25932-11-0

Basic information

• Product Name: BENZENESULFINIC ACID SODIUM SALT DIHYDRATE
• Synonyms: SODIUM BENZENESULFINATE DIHYDRATE;SODIUM BENZENE SULFINIC ACID;SODIUM BENZENESULPHINATE;BENZENESULPHINIC ACID SODIUM SALT;BENZENESULPHINIC ACID SODIUM SALT DIHYDRATE;BENZENESUIFINIC ACID SODIUM SALT;BENZENESULFINIC ACID SODIUM SALT DIHYDRATE;BENESULFINIC ACID SODIUM SALT, DIHYDRATE
• CAS NO: 25932-11-0
• Molecular Formula: C₆H₅O₂S*2H₂O*Na
• Molecular Weight: 164.16
• EINECS: 212-842-8
• Mol File: 25932-11-0.mol
• Article Data: 0

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 339.4 °C at 760 mmHg
• Flash Point: 159.1 °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: almost transparency
• CAS DataBase Reference: BENZENESULFINIC ACID SODIUM SALT DIHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZENESULFINIC ACID SODIUM SALT DIHYDRATE(25932-11-0)
• EPA Substance Registry System: BENZENESULFINIC ACID SODIUM SALT DIHYDRATE(25932-11-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 1
• RTECS: DA9135000
• Hazardous Substances Data: 25932-11-0(Hazardous Substances Data)

Synthetic route

benzenesulfinic acid sodium dihydrate (25932-11-0) + cyanogen chloride (506-77-4) → benzenesulfonyl cyanide (24224-99-5)

Conditions	Yield
In dichloromethane; water	93.8%

1-(nitromethyl)cycloheptene (52315-51-2) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 1-benzenesulfonylmethylcycloheptene (96921-46-9)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 70℃; for 1h;	92%

methyltriphenylbismuthonium tetrafluoroborate (278172-59-1) + benzenesulfinic acid sodium dihydrate (25932-11-0) → Methyl phenyl sulfone (3112-85-4) + triphenylbismuthane (603-33-8)

Conditions	Yield
In N,N-dimethyl-formamide mixt. (Ph3BiMe)(BF4), sodium benzenesulfinate dihydrate, and DMF was stirred at room temp. for 2 h; water and Et2O was added and stirred, organic phase was separated and dried over MgSO4 and evapd.;	A 54% B 91%

benzenesulfinic acid sodium dihydrate (25932-11-0) + 2-Cyano-5-bromopyridine (97483-77-7) → 5-(benzenesulfonyl)pyridin-2-carbonitrile (1424246-19-4)

Conditions	Yield
In dimethyl sulfoxide at 120℃; for 4h;	91%

3-methyl-3-nitro-1-hepten-6-one (81769-16-6) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 5-Benzenesulfonyl-5-methyl-hept-6-en-2-one (96921-53-8)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0); sodium nitrite In N,N-dimethyl-formamide at 25℃; for 21h;	83%

benzyl bromide (100-39-0) + benzenesulfinic acid sodium dihydrate (25932-11-0) → Benzyl phenyl sulfone (3112-88-7)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;	82%

(Z)-2-nitropent-2-ene (27748-51-2) + benzenesulfinic acid sodium dihydrate (25932-11-0) → (E)-1-methyl-2-butenyl phenyl sulfone (97663-40-6)

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at 70℃; for 2h; Product distribution; Study of the palladium catalyzed synthesis of allylic sulfones from various α-nitro olefins and sodium benzenesulfinate in presence of tertiary amine;	81%

methyl 4-methyl-4-nitro-5-hexanoate (81769-17-7) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 4-Benzenesulfonyl-4-methyl-hex-5-enoic acid methyl ester (96921-50-5)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0); sodium nitrite In N,N-dimethyl-formamide at 25℃; for 21h;	79%

linalool acetate (115-95-7) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 3,7-dimethyl-2,6-octadienyl phenyl sulfone (60622-52-8)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 70℃; for 3h;	76%

t-butyl 2-(bromomethyl)oxazole-4-carboxylate (87027-39-2) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 2-benzenesulfonylmethyl-4-t-butoxycarbonyl-1,3-oxazole (86838-78-0)

Conditions	Yield
18-crown-6 ether In acetonitrile for 8h; Ambient temperature;	76%
18-crown-6 ether In acetonitrile

(E)-3-nitrohept-3-ene (93548-36-8) + benzenesulfinic acid sodium dihydrate (25932-11-0) → (E)-3-(phenylsulfonyl)-4-heptene (97663-36-0)

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at 70℃; for 2h;	71%

benzenesulfinic acid sodium dihydrate (25932-11-0) + methyl 4-bromo-2-(bromomethyl)benzoate (78471-43-9) → methyl 4-bromo-2-(phenylsulfonylmethyl)benzoate

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	71%

1-nitrocyclohexene (2562-37-0) + benzenesulfinic acid sodium dihydrate (25932-11-0) → (cyclohex-2-enylsulfonyl)benzene (87413-32-9)

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at 70℃; for 2h;	70%

benzenesulfinic acid sodium dihydrate (25932-11-0) + silver nitrate → silver (I) phenyl sulfinate (7449-23-2)

Conditions	Yield
In ethanol; water N2-atmosphere; treatment of NaSO2Ph (in EtOH) with equimolar amt. of aq.AgNO3 (pptn.); filtration, washing (water, Me2CO), drying (reduced pressure, over P2O5); elem. anal.;	70%

meta-bromobenzyl bromide (823-78-9) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 1-bromo-3-((phenylsulfonyl)methyl)benzene (130891-01-9)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;	70%

dirhodium tetraacetate + benzenesulfinic acid sodium dihydrate (25932-11-0) → disodium tetra-acetatodi(phenylsulphinato)dirhodate(II)-water (1/2)

Conditions	Yield
In methanol N2-atmosphere; addn. of sulphinate to Rh-complex; concn. (vac.), filtration, crystn. (room temp., overnight), filtration, washing (MeOH contg. NaO2SPh, acetone), drying (vac., over P2O5); elem. anal.;	63%

(1Z,2E)-2-(2-(4-chlorobenzoyl)hydrazono)-N'-(4-sulfamoylphenyl)propanehydrazonoyl chloride (1529774-45-5) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 4-(2-(2-(2-chlorobenzoylhydrazono)-1-(phenylsulfonyl)propylidene)hydrazinyl)benzenesulfonamide

Conditions	Yield
In ethanol for 18h; Reflux;	62%

(1Z,2E)-N'-(4-sulfamoylphenyl)-2-(2-(thiophene-2-carbonyl)hydrazono)propanehydrazonoyl chloride (1529774-47-7) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 4-(2-(2-(2-chlorobenzoylhydrazono)-1-(phenylsulfonyl)propylidene)hydrazinyl)benzenesulfonamide

Conditions	Yield
In ethanol for 18h; Reflux;	62%

(E)-3-nitro-2-pentene (68837-74-1) + benzenesulfinic acid sodium dihydrate (25932-11-0) → <(2-pentenyl)sulfonyl> benzene (82234-80-8)

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at 70℃; for 2h;	60%

2,3-di(bromomethyl)naphthalene (38998-33-3) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 2-bromomethyl-3-(phenylsulfonylmethyl)naphthalene

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	60%

(1Z,2E)-2-(2-benzoylhydrazono)-N′-(4-sulfamoylphenyl)propanehydrazonoyl chloride (1529774-44-4) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 4-(2-(2-(2-benzoylhydrazono)-1-(phenylsulfonyl)propylidene)hydrazinyl)benzenesulfonamide

Conditions	Yield
In ethanol for 18h; Reflux;	59%

(1Z,2E)-2-(2-(4-methoxybenzoyl)hydrazono)-N'-(4-sulfamoylphenyl)propanehydrazonoyl chloride (1529774-46-6) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 4-(2-(2-(2-methoxybenzoylhydrazono)-1-(phenylsulfonyl)propylidene)hydrazinyl)benzenesulfonamide

Conditions	Yield
In ethanol for 18h; Reflux;	57%

benzenesulfinic acid sodium dihydrate (25932-11-0) + 1,2-bis(bromomethyl)-4,5-dichlorobenzene (21903-56-0) → 4-bromomethyl-1,2-dichloro-5-(phenylsulfonylmethyl)benzene

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	53%

benzenesulfinic acid sodium dihydrate (25932-11-0) + 2-methyl-3-nitro-2-propene 70percent, 2-methyl-3-nitro-1-propene 30percent → 1-(phenylsulfonyl)-2-methyl-2-propene (49639-05-6)

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at 70℃; for 2h;	50%

trans-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)cyclohexyl carbaldehyde + ethyltriphenylphosphonium bromide (1530-32-1) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 1-((E)-1-propenyl)-trans-4-(trans-4-(trans4-propylcyclohexyl)cyclohexyl)cyclohexane

Conditions	Yield
With hydrogenchloride; potassium tert-butylate; sodium carbonate In tetrahydrofuran; water	41.6%

tert-butyl carbamate (4248-19-5) + phenylacetaldehyde (122-78-1) + benzenesulfinic acid sodium dihydrate (25932-11-0) → tert-butyl 2-phenyl-1-(phenylsulfonyl)ethylcarbamate (774225-32-0)

Conditions	Yield
With formic acid In tetrahydrofuran; water at 20℃; for 65h;	39%

(E)-3-nitrohept-3-ene (93548-36-8) + (Z)-2-nitropent-2-ene (27748-51-2) + benzenesulfinic acid sodium dihydrate (25932-11-0) → (E)-1-methyl-2-butenyl phenyl sulfone (97663-40-6) + (E)-3-(phenylsulfonyl)-4-heptene (97663-36-0)

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at 70℃; for 2h; Product distribution; study of the relative rate of the sulfonylation in competition reaction of various α-nitro olefins;

(E)-3-nitrohept-3-ene (93548-36-8) + 3-penten-2-yl acetate (31001-80-6) + benzenesulfinic acid sodium dihydrate (25932-11-0) → (E)-1-methyl-2-butenyl phenyl sulfone (97663-40-6) + (E)-3-(phenylsulfonyl)-4-heptene (97663-36-0)

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at 70℃; for 2h; Product distribution; study of the relative rate of the sulfonylation in competition reaction of α-nitro olefin and the correspondig allylic acetate;

(E)-3-nitrohex-3-ene (68216-53-5) + benzenesulfinic acid sodium dihydrate (25932-11-0) → 2-(phenylsulfonyl)-3-hexene (97663-37-1) + 3-(phenylsulfonyl)-4-hexene (97663-38-2)

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at 70℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

linalool acetate (115-95-7) + benzenesulfinic acid sodium dihydrate (25932-11-0) → (3,7-dimethylocta-1,6-diene-3-sulfonyl)benzene (91940-11-3) + 3,7-dimethyl-2,6-octadienyl phenyl sulfone (60622-52-8)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0); sodium nitrite In N,N-dimethyl-formamide at 70℃; for 3h; Yield given. Yields of byproduct given;

Downstream Products

• 97663-40-6 (E)-1-methyl-2-butenyl phenyl sulfone 
• 97663-36-0 (E)-3-(phenylsulfonyl)-4-heptene 
• 91940-11-3 (3,7-dimethylocta-1,6-diene-3-sulfonyl)benzene 
• 60622-52-8 phenyl 3,7-dimethyl-2,6-octadienyl sulfone 
• 86838-78-0 2-benzenesulfonylmethyl-4-t-butoxycarbonyl-1,3-oxazole 
• 352281-97-1 N-phenylsulfonylmethyl-3,4-dichloro-5-isothiazolecarboxamide 
• 41856-34-2 (E)-1-benzenesulfonyl-2-methyl-4-bromo-2-butene 
• 141060-78-8 6-benzenesulfonyl-2H-pyridazin-3-one 
• 24224-99-5 benzenesulfonyl cyanide 
• 82651-72-7 ortho-(phenylsulfonylmethyl)benzonitrile 
• 1242161-32-5 tert-butyl ((phenylsulfonyl)methyl)carbamate