100-88-9

Basic information

• Product Name: Cyclamic acid
• Synonyms: sucarylacid;Sulfamic acid, cyclohexyl-;Zyklamat;N-CYCLOHEXYLSULFAMIC ACID;CYCLAMIC ACID;CYCLOHEXYL SULFAMIC ACID;CYCLOHEXANESULFAMIC ACID;cyclamic acid free acid crystalline
• CAS NO: 100-88-9
• Molecular Formula: C₆H₁₃NO₃S
• Molecular Weight: 179.24
• EINECS: 202-898-1
• Product Categories: Amines;Sulfur & Selenium Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonic/Sulfinic Acids;Sulfur Compounds;HEXAMIC ACID
• Mol File: 100-88-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: ~180 °C (dec.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /solid
• Density: 1.149 (estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Refrigerator
• Solubility: dioxane: soluble1g/10 mL, clear, colorless (hot)
• PKA: pKa 2.28(H2O t=RT c=0.056) (Uncertain)
• Water Solubility: 133g/L
• Merck: 14,2703
• BRN: 2208885
• CAS DataBase Reference: Cyclamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclamic acid(100-88-9)
• EPA Substance Registry System: Cyclamic acid(100-88-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 2
• RTECS: GV6950000
• Hazardous Substances Data: 100-88-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

A non-nutritive sweetener.

Definition

ChEBI: A member of the class of sulfamic acids that is sulfamic acid carrying an N-cyclohexyl substituent.

Brand name

Hexamic Acid (Abbott).

General Description

The N-cyclohexylsulfamic acid salts of well?known therapeutic agents were prepared.

Flammability and Explosibility

Notclassified

Safety Profile

Suspected human carcinogen producing bladder tumors. Poison by intravenous route. LWdly toxic by ingestion. When heated to decomposition it emits toxic fumes of SOx and NOx.

InChI:InChI=1/C6H13NO3S/c8-11(9,10)7-6-4-2-1-3-5-6/h6-7H,1-5H2,(H,8,9,10)

Synthetic route

cyclohexylamine (108-91-8) → cyclohexylsulfamic acid (100-88-9)

Conditions	Yield
With chlorosulfonic acid In chloroform for 8h; Ambient temperature;	72%
With chlorosulphuric acid; chloroform
With chlorosulfonic acid
With chlorosulfonic acid In acetonitrile at 20℃; for 2h;

Cyclohexyl isocyanate (3173-53-3) → cyclohexylsulfamic acid (100-88-9)

Conditions	Yield
With sulfuric acid; sulfur trioxide

N-cyclohexyl-hydroxylamine (2211-64-5) → cyclohexylsulfamic acid (100-88-9)

Conditions	Yield
With sulfur dioxide; benzene

1-nitrocyclohexane (1122-60-7) → cyclohexylsulfamic acid (100-88-9)

Conditions	Yield
With sodium dithionite; water; sodium phosphate

cyclohexylamine (108-91-8) + sodium chloro sulfate → cyclohexylsulfamic acid (100-88-9)

cyclohexylsulfamic acid (100-88-9) + (R)-6-methylamino-2-methylheptene (1620401-56-0) → (R)-isometheptene cyclamate

Conditions	Yield
In ethanol at -20℃; Solvent; Temperature;	100%

cyclohexylsulfamic acid (100-88-9) + C43H51N7O9S2 → (x)C6H13NO3S*C43H51N7O9S2

Conditions	Yield
In methanol at 20℃;	95.6%

cyclohexylsulfamic acid (100-88-9) + ziprazidone (122883-93-6, 199191-69-0) → 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one N-cyclohexylsulfamate

Conditions	Yield
In ethanol; water at -15 - 80℃;	95.2%

N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide (706779-91-1) + cyclohexylsulfamic acid (100-88-9) → C25H34FN3O2*H2O*C6H13NO3S

Conditions	Yield
In ethyl acetate at 20 - 42℃; for 5h;	93.7%

cyclohexylsulfamic acid (100-88-9) + dasatanib (302962-49-8) → N-(2-chloro-6-methylphenyl)-2-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-ylamino]-1,3-thiazole-5-carboxamide monocyclamate salt

Conditions	Yield
In methanol at 70℃;	93.4%

cyclohexylsulfamic acid (100-88-9) → cyclohexylsulfamoyl chloride (10314-35-9)

Conditions	Yield
With phosphorus pentachloride In benzene	91%
With phosphorus pentachloride In benzene for 4h; Heating / reflux;	91%
With phosphorus pentachloride	75%

cyclohexylsulfamic acid (100-88-9) + 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (88150-42-9) → amlodipine cyclamate (745013-02-9)

Conditions	Yield
In ethanol; ethyl acetate at 20℃; for 4h;	87%
In ethanol; isopropyl alcohol at 0℃; for 4h;	86%
In methanol; acetonitrile at 20℃; for 4h;	85%
In isopropyl alcohol at 0℃; for 4h;	82%

5-[2-propyloxy-5-(2-(1-methylpyrrolidin-2-yl)ethylaminosulphonyl)phenyl]-1-methyl-3-propyl-6,7-dihydro-1H-pyrazolo(4,3-d)pyrimidin-7-one (268203-93-6) + cyclohexylsulfamic acid (100-88-9) → udenafil cyclamate (1240622-32-5)

Conditions	Yield
In ethyl acetate at 20℃;	83.7%

cyclohexylsulfamic acid (100-88-9) + 5-(4-(tert-butyl)phenyl)-5H-dibenzo[b,d]thiophen-5-ium bromide → 5-(4-(t-butyl)phenyl)-5Η-dibenzo[b,d]thiophen-5-ium cyclohexylamine sulfonate

Conditions	Yield
Stage #1: 5-(4-(tert-butyl)phenyl)-5H-dibenzo[b,d]thiophen-5-ium bromide With silver(l) oxide In methanol Stage #2: cyclohexylsulfamic acid In methanol at 20℃;	80%

cyclohexylsulfamic acid (100-88-9) + triphenylbismuthane (603-33-8) → C18H22BiNO3S + benzene (71-43-2)

Conditions	Yield
In neat (no solvent) at 80℃; for 0.333333h;	A 77% B n/a

cyclohexylsulfamic acid (100-88-9) + 10-ethoxy-6-(methoxymethyl)-8-(morpholinomethyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5(6H)-one → 10-ethoxy-8-(morpholinomethyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5(6H)-one cyclohexylsulphamic acid

Conditions	Yield
In ethanol at 90℃; for 3h;	75%

cyclohexylsulfamic acid (100-88-9) + triphenylbismuthane (603-33-8) → [Bi(CycH)3] + benzene (71-43-2)

Conditions	Yield
In neat (no solvent) at 80℃; for 2.5h;	A 68.6% B n/a

bismuth(III) tert-butoxide + cyclohexylsulfamic acid (100-88-9) → 3C6H11NO3S(2-)*2Bi(3+) + tert-butyl alcohol (75-65-0)

Conditions	Yield
In tetrahydrofuran at -80℃; Inert atmosphere;	A 67.4% B n/a

cyclohexylsulfamic acid (100-88-9) + bismuth(III) oxide (1304-76-3) → 24C6H12NO3S(1-)*14H2O*45O(2-)*38Bi(3+)

Conditions	Yield
In water for 120h; Sonication;	63%

cyclohexylsulfamic acid (100-88-9) + prasugel (150322-43-3) → 5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate cyclamate (1306607-31-7)

Conditions	Yield
In acetone at -10℃; for 12h;	45%
In acetone	45%

cyclohexylsulfamic acid (100-88-9) → potassium N-nitroso-N-cyclohexylsulfamate (138337-16-3)

Conditions	Yield
With potassium nitrite In water at 4℃; for 0.333333h;	44%

cyclohexylsulfamic acid (100-88-9) + triphenylbismuthane (603-33-8) → [Bi(CycH)3] + C18H22BiNO3S + [PhBi(CycH)2] (1422436-55-2)

Conditions	Yield
In neat (no solvent) at 80℃; for 0.333333h;	A 26% B 30% C 44%

Baricitinib (1187594-09-7) + cyclohexylsulfamic acid (100-88-9) → {1-(ethylsulphonyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dicyclamate

Conditions	Yield
In acetone for 0.5h; Reflux;	41.8%

5,6-dihydrospiro[imidazo[2,1-b][3]benzazepine-11[11H],4'-piperidine] (193469-45-3) + formaldehyd (50-00-0) + cyclohexylsulfamic acid (100-88-9) → 6,11-dihydro-1'-methyl-spiro[5H-imidazo[2,1-b][3]benzazepine-11,4'-piperidine] cyclohexylsulfamate (1:2)

Conditions	Yield
Stage #1: 5,6-dihydrospiro[imidazo[2,1-b][3]benzazepine-11[11H],4'-piperidine]; formaldehyd With thiophene; hydrogen; palladium 10% on activated carbon In methanol at 50℃; Stage #2: cyclohexylsulfamic acid In acetone	40%

styrene (292638-84-7) + N-[2-(3,4-dimethoxyphenyl)ethyl]-2-iodo-5-methoxy-N-methylbenzenepropanamine 4-Methylbenzene Sulfonate + cyclohexylsulfamic acid (100-88-9) + palladium diacetate (3375-31-3) + N-[2-(3,4-dimethoxyphenyl)ethyl]-2-iodo-5-methoxy-N-methylbenzenepropanamine (99254-62-3) → N-[2-(3,4-Dimethoxyphenyl)ethyl]-5-methoxy-N-methyl-2E-(2-phenylethenyl)benzenepropanamine Biscyclohexylsulfamate

Conditions	Yield
In nitrogen; triethylamine	38%

5,6-dihydrospiro[imidazo[2,1-b][3]benzazepine-11[11H],4'-piperidine] (193469-45-3) + cyclohexylsulfamic acid (100-88-9) + 1-(3-chloropropoxy)-4-fluorobenzene (1716-42-3) → 1'-[3-(4-fluorophenoxy)propyl]-5,6-dihydrospiro[imidazo[2,1-b][3]benzazepine-11-[11H],4'-piperidine] cyclohexylsulfamate (1:2)

Conditions	Yield
Stage #1: 5,6-dihydrospiro[imidazo[2,1-b][3]benzazepine-11[11H],4'-piperidine]; 1-(3-chloropropoxy)-4-fluorobenzene With sodium carbonate; potassium iodide In 4-methyl-2-pentanone for 18h; Heating / reflux; Stage #2: cyclohexylsulfamic acid In acetone	37%

5,6-dihydrospiro[imidazo[2,1-b][3]benzazepine-11[11H],4'-piperidine] (193469-45-3) + tetrahydro-2-furanmethanol methanesulfonate (ester) (72641-13-5) + cyclohexylsulfamic acid (100-88-9) → 5,6-dihydro-1'-[(tetrahydro-2-furanyl)methyl]spiro[imidazo[2,1-b][3]benzazepine-11-[11H],4'-piperidine] cyclohexylsulfamate (1:2)

Conditions	Yield
Stage #1: 5,6-dihydrospiro[imidazo[2,1-b][3]benzazepine-11[11H],4'-piperidine]; tetrahydro-2-furanmethanol methanesulfonate (ester) With sodium carbonate In 4-methyl-2-pentanone Heating / reflux; Stage #2: cyclohexylsulfamic acid In acetone	20.7%

5,6-dihydrospiro[imidazo[2,1-b][3]benzazepine-11[11H],4'-piperidine] (193469-45-3) + thiophene-2-carbaldehyde (98-03-3) + cyclohexylsulfamic acid (100-88-9) → 5,6-dihydro-1'-(2-thienyl-methyl)spiro[imidazo[2,1-b][3]benzazepine-11-[11H],4'-piperidine] cyclohexylsulfamate (1:1)

Conditions	Yield
Stage #1: 5,6-dihydrospiro[imidazo[2,1-b][3]benzazepine-11[11H],4'-piperidine]; thiophene-2-carbaldehyde With hydrogen; nickel In methanol Stage #2: cyclohexylsulfamic acid In acetone	6.6%

3-aminobutanoic acid ethyl ester (5303-65-1) + cyclohexylsulfamic acid (100-88-9) + [(Z)-2-(4-Oxiranylmethoxy-phenyl)-vinyl]-carbamic acid methyl ester → 3-{2-Hydroxy-3-[4-((E)-2-methoxycarbonylamino-vinyl)-phenoxy]-propylamino}-butyric acid ethyl ester; compound with cyclohexyl-sulfamic acid

Conditions	Yield
(i) MeCN, (ii) /BRN= 2208885/, iPrOH; Multistep reaction;

cyclohexylsulfamic acid (100-88-9) + isopropylamine (75-31-0) + (Z)-2-Acetylamino-3-(4-oxiranylmethoxy-phenyl)-acrylic acid methyl ester → (Z)-2-Acetylamino-3-[4-(2-hydroxy-3-isopropylamino-propoxy)-phenyl]-acrylic acid methyl ester; compound with cyclohexyl-sulfamic acid

Conditions	Yield
(i) THF, (ii) /BRN= 2208885/, acetone; Multistep reaction;

cyclohexylsulfamic acid (100-88-9) + tert-butylamine (75-64-9) + [(E)-2-(4-Oxiranylmethoxy-phenyl)-vinyl]-carbamic acid ethyl ester → {(E)-2-[4-(3-tert-Butylamino-2-hydroxy-propoxy)-phenyl]-vinyl}-carbamic acid ethyl ester; compound with cyclohexyl-sulfamic acid

Conditions	Yield
(i) iPrOH, (ii) /BRN= 2208885/, acetone; Multistep reaction;

Upstream product

• 108-91-8 cyclohexylamine 
• 1122-60-7 1-nitrocyclohexane 
• 3173-53-3 Cyclohexyl isocyanate 
• 2211-64-5 N-cyclohexyl-hydroxylamine 

Downstream Products

• 10314-35-9 cyclohexylsulfamoyl chloride 
• 50529-50-5 hexahydro-2-imino-1-methyl-1H-azepine cyclohexanesulfamate 
• 26365-83-3 2-phenyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-indole 
• 60218-32-8 1-[2-(dimethylamino)ethyl]-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine bis (cyclohexanesulfamate) 
• 108-94-1 cyclohexanone 
• 75-65-0 tert-butyl alcohol 
• 71-43-2 benzene 
• 1422436-55-2 [PhBi(CycH)₂] 
• 1306607-31-7 5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate cyclamate 

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