4405-13-4

Usage

Uses

Used in Pharmaceutical Industry:
GLYOXAL HYDRATE TRIMER is used as a reactant for the synthesis of Aza-analogs of 1,4-naphthoquinones, which act as effectors of plasmodial thioredoxin and glutathione reductase. These Aza-analogs have potential applications in the development of new drugs to combat parasitic diseases.
Used in Chemical Synthesis:
GLYOXAL HYDRATE TRIMER is used as a reactant for the synthesis of substituted side-bridged cyclam derivatives. These derivatives have potential applications in various fields, including the development of new catalysts and ligands for metal complexes.
Used in Polymer Industry:
GLYOXAL HYDRATE TRIMER is used as a reactant for the synthesis of Furandicarboxylic acid di-methyl ester derivatives. These derivatives are of interest in the development of bio-based and sustainable materials, such as polymers with improved properties and reduced environmental impact.

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

• 6032-74-2 diethyl (2E,4E)-2,4-hexadienedioate 
• 4205-06-5 2-(2-nitrophenyl)-1H-imidazole 
• 1414891-61-4 4,5-dihydroxy-1,3-diphenylimidazolidine-2-thione 
• 631-59-4 glyoxyl dimethyl acetal 
• 1609191-04-9 ⁽⁵⁾-tert-butyl 7-(((benzyloxy)carbonyl)amino)-7-(1H-imidazol-2-yl)heptanoate 
• 289506-17-8 2’-(2-hydroxy-5-bromophenyl)imidazole 
• 177781-53-2 1-ethyl-4,5-dihydroxyimidazolidin-2-one 
• 74420-99-8 (2E,4E)-Hexa-2,4-dienedioic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 117255-11-5 2-(1-(carboxymethyl)-1H-imidazol-3-ium-3-yl)acetate 
• 56222-36-7 N,N'-bis(2,4,6-trimethylphenyl)ethanediimine 
• 497841-81-3 C₁₈H₈F₁₂N₂