CAS 69-78-3 5,5'-Dithiobis(2-nitrobenzoic Acid) (HCID 6254)

Overview

Dithionitrobenzoic acid is an organic disulfide that results from the formal oxidative dimerisation of 2-nitro-5-thiobenzoic acid. An indicator used to quantify the number or concentration of thiol groups. It has a role as an indicator. It is a nitrobenzoic acid and an organic disulfide.

Names & identifiers

Preferred name: 5,5'-Dithiobis(2-nitrobenzoic Acid)
IUPAC: 5-[(3-carboxy-4-nitrophenyl)disulfanyl]-2-nitrobenzoic acid
English name: 5,5′-Dithiobis(2-nitrobenzoic acid)
Molecular formula: C14H8N2O8S2
Molecular weight: 396.35

Names & synonyms

69-78-3DTNB5,5'-Dithiobis(2-nitrobenzoic acid)Ellman's ReagentDithionitrobenzoic acidBenzoic acid, 3,3'-dithiobis[6-nitro-Dithiobisnitrobenzoic acid3,3'-Dithiobis(6-nitrobenzoic acid)Ellmans reagentEllman Reagent2,2'-Dinitro-5,5'-dithiodibenzoic acid2,2'-Dinitro-5,5'-dithiodibenzoesaeure

Show more names

5,5'Ellmanns5,5&priMeEllmsn'sreagentELLMANS' REAGENTellmann's reagent

9BZQ3U62JXDTXSID5058779BENZOIC ACID, 3,3'-DITHIOBIS(6-NITRO-BA-2767CHEBI:862283,3'-Dithiobis[6-nitrobenzoic Acid]5,5'-dithiobis[2-nitrobenzoic acid]Reagent, Ellman's

Database identifiers

CAS: 69-78-3
PubChem CID: 6254
DTXSID: DTXSID5058779
ChEMBL: CHEMBL395814
ChEBI: CHEBI:86228
UNII: 9BZQ3U62JX
EC Number: 200-714-4
Nikkaji: J2.332.125D、J4.870D

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 217 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 10
Rotatable bonds: 5
Heavy atoms: 26
Formal charge: 0
Complexity: 528

Experimental & physicochemical properties

Chemical ClassesDyes -> Indicator Dyes

Physical DescriptionYellow solid; [Merck Index] Light yellow powder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point: 240 · 240-245 °C (dec.)(lit.)
Boiling point: 671.9 · 671.9±55.0 °C(Predicted)
bulk density: 290 kg/m3 · 290kg/m3
Density: 1.67 · 1.67
refractive index: 1.69 · 1.6900 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: 8 mg/mL · ethanol: 8mg/mL
form: Yellow solid
pka: 1.57 · 1.57±0.25(Predicted)
color: Pale Yellow to Light Yellow
Water Solubility: Soluble in water and ethanol.
Merck: 14 · 14,3551
BRN: 1896821 · 1896821
Stability: Stable. Incompatible with strong bases, strong oxidizing agents.
InChI: 1S/C14H8N2O8S2/c17-13(18)9-5-7(1-3-11(9)15(21)22)25-26-8-2-4-12(16(23)24)10(6-8)14(19)20/h1-6H,(H,17,18)(H,19,20)
InChIKey: KIUMMUBSPKGMOY-UHFFFAOYSA-N
SMILES: OC(=O)c1cc(SSc2ccc(c(c2)C(O)=O)[N+]([O-])=O)ccc1[N+]([O-])=O
CAS DataBase Reference: 69 · 69-78-3(CAS DataBase Reference)
FDA UNII: 9 BZQ3U62JX · 9BZQ3U62JX
EPA Substance Registry System: 3 · Benzoic acid, 3,3'-dithiobis[6-nitro- (69-78-3)
UNSPSC Code: 12352200 · 12352200
NACRES: 26 · NA.26
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
RTECS: 9650000 · DG9650000
F: 10 · 10
TSCA: TSCA listed
HS Code: 29309070 · 29309070
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 52 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Benzoic acid, 3,3'-dithiobis[6-nitro-

Benzoic acid, 3,3'-dithiobis[6-nitro-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryIntraperitoneal LD50 (mouse) = 2,080 mg/kg; [RTECS] A skin and strong eye irritant; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

F: 10
PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
rtecs: DG9650000
hs_code: 29309070
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationChemical agents that react with SH groups. This is a chemically diverse group that is used for a variety of purposes. Among these are enzyme inhibition, enzyme reactivation or protection, and labelling.

Uses & manufacturing

UsesUsed as an indicator of thiols, cholinesterase, and other enzymes; [Merck Index]

General Manufacturing InformationBenzoic acid, 3,3'-dithiobis[6-nitro-: ACTIVE

Applications · 4 items

UsesReagent for determination of sufhydryl groups.5,5'-dithiobis-(2-nitrobenzoic acid) is widely utilized as a non-fluorescent probe to quantify the number or the concentration of thiol groups in a sample. It acts as a cleavable cross-linking agent. It finds an important application as a sensitive reagent for determining free sulfhydryl content in proteins, peptides, and tissues. It is also employed in high-performance liquid chromatography (HPLC) to determine the alkylthiol content.

Uses5,5′-Dithiobis(2-nitrobenzoic acid) is a water soluble reagent mainly used for the derivatization of sulfhydryl groups.

Uses5,5′-Dithiobis(2-nitrobenzoic acid) is an membrane-impermeant thiol/disulfide exchange blocker. It is also used to quantify the number or concentration of thiol groups in a sample.

General Description5,5′-Dithiobis(2-nitrobenzoic acid) is also called DTNB or Ellman′s reagent. It is a water soluble reagent, which interacts with thiol groups, and can be used conveniently at neutral pH. Thiolate anion (RS-) reacts with Ellman′s reagent (DTNB2-), to produce 2-nitro-5-thiobenzoate anion (TNB2-) and one mixed disulfide (R-S-TNB-). TNB2- has a high molar absorption coefficient, and absorbs at 412nm. This absorption is independent of pH, at pH> 7.3.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

DefinitionChEBI: An organic disulfide that results from the formal oxidative dimerisation of 2-nitro-5-thiobenzoic acid. An indicator used to quantify the number or concentration of thiol groups.