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Synthetic route

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
Stage #1: hexamethylenetetramine With nitric acid at 20℃; for 0.666667h;
Stage #2: With sodium nitrite at 20 - 70℃;
82%
With ammonium nitrate; Iron(III) nitrate nonahydrate; nitric acid; acetic anhydride69%
With nitric acid
hexamethylenetetramine
100-97-0

hexamethylenetetramine

acetic anhydride
108-24-7

acetic anhydride

ethanolamine
141-43-5

ethanolamine

A

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe
71545-63-6

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe

B

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

C

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane
76237-14-4

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane

Conditions
ConditionsYield
With nitric acid In acetic acid at 50 - 60℃; for 1.5h;A n/a
B n/a
C 75%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

ethanolamine
141-43-5

ethanolamine

A

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe
71545-63-6

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe

B

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

C

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane
76237-14-4

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane

Conditions
ConditionsYield
With nitric acid In acetic anhydride; acetic acid at 50 - 60℃; for 1.5h;A n/a
B n/a
C 75%
diammonium 1,3,5,7-tetraazabicyclo[3.3.1]nonane-3,7-disulfonate sulfate

diammonium 1,3,5,7-tetraazabicyclo[3.3.1]nonane-3,7-disulfonate sulfate

A

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

B

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

Conditions
ConditionsYield
With ammonium nitrate; nitric acid In acetic anhydride; acetic acid at 70℃; for 0.333333h;A 70%
B 30%
1,3,5-tripropionylperhydro-1,3,5-triazine
30805-19-7

1,3,5-tripropionylperhydro-1,3,5-triazine

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With nitric acid; trifluoroacetic anhydride In nitromethane at 0 - 20℃; for 4h;63%
1,3,5-tris(2-hydroxyethyl)-1,3,5-triazacyclohexane
4719-04-4

1,3,5-tris(2-hydroxyethyl)-1,3,5-triazacyclohexane

acetic anhydride
108-24-7

acetic anhydride

A

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe
71545-63-6

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe

B

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

C

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane
76237-14-4

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane

Conditions
ConditionsYield
With ammonium nitrate; nitric acid In chloroform at 55 - 60℃; for 1h;A 41.3%
B n/a
C 62%
1,3,5-tris(2-hydroxyethyl)-1,3,5-triazacyclohexane
4719-04-4

1,3,5-tris(2-hydroxyethyl)-1,3,5-triazacyclohexane

A

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe
71545-63-6

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe

B

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

C

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane
76237-14-4

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane

Conditions
ConditionsYield
With ammonium nitrate; nitric acid In chloroform; acetic anhydride at 55 - 60℃; for 1h;A 41.3%
B n/a
C 62%
3,7-diacetyl-1,3,5,7-tetraaza-bicyclo[3.3.1]nonane
32516-05-5

3,7-diacetyl-1,3,5,7-tetraaza-bicyclo[3.3.1]nonane

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With ammonium nitrate; copper(II) nitrate trihydrate; nitric acid; acetic anhydride at 65℃; for 4h; Molecular sieve;62%
1,3,5-tri-acetyl-1,3,5-triaza cyclohexane
26028-46-6

1,3,5-tri-acetyl-1,3,5-triaza cyclohexane

A

1-acetyl-3,5-dinitrohexahydro-1,3,5-triazine
14168-42-4

1-acetyl-3,5-dinitrohexahydro-1,3,5-triazine

B

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With ammonium nitrate; trifluoroacetic anhydride In nitromethane for 0.75h; Ambient temperature;A 61%
B 8%
acetic anhydride
108-24-7

acetic anhydride

C5H11N3O7S2(2-)*2K(1+)

C5H11N3O7S2(2-)*2K(1+)

A

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

B

1,3-dinitro-5-(2-nitro-ethyl)-[1,3,5]triazinane

1,3-dinitro-5-(2-nitro-ethyl)-[1,3,5]triazinane

C

C7H13N7O10

C7H13N7O10

Conditions
ConditionsYield
With nitric acid at 8 - 25℃; for 0.5h; Nitration; Acetoxylation;A n/a
B 41%
C 48%
acetic anhydride
108-24-7

acetic anhydride

C6H13N3O7S2(2-)*2K(1+)

C6H13N3O7S2(2-)*2K(1+)

A

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

B

1,3-dinitro-5-(3-nitro-propyl)-[1,3,5]triazinane

1,3-dinitro-5-(3-nitro-propyl)-[1,3,5]triazinane

C

C8H15N7O10

C8H15N7O10

Conditions
ConditionsYield
With nitric acid at 8 - 25℃; for 0.5h; Nitration; Acetoxylation;A n/a
B 36%
C 45%
acetic anhydride
108-24-7

acetic anhydride

dipotassium 1-methyl-1,3,5-triazacyclohexane-3,5-disulfonate

dipotassium 1-methyl-1,3,5-triazacyclohexane-3,5-disulfonate

A

1-acetoxy-2,4,6-trinitro-2,4,6-triazaheptane
14133-70-1

1-acetoxy-2,4,6-trinitro-2,4,6-triazaheptane

B

1-methyl-3,5-dinitro-1,3,5-triazacyclohexane
98019-34-2

1-methyl-3,5-dinitro-1,3,5-triazacyclohexane

C

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

D

1-acetoxy-2,4-dinitro-2,4-diazapentane

1-acetoxy-2,4-dinitro-2,4-diazapentane

Conditions
ConditionsYield
With nitric acid at 8 - 25℃; for 0.5h; Nitration; Acetoxylation;A 39%
B 4%
C n/a
D n/a
acetic anhydride
108-24-7

acetic anhydride

C5H11N3O6S2(2-)*2K(1+)

C5H11N3O6S2(2-)*2K(1+)

A

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-octane
117920-64-6

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-octane

B

1-ethyl-3,5-dinitro-hexahydro-[1,3,5]triazine
99512-95-5

1-ethyl-3,5-dinitro-hexahydro-[1,3,5]triazine

C

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With nitric acid at 8 - 25℃; for 0.5h; Nitration; Acetoxylation;A 38%
B 30%
C n/a
diammonium 1,3,5,7-tetraazabicyclo[3.3.1]nonane-3,7-disulfonate sulfate

diammonium 1,3,5,7-tetraazabicyclo[3.3.1]nonane-3,7-disulfonate sulfate

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With nitric acid at -40℃; for 1.5h;38%
acetic anhydride
108-24-7

acetic anhydride

C7H15N3O6S2(2-)*2K(1+)

C7H15N3O6S2(2-)*2K(1+)

A

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

B

1-butyl-3,5-dinitro-[1,3,5]triazinane

1-butyl-3,5-dinitro-[1,3,5]triazinane

C

C9H18N6O8

C9H18N6O8

Conditions
ConditionsYield
With nitric acid at 8 - 25℃; for 0.5h; Nitration; Acetoxylation;A n/a
B 25%
C 35%
N,N'-methylene-bis(oxazolidine)
66204-43-1

N,N'-methylene-bis(oxazolidine)

A

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe
71545-63-6

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe

B

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

C

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane
76237-14-4

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane

Conditions
ConditionsYield
With ammonium nitrate; nitric acid In acetic anhydride at 50 - 60℃; for 1.5h; Yield given;A 27%
B n/a
C n/a
N,N'-methylene-bis(oxazolidine)
66204-43-1

N,N'-methylene-bis(oxazolidine)

acetic anhydride
108-24-7

acetic anhydride

A

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe
71545-63-6

1-acetoxy-2-nitro-2-aza-4-nitroxybutabe

B

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

C

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane
76237-14-4

1-acetoxy-2,4,6-trinitro-2,4,6-triaza-8-nitroxyoctane

Conditions
ConditionsYield
With ammonium nitrate; nitric acid at 50 - 60℃; for 1.5h; Yields of byproduct given;A 27%
B n/a
C n/a
With ammonium nitrate; nitric acid at 50 - 60℃; for 1.5h; Yield given;A 27%
B n/a
C n/a
formaldehyd
50-00-0

formaldehyd

MEDINA
14168-44-6

MEDINA

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With ammonium nitrate; acetic anhydride; acetic acid
formaldehyd
50-00-0

formaldehyd

aminomethyl-nitro-(nitroamino-methyl)-amine; nitrate

aminomethyl-nitro-(nitroamino-methyl)-amine; nitrate

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With acetic anhydride
formaldehyd
50-00-0

formaldehyd

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With ammonium nitrate; acetic anhydride
2-thia-1,3,5,7-tetraaza-adamantane-2,2-dioxide
7020-51-1

2-thia-1,3,5,7-tetraaza-adamantane-2,2-dioxide

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With nitric acid
1,3,5-trinitroso-1,3,5-triazinane
13980-04-6

1,3,5-trinitroso-1,3,5-triazinane

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With dihydrogen peroxide; nitric acid at -40℃;
hexamethylenetetramine
100-97-0

hexamethylenetetramine

Propionamid
79-05-0

Propionamid

A

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

B

1‑nitroso‑3,5,7‑trinitro‑1,3,5,7‑tetraazacyclooctane
5755-28-2

1‑nitroso‑3,5,7‑trinitro‑1,3,5,7‑tetraazacyclooctane

Conditions
ConditionsYield
With ammonium nitrate; nitric acid; acetic anhydride; acetic acid
1-nitroso-3,5-dinitro-1,3,5-triazacyclohexane
5755-27-1

1-nitroso-3,5-dinitro-1,3,5-triazacyclohexane

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With sulfuric acid; nitric acid
With dihydrogen peroxide; nitric acid at -40℃;
Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With ammonium nitrate; water; nitric acid; acetic anhydride
acetic anhydride
108-24-7

acetic anhydride

A

1-acetoxy-2,4,6-trinitro-7-nitryloxy-2,4,6-triaza-heptane

1-acetoxy-2,4,6-trinitro-7-nitryloxy-2,4,6-triaza-heptane

B

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With nitric acid
benzamide
55-21-0

benzamide

A

N,N'-methylenebisbenzamide
1575-94-6

N,N'-methylenebisbenzamide

B

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With ammonium nitrate; hexamethylenetetramine; nitric acid at 65℃; weiteres Reagens: Acetanhydrid, Essigsaeure;
hexamethylenetetramine
100-97-0

hexamethylenetetramine

A

3,7-dinitro-1,3,5,7-tetraaza-bicyclo[3.3.1]nonane
949-56-4

3,7-dinitro-1,3,5,7-tetraaza-bicyclo[3.3.1]nonane

B

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

Conditions
ConditionsYield
With nitric acid at 0 - 10℃; Mechanism; isotope labelling experiments;
With nitric acid at 0 - 10℃;
With (2S)-N-methyl-1-phenylpropan-2-amine hydrate; nitric acid 1.) 0 - 10 deg C; Multistep reaction;
3,4,8,9,12,13-Hexaoxa-1,6-diaza-bicyclo[4.4.4]tetradecane
283-66-9

3,4,8,9,12,13-Hexaoxa-1,6-diaza-bicyclo[4.4.4]tetradecane

nitric acid
7697-37-2

nitric acid

NH4NO3

NH4NO3

Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

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%
Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4

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

N,N'-dinitromethylenediamine dipotassium salt

N,N'-dinitromethylenediamine dipotassium salt

Conditions
ConditionsYield
With potassium hydroxide In ethanol; acetone at 20 - 30℃; for 1h;30%

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