C2776
1-Cyano-4-dimethylaminopyridinium tetrafluoroborate
organic cyanylating reagent
Synonym(s):
Cyanopyridinium Agent, CDAP
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About This Item
Empirical Formula (Hill Notation):
C8H10BF4N3
CAS Number:
Molecular Weight:
234.99
Beilstein:
5685616
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.32
Quality Level
form
powder
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.
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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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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
Raphael Simon et al.
PloS one, 8(5), e64680-e64680 (2013-06-07)
Non-typhoidal Salmonella (NTS) serovars S. Enteritidis and S. Typhimurium are a major cause of invasive bacterial disease (e.g., bacteremia, meningitis) in infants and young children in sub-Saharan Africa and also occasionally cause invasive disease in highly susceptible hosts (young infants
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
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