5329-14-6

Basic information

• Product Name: Sulfamic acid
• Synonyms: aminosulfuricacid;Imidosulfonic acid;Jumbo;Kyselina amidosulfonova;Kyselina sulfaminova;kyselinaamidosulfonova;kyselinaamidosulfonova(czech);kyselinasulfaminova
• CAS NO: 5329-14-6
• Molecular Formula: H₃NO₃S
• Molecular Weight: 97.09372
• EINECS: 226-218-8
• Product Categories: Intermediates of Dyes and Pigments;INORGANIC & ORGANIC CHEMICALS;Intermediates;Inorganics;organic acid;fine chemical;pharmaceutical raw material
• Mol File: 5329-14-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: 215-225 °C (dec.)(lit.)
• Boiling Point: -520.47°C (estimate)
• Flash Point: 205oC
• Appearance: White/Crystals or Crystalline Powder
• Density: 2,12 g/cm3
• Vapor Pressure: 0.8Pa at 20℃
• Refractive Index: 1.553
• Storage Temp.: Store below +30°C.
• Solubility: water: soluble213g/L at 20°C
• PKA: -8.53±0.27(Predicted)
• Water Solubility: 146.8 g/L (20 ºC)
• Stability: Stable.
• Merck: 14,8921
• CAS DataBase Reference: Sulfamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Sulfamic acid(5329-14-6)
• EPA Substance Registry System: Sulfamic acid(5329-14-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-52/53
• Safety Statements: 26-28-61-28A
• RIDADR: UN 2967 8/PG 3
• WGK Germany: 1
• RTECS: WO5950000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5329-14-6(Hazardous Substances Data)

Usage

Chemical Properties

Sulfamic acid is a white orthorhombic flaky crystal, odorless, non-volatile and non-hygroscopic. Soluble in water and liquid ammonia, slightly soluble in methanol, insoluble in ethanol and ether, also insoluble in carbon disulfide and liquid sulfur dioxide. Its aqueous solution has the same strong acid properties as hydrochloric acid and sulfuric acid, but its corrosiveness to metals is much lower than that of hydrochloric acid. The toxicity is extremely small, but it should not be in contact with the skin for a long time, and it should not enter the eyes.

Uses

Sulfamic acid is widely used in electroplating, hard-water scale reremovers, acidic cleaning agent, chlorine stabilizers, sulfonating agents, denitrification agents, disinfectants, flame retardants, herbicides, artificial sweeteners and catalysts.Sulfamic acid is a precursor to sweet-tasting compounds. Reaction with cyclohexylamine followed by addition of NaOH gives C6H11NHSO3Na, sodium cyclamate.Sulfamic acid is a water-soluble, moderately strong acid. An intermediate between sulfuric acid and sulfamide, it can be used as a precursor to sweet-tasting compounds, a therapeutic drug component, an acidic cleaning agent, and a catalyst for esterification.

Application

Sulfamic acid, the monoamide of sulfuric acid, is a strong inorganic acid. It is generally used in chemical cleaning processes like removal of nitrites, carbonate- and phosphate-containing deposits.Sulfamic acid can be used as a catalyst in:Friedlander quinoline synthesis.Liquid Beckmann rearrangement for the synthesis of amides from ketoximes.The preparation of α-aminophosphonates via a three-component reaction between aldehydes, amines, and diethyl phosphite.

Definition

ChEBI: Sulfamic acid is the simplest of the sulfamic acids consisting of a single sulfur atom covalently bound by single bonds to hydroxy and amino groups and by double bonds to two oxygen atoms. It is a strong acid, readily forming sulphamate salts, which is extremely soluble in water and normally exists as the zwitterion H3N+. SO3–.

Reactions

Sulfamic acid is a strong acid that reacts with many basic compounds. It is heated to above the melting point (209°C) under normal pressure to begin to decompose, and continues to be heated to above 260°C to decompose into sulfur trioxide, sulfur dioxide, nitrogen, hydrogen and water.(1) Sulfamic acid can react with metals to form transparent crystalline salts. Such as:2H2NSO3H+Zn→Zn(SO3NH2)2+H2.(2) Can react with metal oxides, carbonates and hydroxides:FeO+2HSO3NH2→Fe(SO3NH2)2+H2O2CaCO3+2HSO3NH2→Ca(SO3NH2)2+H2O+CO23Ni(OH)2+2HSO3NH2→Ni(SO3NH2)2+H2O.(3) Can react with nitrate or nitrite:HNO3+HSO3NH2→H2SO4+N2O+H2O2HNO2+HSO3NH2→H2SO4+N2+H2O.(4) Can react with oxidants (such as potassium chlorate, hypochlorous acid, etc.): KClO3+2HSO3NH2→2H2SO4+KCl+N2+H2O22HOCl+HSO3NH2→HSO3NCl2+2H2O

General Description

Sulfamic acid appears as a white crystalline solid. Density 2.1 g / cm3. Melting point 205°C. Combustible. Irritates skin, eyes, and mucous membranes. Low toxicity. Used to make dyes and other chemicals. It is used as a raw material for the preparation of a synthetic sweetener i.e, sodium cyclohexylsulfamate.

Air & Water Reactions

Moderately soluble in water [Hawley].

Reactivity Profile

Sulfamic acid reacts exothermically with bases. Aqueous solutions are acidic and corrosive.

Hazard

Toxic by ingestion.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. A human skin irritant. A corrosive irritant to skin, eyes, and mucous membranes. A substance that migrates to food from packaging materials. Violent or explosive reactions with chlorine, metal nitrates + heat, metal nitrites + heat, fuming HNO3. When heated to decomposition it emits very toxic fumes of SOx and NOx. See also SULFONATES.

Potential Exposure

Sulfamic acid is used in metal and ceramic cleaning, bleaching paper pulp; and textiles metal; in acid cleaning; as a stabilizing agent for chlorine and hypochlorite in swimming pools; cooling towers; and paper mills.

Shipping

UN2967 Sulfamic acid, Hazard class: 8; Labels: 8-Corrosive material.

Purification Methods

Crystallise NH2SO3H from water at 70o (300mL per 25g), after filtering, by cooling a little and discarding the first batch of crystals (about 2.5g) before standing in an ice-salt mixture for 20minutes. The crystals are filtered off by suction, washed with a small quantity of ice cold water, then twice with cold EtOH and finally with Et2O. Dry it in air for 1hour, then store it in a desiccator over Mg(ClO4)2 [Butler et al. Ind Eng Chem (Anal Ed) 10 690 1938]. For the preparation of primary standard material see Pure Appl Chem 25 459 1969.

Incompatibilities

The aqueous solution is a strong acid. Reacts violently with strong acids (especially fuming nitric acid), bases, chlorine. Reacts slowly with water, forming ammonium bisulfate. Incompatible with ammonia, amines, isocyanates, alkylene oxides; epichlorohydrin, oxidizers.

InChI:InChI=1/H3NO3S/c1-5(2,3)4/h(H3,1,2,3,4)

Synthetic route

sulfuric acid (7664-93-9) + urea (57-13-6) → aminosulfonic acid (5329-14-6)

Conditions	Yield
In sulfuric acid byproducts: CO2; urea dild. in 100% H2SO4 (stirring/cooling); addn. of small portions of fuming H2SO4 (temp. shouldn't exceed 45°C/stirring/cooling); heating carefully to 80°C; evolution of CO2; addn. of next portion fuming H2SO4 and repeating;; left for some time; filtration, washing (concd. H2SO4); drying on clay; left overnight in air; recrystn. from water;;	94%
In sulfuric acid heating with excess fuming H2SO4 (80-90°C, depending on SO3-content); vigorous reaction, evolution of heat;;

ammonium sulfamate + ammonium bisulfate (7803-63-6) → ammonium sulfate + triammonium hydrogen disulfate + aminosulfonic acid (5329-14-6)

Conditions	Yield
With air In melt two salts was reacted in melt in air;	A n/a B n/a C 92%

sulfur dioxide (7446-09-5) + acetone oxime (127-06-0) → aminosulfonic acid (5329-14-6)

Conditions	Yield
In water aq. acetoxim soln., containing liquid SO2, (25°C) left for 5 h in autoclave;;	90%
In water aq. acetoxim soln. cooled to -80°C; excess of SO2 condensed; sealing of tube; warming up to 0°C (pressure increases); left for 5.5 h at that temp.;; opened flask releases excess of SO2; filtration; dried by washing (alc., ether);;	77%
In ethanol; water acetoxim dild. in water/ethanol is satd. with SO2 gas (0°C); leftfor three days (0°C); (pptd. solid HSO3NH2 will be removed);; filtration, addn. of SO2; washing (alc., ether); dried in air;;	76%
In water aq. medium; dependence of pressure (1.14-3.52 kg/cm*cm more than atm.) and temp. (5-30°C); formation of liquid SO2 should be avoided; pptn.;;
In water aq. medium; dependence of pressure (1.14-3.52 kg/cm*cm more than atm.) and temp. (5-30°C); formation of liquid SO2 should be avoided; pptn.;;

pyridine-SO3 complex (42824-16-8) + ammonia (7664-41-7) → aminosulfonic acid (5329-14-6)

Conditions	Yield
In water byproducts: pyridine; diln. of C5H5NSO3 in ammonia water (10% NH3) under sepn. of pyridine;; extraction of pyridine (ether); evapn. (water bath); addn. of concd. H2SO4 (cooling); filtration; drying on clay; recrystn from water;;	80%

trimethyl-sulfo-ammonium betaine (63147-26-2) + ammonia (7664-41-7) → aminosulfonic acid (5329-14-6)

Conditions	Yield
In water byproducts: trimethylamine; diln. in ammonia water by short heating under sepn. of (CH3)N;; evapn.; removal of exceeding NH3 and (CH3)3N; addn. of concd. H2SO4; sepn. of HSO3NH2;;	80%

sulfur dioxide (7446-09-5) + sodium nitrite (7632-00-0) → aminosulfonic acid (5329-14-6)

Conditions	Yield
With sodium carbonate In water byproducts: sodium sulfate; aq. soln. of NaNO2/Na2CO3; introduction of SO2 (until acidic/litmus); addn. of a drop concd. H2SO4; formation of N(SO3)(3-); hydrolysis; short heating or left for several hours (stream of air); neutralization (Na2CO3); evapn.; left (12h/0°C);; filtration from sodium sulfate; addn. of concd. H2SO4; immediate pptn. of most HSO3NH2 (left for another day/cooling); dried on clay; washed (ice cold water); recrystn. (hot water);;	75%
With Na2CO3 In water byproducts: sodium sulfate; aq. soln. of NaNO2/Na2CO3; introduction of SO2 (until acidic/litmus); addn. of a drop concd. H2SO4; formation of N(SO3)(3-); hydrolysis; short heating or left for several hours (stream of air); neutralization (Na2CO3); evapn.; left (12h/0°C);; filtration from sodium sulfate; addn. of concd. H2SO4; immediate pptn. of most HSO3NH2 (left for another day/cooling); dried on clay; washed (ice cold water); recrystn. (hot water);;	75%

sulfuric acid (7664-93-9) + sulfur trioxide (7446-11-9) + urea (57-13-6) → aminosulfonic acid (5329-14-6)

Conditions	Yield
In neat (no solvent) byproducts: CO2; vigorous reaction (careful heating/cooling/stirring); temp. dependence on mechanism discussed;;	73.4%
In neat (no solvent) byproducts: CO2; vigorous reaction (careful heating/cooling/stirring); temp. dependence on mechanism discussed;;	73.4%
In not given equimolar amounts;;

hydroxyammonium sulfate + sulfur dioxide (7446-09-5) → aminosulfonic acid (5329-14-6)

Conditions	Yield
In water aq. hydroxylammonium sulfate soln. cooled to -30°C; excess of SO2 condensed into vessel and left for 24 h in autoclave (at common temps.);; removal of SO2 (passing air through soln.); crystallization, filtration;washing (alc., ether); drying (air); further pptn. of HSO3NH2 by addn. of concd. H2SO4 to mother lye (at 0°C);;	72%
In water aq. medium; dependence of pressure (1.14-3.52 kg/cm*cm more than atm.) and temp. (5-30°C); formation of liquid SO2 should be avoided; pptn.;;
In water aq. medium; dependence of pressure (1.14-3.52 kg/cm*cm more than atm.) and temp. (5-30°C); formation of liquid SO2 should be avoided; pptn.;;

potassium pyrosulfate + ammonia (7664-41-7) → aminosulfonic acid (5329-14-6)

Conditions	Yield
In water K2S2O7 (contaminated with 40% KHSO4) dild. in ammonia water (25%/shakingfor 0.5 h/cooling with cold water); until evolution of heat stops; heating (3 min/water bath);; left cooling; filtration, washing (ammonia water); evapn.; addn. of concd. H2SO4; left for several hours (common temps.); filtration; drying on clay; recrystn. from water;;	60%

ammonia (7664-41-7) + dimethylphenylamidosulfonic acid (35478-69-4) → aminosulfonic acid (5329-14-6)

Conditions	Yield
In water byproducts: dimethylaniline; diln. in ice cold ammonia water (10% NH3/) left warming up to common temps. under sepn. of (CH3)2NC6H5;; evapn. (removal of exceeding NH3 and (CH3)2NC6H5/water bath); addn. of concd. H2SO4; sepn. of HSO3NH2;;	58%

sulfuric acid (7664-93-9) + carbamoyl-amidosulfuric acid ; compound with pyridine → aminosulfonic acid (5329-14-6)

Conditions	Yield
In sulfuric acid heating a soln. of 1.1g pyridinium salt of carbamidosulfonic acid in 2.5 ml 100% H2SO4 at 110 °C for 0.5 h;;	50%

trisulfimide (13954-94-4) → sulfuric acid (7664-93-9) + aminosulfonic acid (5329-14-6) + SULFAMIDE (7803-58-9)

Conditions	Yield
With water in the cold, 48 h, 2 M HCl;	A 33% B n/a C n/a
With H2O in the cold, 48 h, 2 M HCl;	A 33% B n/a C n/a
In water decompn. in aq. soln.; 0 and 22°C discussed; presece of acid discussed;;

hydroxylammonium + sulfur dioxide (7446-09-5) → ammonium sulfate + aminosulfonic acid (5329-14-6)

Conditions	Yield
In water introduction of SO2 into aq. hydroxylammonium salt soln.;;	A 10% B n/a
In water introduction of SO2 into aq. hydroxylammonium salt soln.;;	A 10% B n/a

ethanol (64-17-5) + acetone oxime (127-06-0) + SO2 → aminosulfonic acid (5329-14-6)

Conditions	Yield
at 25℃; unter Druck;

water (7732-18-5) + acetone oxime (127-06-0) + SO2 → aminosulfonic acid (5329-14-6)

Conditions	Yield
at 0℃; unter Druck;

(N-acetyl-acetimidoyl)-amidosulfuric acid (70475-81-9) + water (7732-18-5) → N-acetylacetamide (625-77-4) + aminosulfonic acid (5329-14-6)

trimethyl-sulfo-ammonium betaine (63147-26-2) + ammonium hydroxide → aminosulfonic acid (5329-14-6) + trimethylamine (75-50-3)

hydrogenchloride (7647-01-0) + acetyl-amidosulfuric acid ; potassium-compound → sulfuric acid (7664-93-9) + aminosulfonic acid (5329-14-6)

water (7732-18-5) + acetyl-amidosulfuric acid ; potassium-compound → sulfuric acid (7664-93-9) + aminosulfonic acid (5329-14-6)

5-sulfoimino-pent-3-enal; disodium salt + furan-2,3,5(4H)-trione pyridine (1:1) → aminosulfonic acid (5329-14-6) + pentenedial; sodium enolate (1593-50-6)

N,N-dimethyl-aniline; compound with sulfur trioxide + ammonium hydroxide → aminosulfonic acid (5329-14-6) + N,N-dimethyl-aniline (121-69-7)

sulfur trioxide (7446-11-9) + urea (57-13-6) → aminosulfonic acid (5329-14-6)

Conditions	Yield
In sulfuric acid react. of SO3-vapor with urea, sulfatolysis;;
In sulfuric acid aq. H2SO4; react. of SO3-vapor with urea, sulfatolysis;;

sulfur trioxide (7446-11-9) + urea (57-13-6) → carbon dioxide (124-38-9) + aminosulfonic acid (5329-14-6)

Conditions	Yield
With sulfuric acid In sulfuric acid at 80 - 90°C;

chlorosulfonic acid (7790-94-5) + urea (57-13-6) → triuret (556-99-0) + aminosulfonic acid (5329-14-6)

Conditions	Yield
heating on water bath; equimolar amts. of educts; forming small amt. of triuret;

nitromethane (75-52-5) + sulfur trioxide (7446-11-9) → carbon dioxide (124-38-9) + aminosulfonic acid (5329-14-6) + hydroxylamine-O-sulfonic acid (2950-43-8)

Conditions	Yield
above 0°C;

sulfur dioxide (7446-09-5) + ammonia (7664-41-7) → S4N2 (79796-32-0) + aminosulfonic acid (5329-14-6) + sulfur (7704-34-9) + tetrasulfur tetranitride (28950-34-7)

Conditions	Yield
With water In gas excess of SO2, 50-80°C, the solid product hydrolysed by water;

chlorosulfonic acid (7790-94-5) + aminosulfonic acid (5329-14-6) → bis(chlorosulfonyl)amine (15873-42-4)

Conditions	Yield
In thionyl chloride amidosulfuric acid placed into a flask and suspended in thionyl dichloride under dry N2; HSO3Cl added, then the flask fitted with a reflux condenser, connected to a CaCl2 drying tube; heated at 130°C for 24 h; reaction mixture fractionally distilled under vacuum; main fraction collected at 95°C/650 Pa;	99%

Hippuric Acid (495-69-2) + aminosulfonic acid (5329-14-6) + 4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)aniline (143230-70-0) → 2-phenyl-4,5-oxazoledione 4-[4-chloro-3-(2,2,3,3,3,-pentafluoropropoxymethyl)-phenylhydrazone] (143230-69-7)

Conditions	Yield
With hydrogenchloride; sodium acetate; acetic anhydride; acetic acid; sodium nitrite In water	98.1%

thionyl chloride (7719-09-7) + aminosulfonic acid (5329-14-6) → bis(chlorosulfonyl)amine (15873-42-4)

Conditions	Yield
With chlorosulfonic acid at 130℃; for 24h; Inert atmosphere;	98%

Hippuric Acid (495-69-2) + aminosulfonic acid (5329-14-6) + 4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)aniline (143230-70-0) → 2-phenyl-4,5-oxazoledione 4-[4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)phenylhydrazone]

Conditions	Yield
With hydrogenchloride; sodium acetate; acetic anhydride; acetic acid; sodium nitrite In water	97.95%
With hydrogenchloride; sodium acetate; acetic anhydride; acetic acid; sodium nitrite In water	97.1%

mercury(II) nitrate * 2H2O + aminosulfonic acid (5329-14-6) → potassium amidosulfatomercurate(II)

Conditions	Yield
With KOH In water calcd. amts. of educts; mixing cold aq. solns. of educts under stirring; product pptd. after 2-3 d; sucking off, washing with cold H2O, drying;	97%

aminosulfonic acid (5329-14-6) + mercury dichloride → sodium amidosulfatomercurate(II)

Conditions	Yield
With NaOH In water calcd. amts. of educts; pptn. 3-4 d; washing with alc. and ether; drying in vac. over P2O5;	97%
With sodium hydroxide In water 1.5 fold molar excess of NaOH; amidosulfuric acid neutralized with NaOH soln.; adding hot aq. soln. of HgCl2; pptd. after 3-4 d; washing with H2O, alc. and ether; drying in vac.;
With NaOH In water 1.5 fold molar excess of NaOH; amidosulfuric acid neutralized with NaOH soln.; adding hot aq. soln. of HgCl2; pptd. after 3-4 d; washing with H2O, alc. and ether; drying in vac.;

chlorosulfonic acid (7790-94-5) + thionyl chloride (7719-09-7) + aminosulfonic acid (5329-14-6) → bis(chlorosulfonyl)amine (15873-42-4)

Conditions	Yield
at 70 - 130℃; for 24h;	96%
at 130℃; Inert atmosphere;	Ca. 449 g

2,3-difluoroanilline (4519-40-8) + aminosulfonic acid (5329-14-6) + acrylic acid (79-10-7) → 2,4-Difluorocinnamic acid (94977-52-3)

Conditions	Yield
With sulfuric acid; sodium nitrite; palladium diacetate In water	95%

sodium chlorite (7758-19-2) + 4-iodo-α-methylbenzeneacetaldehyde (70991-79-6) + aminosulfonic acid (5329-14-6) + sodium hydrogensulfite → (RS)-2-(4'-iodophenyl)propanoic acid (34645-72-2)

Conditions	Yield
With sodium hydroxide In water; 1,2-dichloro-ethane	94%

sodium chlorite (7758-19-2) + 4-iodo-α-methylbenzeneacetaldehyde (70991-79-6) + aminosulfonic acid (5329-14-6) → (RS)-2-(4'-iodophenyl)propanoic acid (34645-72-2)

Conditions	Yield
With sodium hydroxide; sodium hydrogen sulphite In water; 1,2-dichloro-ethane	94%

aminosulfonic acid (5329-14-6) + mercury(II) oxide → sodium amidosulfatomercurate(II)

Conditions	Yield
With NaOH In water calcd. amts. of educts; adding aq. suspension of freshly prepared HgO into hot neutralized soln. of amidosulfuric acid; cooling, sucking off; washing with cold H2O; drying;	94%
With NaOH In water calcd. amts. of educts; adding boiling aq. soln. of neutralized amidosulfuric acid dropwise into aq. suspension of yellow HgO; product pptd. by cooling after 24 h;	79%

aminosulfonic acid (5329-14-6) + mercury dichloride → potassium amidosulfatomercurate(II)

Conditions	Yield
With KOH In water calcd. amts. of educts; mixing cold aq. solns. of educts under stirring, heating, cooling; decanting with cold H2O; sucking off; product contains Cl;	94%

aminosulfonic acid (5329-14-6) + 3β,7β-dihydroxy-5β-cholan-24-oic acid (78919-26-3) → ursodeoxycholic acid di-ammonium 3,7-disulfate

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 45 - 90℃; for 0.5h;	93.7%

aminosulfonic acid (5329-14-6) + mercury(II) oxide → potassium amidosulfatomercurate(II)

Conditions	Yield
With KOH In water adding amidosulfuric acid into aq. KOH soln.; this soln. adding to aq. suspension of freshly pptd. HgO; shaking for 1 h; filtrate storing for several h; sucking off the ppt.; washing with cold H2O, drying;	92%
With potassium hydroxide In not given calcd. amts. of educts; amidosulfuric acid neutralized with KOH soln., adding more KOH soln. and freshly prepared HgO; heating 1 h on water bath; product pptd. from filtrate at ambient temp.; sucking off; recrystn. from 0.5 % KOH soln.; washing with alc. and ether; drying in air; storage in vac. over P2O5;
With KOH In not given calcd. amts. of educts; amidosulfuric acid neutralized with KOH soln., adding more KOH soln. and freshly prepared HgO; heating 1 h on water bath; product pptd. from filtrate at ambient temp.; sucking off; recrystn. from 0.5 % KOH soln.; washing with alc. and ether; drying in air; storage in vac. over P2O5;

sodium chlorite (7758-19-2) + aminosulfonic acid (5329-14-6) + 2-(benzo[1,3]dioxol-5-yl)-4-chloro-6-isopropoxy-2H-chromene-3-carbaldehyde (203919-39-5) → 2-(benzo[1,3]dioxol-5-yl)-4-chloro-6-isopropoxy-2H-chromene-3-carboxylic acid (203917-92-4)

Conditions	Yield
With sodium hydroxide; sodium sulfite In water; toluene	91%

aminosulfonic acid (5329-14-6) + 2-Chloronitrobenzene (88-73-3) → 2-Nitrochlorobenznen-4-sulfonyl chloride + 3-nitro-4-chlorosulfonyl chloride (97-08-5)

Conditions	Yield
With chlorosulfonic acid	A n/a B 90.8%

aminosulfonic acid (5329-14-6) + 3-cyclopentyloxy-4-methoxybenzylaldehyde (67387-76-2) → 3-cyclopentyloxy-4-methoxy benzoic acid (144036-17-9)

Conditions	Yield
With sodium chloride In water; acetic acid	90%
With sodium In water; acetic acid

sodium chlorite (7758-19-2) + (1-phenyl-cyclopentyl)-acetaldehyde (100611-61-8) + aminosulfonic acid (5329-14-6) → (1-phenyl-cyclopentyl)-acetic acid (70239-29-1)

Conditions	Yield
In tert-butyl alcohol	90%

sodium hydroxide (1310-73-2) + aminosulfonic acid (5329-14-6) + hydrogen bromide (10035-10-6, 12258-64-9) → N-bromosulfamic acid sodium salt (134509-56-1)

Conditions	Yield
Stage #1: hydrogen bromide With dihydrogen peroxide In water at 61.1011℃; Stage #2: aminosulfonic acid In water at 34.99℃; Stage #3: sodium hydroxide With sode de l'acide trichloroisocyanurique Product distribution / selectivity; more than 3 stages;	88.4%
Stage #1: hydrogen bromide With dihydrogen peroxide In water at 61.1011℃; Stage #2: aminosulfonic acid In water at 29.4344 - 34.99℃; Stage #3: sodium hydroxide With trichloroisocyanuric acid Product distribution / selectivity; more than 3 stages;	80.1%
Stage #1: hydrogen bromide With dihydrogen peroxide In water at 61.1011℃; Stage #2: aminosulfonic acid In water at 34.99℃; Stage #3: sodium hydroxide With calcium hypochlorite Product distribution / selectivity; more than 3 stages;	70.8%

aminosulfonic acid (5329-14-6) + 2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → 2-sulfo-4-methoxybenzoic acid (40567-33-7)

Conditions	Yield
With sulfuric acid; sodium nitrite; palladium(II) chloride In water; acetonitrile	88%

aminosulfonic acid (5329-14-6) + potassium hydroxide → potassium sulfamate (13823-50-2)

Conditions	Yield
In water	86%

aminosulfonic acid (5329-14-6) → potassium sulfamate (13823-50-2)

Conditions	Yield
With potassium hydroxide In water at 20℃; for 0.416667h;	86%

sodium hydroxide (1310-73-2) + aminosulfonic acid (5329-14-6) + sodium bromide (7647-15-6) → N-bromosulfamic acid sodium salt (134509-56-1)

Conditions	Yield
Stage #1: sodium hydroxide; aminosulfonic acid; sodium bromide In water at 26.6567 - 32.2122℃; pH=2; Stage #2: With trichloroisocyanuric acid In water for 0.25 - 0.5h; Product distribution / selectivity;	85%
Stage #1: aminosulfonic acid; sodium bromide In water at 26.6567 - 32.2122℃; pH=2; Stage #2: With calcium hypochlorite In water for 0.25 - 0.5h; Stage #3: sodium hydroxide In water at 26.6567 - 32.2122℃; Product distribution / selectivity;

1-(2,6-dinitro-4-trifluoromethylphenyl)-2-chloro-3-cyano-4-dichlorofluoro-methylsulfenyl-5-methylpyrrole (178050-26-5) + aminosulfonic acid (5329-14-6) → 2-chloro-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(dichlorofluoromethylsulfenyl)-5-methylpyrrole (183288-91-7)

Conditions	Yield
With lithium chloride In 1-methyl-pyrrolidin-2-one	85%

aqueous sodium nitrite + 2-amino-6-(1-hydroxyethyl)-benzoic acid (sodium salt) (374562-42-2) + aminosulfonic acid (5329-14-6) + hydrogen sulfide (7783-06-4) → 7-mercapto-3-methyl-3H-isobenzofuran-1-one (135217-37-7)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium hydrogen sulphite; acetic acid; triphenylphosphine In water; toluene	85%

sodium chlorite (7758-19-2) + aminosulfonic acid (5329-14-6) → 2-(4-(4-methoxybenzoyl)piperidinylcarbonyl)-4-methylpyridine-5-carboxylic acid

Conditions	Yield
In water	85%

2,3,4,5-tetrachloroaniline (634-83-3) + aminosulfonic acid (5329-14-6) + acrylic acid (79-10-7) → 2,3,4,5-tetrachlorocinnamic acid

Conditions	Yield
With sulfuric acid; sodium nitrite; palladium diacetate In water	84%

Upstream product

• 64-17-5 ethanol 
• 127-06-0 acetone oxime 
• 7732-18-5 water 
• 70475-81-9 (N-acetyl-acetimidoyl)-amidosulfuric acid 
• 63147-26-2 trimethyl-sulfo-ammonium betaine 
• 13598-45-3 (hydroxylamino)sulfonic acid 
• 7664-93-9 sulfuric acid 
• 21966-07-4 ((NS(O)Cl)(NSCl)2) 
• 69226-51-3 2,2,2-trichloroethyl sulfamate 
• 7647-01-0 hydrogenchloride 
• 7446-09-5 sulfur dioxide 
• 7803-49-8 hydroxylamine 

Downstream Products

• 513-13-3 sulfuric acid monoethyl ester; ammonium compound 
• 575469-65-7 3-(4-bromo-2-fluorophenyl)-2-propenoic acid 
• 94977-52-3 2,4-Difluorocinnamic acid 
• 5079-90-3 (E)-2-styrylbenzoic acid 
• 38453-72-4 (E)-methyl 2-styrylbenzoate 
• 1882-69-5 5-methoxy-2-nitro-benzoic acid 
• 367-83-9 2-fluoro-5-methoxybenzoic acid 
• 167371-42-8 5-Ethyl-7-[N-methyl-N-((2'-(tetrazol-5-yl)biphenyl-4-yl)methyl)amino]pyrazolo[1,5-a]pyrimidine 
• 179343-20-5 N₂-[3-(4-methyl-piperazin-1-yl)-propyl]-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine 
• 179343-38-5 N₂-[3-(4-methyl-piperazin-1-yl)-propyl]-6-(2,3,5,6-tetramethyl-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine 
• 41521-55-5 1-amino-3-methyl-4-nitro-benzene-6-sulphonic acid 
• 34645-72-2 (RS)-2-(4'-iodophenyl)propanoic acid 
• 124-38-9 carbon dioxide 
• 7803-58-9 SULFAMIDE 

Relevant articles and documents

Mechanisms of hydrolysis of phenyl- and benzyl 4-nitrophenyl-sulfamate esters

The kinetics of hydrolysis at medium acid strength (pH interval 2-5) of a series of phenylsulfamate esters 1 have been studied and they have been found to react by an associative SN2(S) mechanism with water acting as a nucleophile attacking at sulfur, cleaving the S-O bond with simultaneous formation of a new S-O bond to the oxygen of a water molecule leading to sulfamic acid and phenol as products. In neutral to moderate alkaline solution (pH ≥ ～ 6-9) a dissociative (E1cB) route is followed that involves i) ionization of the amino group followed by ii) unimolecular expulsion of the leaving group from the ionized ester to give N-sulfonylamine [HNSO2] as an intermediate. In more alkaline solution further ionization of the conjugate base of the ester occurs to give a dianionic species which expels the aryloxide leaving group to yield the novel N-sulfonylamine anion [ -NSO2]; in a final step, rapid attack of hydroxide ion or a water molecule on it leads again to sulfamic acid. A series of substituted benzyl 4-nitrophenylsulfamate esters 4 were hydrolysed in the pH range 6.4-14, giving rise to a Hammett relationship whose reaction constant is shown to be consistent with the E1cB mechanism.

Kappa agonist compounds and pharmaceutical formulations thereof

Compounds having kappa opioid agonist activity, compositions containing them and method of using them as analgesics are provided. The compounds of formula IIIB have the structure: wherein R1, R2, R, Ar and n are as described in the specification.