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87413-09-0

Basic Information
CAS No.: 87413-09-0
Name: Dess-Martin periodinane
Molecular Structure:
Molecular Structure of 87413-09-0 (Dess-Martin periodinane)
Formula: C13H13IO8
Molecular Weight: 424.14
Synonyms: 1,2-Benziodoxol-3(1H)-one, 1,1,1-tris(acetyloxy)-1,1-dihydro-;Martin's reagent;1,1,1-tris-(Acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one;Dess - Martin Periodinane(Triacetoxyperiodinane);(1,1,1-Triacetoxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one;
EINECS: 200-009-0
Density: 1.369 g/mL at 25 °C
Melting Point: 130-133 °C
Boiling Point: 40 °C
Flash Point: >221 °F
Solubility:
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn, OxidizingO, IrritantXi
Risk Codes: 22-36/37/38-40-8-20/21/22
Safety: 26-36-36/37-24/25-23-17-45-36/37/39
Transport Information: UN 1593 6.1/PG 3
PSA: 105.20000
LogP: 1.95370
Synthetic route
108-24-7

acetic anhydride

61717-82-6

1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione

87413-09-0

Dess-Martin periodane

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 80℃; for 0.333333h; Acetylation;98%
In acetic acid at 100℃; for 0.666667h;93%
With acetic acid at 85℃; for 0.333333h;93%
108-24-7

acetic anhydride

64-19-7

acetic acid

61717-82-6

1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione

87413-09-0

Dess-Martin periodane

Conditions
ConditionsYield
1.) r.t. to 85 deg C, 1 h, 2.) 85 deg C, 1.3 h;78%
at 20 - 85℃; for 24h; Inert atmosphere;
88-67-5

2-Iodobenzoic acid

108-24-7

acetic anhydride

87413-09-0

Dess-Martin periodane

Conditions
ConditionsYield
With potassium bromate; acetic acid 2) 85 deg C, 2.5 h, rt, overnight; Yield given. Multistep reaction;
Stage #1: 2-Iodobenzoic acid With potassium peroxomonosulfate In water at 5 - 70℃; for 4.5h;
Stage #2: acetic anhydride With toluene-4-sulfonic acid at 80℃; for 2h; Reflux;
109-02-4

4-methyl-morpholine

(2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) [HATU]

(2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) [HATU]

(R)-1-((S)-2-amino-3-methylbutanoyl)-N-((S)-1-hydroxy-3-methyl-1-(5-phenyl-1,3,4-oxadiazol-2-yl)butan-2-yl)pyrrolidine-2-carboxamide trifluoroacetic acid salt

(R)-1-((S)-2-amino-3-methylbutanoyl)-N-((S)-1-hydroxy-3-methyl-1-(5-phenyl-1,3,4-oxadiazol-2-yl)butan-2-yl)pyrrolidine-2-carboxamide trifluoroacetic acid salt

methylene chloride Dess-Martin Periodinane

methylene chloride Dess-Martin Periodinane

1160871-87-3

6-[(pyridine-2-carbonyl)-amino]-hexanoic acid hydrochloride salt

87413-09-0

Dess-Martin periodane

Conditions
ConditionsYield
In N-methyl-acetamide; dichloromethane
87413-09-0

Dess-Martin periodane

1-Oxo-2-(R)-phenyl-3-(S)-t-butyldimethylsilyloxymethylcyclohexane

Conditions
ConditionsYield
With pyridine; sodium hydrogencarbonate In dichloromethane100%
87413-09-0

Dess-Martin periodane

trans-1-Benzoyl-2-formyl-3-methylpyrrolidine

Conditions
ConditionsYield
With sodium bicarbonate; sodium thiosulfate In dichloromethane; tert-butyl alcohol100%
374795-03-6

tert-butyl 4-[(benzyloxy)methyl]-4-(hydroxymethyl)piperidine-1-carboxylate

87413-09-0

Dess-Martin periodane

374795-04-7

1,1-dimethylethyl 4-ethenyl-4-(phenylmethoxymethyl)-1-piperidinecarboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl 4-[(benzyloxy)methyl]-4-(hydroxymethyl)piperidine-1-carboxylate; Dess-Martin periodane In dichloromethane at 20℃; for 4h;
Stage #2: With sodium hydrogensulfide In dichloromethane; water at 20℃; for 0.0833333h;
Stage #3: With imino(triphenyl)phosphorane In tetrahydrofuran at 20℃; for 16h;
99%
436161-39-6

3-[1-(3-hydroxypropyl)-1H-indazol-3-yl]-4-[1-(3-pyridinyl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione

87413-09-0

Dess-Martin periodane

247128-24-1

3-(indazol-1-yl)propionic acid

Conditions
ConditionsYield
With sodium thiosulfate In dichloromethane; water98%
NaHCO3-brine

NaHCO3-brine

237384-73-5

methyl 4-[N-(2-hydroxy-1-phenylethyl)carbamoyl]-5-methylthiothiophene-2-carboxylate

87413-09-0

Dess-Martin periodane

methyl 5-methylthio-4-[N-(2-oxo-1-phenylethyl)carbamoyl]thiophene-2-carboxylate

Conditions
ConditionsYield
In dichloromethane; ethyl acetate98%
In dichloromethane; ethyl acetate98%
sodium thiosulfate 5-hydrate

sodium thiosulfate 5-hydrate

87413-09-0

Dess-Martin periodane

229010-22-4

(1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methylnaphtho[2,3-c]furan-4-ol

229010-23-5

(1S,3S,3aR,4aS,8aR,9aS)-decahydro-1-methoxy-3-methylnaphtho[2,3-c]furan-4(1H)-one

Conditions
ConditionsYield
With sodium hydrogencarbonate97%
60-29-7

diethyl ether

75-09-2

dichloromethane

2928-43-0

2-biphenylmethanol

87413-09-0

Dess-Martin periodane

1203-68-5

2-Phenylbenzaldehyde

Conditions
ConditionsYield
With sodium hydroxide In tert-butyl alcohol97%

benzofuran-2-carboxylic acid{(S)-1-[(3S,4S,7R)-3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide

87413-09-0

Dess-Martin periodane

benzofuran-2-carboxylic acid{(S)-3-methyl-1-[(4S,7R)-7-methyl-3-oxo-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide

Conditions
ConditionsYield
In dichloromethane97%
In dichloromethane
56014-51-8

1-[2-(3,4-dimethoxyphenyl)ethyl]-1H-pyrrole

87413-09-0

Dess-Martin periodane

1428317-13-8

C21H20INO5

Conditions
ConditionsYield
In dichloromethane at 0℃; for 2h;96%
87413-09-0

Dess-Martin periodane

147252-84-4, 79069-13-9, 106391-86-0, 127516-56-7

tert-butyl (1-hydroxypropan-2-yl)carbamate

105499-11-4

2-(Boc-amino)propionaldehyde

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃;95%
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

87413-09-0

Dess-Martin periodane

A

1829-26-1

1-acetoxy-1,2-benziodoxol-3-one

B

86-81-7

3,4,5-trimethoxy-benzaldehyde

C

64-19-7

acetic acid

Conditions
ConditionsYield
In dichloromethane at 25℃; for 0.333333h; Product distribution; reaction with other alcohols;A n/a
B 94%
C n/a
362671-49-6

(Z)-8-Hydroxy-3-methyl-8-(2-naphthyl)-2-octenoic acid

87413-09-0

Dess-Martin periodane

362671-50-9

(Z)-3-Methyl-7-(2-naphthoyl)-2-heptenoic acid

Conditions
ConditionsYield
In dichloromethane94%
1613402-01-9

tert-Butyl 4-(3-bromophenylthio)-3-hydroxyazepane-1-carboxylate

87413-09-0

Dess-Martin periodane

1613402-02-0

tert-Butyl 4-(3-bromophenylthio)-3-oxoazepane-1-carboxylate

Conditions
ConditionsYield
With sodium hydrogencarbonate; sodium thiosulfate In dichloromethane; water94%

trans-(3RS,4RS)-3-[N-(3-benzyloxybenzoyl)-L-leucinylamino]-4-hydroxytetrahydrofuran

87413-09-0

Dess-Martin periodane

(3RS)-3-[N-(3-benzyloxybenzoyl)-L-leucinylamino]tetrahydrofuran-4-one

Conditions
ConditionsYield
With sodium thiosulfate In dichloromethane93%
87413-09-0

Dess-Martin periodane

104-15-4

toluene-4-sulfonic acid

159950-96-6

1-(p-methylbenzenesulfonyloxy)-1,2-benziodoxol-3(1H)-one

Conditions
ConditionsYield
for 0.25h;93%
5145-71-1

1-(p-methoxyphenyl)pyrrole

87413-09-0

Dess-Martin periodane

1428317-11-6

C18H14INO4

Conditions
ConditionsYield
In dichloromethane at 0℃; for 2h;93%
87413-09-0

Dess-Martin periodane

94054-40-7

1-(4-methylbenzyl)-1H-pyrrole

1428317-12-7

C19H16INO3

Conditions
ConditionsYield
In dichloromethane at 0℃; for 2h;93%

(R)-N-((S)-2-(2,3-difluorophenyl)-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide

87413-09-0

Dess-Martin periodane

(R)-N-((S)-2-(2,3-difluorophenyl)-4-oxobutan-2-yl)-2-methylpropane-2-sulfinamide

Conditions
ConditionsYield
93%
110-63-4

Butane-1,4-diol

87413-09-0

Dess-Martin periodane

1608-67-9

2-acetoxytetrahydrofuran

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.583333h;92%
122253-01-4

2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinemethanol

87413-09-0

Dess-Martin periodane

75-65-0

tert-butyl alcohol

129122-38-9

2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinecarboxaldehyde

Conditions
ConditionsYield
SiO2 In hexane; dichloromethane; acetonitrile92%
121659-65-2

4-(4'-fluorophenyl)-3-hydroxymethyl-2-(1'-methylethyl)-quinoline

87413-09-0

Dess-Martin periodane

121659-66-3

4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinecarboxaldehyde

Conditions
ConditionsYield
SiO2 In hexane; dichloromethane; ethyl acetate; tert-butyl alcohol92%
315688-15-4

N-[(1-methyl-indole-2-carbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

87413-09-0

Dess-Martin periodane

315688-16-5

N-[(1-methyl-indole-2-carbonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

Conditions
ConditionsYield
In dichloromethane92%
Na2 S2 O3

Na2 S2 O3

[1R-(1α,2α,4α,6β)]-6-Methyl-7-oxabicyclo[2.2.1]heptane-1,2-dimethanol

87413-09-0

Dess-Martin periodane

[1R-(1α,2α,4α,6β)]-2-[(2,2-Dimethyl-1-oxobutoxy)methyl]-6-methyl-7-oxabicyclo-[2.2.1]heptane-1-carboxaldehyde

Conditions
ConditionsYield
In dichloromethane; sodium hydrogencarbonate; tert-butyl alcohol91.5%
753926-18-0

(1-isobutyl-1H-indazol-5-yl)-o-tolyl methanol

87413-09-0

Dess-Martin periodane

753926-30-6

(1-isobutyl-1H-indazol-5-yl)-o-tolyl-methanone

Conditions
ConditionsYield
In dichloromethane91.4%

(1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-hydroxymethyl-1-phenyl-8-azabicyclo[3.2.1]octane

87413-09-0

Dess-Martin periodane

(1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-formyl-1-phenyl-8-azabicyclo[3.2.1]octane

Conditions
ConditionsYield
With sodium bicarbonate; sodium hydrogen sulphite In dichloromethane91%
58885-58-8

N-tert-butoxycarbonyl-3-aminopropanol

87413-09-0

Dess-Martin periodane

A

N-{3-r[(H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-propyl]-guanidine (Hydrobromide Salt)

N-{3-r[(H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-propyl]-guanidine (Hydrobromide Salt)

B

58885-60-2

N-(tert-butoxycarbonyl)-3-aminopropanal

Conditions
ConditionsYield
With sodium hydrogencarbonate; sodium thiosulfate In dichloromethaneA 91%
B n/a
87413-09-0

Dess-Martin periodane

88811-36-3

4-(3-hydroxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester

183500-09-6

4-(3-oxo-propyl)-imidazole-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
In dichloromethane91%
1432048-71-9

3-hydroxy-1-[4-(trifluoromethoxy)phenyl]cyclobutanecarbonitrile

87413-09-0

Dess-Martin periodane

1432048-72-0

3-oxo-1-[4-(trifluoromethoxy)phenyl]cyclobutanecarbonitrile

Conditions
ConditionsYield
In dichloromethane at 20℃;91%
Na2 SO3

Na2 SO3

4-hydroxy-9-cis-retinoic acid

144-55-8

sodium hydrogencarbonate

87413-09-0

Dess-Martin periodane

4-keto-9-cis-retinoic acid

Conditions
ConditionsYield
In hexane; dichloromethane90%
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    Product Name: Dess-Martin periodinane Synonyms: Dess-Martin periodinane,D M P, TAPI;dess-martin periodinate;1,1,1-Triacetoxy-1,2-benziodoxole-IV-3(1H)-one; 1,1,1-Tri

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    Dess-Martin periodinane 87413-09-0

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Chemistry

Molecule structure of Dess-Martin periodinane (CAS NO.87413-09-0):

IUPAC Name: (9,9-Diacetyloxy-7-oxo-9λ5-ioda-8-oxabicyclo[4.3.0]nona-1,3,5-trien-9-yl) acetate 
Molecular Weight: 424.14199 g/mol
Molecular Formula: C13H13IO8 
Density: 1.369 g/mL at 25 °C
Melting Point: 130-133 °C(lit.)
Boiling Point: 40 °C
Flash Point: >221 °F
Storage Temp.: 0-6 °C
Sensitive: light sensitive
XLogP3-AA: 2.7
H-Bond Acceptor: 8
Rotatable Bond Count: 6
Exact Mass: 423.96551
MonoIsotopic Mass: 423.96551
Topological Polar Surface Area: 105
Heavy Atom Count: 22
Canonical SMILES: CC(=O)OI1(C2=CC=CC=C2C(=O)O1)(OC(=O)C)OC(=O)C
InChI: InChI=1S/C13H13IO8/c1-8(15)19-14(20-9(2)16,21-10(3)17)12-7-5-4-6-11(12)13(18)22-14/h4-7H,1-3H3
InChIKey: NKLCNNUWBJBICK-UHFFFAOYSA-N
Product Categories: Hypervalent Iodine Compounds; Oxidation; Synthetic Organic Chemistry; Fused Ring Systems; Hypervalent Iodine; Synthetic Reagents

Uses

 Dess-Martin periodinane (CAS NO.87413-09-0) is mainly used as an oxidant for complex, sensitive and multifunctional alcohols. It is a chemical reagent used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones.

Production

 2-Iodobenzoic acid is oxidized preferably by Oxone, or by KBrO3 to 2-iodoxybenzoic acid. The 2-Iodoxybenzoic acid is then treated with a mixture of acetic anhydride, acetic acid and p-toluenesulfonic acid at 80-100 °C for 40 min. The resulted solids can be obtained via filtration and washing with ether.

Safety Profile

Hazard Codes: HarmfulXn, OxidizingO, IrritantXi
Risk Statements: 22-36/37/38-40-8-20/21/22 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R40:Limited evidence of a carcinogenic effect. 
R8 :Contact with combustible material may cause fire. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36-36/37-24/25-23-17-45-36/37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S36/37:Wear suitable protective clothing and gloves. 
S24/25:Avoid contact with skin and eyes. 
S23:Do not breathe vapour. 
S17:Keep away from combustible material. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 1593 6.1/PG 3
WGK Germany: 3
Hazard Note: Harmful/Light sensitive

Specification

 Dess-Martin periodinane (CAS NO.87413-09-0) is also named as 1,2-Benziodoxol-3(1H)-one,1,1,1-tris- (acetyloxy)-1,1-dihydro- ; 1,2-Benziodoxol-3(1H)-one, 1,1,1-tris(acetyloxy)-1,1-dihydro- ; Martin's reagent ; 1,1,1-tris-(Acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one ; Dess - Martin Periodinane(Triacetoxyperiodinane) ; (1,1,1-Triacetoxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one . Dess-Martin periodinane (CAS NO.87413-09-0) is white crystalline powder.