0) → N-phenyl-N',N-dicyclohexylguanidine (4833-42-5)

Conditions	Yield
With Sm[N(TMS)2]2(THF)3 at 20℃; for 0.166667h; Inert atmosphere;	99%
With [Li(THF)(DME)]3La[μ-η2η1(iPrN)2C(NC6H4p-Cl)]3 at 25℃; for 0.5h; Inert atmosphere;	99%
With (Me3SiNC(Ph)N(CH2)3NC(Ph)NSiMe3)Y[O2,6-(tBu)2-4-(Me)C6H2](DME) at 60℃; for 0.5h; Inert atmosphere; Schlenk technique;	99%

Upstream product

• 75-15-0 carbon disulfide 
• 108-91-8 cyclohexylamine 
• 114316-64-2 N,N'-Dicyclohexyl-C-chlor-formamidinium 
• 3173-53-3 Cyclohexyl isocyanate 
• 19573-22-9 cyclohexyl azide 
• 693-13-0 diisopropyl-carbodiimide 
• 931-53-3 Cyclohexyl isocyanide 
• 34656-93-4 N,N'-dicyclohexylselenourea 
• 1122-82-3 isothiocyanatocyclohexane 
• 92366-11-5 C₃₇H₅₇N₂O₂PS₂ 
• 92366-10-4 C₂₅H₃₃N₂O₂PS₂ 
• 83599-89-7 C₂₉H₄₁N₂O₂PS₂ 
• 121-44-8 triethylamine 
• 1212-29-9 1,3-dicyclohexylthiourea 

Downstream Products

• 4004-57-3 uridine 3',5'-cyclic monophosphate 
• 6453-60-7 2'-deoxythymidine 3',5'-cyclic monophosphate 
• 3080-42-0 N-cyclohexyl-N-(cyclohexylcarbamoyl)benzamide 
• 21662-02-2 N,N'-dicyclohexyl-N-(N,N-phthaloyl-phenylalanyl)-urea 
• 76249-23-5 N-(N,N-phthaloyl-DL-phenylalanyl)-glycin-ethyl ester 
• 41957-78-2 9-chloro-3-cyclohexyl-2-cyclohexylimino-2,3-dihydro-[1,3]oxazino[5,6-c]quinolin-4-one 
• 4833-41-4 N,N',N''-tricyclohexylguanidine 
• 93247-20-2 3-cyclohexylimino-2-butanone 
• 109879-46-1 N-cyclohexyl-3-(phenyl)-1,2,4-oxadiazol-5-amine 
• 2387-23-7 1,3-Dicyclohexylurea 
• 15881-58-0 N-(1,1-dioxo-1H-1λ⁶-benzo[d]isothiazol-3-ylamino)-N',N''-dicyclohexyl-guanidine 
• 37497-55-5 1,3-dicyclohexyl-2-(2-morpholin-4-yl-ethyl)-isourea 
• 95807-28-6 N-<2-Heptylmercapto-aethyl>-N',N'-dicyclohexyl-guanidin 
• 80986-14-7 5-aza-5-carbobenzoxy-2-oxa-3-oxo-bicyclo<2.2.1>heptane 

Relevant articles and documents

MIGRATION REVERSIBLE DE PHOSPHORYLE S-P N-P CONTROLEE PAR TRANSFERT DE PROTON, MODELE D'ACTIVATION PAR PHOSPHORYLATION

This work describes the reversible C-addition of a sterically hindered-P thiophosphoric ester to a carbodiimide, as a model of activated biotin.The formed intermediate, is found to be in equilibrium with the corresponding N-phosphorylated thiourea.The entire system is controlled by proton transfer and reversible.

Method for preparing N,N'-dicyclohexylcarbodiimide by using co-reactor

The invention discloses a method for preparing N,N'-dicyclohexylcarbodiimide by using a co-reactor. The method comprises the steps of maintaining an aqueous solution of cyclohexylamine in a strong alkaline environment in the same reactor, adding carbon disulfide into the same reactor, and adding sodium hypochlorite for oxidation to obtain N,N'-dicyclohexylcarbodiimide. According to the method, thetechnological process is simplified through the co-reactor reaction, generation of highly toxic and harmful gas is avoided, the safety risk of production is reduced, and then the purpose of environment-friendly and safe production is achieved.

Microwave-assisted method for synthesizing N,N'-dicyclohexyl carbodiimide

The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing N,N'-dicyclohexyl carbodiimide through a microwave-assisted method. The method comprises the following steps: dissolving N,N'-dicyclohexyl urea in a solvent under microwave radiation, adding an oxidant and a catalyst loaded on a molecular sieve, and carrying out heat preservation reflux; adding a phase transfer catalyst, adjusting the pH value, and carrying out alkaline hydrolysis reaction; filtering, separating liquid, evaporating out the solvent, and carrying out reduced pressure distillation to obtain N,N'-dicyclohexyl carbodiimide. The catalyst loaded on the molecular sieve is large in specific surface area and high in catalytic efficiency; a microwave-assisted method is adopted, and a phase transfer catalyst is added, so that the problems of difficult two-phase reaction and incomplete reaction in the traditional process are solved, the reaction conversion rate is greatly improved, the reaction time is shortened, and the product has the characteristics of high purity and yield.

Method for preparing dicyclohexylcarbodiimide by using vilsmeier reagent

The invention discloses a method for preparing dicyclohexylcarbodiimide by using a vilsmeier reagent. The method comprises the following steps: preparing a vilsmeier reagent by using N, N-dimethylformamide (DMF) and thionyl chloride (SOCl2), reacting the vilsmeier reagent with dicyclohexylurea (DCU), and carrying out aftertreatment to obtain the dicyclohexylcarbodiimide. According to the method, the vilsmeier reagent is adopted, the reaction can be carried out under mild conditions, the process is safe and stable, and the method is suitable for industrial large-scale production.