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
• Article Data: 3

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

General Description

Sodium benzaldehyde-o-sulfonate is a chemical compound that consists of a benzaldehyde molecule with a sulfonate group attached to the ortho position. sodium benzaldehyde-o-sulfonate is used as an intermediate in the synthesis of various organic compounds, and it is also used as a dye precursor in the production of dyes and pigments. Sodium benzaldehyde-o-sulfonate is a water-soluble compound and is often used in aqueous solutions for its various applications in the chemical industry. It is important to handle this compound with care due to its potentially hazardous nature, and proper safety precautions should be taken when working with it.

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

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

Downstream Products

• 10165-84-1 2-(4,4'-bis-dimethylamino-α-hydroxy-benzhydryl)-benzenesulfonic acid 
• 1227623-24-6 BSc₃₉₂₂ 
• 1318796-74-5 C₉H₈N₂O₅S 
• 63254-90-0 2-(1H-benzimidazol-2-yl)-benzenesulfonic acid 
• 21639-41-8 2-formylbenzene-1-sulfonyl chloride 

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.

Certain derivatives of particular 3-thiolated cephalosporins

Compounds of the formula STR1 wherein A is hydrogen, hydroxy, methyl or methoxy, R1 is hydrogen, sodium or potassium, R2 is carboxyl or an aliphatic, aromatic or heterocyclic radical to which there is also attached a strongly acidic group in the form of its sodium or potassium salt, and R3 is 1,2,3-triazol-5-yl, such group being unsubstituted or substituted with one or two lower alkyl groups of one to four carbon atoms are prepared by reacting the appropriate aldehyde with the corresponding amphoteric cephalosporin. A preferred product has the structure STR2