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235563

Sigma-Aldrich

N,N′-Di-tert-butylcarbodiimide

99%

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About This Item

Linear Formula:
(CH3)3CN=C=NC(CH3)3
CAS Number:
691-24-7
Molecular Weight:
154.25
Beilstein:
1758049
EC Number:
211-719-6
MDL number:
MFCD00010231
UNSPSC Code:
12352001
PubChem Substance ID:
24854113
NACRES:
NA.22

Assay

99%

reaction suitability

reaction type: Coupling Reactions

refractive index

n20/D 1.428 (lit.)

bp

48-50 °C/12 mmHg (lit.)

density

0.8 g/mL at 25 °C (lit.)

application(s)

peptide synthesis

SMILES string

CC(C)(C)N=C=NC(C)(C)C

InChI

1S/C9H18N2/c1-8(2,3)10-7-11-9(4,5)6/h1-6H3

InChI key

IDVWLLCLTVBSCS-UHFFFAOYSA-N

Gene Information

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

Application

N,N′-Di-tert-butylcarbodiimide can be used:
  • As a reagent for the guanylation of aryl amines catalyzed by lanthanum amides.
  • To prepare dichloroimidazolidine-4,5-dione by reacting with oxalyl chloride, which is a key intermediate for the synthesis of N,N′-diamidocarbenes.
  • To prepare the iridium complex of benzamidine named Ir(FMeppy)2(N,N′-di-tert-butyl-4-methyl-benzamidine).

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

95.0 °F - closed cup

Flash Point(C)

35 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Jonathan P Moerdyk et al.
Chemical communications (Cambridge, England), 50(35), 4551-4553 (2014-03-29)
The synthesis of the first stable, five-membered N,N'-diamidocarbenes (DACs), including a differentially N-substituted derivative, was achieved via the reduction of a geminal dichloride precursor using potassium. Key differences between the reactivity of the five-membered DACs and their six-membered congeners were
Synthesis, characterization and photophysical properties of iridium complexes with amidinate ligands
Sahin C, et al.
Journal of Organometallic Chemistry, 772, 68-78 (2014)
Qinghai Li et al.
The Journal of organic chemistry, 72(18), 6763-6767 (2007-08-07)
It is demonstrated that the cyclopentadienyl-free simple lanthanide amides [(Me(3)Si)(2)N](3)Ln(mu-Cl)Li(THF)(3)(Ln = La, Sm, Eu, Y, Yb) and Ln[N(SiMe(3))(2)]3 (Ln = Y, Yb) are highly efficient catalysts for the guanylation of both aromatic and secondary amines with a high activity under

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