693-13-0

Basic information

• Product Name: N,N'-Diisopropylcarbodiimide
• Synonyms: N,N'-Diisopropylcarbodiimide≥ 99% (Assay);N,N'-Diisopropylcarbodiimide for synthesis;N,N'-Methanetetraylbis(1-methylethylamine);n,n'-methanetetraylbis(2-propanamine);N,N'-DIISOPROPYLCARBODIIMIDE;N,N-DIISOPROPYLCARBODIIMIDE;PCI;Carbodiimide, diisopropyl-
• CAS NO: 693-13-0
• Molecular Formula: C₇H₁₄N₂
• Molecular Weight: 126.2
• EINECS: 211-743-7
• Product Categories: straight chain compounds;Amino Acid Derivatives;Aliphatics;Peptide Coupling Reagents;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Synthetic Organic Chemistry;Peptide;Protected Amino Acids;Intermediates & Fine Chemicals;Pharmaceuticals;Pharmaceutical intermediates
• Mol File: 693-13-0.mol

Chemical Properties

• Melting Point: 210-2120C (dec)
• Boiling Point: 145-148 °C(lit.)
• Flash Point: 93 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.815 g/mL at 20 °C(lit.)
• Vapor Pressure: 34.9hPa at 55.46℃
• Refractive Index: n20/D 1.433(lit.)
• Storage Temp.: 2-8°C
• Solubility: Soluble in chloroform, methylene chloride, acetonitrile, dioxane
• Sensitive: Moisture Sensitive
• BRN: 878281
• CAS DataBase Reference: N,N'-Diisopropylcarbodiimide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Diisopropylcarbodiimide(693-13-0)
• EPA Substance Registry System: N,N'-Diisopropylcarbodiimide(693-13-0)

Safety Data

• Hazard Codes: T+,T,F,Xn
• Statements: 10-26-36/37/38-41-42/43-37/38
• Safety Statements: 26-36/37/39-45-38-28A-16-22
• RIDADR: UN 2929 6.1/PG 1
• WGK Germany: 3
• RTECS: FF2175000
• F: 10-21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 693-13-0(Hazardous Substances Data)

Usage

Chemical Properties

N,N'-Diisopropylcarbodiimide is colorless to pale yellow liquid. Insoluble in water, soluble in benzene, ethanol, ether.

Uses

N,N'-Diisopropylcarbodiimide is used as a reagent in synthetic organic chemistry. It serves as a chemical intermediate and as a stabilizer for Sarin (chemical weapon). It is also used in the synthesis of peptide and nucleic acid. Further, it is used as an antineoplastic and involved in the treatment of malignant melanoma and sarcomas. In addition to this, it is used in the synthesis of acid anhydride, aldehyde, ketone and isocyanate.

Definition

ChEBI: A carbodiimide compound having an isopropyl substituent on both nitrogen atoms.

General Description

N,N′-Diisopropylcarbodiimide (DIC) is a carbodiimide used as a coupling reagent in the synthesis of amides, peptides, ureas, heterocycles, and unsymmetrical carbodiimides. It is also used in the polymerization reactions as an activator.

Contact allergens

It is used in peptide chemistry as a coupling reagent. It is very toxic and causes contact dermatitis in labora- tory workers.

Synthetic route

Fmoc-hydroxynorleucine (374899-60-2) + C153H224N12O20*ClH → diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.666667h;	100%

1,3-diisopropylthiourea (2986-17-6) → diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
With cyclopentadienyl iron(II) dicarbonyl dimer In tetrahydrofuran at 60℃; for 24h; Reagent/catalyst; Inert atmosphere;	99%
With cervantite; oxygen In 5,5-dimethyl-1,3-cyclohexadiene at 115℃; under 60006 Torr; for 4h; Temperature; Pressure; Reagent/catalyst; Autoclave;	94.55%
With sodium chlorate; N-benzyl-N,N,N-triethylammonium chloride In water; benzene at 55 - 70℃; for 4h; Reagent/catalyst; Large scale;	93%

1,3-diisopropylurea (4128-37-4) + triphenylphosphine (603-35-0) → Triphenylphosphine oxide (791-28-6) + diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
With aluminum oxide In dichloromethane constant current electrolysis;	A n/a B 92%
With aluminum oxide constant current electrolysis;	A n/a B 92%

C29H60N8 → HC[C(Ni-Pr)NHi-Pr]3 (1412904-60-9) + diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
Stage #1: C29H60N8 With hydrogenchloride In tetrahydrofuran; diethyl ether Inert atmosphere; Stage #2: With water; sodium hydroxide In dichloromethane Inert atmosphere;	A 80.7% B n/a

1,3-diisopropylurea (4128-37-4) → i-propyl isocyanide (598-45-8) + Isopropylisocyanid-dichlorid (29119-58-2) + diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
With sodium hydroxide; triethylamine In chloroform for 4h; Heating;	A 18% B 14% C 15%

N1-cyano-N2,N3-diisopropylguanidine (78822-77-2) → 1,3-diisopropylurea (4128-37-4) + diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
With tert-butylhypochlorite; potassium tert-butylate In tetrachloromethane at -75℃; for 3h;	A 10% B 15%

diethyl ether (60-29-7) + N,N'-diisopropylhydrazine (3711-34-0) + mercury oxide → diisopropyl-carbodiimide (693-13-0)

1,2-diisopropylhydrazine hydrochloride (26254-05-7) + copper (II)-oxide → diisopropyl-carbodiimide (693-13-0)

hydrogenchloride (7647-01-0) + 1,2-di-iso-propylhydrazine dihydrochloride (26254-05-7, 76529-44-7, 124891-86-7) + sodium nitrite (excessive) → N,N'-diisopropyl-N-nitroso-hydrazine + diisopropyl-carbodiimide (693-13-0)

hydrogenchloride (7647-01-0) + 1,2-diisopropylhydrazine hydrochloride (26254-05-7) + sodium nitrite (excessive) → N,N'-diisopropyl-N-nitroso-hydrazine + diisopropyl-carbodiimide (693-13-0)

isopropyl-(2,2,2-trichloro-1,3-diisopropyl-2λ5-[1,3,2]diazaphosphetidin-4-ylidene)-amine → N-isopropyl-p-trichloroiminophosphorane (37596-20-6) + diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
In (2)H8-toluene at 61.84℃; Equilibrium constant; Kinetics; Further Variations:; Temperatures;

N′,N″-diisopropyl-N,N-dimethyl guanidine (68897-42-7) → C7H12N2 (1213750-93-6) + C9H19N3 + dimethyl amine (124-40-3) + diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
With copper(ll) bromide; lithium tert-butoxide at 800℃;

1,3,N,N'-tetraisopropyl-[1,3]diazetidine-2,4-diylidenediamine (17433-10-2) → diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
at 150℃; Kinetics;

copper(I) N′,N″-diisopropyl-N,N-dimethyl guanidinate (1213750-71-0, 1213750-82-3, 870990-61-7) → N′,N″-diisopropyl-N,N-dimethyl guanidine (68897-42-7) + diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
In neat (no solvent) at 165℃; Kinetics; Inert atmosphere; Sealed tube;

i-propyl isocyanide (598-45-8) + isopropylamine (75-31-0) → diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
With Cumene hydroperoxide; iodine In tert-butyl methyl ether at 55℃; for 6h;	55 %Chromat.

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

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

1,2-dimethoxyethane (110-71-4) + (2,3-difluorophenyl)boronic acid (121219-16-7) + tetrakis(triphenylphosphine)palladium (0) + acetylacetone (123-54-6) → diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
With sodium carbonate; potassium carbonate In 2-methoxy-ethanol; water

C20H46N8W → dimethyl amine (124-40-3) + diisopropyl-carbodiimide (693-13-0)

Conditions	Yield
at 200℃; under 760.051 Torr; Inert atmosphere; Schlenk technique; Glovebox;

aniline (62-53-3) + diisopropyl-carbodiimide (693-13-0) → 1,3-diisopropyl-2-phenylguanidine (13134-19-5)

Conditions	Yield
With zinc trifluoromethanesulfonate In benzene-d6 at 80℃; for 3h; In air; Sealed tube;	100%
With C47H73ClN3O3Y at 60℃; for 0.5h; Inert atmosphere;	99%
With [Li(THF)(DME)]3La[μ-η2η1(iPrN)2C(NC6H4p-Cl)]3 at 25℃; for 0.5h; Inert atmosphere;	99%

bis(trifluoromethyl)trichlorophosphorane (353-77-5) + diisopropyl-carbodiimide (693-13-0) → C9H14Cl3F6N2P

Conditions	Yield
In tetrachloromethane Heating;	100%

tris(trifluoromethyl)phosphine dichloride (420-72-4) + diisopropyl-carbodiimide (693-13-0) → C10H14Cl2F9N2P

Conditions	Yield
In tetrachloromethane Heating;	100%

Trifluormethyl-phosphor-tetrachlorid (1066-48-4) + diisopropyl-carbodiimide (693-13-0) → C8H14Cl4F3N2P

Conditions	Yield
In tetrachloromethane Heating;	100%

diisopropyl-carbodiimide (693-13-0) → C7H14Cl5N2P

Conditions	Yield
With phosphorus pentachloride In tetrachloromethane Heating;	100%

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (5807-14-7) + diisopropyl-carbodiimide (693-13-0) → (Z)-N,N′-diisopropyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine-1-carboximidamide

Conditions	Yield
at 20℃; for 48h; Inert atmosphere;	100%
With acid	43%

Upstream product

• 3711-34-0 N,N'-diisopropylhydrazine 
• 2986-17-6 1,3-diisopropylthiourea 
• 4128-37-4 1,3-diisopropylurea 
• 603-35-0 triphenylphosphine 
• 78822-77-2 N¹-cyano-N²,N³-diisopropylguanidine 
• 5577-65-1 N-isopropyl-N-trimethylsilylamine 
• 1795-48-8 Isopropyl isocyanate 
• 627-70-3 propan-2-one azine 
• 7732-18-5 water 
• 7705-08-0 iron(III) chloride 
• 127-09-3 sodium acetate 
• 142-71-2 copper diacetate 
• 60-29-7 diethyl ether 
• 26254-05-7 1,2-diisopropylhydrazine hydrochloride 

Downstream Products

• 63460-32-2 N,N’-diisopropyl-O-isopropylisourea 
• 54648-79-2 N,N’-diisopropyl-O-methylisourea 
• 20452-70-4 1-isopropyl-4-isopropylimino-3,3-dimethyl-azetidin-2-one 
• 60683-30-9 ethyl N,N′-diisopropylcarbamimidate 
• 100528-00-5 N,N'-diisopropyl-O-cyclohexylisourea 
• 3711-34-0 N,N'-diisopropylhydrazine 
• 41957-75-9 2-isopropyl-3-isopropylimino-5-phenyl-2,3-dihydro-[1,3]oxazino[6,5-c]quinolin-1-one 
• 19978-10-0 Isopropyl(tosyl)carbodiimid 
• 53722-39-7 N,N'-di-isopropylbenzamidine 
• 24867-12-7 3-isopropyl-2-isopropylimino-1,1-dioxo-5,5-diphenyl-1λ⁶-thiazolidin-4-one 
• 14537-58-7 N-isopropyl-N-(5-phenyl-[1,3,4]thiadiazol-2-yl)-acetamide 
• 14041-93-1 N-Isopropyl-N'-cyclohexyl-N-acetyl-formamidin 
• 14041-91-9 N-Isopropyl-N'-benzyl-N-acetyl-acetamidin 
• 13134-19-5 N-phenyl- N',N''-diisopropylguanidine 

Relevant articles and documents

Process method for increasing yield of N, N '-diisopropylcarbodiimide product

The invention discloses a process method for improving the yield of an N, N '-diisopropylcarbodiimide product, and relates to the technical field of organic chemical synthesis, and the process methodcomprises the following steps: reacting isopropylamine and carbon disulfide by using chlorobenzene as a solvent to generate diisopropylthiourea, and carrying out suction filtration; using hydrogen peroxide as an oxidizing agent, using ethyl tert-butyl ether as a solvent, performing primary oxidation, removing hydrogen sulfideafter oxidation to generate N, N '-diisopropylcarbodiimide and sulfur; carrying out secondary oxidation, removing sulfur by using sodium hydrosulfide, washing with water, drying, evaporating out the solvent, adding potassium carbonate into the DIC crude product without thesolvent, controlling the temperature to be 55-65 DEG C, stirring for 0.3-1 hour, controlling the pressure to be less than -0.08 MPa, and distilling to obtain qualified DIC; by adding potassium carbonate, the stability of N, N '-diisopropylcarbodiimide is facilitated, and the N, N'-diisopropylcarbodiimide is prevented from being decomposed at a high temperature so that the yield is increased.

Method for synthesizing N, N'-diisopropylcarbodiimide by using oxygen as oxidant

The invention relates to a method for synthesizing N, N'-diisopropylcarbodiimide by using oxygen as an oxidant, which comprises the following steps: adding N, N'-diisopropylthiourea and a xylene solvent into a high-pressure reaction kettle in a mass ratio of 1-2:1; adding a MoO3 or Sb2O4 catalyst, wherein the use amount of the MoO3 or Sb2O4 catalyst is 1-3% of the amount of the added materials; introducing oxygen, wherein the mass ratio of the N, N'-diisopropylthiourea to the oxygen is 1:0.2-0.4, and an oxidation reaction is carried out for 3-4 h under the conditions that the pressure is controlled to be 5-10 MPa and the temperature is controlled to be 110-120 DEG C; and cooling to 5-15 DEG C, carrying out suction filtration, decolorizing, and carrying out reduced pressure distillation toobtain the DIC. Oxygen is used as an oxidizing agent, the reaction selectivity is high, the risk is low, meanwhile, the wastewater yield is greatly reduced, treatment is easy, and the problem that waste brine in a traditional process is large in amount and difficult to treat is solved; and the method is easy to control, the reaction yield is increased, and the production cost is reduced.

N,N'-diisopropyl carbodiimide preparation method

The invention belongs to the technical field of organic synthesis and particularly relates to an N,N'-diisopropyl carbodiimide preparation method. The method includes steps: adopting isopropylamine and carbon disulfide to synthesize N,N'-diisopropyl thiourea in a solvent; subjecting the N,N'-diisopropyl thiourea to suction filtration, drying and primary oxidization; performing secondary oxidization reaction, adding a catalyst and an oxidant, and performing reaction for 1h at 60-65 DEG C; performing desulfurizing treatment, adding sodium sulfide solution into oxidation liquid, heating to 70-75DEG C, and performing reaction for 1-2h; adding caustic soda flakes to neutralize, washing, separating a water layer, adding a drying agent for drying, evaporating out the solvent, and performing vacuum rectification to obtain N,N'-diisopropyl carbodiimide. The N,N'-diisopropyl carbodiimide preparation method has advantages that wastewater recycling can be realized, emission is avoided, and accordingly environmental pollution is avoided; simplicity in feeding and aftertreatment, low production cost, high yield and high purity are realized.

Multicomponent Approach to Libraries of Substituted Dihydroorotic Acid Amides

A process featuring a sequential multicomponent reaction followed by a regioselective postcyclization strategy was implemented for the facile synthesis of N,N′-disubstituted dihydroorotic acid amides under mild conditions. We obtained, for the first time, a library of 29 derivatives, encompassing 19 Nα-substituted-N4-dihydroorotyl-4-aminophenylalanine derivatives, a key residue of gonadotropin-releasing hormone antagonist Degarelix. The corresponding products were prepared from easily accessible starting materials in good to excellent yields with broad substrate scope.

Synthesis and Characterization of Tungsten Nitrido Amido Guanidinato Complexes as Precursors for Chemical Vapor Deposition of WNxCy Thin Films

Tungsten nitrido amido guanidinato complexes of the type WN(NR2)[(NR′)2C(NR2)]2 (R = Me, Et; R′ = iPr, Cy) were synthesized as precursors for aerosol-assisted chemical vapor deposition (AACVD) of WNxCy thin films. The reaction of tungsten nitrido amido complexes of the type WN(NR2)3 (R = Me, Et) with two equivalents of a carbodiimide R′N=C=NR′ (R′ = iPr, Cy) resulted in two insertions of a carbodiimide into W–N(amido) bonds, affording bis(guanidinato) amido nitrido tungsten complexes. These compounds were characterized by 14N NMR, indicating distinctive chemical shifts for each type of N-bound ligand. Crystallographic structure determination of WN(NMe2)[(NiPr)2C(NMe2)]2 showed the guanidinato ligands to be non-equivalent. The complex WN(NMe2)[(NiPr)2C(NMe2)]2 was demonstrated to serve as a precursor for AACVD of WNxCy thin films, resulting in featureless, X-ray amorphous thin films for growth temperatures 200–400 °C.

A method of manufacturing a carbodiimide compound

PROBLEM TO BE SOLVED: To provide a novel method that can efficiently produce a carbodiimide compound without using substances that are harmful, hazardous, expensive, or difficult to obtain.SOLUTION: The method of producing a carbodiimide compound includes converting a thiourea compound having a specific structure to a carbodiimide compound having a specific structure in the presence of at least one of an iron compound and a molybdenum compound.

Cross-linked peptides containing non-peptide cross-linked structure, method for synthesizing cross-linked peptides, and novel organic compound used in method

The purpose of the present invention is to provide a cross-linked peptide containing a novel non-peptide cross-linked structure, and a method for synthesizing the same. A cross-linked peptide having a novel non-peptide cross-linked structure, a useful intermediate for synthesizing the cross-linked peptide, and a method for synthesizing the novel cross-linked peptide and the intermediate are provided. The cross-linked peptide is characterized by having an —NR— bond in the cross-linked structure. By using the method for synthesizing the cross-linked peptide, a cross-link can be freely designed and an change can be freely made to a cross-link.

ORGANIC METAL COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE EMPLOYING THE SAME

Organic metal compounds and organic electroluminescence devices employing the same are provided. The organic metal compound has a chemical structure represented below: wherein R1, R2, R3, R4, and R5 are independent and can be hydrogen, halogen, C1-8 alkyl or C1-8alkoxy; L can be acetylacetone ligand, picolinic acid ligand, N,N′-diisopropylbenzamidinate, or N,N′-diisopropyl-diisopropyl-guanidinate.

Stimuli-Responsive Frustrated Lewis-Pair-Type Reactivity of a Tungsten Iminoazaphosphiridine Complex

Reactions of 3-imino-azaphosphiridine complexes 1 a,b with carbodiimides 2 a,b, isocyanates 3 a,b, and carbon dioxide are described. Whereas exchange of the carbodiimide unit occurs in the first case, an overall ring expansion takes place with phenyl isocyanate (3 a) and carbon dioxide to yield complexes 4 and 5 bearing novel 1,3,5-oxazaphospholane ligands; the isopropyl derivative 3 b did not react under these conditions. DFT calculations provide insight into the pathway of the reaction with carbon dioxide with model complex 1 c, revealing effects of initial non-covalent interactions with the substrate onto the ring bonding, thus triggering an initially masked frustrated Lewis-pair-type behavior.

Synthesis of carbodiimides by I2/CHP-mediated cross-coupling reaction of isocyanides with amines under metal-free conditions

An I2/CHP-mediated cross-coupling reaction of isocyanides with readily accessible amines via C-N formation is described for carbodiimide synthesis in moderate to excellent yields. This represents a metal-free strategy for a coupling reaction of isocyanides with amines, and it provides an efficient approach for symmetric and unsymmetric functionalized carbodiimide derivative synthesis under mild conditions.