acetic anhydride
1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione
Dess-Martin periodane
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
acetic acid
1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione
Dess-Martin periodane
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; |
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
(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
6-[(pyridine-2-carbonyl)-amino]-hexanoic acid hydrochloride salt
Dess-Martin periodane
Conditions | Yield |
---|---|
In N-methyl-acetamide; dichloromethane |
Dess-Martin periodane
Conditions | Yield |
---|---|
With pyridine; sodium hydrogencarbonate In dichloromethane | 100% |
Dess-Martin periodane
Conditions | Yield |
---|---|
With sodium bicarbonate; sodium thiosulfate In dichloromethane; tert-butyl alcohol | 100% |
tert-butyl 4-[(benzyloxy)methyl]-4-(hydroxymethyl)piperidine-1-carboxylate
Dess-Martin periodane
1,1-dimethylethyl 4-ethenyl-4-(phenylmethoxymethyl)-1-piperidinecarboxylate
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
Dess-Martin periodane
3-(indazol-1-yl)propionic acid
Conditions | Yield |
---|---|
With sodium thiosulfate In dichloromethane; water | 98% |
methyl 4-[N-(2-hydroxy-1-phenylethyl)carbamoyl]-5-methylthiothiophene-2-carboxylate
Dess-Martin periodane
Conditions | Yield |
---|---|
In dichloromethane; ethyl acetate | 98% |
In dichloromethane; ethyl acetate | 98% |
Dess-Martin periodane
(1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methylnaphtho[2,3-c]furan-4-ol
(1S,3S,3aR,4aS,8aR,9aS)-decahydro-1-methoxy-3-methylnaphtho[2,3-c]furan-4(1H)-one
Conditions | Yield |
---|---|
With sodium hydrogencarbonate | 97% |
diethyl ether
dichloromethane
2-biphenylmethanol
water
Dess-Martin periodane
2-Phenylbenzaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide In tert-butyl alcohol | 97% |
Dess-Martin periodane
Conditions | Yield |
---|---|
In dichloromethane | 97% |
In dichloromethane |
1-[2-(3,4-dimethoxyphenyl)ethyl]-1H-pyrrole
Dess-Martin periodane
C21H20INO5
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 2h; | 96% |
Dess-Martin periodane
tert-butyl (1-hydroxypropan-2-yl)carbamate
2-(Boc-amino)propionaldehyde
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; | 95% |
(3,4,5-trimethoxyphenyl)methanol
Dess-Martin periodane
A
1-acetoxy-1,2-benziodoxol-3-one
B
3,4,5-trimethoxy-benzaldehyde
C
acetic acid
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
Dess-Martin periodane
(Z)-3-Methyl-7-(2-naphthoyl)-2-heptenoic acid
Conditions | Yield |
---|---|
In dichloromethane | 94% |
tert-Butyl 4-(3-bromophenylthio)-3-hydroxyazepane-1-carboxylate
Dess-Martin periodane
tert-Butyl 4-(3-bromophenylthio)-3-oxoazepane-1-carboxylate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; sodium thiosulfate In dichloromethane; water | 94% |
Dess-Martin periodane
Conditions | Yield |
---|---|
With sodium thiosulfate In dichloromethane | 93% |
Dess-Martin periodane
toluene-4-sulfonic acid
1-(p-methylbenzenesulfonyloxy)-1,2-benziodoxol-3(1H)-one
Conditions | Yield |
---|---|
for 0.25h; | 93% |
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 2h; | 93% |
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 2h; | 93% |
Dess-Martin periodane
Conditions | Yield |
---|---|
93% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.583333h; | 92% |
2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinemethanol
Dess-Martin periodane
tert-butyl alcohol
2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
SiO2 In hexane; dichloromethane; acetonitrile | 92% |
4-(4'-fluorophenyl)-3-hydroxymethyl-2-(1'-methylethyl)-quinoline
Dess-Martin periodane
4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinecarboxaldehyde
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
Dess-Martin periodane
N-[(1-methyl-indole-2-carbonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester
Conditions | Yield |
---|---|
In dichloromethane | 92% |
Dess-Martin periodane
Conditions | Yield |
---|---|
In dichloromethane; sodium hydrogencarbonate; tert-butyl alcohol | 91.5% |
(1-isobutyl-1H-indazol-5-yl)-o-tolyl methanol
Dess-Martin periodane
(1-isobutyl-1H-indazol-5-yl)-o-tolyl-methanone
Conditions | Yield |
---|---|
In dichloromethane | 91.4% |
Dess-Martin periodane
Conditions | Yield |
---|---|
With sodium bicarbonate; sodium hydrogen sulphite In dichloromethane | 91% |
N-tert-butoxycarbonyl-3-aminopropanol
Dess-Martin periodane
B
N-(tert-butoxycarbonyl)-3-aminopropanal
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; sodium thiosulfate In dichloromethane | A 91% B n/a |
Dess-Martin periodane
4-(3-hydroxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester
4-(3-oxo-propyl)-imidazole-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
In dichloromethane | 91% |
3-hydroxy-1-[4-(trifluoromethoxy)phenyl]cyclobutanecarbonitrile
Dess-Martin periodane
3-oxo-1-[4-(trifluoromethoxy)phenyl]cyclobutanecarbonitrile
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 91% |
sodium hydrogencarbonate
Dess-Martin periodane
Conditions | Yield |
---|---|
In hexane; dichloromethane | 90% |
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
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.
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.
Hazard Codes: Xn, O, Xi
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
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.
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