2-Nitro-5-thiocyanatobenzoic Acid

Names

[ Name ]:
2-Nitro-5-thiocyanatobenzoic Acid

[Synonym ]:
NTCB
MFCD00007139
2-Nitro-5-thiocyanatobenzoesaeure
EINECS 250-093-9
2-Nitro-5-thiocyanobenzoic acid,NTCB
2-Nitro-5-thiocyanobenzoic acid
2-Nitro-5-thiocyano-benzoesaeure
Benzoic acid,2-nitro-5-thiocyanato

Biological Activity

[Description]:

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].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[In Vitro]

2-Nitro-5-thiocyanatobenzoic acid（NTCB is a highly reactive reagent that transfers its cyano group rapidly to a nucleophilic thiolate. When it is provided to a protein, it will quickly cyanylate the protein cysteine to form S-cyano-cysteine which undergoes reversible intramolecular addition with the cysteine N-amide to generate 1-acyl-2-iminothiazolidine, an intermediate that can undergo nucleophilic acyl substitution[1].

[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.

[2]. Price NC. Alternative products in the reaction of 2-nitro-5-thiocyanatobenzoic acid with thiol groups. Biochem J. 1976;159(1):177-180.

Chemical & Physical Properties

[ Density]:
1.63g/cm3

[ Boiling Point ]:
449ºC at 760mmHg

[ Melting Point ]:
156-157ºC(lit.)

[ Molecular Formula ]:
C₈H₄N₂O₄S

[ Molecular Weight ]:
224.19300

[ Flash Point ]:
225.4ºC

[ Exact Mass ]:
223.98900

[ PSA ]:
132.21000

[ LogP ]:
2.38938

[ Appearance of Characters ]:
powder | yellow

[ Index of Refraction ]:
1.5690 (estimate)

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2930909090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

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J. Am. Chem. Soc. 136(29) , 10349-60, (2014)

Electrostatic interactions play an important role in enzyme catalysis by guiding ligand binding and facilitating chemical reactions. These electrostatic interactions are modulated by conformational ch...

Nonradioactive, ultrasensitive site-specific protein-protein photocrosslinking: interactions of alpha-helix 2 of TATA-binding protein with general transcription factor TFIIA and transcriptional repressor NC2.

Nucleic Acids Res. 36(19) , 6143-54, (2008)

We have developed an approach that enables nonradioactive, ultrasensitive (attamole sensitivity) site-specific protein-protein photocrosslinking, and we have applied the approach to the analysis of in...