CAS 538-75-0|N,N'-DICYCLOHEXYL CARBODIIMIDE|dicyclohexylcarbodiimide|N-(N-cyclohexylcarboximidoyl)cyclohexanamine|DCC|N,N′-Dicyclohexylcarbodiimide solution|N,N′-二环己基碳二亚胺溶液|DCC 溶液|DCC...

General Information

Structure

Molecular Formula

C₁₃H₂₂N₂

Molecular Mass

206.32718

Exact Mass

206.17829871

Charge

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

InChIKey

QOSSAOTZNIDXMA-UHFFFAOYSA-N

Canonic Smiles

C1CCC(CC1)N=C=NC1CCCCC1

Isomeric Smiles

C1CCC(CC1)N=C=NC1CCCCC1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

3.7913857

LogD (pH = 7.4)

3.792248

Log P

3.7922592

Molar Refractivity

62.3204

Polarizability

24.36774

Polar Surface Area

24.72

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

dicyclohexylcarbodiimide

IUPAC name

N-(N-cyclohexylcarboximidoyl)cyclohexanamine

Synonyms

N,N'-DICYCLOHEXYL CARBODIIMIDEDCCN,N′-Dicyclohexylcarbodiimide solutionN,N′-二环己基碳二亚胺溶液DCC 溶液DCC solutionNSC 53373N,N′-DicyclohexylcarbodiimideDicyclohexylcarbodiimide solutionN,N′-Methanetetraylbis[cyclohexanamine]NSC 57182N,N′-二环己基碳二亚胺NSC 30022二环己基碳二亚胺溶液N,N'-DicyclohexylcarbodiimideN,N'-二环己基碳二亚胺

Names and Identifiers

Registration numbers

CAS Number

538-75-0

EC Number

208-704-1

PubChem CID

10868

PubChem SID

16208907324862661248941742486361422435037

Beilstein Number

610662

MDL Number

MFCD00011659

Merck Index

143096

Registration numbers

Properties

Pharmacology Properties

Gene Information

human ... EPHX2(2053)mouse ... Ephx2(13850)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02101556

Peptide condensing agent.

Sigma Aldrich

633267

Packaging
100, 800 mL in glass bottle
Application
Catalyst for Mitsunobu reaction to synthesize tetramethylpyrazine derivatives1Coupling agent for generation of graphene and graphene oxide sheets supported on silica2Endophytic bacterium L14 biomass inhibitor3Used to produce:
• Multifunctional aqueous nanocrystals stabilized by hyperbranched polyglycerol4
• MnO2 nanosheets attached to Au nanoparticles on carbon nantubes5
• Functionalized single-walled carbon nantotube arrays6

D80002

Application
Carboxy group activating reagent for peptide synthesis.1
Packaging
1 kg in poly bottle
25, 100, 500 g in poly bottle
5 kg in poly drum

379115

Packaging
100, 800 mL in Sure/Seal™

36650

Other Notes
Coupling reagent, reagent for dehydrations etc. Modifies bovine heart mitochondrial transhydrogenase;1,2 Inhibition of F1F0-ATPase and other proton-translocating enzymes3

Molecule Details

References

PubChem Literature

From Data Sources

• For ester or thioester formation from an acid and an alcohol, the rate is greatly increased by addition of 4-(Dimethylamino)pyridine, A13016: Angew. Chem. Int. Ed., 17, 522 (1978). For t-butyl esters, see: Org. Prep. Proced. Int., 20, 180 (1988); Org. Synth. Coll., 7, 93 (1990). The same combination has been found useful in macrolactonization reactions: J. Org. Chem., 50, 2394 (1985); and in formation of propynoic esters under mild conditions: Tetrahedron Lett., 30, 4575 (1989).

• For reviews of advances in the chemistry of carbodiimides, see: Chem. Rev., 67, 107 (1967), 81, 589 (1981); Tetrahedron, 37, 233 (1981).

• Promotes a variety of acylation reactions between carboxylic acids and nucleophiles; the dicyclohexylurea by-product is almost insoluble in most solvents:

• In the presence of H₂SO₄ or AlCl₃, Friedel-Crafts cyclohexylation of arenes has been reported: Tetrahedron Lett., 35, 903 (1994).

• DCC has also been used in dehydrations, e.g. carboxylic acids to anhydrides: J. Am. Chem. Soc., 85, 1997 (1963); J. Org. Chem., 54, 1922 (1989); primary amides: J. Org. Chem., 26, 3356 (1961), and aldoximes: Synth. Commun., 3, 101 (1973); 12, 25 (1982) to nitriles; dialkylacetic acids to ketenes (where stable): Synthesis, 568 (1989). The combination with Dimethyl sulfoxide, A13280, is used in the Pfitzner-Moffatt oxidation of alcohols to carbonyl compounds under mild conditions: J. Am. Chem. Soc., 85, 3027 (1963); 87, 5661, 5670 (1965); Org. Synth. Coll., 5, 242 (1973); review: Synthesis, 857 (1990).

• In peptide coupling reactions, various auxiliary reagents have been used to suppress racemization. See, e.g., N-Hydroxysuccinimide, A10312, N-Hydroxyphthalimide, A13862, and endo-N-Hydroxy-5-norbornene-2,3-dicarboximide, A13205. For use of CuCl₂, see: Tetrahedron Lett., 25, 771 (1984); J. Chem. Soc., Chem. Commun., 419 (1988).

• DCC-coupling is frequently used to prepare active esters, e.g. of 4-Nitrophenol, A14376, or Pentafluorophenol, A15574, for peptide coupling; see Appendix 6.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

dicyclohexylcarbodiimide

IUPAC name

N-(N-cyclohexylcarboximidoyl)cyclohexanamine

Synonyms

Registration numbers

CAS Number

538-75-0

EC Number

208-704-1

PubChem CID

10868

PubChem SID

16208907324862661248941742486361422435037

Beilstein Number

MDL Number

Merck Index

Molecule Details

Peptide condensing agent.

Sigma Aldrich

633267

D80002

Application
Carboxy group activating reagent for peptide synthesis.1
Packaging
1 kg in poly bottle
25, 100, 500 g in poly bottle
5 kg in poly drum

379115

Packaging
100, 800 mL in Sure/Seal™

36650

Other Notes
Coupling reagent, reagent for dehydrations etc. Modifies bovine heart mitochondrial transhydrogenase;1,2 Inhibition of F1F0-ATPase and other proton-translocating enzymes3

References

PubChem Literature

From Data Sources

• For reviews of advances in the chemistry of carbodiimides, see: Chem. Rev., 67, 107 (1967), 81, 589 (1981); Tetrahedron, 37, 233 (1981).

• Promotes a variety of acylation reactions between carboxylic acids and nucleophiles; the dicyclohexylurea by-product is almost insoluble in most solvents:

• In the presence of H₂SO₄ or AlCl₃, Friedel-Crafts cyclohexylation of arenes has been reported: Tetrahedron Lett., 35, 903 (1994).

• DCC-coupling is frequently used to prepare active esters, e.g. of 4-Nitrophenol, A14376, or Pentafluorophenol, A15574, for peptide coupling; see Appendix 6.

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Gene Information

human ... EPHX2(2053)mouse ... Ephx2(13850)

Molecule

ID:102408