2-NITRO-5-THIOCYANATOBENZOIC ACID Chemical Properties

Melting point:

156-157 °C(lit.)

Boiling point:

449.0±40.0 °C(Predicted)

Density 

1.63

refractive index 

1.5690 (estimate)

Flash point:

225.4℃

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMF: 25 mg/ml; DMSO: 11 mg/ml; Ethanol: 25 mg/ml; PBS (pH 7.2): 0.3 mg/ml

pka

1.75±0.25(Predicted)

form 

powder

color 

yellow

BRN 

2124001

InChI

InChI=1S/C8H4N2O4S/c9-4-15-5-1-2-7(10(13)14)6(3-5)8(11)12/h1-3H,(H,11,12)

InChIKey

NQUNIMFHIWQQGJ-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(SC#N)=CC=C1[N+]([O-])=O

EPA Substance Registry System

Benzoic acid, 2-nitro-5-thiocyanato- (30211-77-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

8-21

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2-NITRO-5-THIOCYANATOBENZOIC ACID Usage And Synthesis

Chemical Properties

yellow fine crystalline powder

Uses

2-Nitro-5-thiocyanatobenzoic acid (NTCB) is a highly reactive reagent that transfers its cyano group rapidly to a nucleophilic thiolate. 2-Nitro-5-thiocyanatobenzoic acid has been proposed as a reagent for converting thiol groups in proteins into their S-cyano derivatives[1][2].

Biological Activity

2-nitro-5-thiocyanatobenzoic acid (NTCB) is commonly used to cyanylate and cleave proteins at cysteine residues.

References

[1] Qiao Y, et al. Site-Specific Conversion of Cysteine in a Protein to Dehydroalanine Using 2-Nitro-5-thiocyanatobenzoic Acid. Molecules. 2021;26(9):2619. Published 2021 Apr 29. DOI:10.3390/molecules26092619
[2] Price NC. Alternative products in the reaction of 2-nitro-5-thiocyanatobenzoic acid with thiol groups. Biochem J. 1976;159(1):177-180. DOI:10.1042/bj1590177

2-NITRO-5-THIOCYANATOBENZOIC ACID(30211-77-9)Related Product Information

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