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Sigma-Aldrich

N,N′-Diphenylformamidine

98%

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About This Item

Linear Formula:
C6H5NHCH=NC6H5
CAS Number:
622-15-1
Molecular Weight:
196.25
Beilstein:
511953
EC Number:
210-720-9
MDL number:
MFCD00003026
UNSPSC Code:
12352100
PubChem Substance ID:
24849829
NACRES:
NA.22

Assay

98%

mp

136-139 °C (lit.)

storage temp.

2-8°C

SMILES string

N(\C=N\c1ccccc1)c2ccccc2

InChI

1S/C13H12N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h1-11H,(H,14,15)

InChI key

ZQUVDXMUKIVNOW-UHFFFAOYSA-N

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General description

N,N′-Diphenylformamidine is an N,N-disubstituted formamide and it forms adducts with phosgeneand oxalyl chloride.

Application

N,N′-Diphenylformamidine was used in the microwave-assisted synthesis of 5-aminopyrazol-4-yl ketones. It was also used in the preparation of monomethine dyes containing imide functional groups.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chemistry of the adducts of N,N'-diphenylformamidine with oxalyl chloride and phosgene.
Barsa EA and Richter R.
The Journal of Organic Chemistry, 51(23), 4483-4485 (1986)
Frank Würthner et al.
The Journal of organic chemistry, 68(23), 8943-8949 (2003-11-08)
The condensation of the CH acidic heterocycles 4-alkyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile (5a and b) and barbituric acid (15) with electron-rich thiophene aldehydes and benzaldehyde derivatives affords the respective monomethine dyes 10-13 and 17-19. The formylation of 5a,b and 15 with N,N'-diphenylformamidine or dibutylformamide
Mark C Bagley et al.
Bioorganic & medicinal chemistry letters, 18(13), 3745-3748 (2008-06-10)
5-Aminopyrazol-4-yl ketones are prepared rapidly and efficiently using microwave dielectric heating from beta-ketonitriles by treatment with N,N'-diphenylformamidine followed by heterocyclocondensation by irradiation with a hydrazine. The inhibitory activity of RO3201195 prepared by this methodology was confirmed in hTERT-immortalized HCA2 and

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