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Merck
CN

C2776

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
NACRES:
NA.32
UNSPSC Code:
12352108
PubChem Substance ID:
24892528
MDL number:
MFCD00011998
Beilstein/REAXYS Number:
5685616

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Product Name

1-Cyano-4-dimethylaminopyridinium tetrafluoroborate, organic cyanylating reagent

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

SMILES string

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

InChI key

ONCRRSYBEJHQMM-UHFFFAOYSA-M

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

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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.

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.

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Warning

pictograms

Exclamation mark
GHS07

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000519266
0000519266
0000501980
0000501980
0000135496

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A Holmberg et al.
Bioconjugate chemistry, 4(6), 570-573 (1993-11-01)
This study presents a carrier system for boron, potentially useful in boron neutron capture therapy (BNCT). Na2B12H11SH (BSH) was covalently coupled to dextran derivatives. This was accomplished in two ways. The first method comprises activation of dextran with 1-cyano-4-(dimethylamino)pyridine (CDAP)
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
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
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
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
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