4405-13-4

Basic information

• Product Name: GLYOXAL HYDRATE TRIMER
• Synonyms: (1,4)Dioxino[2,3-b]-1,4-dioxin-2,3,6,7-tetrol,hexahydro-;3-b)-p-dioxin-2,3,6,7-tetrol,hexahydro-p-dioxino(;3-b]-p-dioxin-2,3,6,7-tetrol,hexahydro-p-Dioxino[2;4)dioxino(2,3-b)-1,4-dioxin-2,3,6,7-tetrol,hexahydro-(;4)Dioxino[2,3-b]-1,4-dioxin-2,3,6,7-tetrol,hexahydro-(1;Ethanedial,trimer,dihydrate;p-Dioxino[2,3-b]-p-dioxin-2,3,6,7-tetrol,hexahydro-;Triethanedialdihydrate
• CAS NO: 4405-13-4
• Molecular Formula: C₆H₁₀O₈
• Molecular Weight: 210.14
• EINECS: 224-551-3
• Mol File: 4405-13-4.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 453℃
• Flash Point: 228℃
• Appearance: /
• Density: 1.900
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 10.54±0.70(Predicted)
• CAS DataBase Reference: GLYOXAL HYDRATE TRIMER(CAS DataBase Reference)
• NIST Chemistry Reference: GLYOXAL HYDRATE TRIMER(4405-13-4)
• EPA Substance Registry System: GLYOXAL HYDRATE TRIMER(4405-13-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: JH5380000
• Hazardous Substances Data: 4405-13-4(Hazardous Substances Data)

Usage

Uses

Reactant involved in the synthesis of:Aza-analogs of 1,4-naphthoquinones as effectors of plasmodial thioredoxin and glutathione reductaseSubstituted side-bridged cyclam derivativesFurandicarboxylic acid di-methyl ester derivatives

General Description

White powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

GLYOXAL HYDRATE TRIMER is an aldehyde. is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. GLYOXAL HYDRATE TRIMER is incompatible with strong oxidizing agents.

Health Hazard

ACUTE/CHRONIC HAZARDS: GLYOXAL HYDRATE TRIMER may be harmful by inhalation, ingestion or skin absorption. It is irritating to the mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide and carbon dioxide.

Fire Hazard

Flash point data for GLYOXAL HYDRATE TRIMER are not available. GLYOXAL HYDRATE TRIMER is probably combustible.

InChI:InChI=1/C6H10O8/c7-1-2(8)12-6-5(11-1)13-3(9)4(10)14-6/h1-10H/t1-,2-,3-,4+,5?,6?/m1/s1

Synthetic route

(S)-1-phenyl-ethylamine (2627-86-3) + glyoxal trimer dihydrate (4405-13-4) → N,N'-bis<(S)-1-phenylethyl>ethanediimine (138812-17-6)

Conditions	Yield
With magnesium sulfate In dichloromethane for 5h;	100%

glyoxal trimer dihydrate (4405-13-4) + 1,4,7,10-tetraazacyclododecan (294-90-6) → cyclen-glyoxal (74199-09-0, 79236-92-3)

Conditions	Yield
In methanol at 0℃; for 3h;	99%
In methanol at 0 - 20℃; for 2.5h;	94%
In methanol; water at 20℃; for 3h;	82%

(S)-1-(4-methoxyphenyl)ethylamine (6298-96-0, 22038-86-4, 35600-82-9, 41851-59-6) + glyoxal trimer dihydrate (4405-13-4) → (1S,1'S)-N,N'-(ethane-1,2-diylidene)bis[1-(4-methoxyphenyl)ethanamine]

Conditions	Yield
In ethanol for 0.333333h; Reflux;	96%

glyoxal trimer dihydrate (4405-13-4) + 1-methyl-3-phenylthiourea (2724-69-8) → (4S*,5S*)-4,5-dihydroxy-1-methyl-3-phenylimidazolidine-2-thione

Conditions	Yield
In isopropyl alcohol for 1h; Reflux;	96%

glyoxal trimer dihydrate (4405-13-4) + 1-ethyl-3-phenylthiourea (2741-06-2) → (4S,5S)-1-ethyl-4,5-dihydroxy-3-phenylimidazolidine-2-thione

Conditions	Yield
In isopropyl alcohol for 1h; Reflux;	95%

glyoxal trimer dihydrate (4405-13-4) + cyclohexanone (108-94-1) → 1,4-diazaspiro[4.5]deca-1,3-diene

Conditions	Yield
Stage #1: glyoxal trimer dihydrate With ammonium acetate; ammonia In tetrahydrofuran at -78℃; for 0.833333h; Inert atmosphere; Stage #2: cyclohexanone In tetrahydrofuran at -78 - 23℃; for 8h; Inert atmosphere;	90%

glyoxal trimer dihydrate (4405-13-4) + N,N-dimethylthiourea (534-13-4) → C5H10N2O2S (861552-34-3)

Conditions	Yield
With isopropyl alcohol at 50 - 55℃; for 1h;	90%

1,4,8,11-Tetraazacyclotetradecane (295-37-4) + glyoxal trimer dihydrate (4405-13-4) → decahydro-1H,6H-3a,5a,8a,10a-tetraazapyrene (72738-47-7)

Conditions	Yield
In methanol; water at 20℃; for 2h;	87%

N,N'-dimethylsulfamide (22504-72-9) + glyoxal trimer dihydrate (4405-13-4) → 1,3,1',3'-tetramethyl-octahydro-[5,5']bi[4,6-dioxa-2-thia-1,3-diaza-pentalenyl] 2,2,2',2'-tetraoxide

Conditions	Yield
With hydrogenchloride at 35 - 40℃; for 1.5h;	85%

(S)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-8-oxooctanoate (1609191-03-8) + glyoxal trimer dihydrate (4405-13-4) → (5)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-7-(1H-imidazol-2-yl)heptanoate (1609191-04-9)

Conditions	Yield
With ammonia In methanol at 20℃; for 72h; Sealed tube;	85%
With ammonia In methanol at 20℃; for 72h; Sealed tube;

glyoxal trimer dihydrate (4405-13-4) + phenylhydrazine (100-63-0) → glyoxal bis(phenylhydrazone) (1534-21-0, 29841-71-2)

Conditions	Yield
In methanol; water at 20℃; for 13h;	83%

glyoxal trimer dihydrate (4405-13-4) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (5S,10aS)-5-[(5S,10aS)-3-oxo-1,5,10,10a-tetrahydro[1,3]oxazolo[3,4-b]isoquinolin-5-yl]-1,5,10,10a-tetrahydro[1,3]oxazolo[3,4-b]isoquinolin-3-one

Conditions	Yield
With sulfuric acid In chloroform at 20℃; for 12h; Pictet-Spengler Synthesis; diastereoselective reaction;	82%
With sulfuric acid In chloroform for 6h; Reflux;	68.9%

glyoxal trimer dihydrate (4405-13-4) + ethylenediamine (107-15-3) → trans-1,4,6,9-tetraazabicyclo[4.4.0]decane (67919-28-2)

Conditions	Yield
With acetic acid In ethanol Condensation;	80%

glyoxal trimer dihydrate (4405-13-4) + ethylenediamine (107-15-3) → decahydropyrazino[2,3-b]pyrazine

Conditions	Yield
With acetic acid In ethanol at 0 - 80℃; for 0.666667h;	80%

glyoxal trimer dihydrate (4405-13-4) + bis[1-methyl-1-mesitylcyclobutane-3-yl]-3-(1-oxyethyl)sulfide (676235-08-8) → 2,5-di[1-methyl-1-mesitylcyclobutane-3-yloyl]thiophene

Conditions	Yield
Stage #1: glyoxal trimer dihydrate In methanol for 1h; Heating; Stage #2: bis[1-methyl-1-mesitylcyclobutane-3-yl]-3-(1-oxyethyl)sulfide With sodium methylate In 1,4-dioxane; methanol for 0.5h;	78%

glyoxal trimer dihydrate (4405-13-4) + bis[1-methyl-1-(2-tetralino)cyclobutane-3-yl]-3-(1-oxyethyl)sulfide → 2,5-di[1-methyl-1-(2-tetralino)cyclobutane-3-yloyl]thiophene

Conditions	Yield
Stage #1: glyoxal trimer dihydrate In methanol for 1h; Heating; Stage #2: bis[1-methyl-1-(2-tetralino)cyclobutane-3-yl]-3-(1-oxyethyl)sulfide With sodium methylate In 1,4-dioxane; methanol for 0.5h;	75%

formaldehyd (50-00-0) + 3β-amino-17-(1H-benzimidazole-1-yl)androsta-5,16-diene (908581-04-4) + glyoxal trimer dihydrate (4405-13-4) → 3β-(1H-imidazol-1-yl)-17-(1H-benzimidazol-1-yl)-androsta-5,16-diene

Conditions	Yield
With ammonium hydroxide In methanol; water at 70℃; for 5h; Inert atmosphere;	75%
With ammonium hydroxide In methanol; water at 70℃; for 5h;	74.8%

N,N'-dipropylsulfamide (19757-10-9) + glyoxal trimer dihydrate (4405-13-4) → 1,3,1',3'-tetrapropyl-octahydro-[5,5']bi[4,6-dioxa-2-thia-1,3-diaza-pentalenyl] 2,2,2',2'-tetraoxide

Conditions	Yield
With hydrogenchloride at 35 - 40℃; for 1.5h;	74%

N,N'-dibutyl-sulfamide (763-11-1) + glyoxal trimer dihydrate (4405-13-4) → 1,3,1',3'-tetrabutyl-octahydro-[5,5']bi[4,6-dioxa-2-thia-1,3-diaza-pentalenyl] 2,2,2',2'-tetraoxide

Conditions	Yield
With hydrogenchloride at 35 - 40℃; for 1.5h;	72%

glyoxal trimer dihydrate (4405-13-4) + C32H36NP → 1,4-bis(3,5-di-tert-butylphenyl)-1,4-diaza-1,3-butadiene

Conditions	Yield
With 4A molecular sives In tetrahydrofuran Heating;	72%

N,N'-Di-sek.-butyl-schwefelsaeurediamid (23415-21-6) + glyoxal trimer dihydrate (4405-13-4) → 3,3'-bi{6,8-di(1-methylpropyl)-2,4-dioxa-7-thia-6,8-diazabicyclo[3.3.0]octane 7,7-dioxide}

Conditions	Yield
With hydrogenchloride at 35 - 40℃; for 1.5h;	71%

formaldehyd (50-00-0) + 3α-amino-17-(1H-benzimidazole-1-yl)androsta-5,16-diene + glyoxal trimer dihydrate (4405-13-4) → 3α-(1H-imidazol-1-yl)-17-(1H-benzimidazol-1-yl)-androsta-5,16-diene

Conditions	Yield
With ammonium hydroxide In methanol; water at 70℃; for 5h; Inert atmosphere;	71%
With ammonium hydroxide In methanol; water at 70℃; for 5h;	70.7%

glyoxal trimer dihydrate (4405-13-4) + (S)-N-tert-butoxycarbonylvalinal (79069-51-5) → (S)-tert-butyl (1-(1H-imidazol-2-yl)-2-methylpropyl)carbamate (172729-99-6)

Conditions	Yield
With ammonia In methanol at 20℃;	70.1%

glyoxal trimer dihydrate (4405-13-4) + Boc-L-phenylalaninal (72155-45-4) → (S)-tert-butyl (1-(1H-imidazol-2-yl)-2-phenylethyl)carbamate (200070-27-5)

Conditions	Yield
With ammonia In methanol at 0 - 20℃; for 48h; Inert atmosphere;	70%
With ammonia In methanol at 20℃; for 48h;	47%

glyoxal trimer dihydrate (4405-13-4) + N,N-diphenylthiourea (102-08-9) → 4,5-dihydroxy-1,3-diphenylimidazolidine-2-thione + 4,5-dihydroxy-1,3-diphenylimidazolidine-2-thione (1414891-61-4)

Conditions	Yield
With potassium carbonate In water; isopropyl alcohol for 1h; pH=7.5; Reflux; diastereoselective reaction;	A 70% B n/a

glyoxal trimer dihydrate (4405-13-4) + bis[1-methyl-1-phenylcyclobutane-3-yl]-3-(1-oxyethyl)sulfide (676235-09-9) → 2,5-di[1-methyl-1-phenylcyclobutane-3-yloyl]thiophene

Conditions	Yield
Stage #1: glyoxal trimer dihydrate In methanol for 1h; Heating; Stage #2: bis[1-methyl-1-phenylcyclobutane-3-yl]-3-(1-oxyethyl)sulfide With sodium methylate In 1,4-dioxane; methanol for 0.5h;	68%

N-ethyl-N'-methyl-sulfamide (26118-84-3) + glyoxal trimer dihydrate (4405-13-4) → 3,3'-bi(N-ethyl-N'methyl-2,4-dioxa-7-thia-6,8-diazabicyclo[3.3.0]octane 7,7-dioxide)

Conditions	Yield
With hydrogenchloride at 35 - 40℃; for 1.5h;	67%

Downstream Products

• 138812-17-6 N,N'-bis<(S)-1-phenylethyl>ethanediimine 
• 111426-70-1 [1,4]dioxane-2,3,5,6-tetraol 
• 111426-71-2 (4S,5S)-2-Dihydroxymethyl-[1,3]dioxolane-4,5-diol 
• 631-59-4 glyoxyl dimethyl acetal 
• 6032-74-2 diethyl (2E,4E)-2,4-hexadienedioate 
• 122001-39-2 (2Z,4E)-diethyl hexa-2,4-dienedioate 
• 1207167-17-6 C₁₈H₂₀N₂O₂ 
• 1414891-61-4 4,5-dihydroxy-1,3-diphenylimidazolidine-2-thione 
• 177781-53-2 1-ethyl-4,5-dihydroxyimidazolidin-2-one