Product Name

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  • Name

    Hexamethylenetetramine

  • EINECS 202-905-8
  • CAS No. 100-97-0
  • Article Data93
  • CAS DataBase
  • Density 1.428 g/cm3
  • Solubility 895 g/L (20 °C)
  • Melting Point 280 °C (subl.)(lit.)
  • Formula C6H12N4
  • Boiling Point 252.704 °C at 760 mmHg
  • Molecular Weight 140.188
  • Flash Point 103.945 °C
  • Transport Information UN 1328 4.1/PG 3
  • Appearance white crystalline powder
  • Safety 16-22-24-37
  • Risk Codes 11-42/43
  • Molecular Structure Molecular Structure of 100-97-0 (Hexamethylenetetramine)
  • Hazard Symbols FlammableF,HarmfulXn
  • Synonyms Hexamethylenetetramine(8CI);1,3,5,7-Tetraazaadamantane;Aceto HMT;Aminoform;Ammoform;Antihydral;1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane;Formamine;Formin;Heterin;HexaB;Hexamine(heterocycle);Hexasan;Methenamin;Methenamine;NSC 26346;Nocceler H;Preparation AF;Sanceler H;Sanceler HT;Uramin;Uratrine;Uritone;Urodeine;Urotropin;Urotropine;Vulkacit H;Xametrin;
  • PSA 12.96000
  • LogP -1.26820

Synthetic route

octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine
2691-41-0

octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With 1-Benzyl-1,4-dihydronicotinamide In N,N-dimethyl-formamide for 24h; Kinetics; Ambient temperature; Irradiation; other nitramines, var. solvents, var. temperatures;100%
Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

Hexahydro-1,3,5-trinitro-1,3,5-triazine

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With borohydride exchange resin; nickel diacetate In methanol for 3h;100%
C17H30B2O2

C17H30B2O2

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
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%
formaldehyd
50-00-0

formaldehyd

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With ammonium hydroxide In water Schlenk technique; Glovebox; Inert atmosphere;97%
With ammonium hydroxide at 15 - 20℃;83%
With ammonium sulfate
formaldehyd
50-00-0

formaldehyd

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

A

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

B

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 1h;A 93%
B 77%
formaldehyd
50-00-0

formaldehyd

A

1,3,5-dithiazinane
5962-66-3

1,3,5-dithiazinane

B

1,5-dithia-3,7-diazabicyclo<3.3.1>nonane
281-20-9

1,5-dithia-3,7-diazabicyclo<3.3.1>nonane

C

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
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
2035-89-4

N-methyl-N-(methyleneamino)methanamine

acrylonitrile
107-13-1

acrylonitrile

A

dimethylaminomethyleneacetonitrile
34714-77-7

dimethylaminomethyleneacetonitrile

B

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With hydroquinone In acetonitrile at 100℃; for 10h; Product distribution;A 36%
B 12%
(1,2-di-tert-butyldiaziridin-3-ylidene)(methyl)amine

(1,2-di-tert-butyldiaziridin-3-ylidene)(methyl)amine

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With sodium hydride In cyclohexane at 180℃; for 0.583333h;A n/a
B 32%
2-Aminomethylbenzimidazole
5805-57-2

2-Aminomethylbenzimidazole

dichloromethane
75-09-2

dichloromethane

A

hexamethylenetetramine
100-97-0

hexamethylenetetramine

B

7H,16H-8,17-Methano-9H,18H-benzimidazolo<1,2-c><8,2'>-spiro-benzimidazolidino<1,3,6>triazonin

7H,16H-8,17-Methano-9H,18H-benzimidazolo<1,2-c><8,2'>-spiro-benzimidazolidino<1,3,6>triazonin

Conditions
ConditionsYield
With ammonia at 40℃; for 10h;A 12%
B 27%
methane
34557-54-5

methane

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With ammonia; oxygen; copper at 500 - 700℃;
With silver copper; ammonia; oxygen at 500 - 700℃;
dichloromethane
75-09-2

dichloromethane

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With ammonium hydroxide at 100 - 120℃;
With sodium hydroxide; ammonia at 100 - 120℃;
With ammonium hydroxide at 100 - 120℃;
hexamethylenetetramine; compound with phenol
26940-74-9, 59481-40-2, 59481-41-3, 81646-16-4

hexamethylenetetramine; compound with phenol

benzene
71-43-2

benzene

A

hexamethylenetetramine
100-97-0

hexamethylenetetramine

B

phenol
108-95-2

phenol

β-naphthol
135-19-3

β-naphthol

A

hexamethylenetetramine
100-97-0

hexamethylenetetramine

B

bis(2-hydroxy-1-naphthyl)methane
1096-84-0

bis(2-hydroxy-1-naphthyl)methane

C

1,3-diformyl-2-naphthol
77204-14-9

1,3-diformyl-2-naphthol

D

2-formyl-2,3-dihydro-1H-naphth<1,2-e><1,3>oxazine
77204-15-0

2-formyl-2,3-dihydro-1H-naphth<1,2-e><1,3>oxazine

Conditions
ConditionsYield
With hydrogenchloride; acetic acid 1) 2h, steambath, 2) 30 min.; Yield given. Multistep reaction. Yields of byproduct given;
2-c,3-t-diisopropyl-1-r-methyltriaziridin

2-c,3-t-diisopropyl-1-r-methyltriaziridin

A

azobisisopropane
15464-00-3

azobisisopropane

B

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
for 10h; Product distribution; thermolysis;
2-chloromethyl-1H-benzimidazole
4857-04-9

2-chloromethyl-1H-benzimidazole

dichloromethane
75-09-2

dichloromethane

A

hexamethylenetetramine
100-97-0

hexamethylenetetramine

B

7H,16H-8,17-Methano-9H,18H-benzimidazolo<1,2-c><8,2'>-spiro-benzimidazolidino<1,3,6>triazonin

7H,16H-8,17-Methano-9H,18H-benzimidazolo<1,2-c><8,2'>-spiro-benzimidazolidino<1,3,6>triazonin

Conditions
ConditionsYield
With ammonia at 40℃; for 10h; Yield given. Yields of byproduct given;
formaldehyd
50-00-0

formaldehyd

methylamine
74-89-5

methylamine

A

hexamethylenetetramine
100-97-0

hexamethylenetetramine

B

N-methylhexamethylenetetrammonium fluoride

N-methylhexamethylenetetrammonium fluoride

Conditions
ConditionsYield
With hydrogen fluoride; ammonia In methanol
glycerol
56-81-5

glycerol

A

hexamethylenetetramine
100-97-0

hexamethylenetetramine

B

barium formate
541-43-5

barium formate

Conditions
ConditionsYield
With barium dihydroxide; phosphoric acid; ammonia; periodic acid Product distribution; multistep reaction;
formaldehyd
50-00-0

formaldehyd

ammonium carbonate

ammonium carbonate

hexamethylenetetramine
100-97-0

hexamethylenetetramine

carbon monoxide

carbon monoxide

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With nickel kieselguhr; ammonia; hydrogen at 250 - 280℃;
methanol
67-56-1

methanol

NH3

NH3

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With water bei der Beruehrung mit einem gluehenden Nickel-Draht;
formaldehyd
50-00-0

formaldehyd

NH3

NH3

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With water
ethanol
64-17-5

ethanol

NH3

NH3

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
bei der Einwirkung dunkler elektrischer Entladungen;
dichloromethane
75-09-2

dichloromethane

NH3

NH3

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With ethanol at 125℃;
bis(benzoyloxy)methane
5342-31-4

bis(benzoyloxy)methane

NH3

NH3

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With ethanol
methylene glycol diacetate

methylene glycol diacetate

NH3

NH3

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With ethanol
polyoxymethylene

polyoxymethylene

NH3

NH3

hexamethylenetetramine
100-97-0

hexamethylenetetramine

ammonia
7664-41-7

ammonia

sodium amide

sodium amide

epichlorohydrin
106-89-8

epichlorohydrin

A

(E)-2-penten-4-yn-1-ol
35042-52-5

(E)-2-penten-4-yn-1-ol

B

hexamethylenetetramine
100-97-0

hexamethylenetetramine

C

propargyl alcohol
107-19-7

propargyl alcohol

5-methyl-4-oxo-1,3-dioxolane
13372-32-2

5-methyl-4-oxo-1,3-dioxolane

ammonia
7664-41-7

ammonia

A

hexamethylenetetramine
100-97-0

hexamethylenetetramine

tris(chloromethyl)-s-triazinetrione
63579-00-0

tris(chloromethyl)-s-triazinetrione

ammonia
7664-41-7

ammonia

A

hexamethylenetetramine
100-97-0

hexamethylenetetramine

B

ammonium chloride

ammonium chloride

C

isocyanuric acid
108-80-5

isocyanuric acid

Conditions
ConditionsYield
at 100℃;
Z-1,4-dichlorobutene
1476-11-5

Z-1,4-dichlorobutene

hexamethylenetetramine
100-97-0

hexamethylenetetramine

1-<(Z)-4-Chloro-2-butenyl>-1-azonia-3,5,7-triazatricyclo<3.3.1.1.3,7>decane chloride
117175-09-4

1-<(Z)-4-Chloro-2-butenyl>-1-azonia-3,5,7-triazatricyclo<3.3.1.1.3,7>decane chloride

Conditions
ConditionsYield
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
19381-40-9

1-(3-(benzyloxy)phenyl)-2-bromoethanone

hexamethylenetetramine
100-97-0

hexamethylenetetramine

1-[2-(3-Benzyloxy-phenyl)-2-oxo-ethyl]-3,5,7-triaza-1-azonia-tricyclo[3.3.1.13,7]decane; bromide
115851-98-4

1-[2-(3-Benzyloxy-phenyl)-2-oxo-ethyl]-3,5,7-triaza-1-azonia-tricyclo[3.3.1.13,7]decane; bromide

Conditions
ConditionsYield
In diethyl ether; chloroform Ambient temperature;100%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

1,4-bis(chloromethyl)-2,5-dimethoxybenzene
3752-97-4

1,4-bis(chloromethyl)-2,5-dimethoxybenzene

1,1'-(2,5-dimethoxy-p-xylylene)-bis-hexamethylenetetraminium; dichloride
114558-97-3

1,1'-(2,5-dimethoxy-p-xylylene)-bis-hexamethylenetetraminium; dichloride

Conditions
ConditionsYield
In dichloromethane for 16h; Heating;100%
In chloroform 1.) reflux, 30 min, 2.) r.t., overnight;
In chloroform at 90℃; for 24h;
hexamethylenetetramine
100-97-0

hexamethylenetetramine

4-Nitrophenacyl bromide
99-81-0

4-Nitrophenacyl bromide

(4-nitrophenacyl)hexaminium bromide
88260-40-6

(4-nitrophenacyl)hexaminium bromide

Conditions
ConditionsYield
In chloroform for 2h;100%
In chloroform at 20℃; for 12h; Delepine reaction;
hexamethylenetetramine
100-97-0

hexamethylenetetramine

2-chloro-N-(4-chlorophenyl)acetamide
3289-75-6

2-chloro-N-(4-chlorophenyl)acetamide

N,N'-methylenebis<3-(4-chlorophenyl)>-4-imidazolidinone
79988-56-0

N,N'-methylenebis<3-(4-chlorophenyl)>-4-imidazolidinone

Conditions
ConditionsYield
In ethanol 60 deg C, 1 h, then reflux, 1.5 h;100%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

methyl iodide
74-88-4

methyl iodide

N-methylhexamethylenetetrammonium iodide
50982-79-1

N-methylhexamethylenetetrammonium iodide

Conditions
ConditionsYield
In chloroform at 20℃;100%
at 80℃; for 7h; Temperature;95.8%
In ethanol
In chloroform
hexamethylenetetramine
100-97-0

hexamethylenetetramine

4-tert-butyl-2-(diphenyl-phosphinoyl)-phenol
60254-03-7

4-tert-butyl-2-(diphenyl-phosphinoyl)-phenol

5-tert-butyl-3-(diphenyl-phosphinoyl)-2-hydroxy-benzaldehyde

5-tert-butyl-3-(diphenyl-phosphinoyl)-2-hydroxy-benzaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid for 20h; Heating;100%
1-benzo[1,3]dioxol-5-yl-2-(2,5-dichloro-phenyl)-ethane-1,2-dione
858037-60-2

1-benzo[1,3]dioxol-5-yl-2-(2,5-dichloro-phenyl)-ethane-1,2-dione

hexamethylenetetramine
100-97-0

hexamethylenetetramine

5-benzo[1,3]dioxol-5-yl-4-(2,5-dichloro-phenyl)-1H-imidazole
858037-61-3

5-benzo[1,3]dioxol-5-yl-4-(2,5-dichloro-phenyl)-1H-imidazole

Conditions
ConditionsYield
With ammonium acetate In acetic acid at 95℃; for 2.5h;100%
2-(2-Hydroxyphenyl)benzoxazole
835-64-3

2-(2-Hydroxyphenyl)benzoxazole

hexamethylenetetramine
100-97-0

hexamethylenetetramine

5-(1,3-benzoxazol-2-yl)-4-hydroxyisophthalic aldehyde
1275589-01-9

5-(1,3-benzoxazol-2-yl)-4-hydroxyisophthalic aldehyde

Conditions
ConditionsYield
With trifluoroacetic acid for 48h; Reflux;100%
With acetic acid In toluene for 18h; Duff reaction; Reflux;91%
With trifluoroacetic acid Reflux;91%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

2-chloro-1,4-dimethoxybenzene
2100-42-7

2-chloro-1,4-dimethoxybenzene

2,5-dimethoxy-4-chlorobenzaldehyde
90064-48-5

2,5-dimethoxy-4-chlorobenzaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid at 95℃; for 5h;100%
With trifluoroacetic acid at 95℃;72.7%
Ethyl 4-hydroxybenzoate
120-47-8

Ethyl 4-hydroxybenzoate

hexamethylenetetramine
100-97-0

hexamethylenetetramine

3,5-diformyl-4-hydroxybenzoic acid ethyl ester
329904-04-3

3,5-diformyl-4-hydroxybenzoic acid ethyl ester

Conditions
ConditionsYield
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
100-97-0

hexamethylenetetramine

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

3,5-diformyl-4-hydroxybenzoic acid
1384440-57-6

3,5-diformyl-4-hydroxybenzoic acid

Conditions
ConditionsYield
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%
cyclopentadienecarboxylic acid manganese tricarbonyl

cyclopentadienecarboxylic acid manganese tricarbonyl

hexamethylenetetramine
100-97-0

hexamethylenetetramine

C9H5MnO5*C6H12N4
1416228-92-6

C9H5MnO5*C6H12N4

Conditions
ConditionsYield
In methanol at 20 - 60℃; Darkness;100%
α-chloro-2',5'-difluoroacetophenone
60468-36-2

α-chloro-2',5'-difluoroacetophenone

hexamethylenetetramine
100-97-0

hexamethylenetetramine

1-(2,5-difluorophenyl)ethanone-2-hexamethylentetrammonium chloride

1-(2,5-difluorophenyl)ethanone-2-hexamethylentetrammonium chloride

Conditions
ConditionsYield
In chloroform Solvent; Temperature; Reflux;100%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

2-bromo-1-cyclopropylethan-1-one
69267-75-0

2-bromo-1-cyclopropylethan-1-one

1-(2-cyclopropyl-2-oxoethyl)-3,5,7-triaza-1-azoniatricyclo[3.3.1.13,7]decane bromide

1-(2-cyclopropyl-2-oxoethyl)-3,5,7-triaza-1-azoniatricyclo[3.3.1.13,7]decane bromide

Conditions
ConditionsYield
In chloroform at 20℃; for 12h;100%
In chloroform at 20℃; for 12h;100%
E/Z-1,3-Dichloropropene
542-75-6

E/Z-1,3-Dichloropropene

hexamethylenetetramine
100-97-0

hexamethylenetetramine

1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride

1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride

Conditions
ConditionsYield
In chloroform at 60℃; for 12h;99.9%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

2,4-difluorobenzyl chloride
452-07-3

2,4-difluorobenzyl chloride

(2,4-difluoro-benzyl)-hexamethylenetetraminium; chloride

(2,4-difluoro-benzyl)-hexamethylenetetraminium; chloride

Conditions
ConditionsYield
In toluene for 2h; Solvent; Reflux; Industrial scale;99.9%
1,1,2,3-Tetrachloropropene
10436-39-2

1,1,2,3-Tetrachloropropene

hexamethylenetetramine
100-97-0

hexamethylenetetramine

N-β,γ,γ-trichloroallylhexamethylenetetramine chloride

N-β,γ,γ-trichloroallylhexamethylenetetramine chloride

Conditions
ConditionsYield
In chloroform at 60℃; for 12h;99.6%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

tris-(chloromethyl)amine
16395-67-8

tris-(chloromethyl)amine

Conditions
ConditionsYield
With phosphorus pentachloride at 100℃; for 5.5h; Neat (no solvent);99%
With phosphorus pentachloride
With phosphorus pentachloride
2-bromoacetyl-1-methyl-5-nitropyrrole
63158-38-3

2-bromoacetyl-1-methyl-5-nitropyrrole

hexamethylenetetramine
100-97-0

hexamethylenetetramine

1-[2-(1-methyl-5-nitro-1H-pyrrol-2-yl)-2-oxo-ethyl]-3,5,7-triaza-1-azonia-tricyclo[3.3.1.13,7]decane; bromide

1-[2-(1-methyl-5-nitro-1H-pyrrol-2-yl)-2-oxo-ethyl]-3,5,7-triaza-1-azonia-tricyclo[3.3.1.13,7]decane; bromide

Conditions
ConditionsYield
In chloroform Alkylation;99%
In chloroform99%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

2-bromo-1-[5-fluoro-2-(methylthio)phenyl]ethanone
256950-23-9

2-bromo-1-[5-fluoro-2-(methylthio)phenyl]ethanone

1-[5-fluoro-2-(methylthio)phenyl]ethanone-2-hexaminium bromide

1-[5-fluoro-2-(methylthio)phenyl]ethanone-2-hexaminium bromide

Conditions
ConditionsYield
In chloroform at 20℃;99%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

2-Bromo-1-(3,4-dimethoxyphenyl)ethanone
1835-02-5

2-Bromo-1-(3,4-dimethoxyphenyl)ethanone

2-hexamethylenetetramino-1-(3,4-dimethoxyphenyl)ethanone-2-ium bromide
1234216-77-3

2-hexamethylenetetramino-1-(3,4-dimethoxyphenyl)ethanone-2-ium bromide

Conditions
ConditionsYield
In chloroform at 20℃; for 4h;99%
In chloroform at 20℃;
hexamethylenetetramine
100-97-0

hexamethylenetetramine

C76H120O4
1528493-04-0

C76H120O4

C78H120O6
1528492-99-0

C78H120O6

Conditions
ConditionsYield
Stage #1: hexamethylenetetramine; C76H120O4 With trifluoroacetic acid at 125℃; for 4h;
Stage #2: With hydrogenchloride; water In dichloromethane at 20℃; for 3h;
99%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

4-Bromoacetyl-1-(t-butoxycarbonyl)piperidine
301221-79-4

4-Bromoacetyl-1-(t-butoxycarbonyl)piperidine

1-[2-(1-tert-butoxycarbonyl-piperidin-4-yl)-2-oxo-ethyl]-3,5,7-triaza-1-azonia-tricyclo[3.3.1.13,7]decane bromide

1-[2-(1-tert-butoxycarbonyl-piperidin-4-yl)-2-oxo-ethyl]-3,5,7-triaza-1-azonia-tricyclo[3.3.1.13,7]decane bromide

Conditions
ConditionsYield
In chloroform at 50℃; for 1h;99%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

(Z)-3-chloro-2-fl uoro-1-phenylpropene

(Z)-3-chloro-2-fl uoro-1-phenylpropene

(Z)-N-(2-fluoro-3-phenylallyl)urotropinium chloride

(Z)-N-(2-fluoro-3-phenylallyl)urotropinium chloride

Conditions
ConditionsYield
In dichloromethane for 24h; Reflux;99%
6-ethyl-1H-pyrrolo[2,3-b]pyridine
533939-04-7

6-ethyl-1H-pyrrolo[2,3-b]pyridine

hexamethylenetetramine
100-97-0

hexamethylenetetramine

6-ethyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

6-ethyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Conditions
ConditionsYield
With acetic acid In water at 120℃; for 8h;99%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

2-bromo-1-(tetrahydro-2H-pyran-3-yl)ethan-1-one

2-bromo-1-(tetrahydro-2H-pyran-3-yl)ethan-1-one

rac-1-{2-[oxan-3-yl]-2-oxoethyl}-1,3,5,7-tetraazatricyclo[3.3.1.13,7]decan-1-ium bromide

rac-1-{2-[oxan-3-yl]-2-oxoethyl}-1,3,5,7-tetraazatricyclo[3.3.1.13,7]decan-1-ium bromide

Conditions
ConditionsYield
In chloroform at 20℃; for 12h;99%
7-Azaindole
271-63-6

7-Azaindole

hexamethylenetetramine
100-97-0

hexamethylenetetramine

1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde
4649-09-6

1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde

Conditions
ConditionsYield
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%

Hexamethylenetetramine Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Hexamethylenetetramine Standards and Recommendations

DOT Classification:  4.1; Label: Flammable Solid

Hexamethylenetetramine Specification

The Hexamethylenetetramine is an organic compound with the formula C6H12N4. The systematic name of this chemical is 1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane. With the CAS registry number 100-97-0, it is also named as 1,3,5,7-tetraazaadamantane. The product's categories are Organics; Amination; Synthetic Organic Chemistry; Organic Chemicals. Besides, it is a white crystalline powder, which should be stored in a cool and ventilated place.

The Hexamethylenetetramine is used in the plastics indusrty, as a solid fuel and in some drugs. The term methenamine (an International Nonproprietary Name) is more common in its medicinal uses, and hexamine is more common in commercial uses. The primary use of Hexamethylenetetramine is in the manufacture of powdery or liquid preparations of phenolic resins and phenolic resin moulding compounds, where hexamine is added as a hardening component. These products are used as binders, e.g. in brake and clutch linings, abrasive products, non-woven textiles, formed parts produced by moulding processes, and fireproof materials. Hexamethylenetetramine is also used as an accelerator for rubber. It is used to some extent in medicine as an internal.

Physical properties about Hexamethylenetetramine are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 12.039; (4)ACD/KOC (pH 7.4): 19.127; (5)#H bond acceptors: 4; (6)Polar Surface Area: 12.96 Å2; (7)Index of Refraction: 1.731; (8)Molar Refractivity: 39.223 cm3; (9)Molar Volume: 98.175 cm3; (10)Polarizability: 15.549×10-24cm3; (11)Surface Tension: 73.069 dyne/cm; (12)Density: 1.428 g/cm3; (13)Flash Point: 103.945 °C; (14)Enthalpy of Vaporization: 49.006 kJ/mol; (15)Boiling Point: 252.704 °C at 760 mmHg; (16)Vapour Pressure: 0.019 mmHg at 25°C.

Preparation: this chemical can be prepared by 1,3,5,7-tetranitro-[1,3,5,7]tetrazocane. This reaction will need reagent 1-benzyl-1,4-dihydronicotinamide (BNAH, 1) and solvent dimethylformamide. The reaction time is 24 hours. The yield is about 100%.



Uses of Hexamethylenetetramine: it can be used to produce 5-tert-butyl-2-hydroxy-isophthalaldehyde by heating. It will need reagent TFA with reaction time of 24 hours. The yield is about 65%.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable. Besides, this chemical may cause sensitisation by inhalation and skin contact. When you are using it, Wear suitable gloves, do not breathe dust, avoid contact with skin and keep away from sources of ignition - No smoking.

You can still convert the following datas into molecular structure:
(1)SMILES: C1N2CN3CN1CN(C2)C3
(2)InChI: InChI=1/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2 CopyCopied
(3)InChIKey: VKYKSIONXSXAKP-UHFFFAOYAW
(4)Std. InChI: InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
(5)Std. InChIKey: VKYKSIONXSXAKP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo parenteral 200mg/kg (200mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
cat LDLo subcutaneous 200mg/kg (200mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 84, 1955.
guinea pig LDLo subcutaneous 300mg/kg (300mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 84, 1955.
mammal (species unspecified) LDLo parenteral 300mg/kg (300mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
mouse LD50 intravenous 17700uL/kg (17.7mL/kg)   Antibiotiki. Vol. 20, Pg. 891, 1975.
mouse LD50 oral 569mg/kg (569mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 35(3), Pg. 115, 1970.
mouse LD50 subcutaneous 215mg/kg (215mg/kg) BEHAVIORAL: TREMOR

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 225, Pg. 428, 1955.
mouse LDLo parenteral 450mg/kg (450mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
rat LD50 intravenous 9200mg/kg (9200mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 221, Pg. 166, 1954.
rat LDLo parenteral 200mg/kg (200mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
rat LDLo subcutaneous 200mg/kg (200mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 84, 1955.

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