91-25-8

Basic information

• Product Name: sodium benzaldehyde-o-sulfonate
• Synonyms: Benzaldehyde-o-sulfonic acid;o-Sulfobenzaldehyde;2-methanoylbenzenesulfonic acid;sodium benzaldehyde-o-sulfonate
• CAS NO: 91-25-8
• Molecular Formula: C₇H₆O₄S
• Molecular Weight: 208.16697
• EINECS: 202-053-7
• Mol File: 91-25-8.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.503g/cm³
• CAS DataBase Reference: sodium benzaldehyde-o-sulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: sodium benzaldehyde-o-sulfonate(91-25-8)
• EPA Substance Registry System: sodium benzaldehyde-o-sulfonate(91-25-8)

Safety Data

• Hazardous Substances Data: 91-25-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Sodium benzaldehyde-o-sulfonate is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block for the creation of a wide range of chemical products.
Used in Dye and Pigment Production:
Sodium benzaldehyde-o-sulfonate is used as a dye precursor in the production of dyes and pigments. Its ability to form various organic compounds makes it a valuable component in the development of new dyes and pigments with specific properties.
Used in Chemical Industry:
Sodium benzaldehyde-o-sulfonate is used in various applications within the chemical industry, taking advantage of its water solubility and reactivity. Its use in this sector highlights its importance in the synthesis of a diverse range of chemical products.
Safety Precautions:
It is important to handle sodium benzaldehyde-o-sulfonate with care due to its potentially hazardous nature. Proper safety precautions should be taken when working with this compound to ensure the safety of individuals and the environment.

InChI:InChI=1/C7H6O4S.Na.2H2O/c8-5-6-3-1-2-4-7(6)12(9,10)11;;;/h1-5H,(H,9,10,11);;2*1H2/q;+1;;/p-1

Synthetic route

2-chloro-benzaldehyde (89-98-5) → 2-sulfobenzaldehyde (91-25-8)

Conditions	Yield
Stage #1: 2-chloro-benzaldehyde With tert-butylammonium hydrogen sulphate In water at 60℃; under 760.051 Torr; for 0.166667h; Stage #2: With potassium pyrosulfite In water at 70℃; under 760.051 Torr; for 12.5h; Reagent/catalyst;	88.9%
With sodium sulfite at 190 - 200℃;

o-toluenesulfonic acid (88-20-0) → 2-sulfobenzaldehyde (91-25-8)

Conditions	Yield
With manganese(IV) oxide; sulfuric acid

2,2″-([1,1′-biphenyl]-4,4′-diyldi-2,1-ethenediyl)bis-benzenesulfonic acid (38775-22-3) → 4,4'-diformylbiphenyl (66-98-8) + 2-sulfobenzaldehyde (91-25-8) + 4-Aldehyde-4'-(2-sulfostyryl)biphenyl

Conditions	Yield
With oxygen; phenol In phosphate buffer at 25℃; pH=8.0; Kinetics; Quantum yield; Further Variations:; Reagents; source of irradiation; Decomposition; Photolysis;

water (7732-18-5) + 2-chloro-benzaldehyde (89-98-5) + sulfite(2-) (14265-45-3) → 2-sulfobenzaldehyde (91-25-8)

Conditions	Yield
at 110℃; unter Druck;

stilbene-disulfonic acid-(2.2') → 2-sulfobenzaldehyde (91-25-8)

Conditions	Yield
With permanganate(VII) ion

trans-stilbene-disulfonic acid-(2,2') (28097-15-6) + KMnO4 → 2-sulfobenzaldehyde (91-25-8)

1,10-phenanthroline-5,6-dione (27318-90-7) + 2-sulfobenzaldehyde (91-25-8) → 2-(2-sulfophenyl)imidazo(4,5-f)(1,10)-phenanthroline

Conditions	Yield
With ammonium acetate; acetic acid at 100℃; for 0.333333h; Microwave irradiation;	87%

2-sulfobenzaldehyde (91-25-8) + 1,2-diamino-benzene (95-54-5) → 2-(1H-benzimidazol-2-yl)-benzenesulfonic acid (63254-90-0)

Conditions	Yield
With oxygen at 20℃; for 3h; pH=6; aq. phosphate buffer;	80%

2-sulfobenzaldehyde (91-25-8) + 3-(2-aminophenyl)-6-(4-isopropylphenyl)-1,2,4-triazin-5(2H)-one → 2-[3-(4-isopropylphenyl)-2-oxo-6,7-dihydro-2H-[1,2,4]-triazino[2,3-c]quinazolin-6-yl]benzenesulfonic acid

Conditions	Yield
With acetic acid for 3h; Reflux;	68%

2-sulfobenzaldehyde (91-25-8) + acetone (67-64-1) → C10H10O4S

Conditions	Yield
With water; sodium hydroxide In methanol	60%

methyl-3-pyridylketone (350-03-8) + 2-sulfobenzaldehyde (91-25-8) → 2-(3,2':6',3''-terpyridin-4'-yl)benzenesulfonic acid

Conditions	Yield
With ammonium hydroxide; sodium hydroxide In ethanol at 0 - 50℃; for 27h;	44%

5-chloro-indolin-2-one (17630-75-0) + 2-sulfobenzaldehyde (91-25-8) → BSc3922 (1227623-24-6)

Conditions	Yield
With piperidine In methanol at 100℃; for 0.5h; Knoevenagel condensation; Microwave irradiation; optical yield given as %de;	43%

potassium cyanide + 2-sulfobenzaldehyde (91-25-8) + ammonium carbonate (506-87-6) → C9H8N2O5S (1318796-74-5)

Conditions	Yield
In methanol; water at 50 - 60℃; for 3h; Bucherer-Bergs reaction;	42%

antipyrine (60-80-0) + 2-sulfobenzaldehyde (91-25-8) → 2-[bis-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-methyl]-benzenesulfonic acid

Conditions	Yield
With hydrogenchloride

nitromethane (75-52-5) + 2-sulfobenzaldehyde (91-25-8) → 2-(2-nitro-vinyl)-benzenesulfonic acid ; sodium-salt

Conditions	Yield
With potassium hydroxide
With methanol; sodium hydroxide

3-methylsalicylic acid (83-40-9) + 2-sulfobenzaldehyde (91-25-8) → eriochrome cyanine R (14674-54-5)

Conditions	Yield
With sulfuric acid at 120 - 125℃; Und oxydiert die erhaltene Leukoverbindung mit Nitrosylschwefelsaeure bei 20grad;
With sulfuric acid at 120 - 125℃; Und oxydiert die erhaltene Leukoverbindung mit 4-Nitro-phenol in konz.Schwefelsaeure bei 90-100grad;

1,2,4-triacetoxybenzene (613-03-6) + 2-sulfobenzaldehyde (91-25-8) → 1,1-dioxo-1λ6-spiro[benz[c][1,2]oxathiol-3,9'-xanthene]-2',3',6',7'-tetraol (53510-54-6)

Conditions	Yield
With hydrogenchloride; ethanol anschliessend Hydrolyse bei pH 4;

2-sulfobenzaldehyde (91-25-8) + 4-(N-ethyl-anilinomethyl)-benzenesulfonic acid (92-60-4) → 2-{4,4'-bis-[ethyl-(3-sulfo-benzyl)-amino]-α-hydroxy-benzhydryl}-benzenesulfonic acid

Conditions	Yield
Oxydation der erhaltenen Leukoverbindung mit Bleidioxyd in salzsaurer Loesung;
Oxydation der erhaltenen Leukoverbindung mit Bleidioxyd in salzsaurer Loesung;

2-sulfobenzaldehyde (91-25-8) + ortho-cresol (95-48-7) → 2-(4,4'-dihydroxy-3,3'-dimethyl-benzhydryl)-benzenesulfonic acid (871593-39-4)

Conditions	Yield
With sulfuric acid

2-sulfobenzaldehyde (91-25-8) + N,N-dimethyl-aniline (121-69-7) → 2-(4,4'-bis-dimethylamino-α-hydroxy-benzhydryl)-benzenesulfonic acid (10165-84-1)

Conditions	Yield
With sulfuric acid man macht alkalisch, saeuert mit Salzsaeure oder Essigsaeure an und oxydiert die erhaltene Leukoverbindung mit Bleidioxyd;

2-sulfobenzaldehyde (91-25-8) + 3-diethylaminophenol (91-68-9) + acid → bis-diethylamino-dioxy-triphenylmethane-sulfonic acid

sulfuric acid (7664-93-9) + 2-sulfobenzaldehyde (91-25-8) + 2,4,6-Trichlorophenol (88-06-2) → 3-<2,4,6-Trichlor-3-hydroxy-phenyl>-2,1,3-benzoxathiol-S,S-dioxid (99585-51-0)

sulfuric acid (7664-93-9) + 2-sulfobenzaldehyde (91-25-8) + ortho-cresol (95-48-7) → 2-(4,4'-dihydroxy-3,3'-dimethyl-benzhydryl)-benzenesulfonic acid (871593-39-4)

phosphorus pentachloride (10026-13-8, 874483-75-7) + 2-sulfobenzaldehyde (91-25-8) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → saccharin (81-07-2)

Conditions	Yield
Erhitzen des entstehenden, bei 114grad schmelzende Verbindung mit Ammoniak unter Druck auf 100-150grad;

2-sulfobenzaldehyde (91-25-8) + water (7732-18-5) + KOH → benzoic acid (65-85-0) + salicylic acid (69-72-7)

Conditions	Yield
at 220 - 240℃;

2-sulfobenzaldehyde (91-25-8) + m-diethylamino-phenol → bis-diethylamino-dioxy-triphenylmethane-monosulfonic acid

3-methylsalicylic acid (83-40-9) + 2-sulfobenzaldehyde (91-25-8) → Eriochrome Cyanin

Conditions	Yield
Oxydation der entstehenden Leukoverbindung;

Upstream product

• 38775-22-3 2,2″-([1,1′-biphenyl]-4,4′-diyldi-2,1-ethenediyl)bis-benzenesulfonic acid 
• 28097-15-6 trans-stilbene-disulfonic acid-(2,2') 
• 7732-18-5 water 
• 89-98-5 2-chloro-benzaldehyde 
• 14265-45-3 sulfite^(2-) 
• 88-20-0 o-toluenesulfonic acid 

Downstream Products

• 871593-39-4 2-(4,4'-dihydroxy-3,3'-dimethyl-benzhydryl)-benzenesulfonic acid 
• 99585-51-0 3-<2,4,6-Trichlor-3-hydroxy-phenyl>-2,1,3-benzoxathiol-S,S-dioxid 
• 21639-41-8 2-formylbenzene-1-sulfonyl chloride 
• 1227623-24-6 BSc₃₉₂₂ 
• 63254-90-0 2-(1H-benzimidazol-2-yl)-benzenesulfonic acid 
• 1318796-74-5 C₉H₈N₂O₅S 

Relevant articles and documents

Method for synthesizing O-sulfonic acid benzaldehyde under normal pressure

The invention relates to a method for synthesizing o-sulfonic acid benzaldehyde under normal pressure. The method comprises the following steps: by using o-chlorobenzaldehyde as a raw material and metasulfite as a sulfonating agent, carrying out sulfonation reaction under the catalytic action of tert-butylamine salt or quaternary ammonium salt to generate benzaldehyde-2-sulfonate, and acidifying to obtain the o-benzaldehyde sulfonate. The preparation method is mild in condition, capable of preparing the o-sulfonic acid benzaldehyde at normal pressure and low temperature, few in side reaction,high in yield, simple in post-treatment, high in safety, low in cost, simple to operate and easy to control in industrial production.

Degradation of fluorescent whitening agents in sunlit natural waters

Stilbene-type fluorescent whitening agents (FWAs), such as the distyryl biphenyl (DSBP) and the diaminostilbene types (DAS 1 and DAS 2), are commonly used in detergents and papers. They are not readily biodegradable, but due to their ability to absorb part of the terrestrial sunlight, they can be photochemically degraded in natural surface waters. Following a fast preceding photoisomerization, the three compounds are degraded by direct photochemical processes yielding mainly aldehydes and alcohols. Their degradation quantum yields are similar, about 10"SUP -4" . Nevertheless, in samples of a eutrophic Swiss lake water, DSBP is photochemically degraded three times faster (t"SUB 1/2" =87 min) in summer noon terrestrial sunlight at 25 degrees C than DAS 1 and DAS 2 (t"SUB 1/2" =278 and 313 min) because of a higher rate of sunlight absorption by the DSBP isomer mixture. All FWAs are degraded faster if the oxygen concentration is increased. Dissolved natural organic material partly inhibits the degradation of DSBP in the reaction with molecular oxygen. The behavior of these compounds illustrates the influence of a preceding isomer equilibrium on degradation rate coefficients. (Authors)

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