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Merck
CN

C2776

Sigma-Aldrich

1-Cyano-4-dimethylaminopyridinium tetrafluoroborate

greener alternative

organic cyanylating reagent

Synonym(s):

Cyanopyridinium Agent, CDAP

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About This Item

Empirical Formula (Hill Notation):
C8H10BF4N3
CAS Number:
59016-56-7
Molecular Weight:
234.99
Beilstein:
5685616
MDL number:
MFCD00011998
UNSPSC Code:
12352108
PubChem Substance ID:
24892528
NACRES:
NA.32

Key Documents

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Quality Level

300

Assay

≥97.00% (TLC)

form

powder

mol wt

234.99 g/mol

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concentration

90-100 % (w/w) (1-Cyano-4-dimethylammoniumpyridinium tetrafluoroborate)

color

white to yellow

solubility

acetonitrile: 49.00-51.00 mg/mL, clear to slightly hazy, colorless to yellow

λmax

298-302 nm (0.1 N HCl)

fluorescence

(EmM at Lambda max 28.00 - 32.00)

greener alternative category

Aligned

storage temp.

−20°C

SMILES string

[F-].FB(F)F.CN(C)c1cc[n+](cc1)C#N

InChI

1S/C8H10N3.BF3.FH/c1-10(2)8-3-5-11(7-9)6-4-8;2-1(3)4;/h3-6H,1-2H3;;1H/q+1;;/p-1

InChI key

ONCRRSYBEJHQMM-UHFFFAOYSA-M

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General description

1-Cyano-4-dimethylaminopyridinium tetrafluoroborate is an organic cyanylating agent also termed CDAP. It is a unique cystine-labeling reagent due to its reactive nature under acidic conditions. This feature provides CDAP an advantage over other sulfhydryl labeling agents, as it can avoid potential thiol-disulfide exchange.
We are committed to bringingyou greener alternative products, which adhere to one or more of the 12Principles of Greener Chemistry. 1-Cyano-4-DimethylaminopyridineTetrafluoroborate (CDAP) is a safer alternative to cyanogen bromide (CNBr) foractivating soluble polysaccharides in vaccine development. It operates at lowerpH levels, reducing toxicity and side reactions. CDAP enables quick activationfor protein-polysaccharide conjugate vaccines, bioconjugation, and drugdelivery, promoting sustainable practices in biochemistry and pharmaceuticals. Click here for more information.

Application

1-Cyano-4-dimethylaminopyridinium (CDAP) has been used in the synthesis of conjugate vaccines as a cyanylating agent. Activation of cellulose dialysis membrane for immunosensor applications used CDAP as an activation agent.

Features and Benefits

When compared to Cyanogen Bromide (CNBr), a similar reagent, CDAP is:

  • Easier to use.
  • Can operate at lower pH levels.
  • Fewer side reactions.
  • Cyanogen Bromide is hazardous in nature.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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
0000505846
0000505846
0000504506
0000504506
0000493478

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S Bystrický et al.
Glycoconjugate journal, 17(10), 677-680 (2001-06-27)
The possibility of using 1-cyano-4-dimethylaminopyridinium tetrafluoroborate (CDAP) for activation of saccharide hydroxyl groups (instead of hazardous cyanogen bromide) is examined with cell-surface mannans of the yeasts Candida albicans, Candida tropicalis, Candida lambica and galactoglucoxylomannan of Cryptococcus laurentii. Direct conjugation with
J Qi et al.
Biochemistry, 40(15), 4531-4538 (2001-04-11)
The disulfide structure of sillucin, a highly knotted, cysteine-rich, antimicrobial peptide, isolated from Rhizomucor pusillus, has been determined to be Cys2--Cys7, Cys12--Cys24, Cys13--Cys30, and Cys14--Cys21 by disulfide mass mapping based on partial reduction and CN-induced cleavage enabled by cyanylation. The
E Konadu et al.
Infection and immunity, 64(7), 2709-2715 (1996-07-01)
Salmonella paratyphi A, the second most common cause of enteric fever in Southeast Asia, is a habitant of and a pathogen for humans only. Lipopolysaccharides (LPS) are both essential virulence factors and protective antigens for systemic infections caused by groups
L J Shore et al.
The Journal of biological chemistry, 272(19), 12536-12543 (1997-05-09)
Ornithine decarboxylase (ODC) is the key initial enzyme in the biosynthesis of polyamines. Since polyamines have been shown to enhance protein kinase CK2 activity in vitro, ODC was overexpressed to examine the role of polyamines in CK2 regulation in vivo.
A Andersson et al.
International journal of cancer, 47(3), 439-444 (1991-02-01)
Some gliomas, melanomas and squamous carcinomas have large numbers of EGF receptors which could, in these cases, be used for targeting with toxic agents. We investigated whether EGF could be conjugated to dextran, which is a suitable carrier for toxic
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