Product Name

  • Name

    ISOPROPYL METHANESULFONATE

  • EINECS 213-132-0
  • CAS No. 926-06-7
  • Article Data20
  • CAS DataBase
  • Density 1.145
  • Solubility
  • Melting Point 7°C(lit.)
  • Formula C4H10 O3 S
  • Boiling Point 82 °C (6 mmHg)
  • Molecular Weight 138.188
  • Flash Point 104 °C
  • Transport Information
  • Appearance clear, colorless liquid.
  • Safety Poison by ingestion. An experimental teratogen. Experimental reproductive effects. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Human mutation data reported. When heated to decomposition it emits toxic fumes of SOx. See also SULFONATES.
  • Risk Codes 68-40-34-22
  • Molecular Structure Molecular Structure of 926-06-7 (ISOPROPYL METHANESULFONATE)
  • Hazard Symbols CorrosiveC
  • Synonyms Methanesulfonicacid, isopropyl ester (6CI,7CI,8CI); 2-Propyl methanesulfonate; Isopropylmesylate; Isopropyl methanesulfonate; Isopropyl methanesulphonate
  • PSA 51.75000
  • LogP 1.45180

Synthetic route

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

Conditions
ConditionsYield
With sodium hydroxide; potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate In benzene at 15 - 20℃; for 1h;94%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;94%
With pyridine 1.) from -20 deg C to 30 deg C, 2.) room temp., 2 h;63%
methanesulfonic acid
75-75-2

methanesulfonic acid

propene
187737-37-7

propene

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

Conditions
ConditionsYield
under 2206.5 Torr;
sodium isopropylate
683-60-3

sodium isopropylate

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

Conditions
ConditionsYield
With isopropyl alcohol
diazomethane
186581-53-3, 908094-01-9

diazomethane

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

Conditions
ConditionsYield
With sulfur dioxide In Petroleum ether at -15℃;12 g
O,O-diethyl S-methyl phosphorothioate
2404-05-9

O,O-diethyl S-methyl phosphorothioate

isopropyl alcohol
67-63-0

isopropyl alcohol

A

methanesulfonic acid
75-75-2

methanesulfonic acid

B

Diethyl phosphate
598-02-7

Diethyl phosphate

C

diethyl 2-propyl phosphate
2736-99-4

diethyl 2-propyl phosphate

D

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acidA n/a
B 41 % Spectr.
C 59 % Spectr.
D n/a
...Expand
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

1-(1H-imdiazol-1-yl)-2-methyl-2-propanol
924638-97-1

1-(1H-imdiazol-1-yl)-2-methyl-2-propanol

1-(2-hydroxy-2-methyl-n-propyl)-3-isopropylimidazolium mesylate
1006900-61-3

1-(2-hydroxy-2-methyl-n-propyl)-3-isopropylimidazolium mesylate

Conditions
ConditionsYield
In acetonitrile at 90℃; for 24h;100%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

methyl 2,3-O-isopropylidene-α-D-mannopyranoside-4,6-cyclic sulfate
139978-82-8

methyl 2,3-O-isopropylidene-α-D-mannopyranoside-4,6-cyclic sulfate

C8H16O8S
1097263-89-2

C8H16O8S

Conditions
ConditionsYield
Stage #1: isopropyl methanesulfonate; methyl-2,3-O-isopropylidene-4,6-cyclic sulfate-α-D-mannopyranoside With 1,1-Diphenylethylene; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran
Stage #2: In tetrahydrofuran; methanol regioselective reaction;		100%
5-(4-tert-butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1H-indole-2-carboxylic acid ethyl ester
952800-18-9

5-(4-tert-butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1H-indole-2-carboxylic acid ethyl ester

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

5-(4-tert-butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester
952800-17-8

5-(4-tert-butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 95℃;93%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

5-benzyloxy-1H-indole-2-carboxylic acid ethyl ester
37033-95-7

5-benzyloxy-1H-indole-2-carboxylic acid ethyl ester

5-Benzyloxy-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester
938081-51-7

5-Benzyloxy-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With caesium carbonate In acetonitrile for 18h; Heating / reflux;90%
With caesium carbonate In acetonitrile for 18h; Reflux;89%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

isopropyl diethylphosphonylmethanesulphonate
114086-63-4

isopropyl diethylphosphonylmethanesulphonate

Conditions
ConditionsYield
Stage #1: isopropyl methanesulfonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.33h;
Stage #2: diethyl chlorophosphate In tetrahydrofuran; hexane at -50℃; for 1.5h;		87%
With n-butyllithium 1) THF, hexane, -78 deg C, 15 min, 2) THF, hexane, -78 to -50 deg C; Yield given. Multistep reaction;
With n-butyllithium In tetrahydrofuran5.20 g (67%)
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

2-hydroxy-2-(4-nitrophenyl)ethanesulfonic acid isopropyl ester
639008-17-6

2-hydroxy-2-(4-nitrophenyl)ethanesulfonic acid isopropyl ester

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -78℃; for 4.5h;86%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

(4aS*,8aS*)-1,2,3,4,4a,5,6,7,8,8a-perhydroisoquinoline
2744-08-3, 2744-09-4, 6329-61-9

(4aS*,8aS*)-1,2,3,4,4a,5,6,7,8,8a-perhydroisoquinoline

N-isopropyl-cis-decahydroisoquinoline
90653-73-9, 90653-80-8

N-isopropyl-cis-decahydroisoquinoline

Conditions
ConditionsYield
With triethylamine In benzene for 48h; Heating;81%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

N-(tert-butoxycarbonyl)-D-tyrosine methyl ester
76757-90-9

N-(tert-butoxycarbonyl)-D-tyrosine methyl ester

Boc-D-Tyr(i-Pr)
80131-85-7

Boc-D-Tyr(i-Pr)

Conditions
ConditionsYield
With crown ether In N,N-dimethyl-formamide; benzene for 7h;72.3%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

Acetanilid
103-84-4

Acetanilid

N-isopropyl-N-phenyl-acetamide
5461-51-8

N-isopropyl-N-phenyl-acetamide

Conditions
ConditionsYield
With tetraethylammonium tosylate In N,N-dimethyl-formamide electroreduction;71%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

(1R,3R,5S)-3-{2-[4-(4-trifluoromethyl-benzenesulfonyl)-piperazine-1-carbonyl]-1H-indol-5-yloxy}-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
1044761-07-0

(1R,3R,5S)-3-{2-[4-(4-trifluoromethyl-benzenesulfonyl)-piperazine-1-carbonyl]-1H-indol-5-yloxy}-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

(1R,3r,5S)-3-{1-Isopropyl-2-[4-(4-trifluoromethyl-benzenesulfonyl)-piperazine-1-carbonyl]-1H-indol-5-yloxy}-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
1044761-06-9

(1R,3r,5S)-3-{1-Isopropyl-2-[4-(4-trifluoromethyl-benzenesulfonyl)-piperazine-1-carbonyl]-1H-indol-5-yloxy}-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 95℃; for 24h;66%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

N-(4-methylphenylsulfonyl)-4-[(trifluoromethanesulfonyl)oxy]-1,2,3,6-tetrahydropyridine
606926-42-5

N-(4-methylphenylsulfonyl)-4-[(trifluoromethanesulfonyl)oxy]-1,2,3,6-tetrahydropyridine

C15H21NO2S

C15H21NO2S

Conditions
ConditionsYield
With 2,2':6,2''-terpyridine; manganese; sodium iodide In N,N-dimethyl acetamide at 100℃; for 12h;66%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

sodium ethyl N-hydroxyacetimidate
120940-23-0

sodium ethyl N-hydroxyacetimidate

N-isopropoxy-acetimidic acid ethyl ester
18498-62-9

N-isopropoxy-acetimidic acid ethyl ester

Conditions
ConditionsYield
at 20℃;65%
6-methyl-5-nitropyridin-2-ol
28489-45-4

6-methyl-5-nitropyridin-2-ol

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

6-methyl-5-nitro-2-(prop-2-yloxy)pyridine

6-methyl-5-nitro-2-(prop-2-yloxy)pyridine

Conditions
ConditionsYield
Stage #1: 6-methyl-5-nitropyridin-2-ol With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: isopropyl methanesulfonate In N,N-dimethyl-formamide at 80℃; for 2h;		63%
4-bromo-1H-piperidine
90633-18-4

4-bromo-1H-piperidine

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

4-bromo-1-isopropylpiperidine
90633-21-9

4-bromo-1-isopropylpiperidine

Conditions
ConditionsYield
With triethylamine In benzene for 48h; Heating;58%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

[6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone
1044760-49-7

[6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone

[6-bromo-1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone
1044760-52-2

[6-bromo-1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone

Conditions
ConditionsYield
With caesium carbonate In acetonitrile for 18h; Heating / reflux;56%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

N-hydroxypyridine-2(1H)-thione tetraethylammonium salt
22574-14-7

N-hydroxypyridine-2(1H)-thione tetraethylammonium salt

N-(isopropyloxy)pyridine-2(1H)-thione
122333-46-4

N-(isopropyloxy)pyridine-2(1H)-thione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40℃; for 1h;54%
2-(trimethylsilyl)ethyl 3,3-difluoro-2-[(4-methoxyphenyl)imino]-5-hexenoate
1039136-57-6

2-(trimethylsilyl)ethyl 3,3-difluoro-2-[(4-methoxyphenyl)imino]-5-hexenoate

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

isopropyl (E)-3,3-difluoro-2-[(4-methoxyphenyl)imino]-5-hexenoate
1039136-71-4

isopropyl (E)-3,3-difluoro-2-[(4-methoxyphenyl)imino]-5-hexenoate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 24h;48%
(1,1-dioxo-1λ6-thiomorpholin-4-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-methanone
938081-30-2

(1,1-dioxo-1λ6-thiomorpholin-4-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-methanone

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

(1,1-dioxo-1λ6-thiomorpholin-4-yl)-[1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-methanone

(1,1-dioxo-1λ6-thiomorpholin-4-yl)-[1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-methanone

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 95℃; for 22h;47%
With caesium carbonate In acetonitrile at 95℃; for 22h;47%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

Azobenzene
1227476-15-4

Azobenzene

N,N'-diisopropyl-N,N'-diphenylhydrazine
63378-85-8

N,N'-diisopropyl-N,N'-diphenylhydrazine

Conditions
ConditionsYield
Stage #1: Azobenzene With sodium In tetrahydrofuran for 24h;
Stage #2: isopropyl methanesulfonate In tetrahydrofuran for 24h;		41%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

(4-benzenesulfonyl-piperazin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone
1043528-45-5

(4-benzenesulfonyl-piperazin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

(4-benzenesulfonyl-piperazin-1-yl)-[1-isopropyl-5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone
1043528-62-6

(4-benzenesulfonyl-piperazin-1-yl)-[1-isopropyl-5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

Conditions
ConditionsYield
With caesium carbonate In acetonitrile for 16h; Heating / reflux;39%
1H-indol-2-ylcarboxaldehyde
19005-93-7

1H-indol-2-ylcarboxaldehyde

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

1-(1-methylethyl)-1H-indole-2-carbaldehyde

1-(1-methylethyl)-1H-indole-2-carbaldehyde

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 20 - 95℃; for 17h;34%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

11-azide-1-{(methylsulfonyl)oxy}-3,6,9-trioxaundecane
134179-43-4

11-azide-1-{(methylsulfonyl)oxy}-3,6,9-trioxaundecane

4,4'-dihydroxy-2,2'-dipyridine
90770-88-0

4,4'-dihydroxy-2,2'-dipyridine

A

4-(tetra(ethyleneglycol)azido)-4'-isopropoxy-2,2'-bipyridine

4-(tetra(ethyleneglycol)azido)-4'-isopropoxy-2,2'-bipyridine

B

C26H38N8O8

C26H38N8O8

C

C16H20N2O2

C16H20N2O2

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate for 66h; Inert atmosphere; Reflux;A 32%
B n/a
C n/a
...Expand
ethyl 5-(3-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylate
952800-09-8

ethyl 5-(3-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylate

isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

5-(3-dimethylamino-piperidine-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester
952800-11-2

5-(3-dimethylamino-piperidine-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With caesium carbonate In acetonitrile Heating / reflux;31%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

N-[(5Z)-2-tert-butyl-4-(hydroxymethyl)isothiazol-5(2H)-ylidene]-5-chloro-2-methoxybenzamide
1075241-98-3

N-[(5Z)-2-tert-butyl-4-(hydroxymethyl)isothiazol-5(2H)-ylidene]-5-chloro-2-methoxybenzamide

N-[(5Z)-2-tert-butyl-4-(isopropoxymethyl)isothiazol-5(2H)-ylidene]-5-chloro-2-methoxybenzamide
1075242-69-1

N-[(5Z)-2-tert-butyl-4-(isopropoxymethyl)isothiazol-5(2H)-ylidene]-5-chloro-2-methoxybenzamide

Conditions
ConditionsYield
Stage #1: N-[(5Z)-2-tert-butyl-4-(hydroxymethyl)isothiazol-5(2H)-ylidene]-5-chloro-2-methoxybenzamide With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 0.166667h;
Stage #2: isopropyl methanesulfonate In 1,4-dioxane; mineral oil at 85℃; for 12h;		9%
Stage #1: N-[(5Z)-2-tert-butyl-4-(hydroxymethyl)isothiazol-5(2H)-ylidene]-5-chloro-2-methoxybenzamide With sodium hydride In 1,4-dioxane at 20℃; for 0.166667h;
Stage #2: isopropyl methanesulfonate In 1,4-dioxane at 85℃; for 12h;		9%
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

β-naphthol
135-19-3

β-naphthol

2-isopropoxynaphthalene
15052-09-2

2-isopropoxynaphthalene

Conditions
ConditionsYield
With sodium carbonate; acetone
isopropyl methanesulfonate
926-06-7

isopropyl methanesulfonate

benzene
71-43-2

benzene

1,3,5-triisopropyl benzene
717-74-8

1,3,5-triisopropyl benzene

Conditions
ConditionsYield
With methanesulfonic acid at 80 - 100℃;

Isopropyl methanesulfonate Chemical Properties

IUPAC Name: Propan-2-yl methanesulfonate
CAS: 926-06-7
EINECS: 213-132-0
Following is the Molecular Structure of Isopropyl methanesulfonate (926-06-7):

SMILES: O=S(=O)(OC(C)C)C
InChI: InChI=1/C4H10O3S/c1-4(2)7-8(3,5)6/h4H,1-3H3
InChIKey: SWWHCQCMVCPLEQ-UHFFFAOYAF
Std.InChI: InChI=1S/C4H10O3S/c1-4(2)7-8(3,5)6/h4H,1-3H3
Std.InChIKey: SWWHCQCMVCPLEQ-UHFFFAOYSA-N
Molecular Formula: C4H10O3S
Molecular Weight: 138.19
Boiling Point: 220℃ at 760mmHg
Flash Point: 86.9℃
Molar Volume: 122.3cm3
Density: 1.129g/cm3
Index of Refraction: 1.422
Molar Refractivity: 31.09cm3
Surface Tension: 32.2dyne/cm
Polarizability: 12.32 10-24cm3
Enthalpy of Vaporization: 43.78kJ/mol
Vapour Pressure: 0.171mmHg at 25℃

Isopropyl methanesulfonate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 287mg/kg (287mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

Isopropyl methanesulfonate Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Isopropyl methanesulfonate Safety Profile

Hazard Codes: C Corrosive.
Risk Statements: 68-40-34-22
R68: Possible risk of irreversible effects.
R40: Limited evidence of a carcinogenic effect.
R34: Causes burns.
R22: Harmful if swallowed.
Safety Statements: 45-36/37/39-26
S45: In case of accident or if you feel unwell,seek medical advice immediately (show label where possible).
S36/37/39: Wear suitable protective clothing,gloves and eye/face protection.
S26: In case of contact with eyes,rinse immediately with plenty of water and seek medical advice.
Poison by ingestion. An experimental teratogen. Experimental reproductive effects. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Human mutation data reported.

Isopropyl methanesulfonate Specification

 Isopropyl methanesulfonate (926-06-7),which also can be called for 2-Propyl methanesulphonate ; 2-Propylmethanesulphonate ; IMS ; Isopropyl mesylate ; Isopropyl methane sulphonate ; Isopropyl methanesulfate ; Isopropylmesylate ; Isopropylmethanesulphonate .When Isopropyl methanesulfonate (926-06-7) was heated, it emits toxic fumes of SOx .This chemical is a clear colourless liquid and it should be stored at 0℃-6℃.

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