Conditions | Yield |
---|---|
With 1-Benzyl-1,4-dihydronicotinamide In N,N-dimethyl-formamide for 24h; Kinetics; Ambient temperature; Irradiation; other nitramines, var. solvents, var. temperatures; | 100% |
Conditions | Yield |
---|---|
With borohydride exchange resin; nickel diacetate In methanol for 3h; | 100% |
hexamethylenetetramine
Conditions | Yield |
---|---|
With ammonium hydroxide; Fe(H)2(1,2-bis(dimethylphosphino)ethane)2 In tetrahydrofuran at 20 - 60℃; for 36h; Reagent/catalyst; Schlenk technique; Glovebox; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With ammonium hydroxide In water Schlenk technique; Glovebox; Inert atmosphere; | 97% |
With ammonium hydroxide at 15 - 20℃; | 83% |
With ammonium sulfate |
formaldehyd
1,1,1,3,3,3-hexamethyl-disilazane
A
Hexamethyldisiloxane
B
hexamethylenetetramine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 1h; | A 93% B 77% |
formaldehyd
A
1,3,5-dithiazinane
B
1,5-dithia-3,7-diazabicyclo<3.3.1>nonane
C
hexamethylenetetramine
Conditions | Yield |
---|---|
With ammonium hydroxide; hydrogen sulfide In water at 15℃; | A 4% B 44% C 29% |
With ammonium hydroxide; hydrogen sulfide In water at 40℃; | A 5% B 19% C 42% |
N-methyl-N-(methyleneamino)methanamine
acrylonitrile
A
dimethylaminomethyleneacetonitrile
B
hexamethylenetetramine
Conditions | Yield |
---|---|
With hydroquinone In acetonitrile at 100℃; for 10h; Product distribution; | A 36% B 12% |
Conditions | Yield |
---|---|
With sodium hydride In cyclohexane at 180℃; for 0.583333h; | A n/a B 32% |
Conditions | Yield |
---|---|
With ammonia at 40℃; for 10h; | A 12% B 27% |
methane
hexamethylenetetramine
Conditions | Yield |
---|---|
With ammonia; oxygen; copper at 500 - 700℃; | |
With silver copper; ammonia; oxygen at 500 - 700℃; |
Conditions | Yield |
---|---|
With ammonium hydroxide at 100 - 120℃; | |
With sodium hydroxide; ammonia at 100 - 120℃; | |
With ammonium hydroxide at 100 - 120℃; |
hexamethylenetetramine; compound with phenol
benzene
A
hexamethylenetetramine
B
phenol
β-naphthol
A
hexamethylenetetramine
B
bis(2-hydroxy-1-naphthyl)methane
C
1,3-diformyl-2-naphthol
D
2-formyl-2,3-dihydro-1H-naphth<1,2-e><1,3>oxazine
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid 1) 2h, steambath, 2) 30 min.; Yield given. Multistep reaction. Yields of byproduct given; |
A
azobisisopropane
B
hexamethylenetetramine
Conditions | Yield |
---|---|
for 10h; Product distribution; thermolysis; |
Conditions | Yield |
---|---|
With ammonia at 40℃; for 10h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With hydrogen fluoride; ammonia In methanol |
Conditions | Yield |
---|---|
With barium dihydroxide; phosphoric acid; ammonia; periodic acid Product distribution; multistep reaction; |
hexamethylenetetramine
Conditions | Yield |
---|---|
With nickel kieselguhr; ammonia; hydrogen at 250 - 280℃; |
Conditions | Yield |
---|---|
With water bei der Beruehrung mit einem gluehenden Nickel-Draht; |
Conditions | Yield |
---|---|
With water |
Conditions | Yield |
---|---|
bei der Einwirkung dunkler elektrischer Entladungen; |
Conditions | Yield |
---|---|
With ethanol at 125℃; |
Conditions | Yield |
---|---|
With ethanol |
Conditions | Yield |
---|---|
With ethanol |
ammonia
epichlorohydrin
A
(E)-2-penten-4-yn-1-ol
B
hexamethylenetetramine
C
propargyl alcohol
5-methyl-4-oxo-1,3-dioxolane
ammonia
A
hexamethylenetetramine
B
(+/-)-lactamide
tris(chloromethyl)-s-triazinetrione
ammonia
A
hexamethylenetetramine
C
isocyanuric acid
Conditions | Yield |
---|---|
at 100℃; |
Z-1,4-dichlorobutene
hexamethylenetetramine
1-<(Z)-4-Chloro-2-butenyl>-1-azonia-3,5,7-triazatricyclo<3.3.1.1.3,7>decane chloride
Conditions | Yield |
---|---|
In dichloromethane for 5h; Reflux; Large scale reaction; | 100% |
In ethanol; chloroform for 4h; Heating; | 99% |
In chloroform at 60℃; for 4h; | 94% |
In chloroform for 4h; Heating; | 91% |
In chloroform for 4h; Reflux; | 91% |
1-(3-(benzyloxy)phenyl)-2-bromoethanone
hexamethylenetetramine
1-[2-(3-Benzyloxy-phenyl)-2-oxo-ethyl]-3,5,7-triaza-1-azonia-tricyclo[3.3.1.13,7]decane; bromide
Conditions | Yield |
---|---|
In diethyl ether; chloroform Ambient temperature; | 100% |
hexamethylenetetramine
1,4-bis(chloromethyl)-2,5-dimethoxybenzene
1,1'-(2,5-dimethoxy-p-xylylene)-bis-hexamethylenetetraminium; dichloride
Conditions | Yield |
---|---|
In dichloromethane for 16h; Heating; | 100% |
In chloroform 1.) reflux, 30 min, 2.) r.t., overnight; | |
In chloroform at 90℃; for 24h; |
hexamethylenetetramine
4-Nitrophenacyl bromide
(4-nitrophenacyl)hexaminium bromide
Conditions | Yield |
---|---|
In chloroform for 2h; | 100% |
In chloroform at 20℃; for 12h; Delepine reaction; |
hexamethylenetetramine
2-chloro-N-(4-chlorophenyl)acetamide
N,N'-methylenebis<3-(4-chlorophenyl)>-4-imidazolidinone
Conditions | Yield |
---|---|
In ethanol 60 deg C, 1 h, then reflux, 1.5 h; | 100% |
hexamethylenetetramine
methyl iodide
N-methylhexamethylenetetrammonium iodide
Conditions | Yield |
---|---|
In chloroform at 20℃; | 100% |
at 80℃; for 7h; Temperature; | 95.8% |
In ethanol | |
In chloroform |
hexamethylenetetramine
4-tert-butyl-2-(diphenyl-phosphinoyl)-phenol
Conditions | Yield |
---|---|
With trifluoroacetic acid for 20h; Heating; | 100% |
1-benzo[1,3]dioxol-5-yl-2-(2,5-dichloro-phenyl)-ethane-1,2-dione
hexamethylenetetramine
5-benzo[1,3]dioxol-5-yl-4-(2,5-dichloro-phenyl)-1H-imidazole
Conditions | Yield |
---|---|
With ammonium acetate In acetic acid at 95℃; for 2.5h; | 100% |
2-(2-Hydroxyphenyl)benzoxazole
hexamethylenetetramine
5-(1,3-benzoxazol-2-yl)-4-hydroxyisophthalic aldehyde
Conditions | Yield |
---|---|
With trifluoroacetic acid for 48h; Reflux; | 100% |
With acetic acid In toluene for 18h; Duff reaction; Reflux; | 91% |
With trifluoroacetic acid Reflux; | 91% |
hexamethylenetetramine
2-chloro-1,4-dimethoxybenzene
2,5-dimethoxy-4-chlorobenzaldehyde
Conditions | Yield |
---|---|
With trifluoroacetic acid at 95℃; for 5h; | 100% |
With trifluoroacetic acid at 95℃; | 72.7% |
Ethyl 4-hydroxybenzoate
hexamethylenetetramine
3,5-diformyl-4-hydroxybenzoic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: Ethyl 4-hydroxybenzoate; hexamethylenetetramine With trifluoroacetic acid Reflux; Stage #2: With water at 20 - 80℃; for 2h; | 100% |
With trifluoroacetic acid | |
With trifluoroacetic acid Duff Aldehyde Synthesis; Reflux; | |
With trifluoroacetic acid Duff Aldehyde Synthesis; |
hexamethylenetetramine
4-hydroxy-benzoic acid
3,5-diformyl-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: hexamethylenetetramine; 4-hydroxy-benzoic acid With trifluoroacetic acid for 72h; Reflux; Stage #2: With water at 20 - 80℃; for 4h; | 100% |
With trifluoroacetic acid at 110℃; for 48h; | 70% |
With trifluoroacetic acid at 110℃; for 48h; | 70% |
hexamethylenetetramine
C9H5MnO5*C6H12N4
Conditions | Yield |
---|---|
In methanol at 20 - 60℃; Darkness; | 100% |
α-chloro-2',5'-difluoroacetophenone
hexamethylenetetramine
Conditions | Yield |
---|---|
In chloroform Solvent; Temperature; Reflux; | 100% |
hexamethylenetetramine
2-bromo-1-cyclopropylethan-1-one
Conditions | Yield |
---|---|
In chloroform at 20℃; for 12h; | 100% |
In chloroform at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
In chloroform at 60℃; for 12h; | 99.9% |
Conditions | Yield |
---|---|
In toluene for 2h; Solvent; Reflux; Industrial scale; | 99.9% |
1,1,2,3-Tetrachloropropene
hexamethylenetetramine
Conditions | Yield |
---|---|
In chloroform at 60℃; for 12h; | 99.6% |
hexamethylenetetramine
tris-(chloromethyl)amine
Conditions | Yield |
---|---|
With phosphorus pentachloride at 100℃; for 5.5h; Neat (no solvent); | 99% |
With phosphorus pentachloride | |
With phosphorus pentachloride |
2-bromoacetyl-1-methyl-5-nitropyrrole
hexamethylenetetramine
Conditions | Yield |
---|---|
In chloroform Alkylation; | 99% |
In chloroform | 99% |
hexamethylenetetramine
2-bromo-1-[5-fluoro-2-(methylthio)phenyl]ethanone
Conditions | Yield |
---|---|
In chloroform at 20℃; | 99% |
hexamethylenetetramine
2-Bromo-1-(3,4-dimethoxyphenyl)ethanone
2-hexamethylenetetramino-1-(3,4-dimethoxyphenyl)ethanone-2-ium bromide
Conditions | Yield |
---|---|
In chloroform at 20℃; for 4h; | 99% |
In chloroform at 20℃; |
Conditions | Yield |
---|---|
Stage #1: hexamethylenetetramine; C76H120O4 With trifluoroacetic acid at 125℃; for 4h; Stage #2: With hydrogenchloride; water In dichloromethane at 20℃; for 3h; | 99% |
hexamethylenetetramine
4-Bromoacetyl-1-(t-butoxycarbonyl)piperidine
Conditions | Yield |
---|---|
In chloroform at 50℃; for 1h; | 99% |
hexamethylenetetramine
Conditions | Yield |
---|---|
In dichloromethane for 24h; Reflux; | 99% |
6-ethyl-1H-pyrrolo[2,3-b]pyridine
hexamethylenetetramine
Conditions | Yield |
---|---|
With acetic acid In water at 120℃; for 8h; | 99% |
hexamethylenetetramine
Conditions | Yield |
---|---|
In chloroform at 20℃; for 12h; | 99% |
7-Azaindole
hexamethylenetetramine
1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde
Conditions | Yield |
---|---|
With propionic acid In ethanol at 80℃; for 6h; Temperature; | 98.9% |
Stage #1: 7-Azaindole; hexamethylenetetramine With acetic acid for 6h; Duff reaction; Heating; Stage #2: With water at 20℃; Further stages.; | 77% |
With acetic acid In water for 12h; Heating / reflux; | 76% |
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