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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.)

functional group

amine

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL2766
STBK6712
STBK2155
STBJ7195
STBH8325

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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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