87413-09-0

Basic information

• Product Name: Dess-Martin periodinane
• Synonyms: DESS-MARTIN;DESS-MARTIN PERIODINANE;DESS-MARTIN REAGENT;DESSS-MARTIN PERIODINANE;1,1-DIHYDRO-1,1,1-TRIACETOXY-1,2-BENZOIODOOXOL-3(1H)-ONE;1,1,1-TRIACETOXY-1,1-DIHYDRO-1,2-BENZIODOXOL-3(1H)-ONE;1,1,1-TRIS(ACETYLOXY)-1,1-DIHYDRO-1,2-BENZIODOXOL-3-(1H)-ONE;ACETIC ACID 1,1-DIACETOXY-3-OXO-1L5-IODA-2-OXA-INDAN-1-YL ESTER
• CAS NO: 87413-09-0
• Molecular Formula: C₁₃H₁₃IO₈
• Molecular Weight: 424.14
• EINECS: 200-009-0
• Product Categories: Hypervalent Iodine Compounds;Oxidation;Synthetic Organic Chemistry;Fused Ring Systems;Hypervalent Iodine;Synthetic Reagents
• Mol File: 87413-09-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 130-133 °C(lit.)
• Boiling Point: 40 °C
• Flash Point: >221 °F
• Appearance: Colorless to light yellow/Liquid
• Density: 1.369 g/mL at 25 °C
• Storage Temp.: 0-6°C
• Solubility: Soluble in chloroform, acetone, acetonitrile and methylene chlor
• Sensitive: Light Sensitive
• Merck: 14,2933
• BRN: 4548207
• CAS DataBase Reference: Dess-Martin periodinane(CAS DataBase Reference)
• NIST Chemistry Reference: Dess-Martin periodinane(87413-09-0)
• EPA Substance Registry System: Dess-Martin periodinane(87413-09-0)

Safety Data

• Hazard Codes: Xn,O,Xi
• Statements: 22-36/37/38-40-8-20/21/22-44
• Safety Statements: 26-36-36/37-24/25-23-17-45-36/37/39
• RIDADR: UN 1593 6.1/PG 3
• WGK Germany: 3
• TSCA: No
• HazardClass: 5.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 87413-09-0(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline powder

Uses

Different sources of media describe the Uses of 87413-09-0 differently. You can refer to the following data:
1. Dess-Martin Periodinaneis a very usefulreagent used in the oxidation of primary alcohols to aldehydes and secondary alcohols to ketones.
2. Dess Martin periodinane is used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. It is also used as an oxidant for complexes with multifunctional alcohols. It is actively involved in the oxidation of N-protected-amino alcohols without epimerization and allylic alcohols.

InChI:InChI=1/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

Synthetic route

acetic anhydride (108-24-7) + 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione (61717-82-6) → Dess-Martin periodane (87413-09-0)

Conditions	Yield
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%

acetic anhydride (108-24-7) + acetic acid (64-19-7) + 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione (61717-82-6) → Dess-Martin periodane (87413-09-0)

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

2-Iodobenzoic acid (88-67-5) + acetic anhydride (108-24-7) → Dess-Martin periodane (87413-09-0)

Conditions	Yield
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;

4-methyl-morpholine (109-02-4) + (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 + methylene chloride Dess-Martin Periodinane + 6-[(pyridine-2-carbonyl)-amino]-hexanoic acid hydrochloride salt (1160871-87-3) → Dess-Martin periodane (87413-09-0)

Conditions	Yield
In N-methyl-acetamide; dichloromethane

Dess-Martin periodane (87413-09-0) → 1-Oxo-2-(R)-phenyl-3-(S)-t-butyldimethylsilyloxymethylcyclohexane

Conditions	Yield
With pyridine; sodium hydrogencarbonate In dichloromethane	100%

Dess-Martin periodane (87413-09-0) → trans-1-Benzoyl-2-formyl-3-methylpyrrolidine

Conditions	Yield
With sodium bicarbonate; sodium thiosulfate In dichloromethane; tert-butyl alcohol	100%

tert-butyl 4-[(benzyloxy)methyl]-4-(hydroxymethyl)piperidine-1-carboxylate (374795-03-6) + Dess-Martin periodane (87413-09-0) → 1,1-dimethylethyl 4-ethenyl-4-(phenylmethoxymethyl)-1-piperidinecarboxylate (374795-04-7)

Conditions	Yield
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%

3-[1-(3-hydroxypropyl)-1H-indazol-3-yl]-4-[1-(3-pyridinyl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione (436161-39-6) + Dess-Martin periodane (87413-09-0) → 3-(indazol-1-yl)propionic acid (247128-24-1)

Conditions	Yield
With sodium thiosulfate In dichloromethane; water	98%

NaHCO3-brine + methyl 4-[N-(2-hydroxy-1-phenylethyl)carbamoyl]-5-methylthiothiophene-2-carboxylate (237384-73-5) + Dess-Martin periodane (87413-09-0) → methyl 5-methylthio-4-[N-(2-oxo-1-phenylethyl)carbamoyl]thiophene-2-carboxylate

Conditions	Yield
In dichloromethane; ethyl acetate	98%
In dichloromethane; ethyl acetate	98%

sodium thiosulfate 5-hydrate + Dess-Martin periodane (87413-09-0) + (1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methylnaphtho[2,3-c]furan-4-ol (229010-22-4) → (1S,3S,3aR,4aS,8aR,9aS)-decahydro-1-methoxy-3-methylnaphtho[2,3-c]furan-4(1H)-one (229010-23-5)

Conditions	Yield
With sodium hydrogencarbonate	97%

diethyl ether (60-29-7) + dichloromethane (75-09-2) + 2-biphenylmethanol (2928-43-0) + water (7732-18-5) + Dess-Martin periodane (87413-09-0) → 2-Phenylbenzaldehyde (1203-68-5)

Conditions	Yield
With sodium hydroxide In tert-butyl alcohol	97%

benzofuran-2-carboxylic acid{(S)-1-[(3S,4S,7R)-3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide + Dess-Martin periodane (87413-09-0) → benzofuran-2-carboxylic acid{(S)-3-methyl-1-[(4S,7R)-7-methyl-3-oxo-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide

Conditions	Yield
In dichloromethane	97%
In dichloromethane

1-[2-(3,4-dimethoxyphenyl)ethyl]-1H-pyrrole (56014-51-8) + Dess-Martin periodane (87413-09-0) → C21H20INO5 (1428317-13-8)

Conditions	Yield
In dichloromethane at 0℃; for 2h;	96%

Dess-Martin periodane (87413-09-0) + tert-butyl (1-hydroxypropan-2-yl)carbamate (147252-84-4, 79069-13-9, 106391-86-0, 127516-56-7) → 2-(Boc-amino)propionaldehyde (105499-11-4)

Conditions	Yield
In dichloromethane at 0 - 20℃;	95%

(3,4,5-trimethoxyphenyl)methanol (3840-31-1) + Dess-Martin periodane (87413-09-0) → 1-acetoxy-1,2-benziodoxol-3-one (1829-26-1) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) + acetic acid (64-19-7)

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

(Z)-8-Hydroxy-3-methyl-8-(2-naphthyl)-2-octenoic acid (362671-49-6) + Dess-Martin periodane (87413-09-0) → (Z)-3-Methyl-7-(2-naphthoyl)-2-heptenoic acid (362671-50-9)

Conditions	Yield
In dichloromethane	94%

tert-Butyl 4-(3-bromophenylthio)-3-hydroxyazepane-1-carboxylate (1613402-01-9) + Dess-Martin periodane (87413-09-0) → tert-Butyl 4-(3-bromophenylthio)-3-oxoazepane-1-carboxylate (1613402-02-0)

Conditions	Yield
With sodium hydrogencarbonate; sodium thiosulfate In dichloromethane; water	94%

trans-(3RS,4RS)-3-[N-(3-benzyloxybenzoyl)-L-leucinylamino]-4-hydroxytetrahydrofuran + Dess-Martin periodane (87413-09-0) → (3RS)-3-[N-(3-benzyloxybenzoyl)-L-leucinylamino]tetrahydrofuran-4-one

Conditions	Yield
With sodium thiosulfate In dichloromethane	93%

Dess-Martin periodane (87413-09-0) + toluene-4-sulfonic acid (104-15-4) → 1-(p-methylbenzenesulfonyloxy)-1,2-benziodoxol-3(1H)-one (159950-96-6)

Conditions	Yield
for 0.25h;	93%

1-(p-methoxyphenyl)pyrrole (5145-71-1) + Dess-Martin periodane (87413-09-0) → C18H14INO4 (1428317-11-6)

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

Dess-Martin periodane (87413-09-0) + 1-(4-methylbenzyl)-1H-pyrrole (94054-40-7) → C19H16INO3 (1428317-12-7)

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

(R)-N-((S)-2-(2,3-difluorophenyl)-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide + Dess-Martin periodane (87413-09-0) → (R)-N-((S)-2-(2,3-difluorophenyl)-4-oxobutan-2-yl)-2-methylpropane-2-sulfinamide

Conditions	Yield
	93%

Butane-1,4-diol (110-63-4) + Dess-Martin periodane (87413-09-0) → 2-acetoxytetrahydrofuran (1608-67-9)

Conditions	Yield
In dichloromethane at 20℃; for 0.583333h;	92%

2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinemethanol (122253-01-4) + Dess-Martin periodane (87413-09-0) + tert-butyl alcohol (75-65-0) → 2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinecarboxaldehyde (129122-38-9)

Conditions	Yield
SiO2 In hexane; dichloromethane; acetonitrile	92%

4-(4'-fluorophenyl)-3-hydroxymethyl-2-(1'-methylethyl)-quinoline (121659-65-2) + Dess-Martin periodane (87413-09-0) → 4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinecarboxaldehyde (121659-66-3)

Conditions	Yield
SiO2 In hexane; dichloromethane; ethyl acetate; tert-butyl alcohol	92%

N-[(1-methyl-indole-2-carbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (315688-15-4) + Dess-Martin periodane (87413-09-0) → N-[(1-methyl-indole-2-carbonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (315688-16-5)

Conditions	Yield
In dichloromethane	92%

Na2 S2 O3 + [1R-(1α,2α,4α,6β)]-6-Methyl-7-oxabicyclo[2.2.1]heptane-1,2-dimethanol + Dess-Martin periodane (87413-09-0) → [1R-(1α,2α,4α,6β)]-2-[(2,2-Dimethyl-1-oxobutoxy)methyl]-6-methyl-7-oxabicyclo-[2.2.1]heptane-1-carboxaldehyde

Conditions	Yield
In dichloromethane; sodium hydrogencarbonate; tert-butyl alcohol	91.5%

(1-isobutyl-1H-indazol-5-yl)-o-tolyl methanol (753926-18-0) + Dess-Martin periodane (87413-09-0) → (1-isobutyl-1H-indazol-5-yl)-o-tolyl-methanone (753926-30-6)

Conditions	Yield
In dichloromethane	91.4%

(1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-hydroxymethyl-1-phenyl-8-azabicyclo[3.2.1]octane + Dess-Martin periodane (87413-09-0) → (1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-formyl-1-phenyl-8-azabicyclo[3.2.1]octane

Conditions	Yield
With sodium bicarbonate; sodium hydrogen sulphite In dichloromethane	91%

N-tert-butoxycarbonyl-3-aminopropanol (58885-58-8) + Dess-Martin periodane (87413-09-0) → N-{3-r[(H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-propyl]-guanidine (Hydrobromide Salt) + N-(tert-butoxycarbonyl)-3-aminopropanal (58885-60-2)

Conditions	Yield
With sodium hydrogencarbonate; sodium thiosulfate In dichloromethane	A 91% B n/a

Dess-Martin periodane (87413-09-0) + 4-(3-hydroxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester (88811-36-3) → 4-(3-oxo-propyl)-imidazole-1-carboxylic acid tert-butyl ester (183500-09-6)

Conditions	Yield
In dichloromethane	91%

3-hydroxy-1-[4-(trifluoromethoxy)phenyl]cyclobutanecarbonitrile (1432048-71-9) + Dess-Martin periodane (87413-09-0) → 3-oxo-1-[4-(trifluoromethoxy)phenyl]cyclobutanecarbonitrile (1432048-72-0)

Conditions	Yield
In dichloromethane at 20℃;	91%

Na2 SO3 + 4-hydroxy-9-cis-retinoic acid + sodium hydrogencarbonate (144-55-8) + Dess-Martin periodane (87413-09-0) → 4-keto-9-cis-retinoic acid

Conditions	Yield
In hexane; dichloromethane	90%

Upstream product

• 109-02-4 4-methyl-morpholine 
• 1160871-87-3 6-[(pyridine-2-carbonyl)-amino]-hexanoic acid hydrochloride salt 
• 88-67-5 2-Iodobenzoic acid 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 61717-82-6 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione 

Downstream Products

• 502-49-8 cycloactanone 
• 1829-26-1 1-acetoxy-1,2-benziodoxol-3-one 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 64-19-7 acetic acid 
• 1608-67-9 2-acetoxytetrahydrofuran 
• 106421-03-8 oxepan-2-yl acetate 
• 1072-21-5 hexanedial 
• 18328-11-5 3-benzyl propionaldehyde 
• 509093-81-6 N-[5-(2-Oxo-pyrrolidin-1-ylmethyl)-1-phenyl-1H-benzoimidazol-2-yl]-3-trifluoromethylbenzamide 
• 120690-80-4 3-(pyridin-4-yl)propionaldehyde 
• 1374994-89-4 [4-(2-pyrimidinyl)phenyl]-2-propynal 
• 199599-68-3 2-dimethylaminomethylthiazole-4-carboxaldehyde 

Relevant articles and documents

An Improved Procedure for the Preparation of the Dess-Martin Periodinane

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Changes in the Key Odorants and Aroma Profiles of Hamlin and Valencia Orange Juices Not from Concentrate (NFC) during Chilled Storage

Application of the aroma extract dilution analysis (AEDA) on the volatiles isolated by extraction/SAFE distillation from NFC (not from concentrate) juice from Hamlin oranges revealed 51 odor-active constituents in the flavor dilution (FD) factor range of 8 to 8192 among which vanillin, wine lactone, and (R)-linalool appeared with the highest FD factors. The AEDA applied on the volatile fraction of the same batch of juice stored at 0 °C for 10 months under aseptic conditions showed clear changes in the aroma profile as well as in the FD factors of key odorants. The reduction in the intensity of the citrus-like, pungent, green odor attributes in the aroma profile correlated with the loss of 1-penten-3-one, acetaldehyde, and (Z)-3-hexenal and a clear decrease in hexanal, octanal, nonanal, decanal, and (E,E)-2,4-decadienal. Quantitation done by stabile isotope dilution assays followed by a calculation of odor activity values (ratio of concentration to odor thresholds in citrate buffer) confirmed that the quick loss of 1-penten-3-one and acetaldehyde already within a few weeks and a significant reduction in nearly all aldehydes over the storage time of 10 months were responsible for the changes in the overall aroma profile of the juice. The same approach applied on Hamlin juice from the next harvest year as well as on chilled stored NFC juice from Valencia oranges confirmed the results for another harvest year and another orange variety.

The crystal structure of the Dess-Martin periodinane

We report the elusive X-ray structure of the Dess-Martin periodinane (DMP), a hypervalent iodine reagent popular amongst synthetic chemists. In the solid state, the highly crystalline compound forms an intricate coordination polymer held together by intermolecular halogen and hydrogen bonds.