726-42-1

Basic information

• Product Name: 1,3-DI-P-TOLYLCARBODIIMIDE
• Synonyms: N,N'-DI-P-TOLYLCARBODIIMIDE;N,N'-DI-P-TOLYLCARBODIMIDE;1,3-DI-P-TOLYLCARBODIIMIDE;di-p-tolylcarbodiimide;DI-PARA-TOLYLCARBODIIMIDE;DI-P-TOLY CARBODIIMIDE;1,3-Bis(p-tolyl)carbodiimide;Bis(4-methylphenyl)carbodiimide
• CAS NO: 726-42-1
• Molecular Formula: C₁₅H₁₄N₂
• Molecular Weight: 222.29
• EINECS: 211-971-7
• Product Categories: Carbodiimides;CarbodiimidesSynthetic Reagents;Coupling;Peptide Synthesis
• Mol File: 726-42-1.mol

Chemical Properties

• Melting Point: 56-58 °C(lit.)
• Boiling Point: 221-223 °C20 mm Hg(lit.)
• Flash Point: 173.8°C
• Appearance: /
• Density: 1.1500
• Vapor Pressure: 4.28E-05mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,3-DI-P-TOLYLCARBODIIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DI-P-TOLYLCARBODIIMIDE(726-42-1)
• EPA Substance Registry System: 1,3-DI-P-TOLYLCARBODIIMIDE(726-42-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 726-42-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,3-DI-P-TOLYLCARBODIIMIDE is used as a reactant for the synthesis of various organic compounds, including cyclic guanidines, five-membered heterometallacycloallenes, benzimidazoles or quinazolines via nucleophilic addition and intramolecular C-C bond formation, benzoxazole and benzimidazole derivatives via cross-coupling reactions, and gem-difluorodihydrouracil derivatives via addition reactions.
Used in Pharmaceutical Chemistry:
In the pharmaceutical industry, 1,3-DI-P-TOLYLCARBODIIMIDE is used as a reactant for ketene cycloadditions, which are important reactions in the synthesis of various pharmaceutical compounds. Its ability to form stable complexes with biopolymers and macromolecules makes it a valuable tool in the development of new drugs and drug delivery systems.
Used in Material Science:
1,3-DI-P-TOLYLCARBODIIMIDE can also be used in the development of new materials, such as polymers and composites, due to its reactivity and ability to form stable complexes with other molecules. This application can lead to the creation of innovative materials with improved properties and performance in various industries, including automotive, aerospace, and electronics.

InChI:InChI=1/C15H14N2/c1-12-3-7-14(8-4-12)16-11-17-15-9-5-13(2)6-10-15/h3-10H,1-2H3

Upstream product

• 73901-66-3 N,N-di-p-tolyl-thiourea 
• 20584-08-1 S-ethyl-N,N'-di-p-tolyl-isothiourea 
• 75-15-0 carbon disulfide 
• 2327-67-5 N-(p-tolyl)-P,P,P-triphenylphosphine imide 
• 124-38-9 carbon dioxide 
• 33535-76-1 bis(p-tolyl-imino-diphenylphosphoranyl)methane 
• 65423-89-4 triphenylarsazo-p-tolyl 
• 160060-64-0 N,N'-Di-p-tolyl-5H-4b,10,11-triaza-benzo[b]fluorene-10-carboxamidine 
• 546-68-9 titanium(IV)isopropoxide 
• 103-71-9 phenyl isocyanate 
• 622-58-2 p-Tolylisocyanate 
• 75102-51-1 (C₅H₅)2V(CH₃C₆H₄NCNC₆H₄CH₃) 
• 24424-99-5 di-tert-butyl dicarbonate 
• 621-01-2 N,N'-Bis(p-tolyl)thiourea 

Downstream Products

• 34982-41-7 p-tolyl-(3-p-tolyl-3H-[1,2,3]triazol-4-yl)-amine 
• 109044-99-7 diphosphoric acid-1,2-dimethyl ester-1,2-bis-(4-nitro-phenyl ester) 
• 52625-61-3 diphosphoric acid tetrakis-(4-nitro-phenyl ester) 
• 124129-81-3 diphosphoric acid tetrakis-(4-bromo-benzyl ester) 
• 124129-83-5 diphosphoric acid tetrakis-(4-iodo-benzyl ester) 
• 13471-32-4 N,N’-di-p-tolyl-O-methylisourea 
• 73565-31-8 p-tolyl-(1-p-tolyl-1H-tetrazol-5-yl)-amine 
• 16519-45-2 N,N'-di-p-tolylselenourea 
• 101574-68-9 1-acetyl-1,3-di-p-tolylurea 

Relevant articles and documents

Catalytic Imido-Transfer Reactions of Well-Defined Silica-Supported Titanium Imido Complexes Prepared via Surface Organometallic Chemistry

We expand the series of well-defined silica-supported titanium imido complexes of general formula (SiO)Ti(═NtBu)X(py)n prepared via surface organometallic chemistry in order to analyze the effect of the X ligand on their catalytic properties. Two new surface complexes, (SiO)Ti(═NtBu)Cl(py)2 (2s) and (SiO)Ti(═NtBu)Cp(py) (3s), have been prepared and characterized with physicochemical techniques, and their performance in oxo/imido heterometathesis and other catalytic imido-transfer reactions has been studied and compared to that of the previously reported catalyst (SiO)Ti(═NtBu)(Me2Pyr)(py)2 (1s; Me2Pyr = 2,5-dimethylpyrrolyl).

A facile method for the preparation of carbodiimides from thioureas and (Boc)2O

A concise method for the preparation of carbodiimides from thioureas using di-tert-butyl dicarbonate [(Boc)2O] as the dehydrosulfurizative reagent has been developed. Using DMAP as the catalyst, a variety of symmetric and asymmetric 1,3-diaryl thioureas were converted into the corresponding carbodiimides efficiently in a short time.

RE[N(SiMe3)2]3-Catalyzed Guanylation/Cyclization of Amino Acid Esters and Carbodiimides

The example of rare-earth metal-catalyzed guanylation/cyclization of amino acid esters and carbodiimides is well-established, forming 4(3H)-2-alkylaminoquinazolinones in 65-96% yields. The rare-earth metal amides RE[N(TMS)2]3 (RE = Y, Yb, Nd, Sm, La; TMS = SiMe3) showed high activities, and La[N(TMS)2]3 performed best for a wide scope of the substrates.

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

Ultrasonic-assisted synthesis of carbodiimides from N,N′-disubstituted thioureas and ureas

A facile and efficient sonochemical method for the preparation of carbodiimides from their corresponding thioureas or ureas was described. Using Ph3P–I2 combination in the presence of triethylamine, various diaryl, aryl–alkyl, as well as dialkyl substituted substrates could be converted into carbodiimides in good-to-excellent yields within short reaction times under mild conditions with simple experimental setup. Graphical abstract: [Figure not available: see fulltext.]

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.

Dehydrogenative desulfurization of thiourea derivatives to give carbodiimides, using hydrosilane and an iron complex

Dehydrogenative desulfurization of thiourea derivatives (RNHC(S)NHR′) has been achieved, to give carbodiimides (RNCNR′), in the reaction with hydrosilane and (η5-C5H5)Fe(CO) 2Me. The obtained carbodiimide reacted with (η5-C 5H5)Fe(CO)(SiR3) formed in the reaction to give an N-silylated η2-amidino iron complex, which was isolated and then characterized by X-ray analysis.

A New synthetic protocol for the preparation of carbodiimides using a hypervalent iodine(III) reagent

A new, simple, and efficient preparation of symmetrical and unsymmetrical carbodiimides from the corresponding thioureas via dehydrosulfurization using a hypervalent iodine(III) reagent is described. The oxidation afforded carbodiimides in excellent yields and high selectivity. A possible mechanism for the transformation is proposed. Georg Thieme Verlag Stuttgart New York.

Synthesis and X-ray crystal structures of imido and ureato derivatives of titanium(iv) phthalocyanine and their application in the catalytic formation of carbodiimides by metathesis from isocyanates

The imido titanium phthalocyanine complex [PcTi(NDip)] (Dip = 2,6-diisopropylphenyl) 2a was synthesized from [PcTiO] 1 and one eq. of DipNCO. Due to the steric demand of the Dip group, addition of another isocyanate molecule to the TiN functionality of 2a does not occur even at high molar ratios of DipNCO. However, 1 reacts with 2 eq. of arylisocyanates containing sterically less demanding aryl groups producing N,N′- diarylureatotitanium(iv)phthalocyanines [PcTi{κ2-(NR)C(O) (N′R)}] (R = p-tolyl (Tol) 3a or mesityl (Mes) 3b). The N,N′ coordination (III) of the ureato ligand in 3a and 3b was proven by a single set of resonances for the aryl groups in their 1H-NMR spectra. An N,O coordination (IV) can therefore be excluded. This is also confirmed by the X-ray crystal structure of 3a. Upon heating [PcTiO] and an excess of aryl isocyanates for 6 days, a steady evolution of CO2 was observed and a white precipitate, identified as the corresponding diarylcarbodiimides (V), could be isolated. Therefore this reaction was applied in the metathetic conversion of two isocyanate molecules into diarylcarbodiimides (V) and CO2. Additionally, imido titanium Pc's 2b (R = tBu) and 2c (R = Mes) were prepared by a more general synthetic strategy, reacting the potassium salt of the ligand PcK2 with appropriate imido titanium precursors.

Manganese-catalyzed cleavage of a carbon-carbon single bond between carbonyl carbon and α-carbon atoms of ketones

Singled out: Treatment of ketones with carbodiimides in the presence of a catalytic amount of either [{HMn(CO)4}3] or [Mn 2(CO)10] gave amides in good to excellent yields. In this reaction, the carbon-carbon single bond of a ketone is cleaved efficiently. The reaction also proceeded by using isocyanates instead of carbodiimides. Copyright