2508-19-2

Basic information

• Product Name: 2,4,6-TRINITROBENZENESULFONIC ACID
• Synonyms: 2,4,6-TRINITOBENZENESULFONIC ACID;Trinitrobenzene sulphonic acid;TNBS;TNBSA;PICRYLSULFONIC ACID;2,4,6-trinitro-benzenesulfonicaci;2,4,6-trinitrobenzenesulfonicacidsol.;trinitrobenzenesulfonicacid
• CAS NO: 2508-19-2
• Molecular Formula: C₆H₃N₃O₉S
• Molecular Weight: 293.17
• EINECS: 219-717-7
• Product Categories: Combinatorial Chemistry;Detection of Amines for Primary Amines (for Detection of Free Amine on the Resins);Synthetic Organic Chemistry
• Mol File: 2508-19-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: 58 °C
• Appearance: CLEAR TO SLIGHTLY HAZY YELLOW LIQUID
• Density: 1.14 g/mL at 20 °C
• Refractive Index: n20/D 1.431
• Storage Temp.: 2-8°C
• PKA: -3.05±0.50(Predicted)
• BRN: 572358
• CAS DataBase Reference: 2,4,6-TRINITROBENZENESULFONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRINITROBENZENESULFONIC ACID(2508-19-2)
• EPA Substance Registry System: 2,4,6-TRINITROBENZENESULFONIC ACID(2508-19-2)

Safety Data

• Hazard Codes: T,Xn,C,F
• Statements: 61-20/21-36-43-36/38-22-1-34-25-11
• Safety Statements: 53-26-36/37-45-36/37/39-16-35
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 1
• RTECS: DA9138500
• HazardClass: 1.1D
• PackingGroup: Ⅱ
• Hazardous Substances Data: 2508-19-2(Hazardous Substances Data)

Usage

Definition

ChEBI: The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.

General Description

A detonating explosive substance derived from an organic sulfonic acid. Primary hazard is blast of an instantaneous explosion, not flying projectiles or fragments. Under prolonged exposure to fire or heat the containers may explode violently.

Air & Water Reactions

Soluble in water. Solution exhibits a strong acidic reaction.

Reactivity Profile

2,4,6-TRINITROBENZENESULFONIC ACID is a nitroaryl oxidizing acid. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups.

Health Hazard

Fire may produce irritating, corrosive and/or toxic gases.

Fire Hazard

MAY EXPLODE AND THROW FRAGMENTS 1600 meters (1 MILE) OR MORE IF FIRE REACHES CARGO.

Purification Methods

Recrystallise TNBS from 1M HCl, or a mixture of EtOH (50mL), H2O (30mL) and conc HCl (70mL) for 65g of acid, and dry it at 100o. The diethanolamine salt had m 182-183o [Golumbic J Org Chem 11 518 1946]. [Beilstein 11 III 161.]

InChI:InChI=1/C6H3N3O9S/c10-7(11)3-1-2-4(19(16,17)18)6(9(14)15)5(3)8(12)13/h1-2H,(H,16,17,18)

Synthetic route

2,4,6-trinitrochlorobenzene (88-88-0) → 2,4,6-trinitrobenzensulfonate (2508-19-2)

Conditions	Yield
Stage #1: 2,4,6-trinitrochlorobenzene With sodium metabisulfite In ethanol for 4h; Reflux; Stage #2: With hydrogenchloride In acetone for 0.25h;	95%
With ethanol; sodium sulfite
With sodium hydrogensulfite
With sodium metabisulfite In ethanol

silver nitrate + 2,4,6-trinitrobenzensulfonate (2508-19-2) → silver 2,4,6-trinitrobenzenesulfonate (18681-53-3)

Conditions	Yield
In water at 50℃; for 0.5h; Darkness;	98%

N-acetyl-1,6-anhydromuramyl-L-Ala-γ-D-Glu-L-Lys (1222520-56-0) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → N-acetyl-1,6-anhydromuramyl-L-Ala-γ-D-Glu-[N-ε-(2,4,6-trinitrophenyl)-L-lysine] (1257317-25-1)

Conditions	Yield
In methanol; water at 37℃; for 3h; pH=9.5; carbonate buffer;	97%

1,3-Propandiylbis(dimethylsulfonium)-bis(tetrafluoroborat) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → 1,3-Bis-propan-bis<2,4,6-trinitrobenzosulfonat>

Conditions	Yield
	92%

tetra-S-methyl-S,S'-ethane-1,2-diyl-bis-sulfonium; bis-tetrafluoroborate + 2,4,6-trinitrobenzensulfonate (2508-19-2) → 1,2-Bis-ethan-bis<2,4,6-trinitrobenzosulfonat>

Conditions	Yield
	80%

iodine tris(trifluoroacetate) (14353-86-7) + Pentafluorobenzene (363-72-4) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → bis(pentafluorophenyl)iodine 2,4,6-trinitrobenzenesulfonate

Conditions	Yield
In trifluoroacetic acid 1.) 0 deg C, 1 h, 2.) RT, 72 h;	75%

D-Tyr-Val-Gly + 2,4,6-trinitrobenzensulfonate (2508-19-2) → TNP-D-Tyr-L-Val-Gly (137856-43-0)

Conditions	Yield
Stage #1: D-Tyr-Val-Gly; 2,4,6-trinitrobenzensulfonate With triethylamine In methanol; water Darkness; Stage #2: With hydrogenchloride In methanol; water pH=2;	50%

2,4,6-trinitrobenzensulfonate (2508-19-2) + C37H50N4O10S3 → C43H51N7O16S3

Conditions	Yield
In water for 0.5h; Ambient temperature; pH 9.0;	35%

[Sb(μ2-oxo)(phenyl)3]2 (102614-53-9) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → (((NO2)3C6H2SO3)(C6H5)3SbO)2Sb(C6H5)3

Conditions	Yield
With 2,2-dimethoxypropane In acetone suspending of Sb-compd. and sulfonic acid in acetone (room temp.), addn. of dimethoxypropane, stirring (12 h); partial evapn. (vac.), filtration, washing (ether);	32%

2,4,6-trinitrobenzensulfonate (2508-19-2) + kanamycin A (59-01-8) → tetra N-(2,4,6-trinitrophenyl)kanamycin A

Conditions	Yield
With pyridine In water at 70℃; for 0.333333h;	29%

diazomethane (186581-53-3, 908094-01-9) + Dimethyl ether (115-10-6) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → 2,4,6-trinitro-benzenesulfonic acid ; trimethyloxonium salt (13700-00-0)

1-(2-chloro-ethyl)-[1,4]dithianium; chloride (30843-67-5) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → 1-vinyl-[1,4]dithianium; 2,4,6-trinitro-benzenesulfonate

2-methyl-1,2-epoxypropane (558-30-5) + dimethyl sulfoxide (67-68-5) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → C6H15O2S(1+)*C6H2N3O9S(1-)

ethyloxirane (106-88-7) + dimethyl sulfoxide (67-68-5) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → C6H15O2S(1+)*C6H2N3O9S(1-)

ethyloxirane (106-88-7) + dimethyl sulfoxide (67-68-5) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → C6H15O2S(1+)*C6H2N3O9S(1-)

epoxybutene (930-22-3) + dimethyl sulfoxide (67-68-5) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → C6H13O2S(1+)*C6H2N3O9S(1-)

styrene oxide (96-09-3) + dimethyl sulfoxide (67-68-5) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → C10H15O2S(1+)*C6H2N3O9S(1-)

cyclohexane-1,2-epoxide (286-20-4) + dimethyl sulfoxide (67-68-5) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → C8H17O2S(1+)*C6H2N3O9S(1-)

methanol (67-56-1) + dimethyl sulfoxide (67-68-5) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → C6H2N3O9S(1-)*C3H9OS(1+)

Conditions	Yield
(i) ethyloxirane, (ii) /BRN= 1098229/; Multistep reaction;

2-bromo-3-methylbut-2-ene (3017-70-7) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → Trimethylvinyl-2,4,6-trinitrobenzolsulfonat (35552-98-8)

Conditions	Yield
(i) Li, Et2O, (ii) PhN3, (iii) /BRN= 572358/, CH2Cl2; Multistep reaction;

N-<2-Chlor-ethyl>-3.3'-dichlor-dipropylamin + 2,4,6-trinitrobenzensulfonate (2508-19-2) → N-<2-Chlorethyl>-N-<3-Chlor-propyl>-isoxazolidinium

Conditions	Yield
(i) H2O2, Ac2O, (ii) /BRN= 572358/; Multistep reaction;

p-Methoxy-benzyl-dimethylsulfoniumbromid (14181-52-3) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → 2,4,6-Trinitro-benzenesulfonate(4-methoxy-benzyl)-dimethyl-sulfonium; (109498-18-2)

Triethyl-morpholin-4-ylmethyl-phosphonium; bromide (38021-60-2) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → 2,4,6-Trinitro-benzenesulfonatetriethyl-morpholin-4-ylmethyl-phosphonium; (38021-61-3)

2,4,6-trinitrobenzensulfonate (2508-19-2) + (S)-Ethyl-methyl-((E)-propenyl)-sulfonium; chloride → (S)-Ethylmethylpropylsulfonium-2,4,6-trinitrobenzolsulfonat (57691-35-7)

Conditions	Yield
(i) H2, Pd, MeOH, (ii) /BRN= 572358/; Multistep reaction;

2,4,6-trinitrobenzensulfonate (2508-19-2) + C24H20B(1-)*C8H15O2S(1+) (71232-92-3) → 2,4,6-Trinitro-benzenesulfonatecarboxymethyl-ethyl-((E)-propenyl)-sulfonium;

Conditions	Yield
(i) nBu4N(1+)*ClO4(1-), acetone, (ii) aq. NaOH, (iii) /BRN= 572358/; Multistep reaction;

2,4,6-Trinitro-benzenesulfonatecarboxymethyl-ethyl-((E)-propenyl)-sulfonium; + 2,4,6-trinitrobenzensulfonate (2508-19-2) → 2,4,6-Trinitro-benzenesulfonateethyl-methyl-((E)-propenyl)-sulfonium;

Conditions	Yield
(i) nBu3N, acetone, (ii) /BRN= 572358/; Multistep reaction;

2,4,6-trinitrobenzensulfonate (2508-19-2) + (2S,4S)-4-Ethyl-2-methyl-6-oxo-[1,4]oxathian-4-ium; perchlorate → (S)-Ethylmethylpropylsulfonium-2,4,6-trinitrobenzolsulfonat (57691-35-7)

Conditions	Yield
Multistep reaction;

dimethyl sulfoxide (67-68-5) + 2,4,6-trinitrobenzensulfonate (2508-19-2) + rac-1,2,3,4-diepoxybutane (1464-53-5) → C8H20O4S2(2+)*2C6H2N3O9S(1-)

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → caffeine-picrylsulfonate ion-pair (94944-47-5)

Conditions	Yield
In water for 0.333333h;

Methyl fluorosulfonate (421-20-5) + 3,5-diacetoxy-4-phenyl-benzo[b]thiepine (13200-08-3) + 2,4,6-trinitrobenzensulfonate (2508-19-2) → 3,5-Diacetoxy-1-methyl-4-phenyl-1-benzothiepinium-trinitrobenzolsulfonat (64807-46-1)

Conditions	Yield
1) ether, -10 deg C, 7d, 2) aceton, room temp.; Yield given. Multistep reaction;

Upstream product

• 88-88-0 2,4,6-trinitrochlorobenzene 

Downstream Products

• 13700-00-0 2,4,6-trinitro-benzenesulfonic acid ; trimethyloxonium salt 
• 88-88-0 2,4,6-trinitrochlorobenzene 
• 88-89-1 2,4,6-Trinitrophenol 
• 53541-31-4 methyl 2,4,6-trinitrobenzenesulfonate 
• 1287795-66-7 C₆H₂N₃O₉S^(1-)*C₈H₂₀N⁽¹⁺⁾ 
• 137856-43-0 TNP-D-Tyr-L-Val-Gly 
• 18681-53-3 silver 2,4,6-trinitrobenzenesulfonate 
• 2493-31-4 N,N-dimethyl-2,4,6-trinitro-aniline 
• 1257317-25-1 N-acetyl-1,6-anhydromuramyl-L-Ala-γ-D-Glu-[N-ε-(2,4,6-trinitrophenyl)-L-lysine] 
• 140215-96-9 (2,4,6-Trinitro-benzenesulfonylamino)-acetic acid 

Relevant articles and documents

Fluoromethyl-2,4,6-trinitrophenylsulfonate: A New Electrophilic Monofluoromethylating Reagent

Fluoromethyl-2,4,6-trinitrophenylsulfonate has been prepared for the first time and qualified as a simple to use monofluoromethylating reagent. Its molecular structure in the solid state has been determined by single-crystal X-ray diffraction studies. This reagent proves to be effective for the electrophilic introduction of a CH2F group into selected chalcogen and nitrogen nucleophiles. Monofluoromethyl derivatives of various bifunctional N,O-nucleophiles have been synthesized using fluoromethyl-2,4,6-trinitrophenylsulfonate. Due to the good crystallizing properties of the anion, the fluoromethylated products as well as side products that are difficult to identify by nuclear magnetic resonance spectroscopy can readily be characterized by X-ray crystallographic techniques.