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159646

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

Quality Level

100

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

159646-BULK:
159646-100G:
159646-VAR:
159646-25G:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK6712
STBK2155
STBJ7195
STBH8325
STBG8649

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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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