3D Mol Similar

Dicyclohexylcarbodiimide

: Iupac Name：N,N'-dicyclohexylmethanediimine; CAS No.: 538-75-0; Molecular Weight：206.32718; Modify Date.: 2022-11-07 10:19; Introduction: Dicydohexyl carbodiimide is used in peptide chemistryas a coupling reagent. It is both an irritant and asensitizer, and caused contact dermatitis in pharmacistsand chemists. View more+

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1. Names and Identifiers

: 1.1 Name; Dicyclohexylcarbodiimide; 1.2 Synonyms; 1,3-dicyclohexylcarbodiimide 1,3-di-cyclohexylcarbodiimide bis-cyclohexylcarbodiimide Carbodicyclohexylimide Carbodiimide, dicyclohexyl- Cyclohexanamine, N-(cyclohexylcarbonimidoyl)- Cyclohexanamine, N,N'-methanetetraylbis- DCC DCC Dicyclohexylcarbodiimide dcc solution DCC/DCCI DCCD DCCI Dicyclimide dicyclohexyl-carbodiimide EINECS 208-704-1 Methanediimine, N,N'-dicyclohexyl- MFCD00011659 N-(N-cyclohexylcarboximidoyl)cyclohexanamine N,N&lsquo-Dicyclohexylcarbodiimide N,N&lsquo-Dicyclohexylcarbodimide N,N&rsquo-Dicyclohexylcarbodiimide (DCC) N,N″-Dicyclohexylcarbodiimide N,N'-Dicyclohexylcarbodiimide N,N'-Dicyclohexylcarbodiimide [for Peptide Synthesis] n,n'-dicyclohexylcarbodiimide solution N,N'-Dicyclohexylcarbodiimide, 0.1M sol.in DCM, peptide synthesis grade N,N'-Dicyclohexylcarbodiimide, 1 M solution in dichloromethane N,N'-Dicyclohexylcarbodiimide, 1M sol. In N-methylpyrrolidone,peptide synth.grade N,N'-Dicyclohexylcarbodimide N,N'-Methanediylidenedicyclohexanamine N,N'-Methanetetraylbiscyclohexanamine; View all

1.3 CAS No.: 538-75-0

1.4 CID: 10868

1.5 EINECS(EC#): 208-704-1

1.6 Molecular Formula: C13H22N2 (isomer)

1.7 Inchi: InChI=1S/C13H22N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h12-13H,1-10H2

1.8 InChIkey: QOSSAOTZNIDXMA-UHFFFAOYSA-N

1.9 Canonical Smiles: C1CCC(CC1)N=C=NC2CCCCC2

1.10 Isomers Smiles: C1CCC(CC1)N=C=NC2CCCCC2

2. Properties

2.1 Density: 1.325

2.1 Melting point: 33-35℃

2.1 Boiling point: 122-124℃ (6 torr)

2.1 Refractive index: n20/D 1.48

2.1 Flash Point: 87℃

2.1 Precise Quality: 206.17800

2.1 PSA: 24.72000

2.1 logP: 3.82570

2.1 Solubility: methylene chloride: 0.1?g/mL, clear, colorless

2.2 Appearance: colorless solid

2.3 Storage: Moisture Sensitive. Store under Nitrogen. Ambient temperatures.

2.4 Chemical Properties: Colorless solid

2.5 Color/Form: White to pale yellow

2.6 Contact Allergens: Used in peptide chemistry as a coupling reagent. It is both an irritant and a sensitizer and has caused contact dermatitis in pharmacists and chemists.

2.7 Corrosivity: Corrosive to tissue

2.8 Decomposition: When heated to decomposition it emits toxic vapors of /oxides of nitrogen/.

2.9 Odor: Heavy sweet odor

2.10 Water Solubility: Reaction

2.11 Stability: Stable, but moisture sensitive. Combustible. Incompatible with strong oxidizing agents. Avoid exposure to air or moisture.

2.12 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 Definition: ChEBI: A carbodiimide compound having a cyclohexyl substituent on both nitrogen atoms.

3.2 General Description: White crystalline solid with a heavy sweet odor.

3.3 Potential Exposure: Laboratory reagent

3.4 Purification Methods: It is sampled as a liquid after melting in warm H2O. It is sensitive to air, and it is a potent skin irritant. It can be distilled in a vacuum and is best stored in a tightly stoppered flask in a freezer. It is very soluble in CH2Cl2 and pyridine where the reaction product with H2O, after condensation, is dicyclohexyl urea which is insoluble and can be filtered off. Alternatively dissolve it in CH2Cl2, add powdered anhydrous MgSO4, shake for 4hours, filter, evaporate and distil at 0.6mm pressure and oil bath temperature of 145o. [Bodansky et al. Biochemical Preparations 10, 122 1963, Schmidt & Seefelder Justus Liebigs Ann Chem 571 83 1951, Schmidt et al. Justus Liebigs Ann Chem 612 11 1958, Beilstein 12 IV 72.]

3.5 Shipping: UN2928 Toxic solids, corrosive, organic, n.o.s.,Hazard Class: 6.1; Labels: 6.1-Poisonous materials, 8-Corrosive material, Technical Name Required. UN2811Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

3.6 Usage: In the synthesis of peptides.

3.7 Waste Disposal: Whatever cannot be saved forrecovery or recycling should be managed in an appropriateand approved waste facility. Although not a listed RCRAhazardous waste, this material may exhibit one or morecharacteristics of a hazardous waste and require appropriateanalysis to determine specific disposal requirements.Processing, use or contamination of this product maychange the waste management options. State and localdisposal regulations may differ from federal disposalregulations. Dispose of container and unused contents inaccordance with federal, state and local requirements Dicyclohexylcarbodiimide Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 Symbol: GHS05;GHS06;GHS08;

4.1 Hazard Codes: Xn

4.1 Signal Word: DANGER

4.1 Risk Statements: R21;R36/38;R41;R43

4.1 Safety Statements: S24;S26;S36/37/39;S41

4.1 Packing Group: II

4.1 Fire Hazard: Dicyclohexylcarbodiimide is probably combustible.

4.2 Hazard Class: 6.1

4.2 Hazard Declaration: H302; H311; H317; H318; H351

4.2 RIDADR: 20kgs

4.2 Caution Statement: P260-P280-P301 + P312 + P330-P305 + P351 + P338 + P310

4.2 Incompatibilities: Dust may for explosive mixturewith air. Reacts with steam and water. N,N0-Dicyclohexylcarbodiimide is an amine/imide: contactwith strong oxidizers may cause fire and explosions.Incompatible with acids, strong bases, strong reducingagents (may form flammable gasses); azo and diazo compounds (may form toxic gases); chlorinated hydrocarbons;nitro compounds. Contact with mixture of acetic acid 1dinitrogen trioxide may cause explosion. The combustionof amide compounds generate nitrogen oxides (NOx).In the presence of moisture, may attack metals and plastics.

4.3 WGK Germany: 3

4.3 RTECS: FF2160000

4.3 Safety: Hazard Codes: T,Xn
Risk Statements: 23/24/25-34-40-43-41-36/38-21-24-22-62-37/38-10-61
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed
R34: Causes burns
R40: Limited evidence of a carcinogenic effect
R43: May cause sensitization by skin contact
R41: Risk of serious damage to eyes
R36/38: Irritating to eyes and skin
R21: Harmful in contact with skin
R24: Toxic in contact with skin
R22: Harmful if swallowed
R62: Possible risk of impaired fertility
R37/38: Irritating to respiratory system and skin
R10: Flammable
R61: May cause harm to the unborn child
Safety Statements: 26-36/37/39-45-41-24-37/39-24/25-36-16-53
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
S41: In case of fire and/or explosion do not breathe fumes
S24: Avoid contact with skin
S37/39: Wear suitable gloves and eye/face protection
S24/25: Avoid contact with skin and eyes
S36: Wear suitable protective clothing
S16: Keep away from sources of ignition - No smoking
S53: Avoid exposure - obtain special instruction before use
RIDADR: UN 2922 8/PG 2
WGK Germany: 3
RTECS: FF2160000
F: 3-8-10-21: Hygroscopic. Photosensitive. Keep under argon. Sensitive to humidity.
HazardClass: 6.1
PackingGroup: II; View all

4.4 Sensitive: Moisture Sensitive

4.5 Specification: Dicyclohexylcarbodiimide (CAS NO.538-75-0) is also named as 1,3-Dicyclohexylcarbodiimide ; Bis(cyclohexyl)carbodiimide ; Carbodicyclohexylimide ; DCC ; DCCD ; DCCI ; N,N'-Dicyclohexylcarbodiimide ; N,N'-Methanetetraylbiscyclohexaamine ; NSC 30022 . Dicyclohexylcarbodiimide (CAS NO.538-75-0) is colorless solid with a heavy sweet odor. Dicyclohexylcarbodiimide is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P₂O₅ or SOCl₂ generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NO_x). Dicyclohexylcarbodiimide is incompatible with acids and oxidizing agents. It is probably combustible.; View all

4.6 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LD50	skin	10mL/kg (10mL/kg)		National Technical Information Service. Vol. OTS0555962,
mouse	LD50	intraperitoneal	> 800mg/kg (800mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS SKIN AND APPENDAGES (SKIN): HAIR: OTHER	National Technical Information Service. Vol. OTS0555962,
mouse	LD50	oral	> 800mg/kg (800mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS SKIN AND APPENDAGES (SKIN): HAIR: OTHER	National Technical Information Service. Vol. OTS0555962,
rat	LC50	inhalation	159mg/m³/6H (159mg/m³)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION SKIN AND APPENDAGES (SKIN): HAIR: OTHER	National Technical Information Service. Vol. OTS0555962,
rat	LD50	intraperitoneal	10mg/kg (10mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: CYANOSIS	National Technical Information Service. Vol. OTS0555962,
rat	LD50	oral	400mg/kg (400mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" SKIN AND APPENDAGES (SKIN): HAIR: OTHER	National Technical Information Service. Vol. OTS0555962,

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 3

Serious eye damage, Category 1

Skin sensitization, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H311 Toxic in contact with skin H318 Causes serious eye damage H317 May cause an allergic skin reaction
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

Predict 1H proton NMR

SOLUTION (10% IN CCl4 FOR 3800-1333, 10% IN CS2 FOR 1333-400 CM-1)

Raman : 4880 A,200 M,powder

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

538-75-0Total: 16 Synthesis Route

108-91-8 233 Suppliers

538-75-0 406 Suppliers

Literatures:
Bulletin de la Societe Chimique de France, , p. 1360
Yield: null

931-53-3 25 Suppliers

538-75-0 406 Suppliers

Literatures:
Synlett, , # 1 p. 75 - 76
Yield: null

2387-23-7 31 Suppliers

538-75-0 406 Suppliers

Literatures:
Schlama; Gouverneur; Mioskowski Tetrahedron Letters, 1996 , vol. 37, # 39 p. 7047 - 7048
Yield: ~99%

View all

8. Precursor and Product

precursor:

24901-29-9

34656-93-4

1212-29-9

2387-23-7

603-35-0

98-59-9

3173-53-3

931-53-3

1122-82-3

108-91-8

product :

7506-46-9

587-03-1

63-39-8

98183-15-4

5807-14-7

6407-36-9

6628-00-8

1212-29-9

2387-23-7

36049-77-1

13094-51-4

53205-66-6

58-98-0

109879-46-1

70118-40-0

68406-57-5

1124-53-4

3080-42-0

114316-64-2

15989-99-8

4833-41-4

827-52-1

108-94-1

3173-53-3

52770-86-2

619-73-8

View all

9. Other Information

9.0 Merck: 14,3096

9.1 BRN: 610662

9.2 Description: Dicydohexyl carbodiimide is used in peptide chemistry as a coupling reagent. It is both an irritant and a sensitizer, and caused contact dermatitis in pharmacists and chemists.

9.3 Chemical Properties: Colorless solid

9.4 Chemical Properties: N,N0 -Dicyclohexylcarbodiimide (DCC) is a white crystalline solid. Odor is sweet and heavy.

9.5 Uses: In the synthesis of peptides.

9.6 Uses: This product is mainly used in amikacin, glutathione dehydrants, as well as in synthesis of acid anhydride, aldehyde, ketone, isocyanate; when it is used as dehydrating condensing agent, it reacts to dicyclohexylurea through short-time reaction under normal temperature. This product can also be used in synthesis of peptide and nucleic acid. It is easy to use this product to react with compound of free carboxy and amino-group into peptide. This product is widely used in medical, health, make-up and biological products, and other synthetic fields.

9.7 Uses: N,N'-Dicyclohexylcarbodiimide is a carbodiimide used to couple amino acids during peptide synthesis. N,N'-Dicyclohexylcarbodiimide is used as a dehydrating agent for the preparation of amides, ketones , nitriles as well as in the inversion and esterification of secondary alcohols.

9.8 Uses: dicyclohexylcarbodiimide is used as a dehydrating agent at room temperature after a short reaction time, after the reaction product is dicyclohexylurea. the product is very small solubility in an organic solvent, so that easy separation of the reaction product.

9.9 Definition: ChEBI: A carbodiimide compound having a cyclohexyl substituent on both nitrogen atoms.

9.10 Preparation: A stirred mixture of N,N′-dicyclohexylurea (19.7 g), phosphorus pentoxide (100 g), sand (175 g), and pyridine (700 mL) was refluxed for 2.25 h. Stirring was no longer possible after about 30 min. The mixture was filtered and the residue was extracted with pyridine (100 mL). Pyridine was removed from the combined solutions on a flash evaporator, and the residual oil was extracted with boiling petroleum ether (bp 60–80 C°) (2 × 100 mL), and then with diethyl ether (100 mL). The combined extracts were washed with iced water (3×80 mL), dried over calcium chloride, and filtered. The solvents were removed from the filtrate under reduced pressure to give 17.4 g of an oil, which on distillation yielded 13.7 g (76%) of a clear liquid; bp 143 C° (3.5 mmHg), which solidified in the receiver; mp 34–35 C°.
Another method for producing DCC from dicyclohexylurea is a two-step process using phosphoryl chloride in dichloromethane at 40 C° for 4 h under non-basic conditions followed by removal of acidic components with aq. sodium hydroxide. This method, which gives an 89% yield of DCC, has been presented in a patent application.; View all

9.11 Preparation: Palladium acetate (22 mg, 0.1 mmol), iodine (50 mg, 0.2 mmol), and anhydrous sodium carbonate (320 mg, 3.0 mmol) were placed in a pressure vessel. Cyclohexylamine (0.11 mL, 1.0 mmol) and cyclohexyl isocyanide (0.1 mL, 0.8 mmol) were dissolved in acetonitrile (10 mL) and this solution was added to the reaction vessel, which was then pressurized with oxygen (40 psi) and heated to 100 C° for 3 h. The initially deep-red reaction mixture turned yellow-orange; no Pd black precipitation was observed. There was no obvious reaction rate dependence on oxygen pressure. The mixture was cooled to ambient temperature, depressurized, filtered, and analyzed by GC. DCC was isolated by evaporating the solvent and residual amine, followed by vacuum distillation.
Palladium(II) complexes with a carbodiimide ligand, in which a nitrogen of the linear NbCbN moiety is bonded to the metal center, and bis(carbodiimido)palladium(II) complexes, both derived from isocyanides, have been described.

9.12 General Description: White crystalline solid with a heavy sweet odor.

9.13 Air & Water Reactions: Sensitive to moisture.

9.14 Reactivity Profile: Dicyclohexylcarbodiimide is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). Dicyclohexylcarbodiimide is incompatible with acids and oxidizing agents. Dicyclohexylcarbodiimide reacts with water.

9.15 Hazard: A poison by skin contact. Moderately toxic by ingestion and inhalation.

9.16 Fire Hazard: Dicyclohexylcarbodiimide is probably combustible.

9.17 Contact allergens: Used in peptide chemistry as a coupling reagent. It is both an irritant and a sensitizer and has caused contact dermatitis in pharmacists and chemists.

9.18 Potential Exposure: Laboratory reagent

9.19 Shipping: UN2928 Toxic solids, corrosive, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, 8- Corrosive material, Technical Name Required. UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1- Poisonous materials, Technical Name Required

9.20 Purification Methods: It is sampled as a liquid after melting in warm H2O. It is sensitive to air, and it is a potent skin irritant. It can be distilled in a vacuum and is best stored in a tightly stoppered flask in a freezer. It is very soluble in CH2Cl2 and pyridine where the reaction product with H2O, after condensation, is dicyclohexyl urea which is insoluble and can be filtered off. Alternatively dissolve it in CH2Cl2, add powdered anhydrous MgSO4, shake for 4hours, filter, evaporate and distil at 0.6mm pressure and oil bath temperature of 145o. [Bodansky et al. Biochemical Preparations 10, 122 1963, Schmidt & Seefelder Justus Liebigs Ann Chem 571 83 1951, Schmidt et al. Justus Liebigs Ann Chem 612 11 1958, Beilstein 12 IV 72.]

9.21 Incompatibilities: Dust may for explosive mixture with air. Reacts with steam and water. N,N0 - Dicyclohexylcarbodiimide is an amine/imide: contact with strong oxidizers may cause fire and explosions. Incompatible with acids, strong bases, strong reducing agents (may form flammable gasses); azo and diazo compounds (may form toxic gases); chlorinated hydrocarbons; nitro compounds. Contact with mixture of acetic acid 1 dinitrogen trioxide may cause explosion. The combustion of amide compounds generate nitrogen oxides (NOx). In the presence of moisture, may attack metals and plastics.

9.22 Waste Disposal: Whatever cannot be saved for recovery or recycling should be managed in an appropriate and approved waste facility. Although not a listed RCRA hazardous waste, this material may exhibit one or more characteristics of a hazardous waste and require appropriate analysis to determine specific disposal requirements. Processing, use or contamination of this product may change the waste management options. State and local disposal regulations may differ from federal disposal regulations. Dispose of container and unused contents in accordance with federal, state and local requirements

9.23 Usage: N,N'-Dicyclohexylcarbodiimide is a carboxyl activating reagent used in peptide synthesis. It acts as a dehydrating agent for the preparation of amides, ketones and nitriles. It is involved in the preparation of esters by reacting tertiary alcohols with carboxylic acid. It is utilized for the stereo chemical inversion of secondary alcohols by forming formyl ester followed by saponification. It is associated with dimethyl sulfoxide and used in Pfitzner-Moffatt oxidation to convert alcohols into aldehydes and ketones.

10. Computational chemical data

Molecular Weight: 206.32718g/mol
Molecular Formula: C₁₃H₂₂N₂
Compound Is Canonicalized: False
XLogP3-AA: 4.7
Exact Mass: 206.178298710
Monoisotopic Mass: 206.178298710
Complexity: 201
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 24.7
Heavy Atom Count: 15
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBzAAAAAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAAAAAAAHAAAAAAACCjBAAQBAAIAAAAgAAAAJAAAAAAAAAAAAAAAAAAAAAIAgAAAAAAAAAAAAAEQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

How can Dicyclohexylcarbodiimide (DCC) be regenerated from N,N'-Dicyclohexylurea (DCU)? Nov 09 2022
Background Technology Dicyclohexylcarbodiimide (DCC), N,N'-Dicyclohexylurea (DCU), and 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (EDCI) are three commonly used dehydration coupling agents. DCC, as..
The reactions of N,N'-Dicyclohexylcarbodiimide May 13 2021
N,N'-Dicyclohexylcarbodiimide (DCC)is an organic compound with the chemical formula (C6H11N)2C. It is a waxy white solid with a sweet odor. Its primary use is to couple amino acids during artifici..
What is N,N'-Dicyclohexylcarbodiimide (DCC) and its Applications? Aug 29 2019
N,N'-Dicyclohexylcarbodiimide (DCC) is a waxy white solid with a sweet odor, commonly used in artificial peptide synthesis to couple amino acids. Its low melting point allows for easy handling, and it..

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13. Realated Product Infomation

36049-77-1 N,N'-DICYCLOHEXYLCARBODIIMIDE METHIODIDE

Recently Updated : 1009119-62-3 2446484-57-5 2446481-80-5 1118567-46-6 1447940-07-9 2947584-56-5 32259-88-4 1372158-13-8 2813950-07-9 849481-53-4