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Name
HEXAHYDRO-1,3,5-TRINITRO-1,3,5-TRIAZINE
EINECS 204-500-1
CAS No. 121-82-4
Article Data42
CAS DataBase
Density 1.89g/cm³
Solubility insoluble
Melting Point 205 C
Formula C3H6 N6 O6
Boiling Point 747°Cat760mmHg
Molecular Weight 222.117
Flash Point 405.6°C
Transport Information
Appearance
Safety Poison by ingestion, intraperitoneal, and intravenous routes. An experimental teratogen. Other experimental reproductive effects. A corrosive irritant to skin, eyes, and mucous membranes. Cases of epileptiform convulsions have been reported from exposure. It is one of the most powerful high explosives in use today. Has more shattering power than TNT and is often mixed with TNT as a bursting charge for aerial bombs, mines, and torpedoes. It is easily initiated by mercury fulminate, which may be used as a booster. When heated to decomposition it emits toxic fumes of NO_x. See also AMINES, NITRATES, and EXPLOSIVES, HIGH.
Risk Codes 11-23/24/25-36/37/38
Molecular Structure
Hazard Symbols High explosive, easily initiated by mercury fulminate. Toxic by inhalation and skin contact. TLV: 1.5 mg/m³.
Synonyms s-Triazine,hexahydro-1,3,5-trinitro- (8CI);1,3,5-Triaza-1,3,5-trinitrocyclohexane;1,3,5-Trinitro-1,3,5-triazacyclohexane;1,3,5-Trinitrohexahydro-1,3,5-triazine;1,3,5-Trinitrohexahydro-s-triazine;1,3,5-Trinitroperhydro-1,3,5-triazine;A 3;A 3 (explosive);A-IX 1;A-IX 2;CH 6 (explosive);CPX 301;CX 84A;Composition A 3;Cyclonite;Cyclotrimethylenenitramine;Cyclotrimethylenetrinitramine;Giekfol;Heksoflen;Hexahydro-1,3,5-trinitro-1,3,5-s-triazine;Hexahydro-1,3,5-trinitro-1,3,5-triazine;Hexahydro-1,3,5-trinitro-s-triazine;Hexogen;Hexogen (explosive);Hexogen 5W;NSC 312447;PBX 9407;PBX(AF) 108;PBX-B 2238;PBX-C 117;PBX-L 3;PBX-L 5;PBX-MC;PBX-MVF;PBX-W 108;PBXC 116;PBXN 107;PBXN 107A;PBXN 108;PBXN 201;PBXN 6;PBXN 8;PBXN(AF) 108;PBXW108(E);PE 4;PE 4 (explosive);PHX 34;PMW 8;RDX;T4;TS 1;TS 1(propellant);Trimethylenetrinitramine;V 29;V 29 (propellant);
PSA 147.18000
LogP -0.26310

Synthetic route

: 100-97-0
hexamethylenetetramine

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

Conditions

Conditions	Yield
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 anhydride	69%
With nitric acid

: 100-97-0
hexamethylenetetramine

: 108-24-7
acetic anhydride

: 141-43-5
ethanolamine

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

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

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

Conditions

Conditions	Yield
With nitric acid In acetic acid at 50 - 60℃; for 1.5h;	A n/a B n/a C 75%

...Expand

: 100-97-0
hexamethylenetetramine

: 141-43-5
ethanolamine

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

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

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

Conditions

Conditions	Yield
With nitric acid In acetic anhydride; acetic acid at 50 - 60℃; for 1.5h;	A n/a B n/a C 75%

...Expand

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

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

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

Conditions

Conditions	Yield
With ammonium nitrate; nitric acid In acetic anhydride; acetic acid at 70℃; for 0.333333h;	A 70% B 30%

: 30805-19-7
1,3,5-tripropionylperhydro-1,3,5-triazine

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

Conditions

Conditions	Yield
With nitric acid; trifluoroacetic anhydride In nitromethane at 0 - 20℃; for 4h;	63%

: 4719-04-4
1,3,5-tris(2-hydroxyethyl)-1,3,5-triazacyclohexane

: 108-24-7
acetic anhydride

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

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

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

Conditions

Conditions	Yield
With ammonium nitrate; nitric acid In chloroform at 55 - 60℃; for 1h;	A 41.3% B n/a C 62%

...Expand

: 4719-04-4
1,3,5-tris(2-hydroxyethyl)-1,3,5-triazacyclohexane

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

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

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

Conditions

Conditions	Yield
With ammonium nitrate; nitric acid In chloroform; acetic anhydride at 55 - 60℃; for 1h;	A 41.3% B n/a C 62%

...Expand

: 32516-05-5
3,7-diacetyl-1,3,5,7-tetraaza-bicyclo[3.3.1]nonane

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

Conditions

Conditions	Yield
With ammonium nitrate; copper(II) nitrate trihydrate; nitric acid; acetic anhydride at 65℃; for 4h; Molecular sieve;	62%

: 26028-46-6
1,3,5-tri-acetyl-1,3,5-triaza cyclohexane

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

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

Conditions

Conditions	Yield
With ammonium nitrate; trifluoroacetic anhydride In nitromethane for 0.75h; Ambient temperature;	A 61% B 8%

: 108-24-7
acetic anhydride

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

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

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

C: C7H13N7O10

Conditions

Conditions	Yield
With nitric acid at 8 - 25℃; for 0.5h; Nitration; Acetoxylation;	A n/a B 41% C 48%

...Expand

: 108-24-7
acetic anhydride

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

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

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

C: C8H15N7O10

Conditions

Conditions	Yield
With nitric acid at 8 - 25℃; for 0.5h; Nitration; Acetoxylation;	A n/a B 36% C 45%

...Expand

: 108-24-7
acetic anhydride

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

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

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

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

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

Conditions

Conditions	Yield
With nitric acid at 8 - 25℃; for 0.5h; Nitration; Acetoxylation;	A 39% B 4% C n/a D n/a

...Expand

: 108-24-7
acetic anhydride

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

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

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

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

Conditions

Conditions	Yield
With nitric acid at 8 - 25℃; for 0.5h; Nitration; Acetoxylation;	A 38% B 30% C n/a

...Expand

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

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

Conditions

Conditions	Yield
With nitric acid at -40℃; for 1.5h;	38%

: 108-24-7
acetic anhydride

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

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

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

C: C9H18N6O8

Conditions

Conditions	Yield
With nitric acid at 8 - 25℃; for 0.5h; Nitration; Acetoxylation;	A n/a B 25% C 35%

...Expand

: 66204-43-1
N,N'-methylene-bis(oxazolidine)

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

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

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

Conditions

Conditions	Yield
With ammonium nitrate; nitric acid In acetic anhydride at 50 - 60℃; for 1.5h; Yield given;	A 27% B n/a C n/a

...Expand

: 66204-43-1
N,N'-methylene-bis(oxazolidine)

: 108-24-7
acetic anhydride

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

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

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

Conditions

Conditions	Yield
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

...Expand

: 50-00-0
formaldehyd

: 14168-44-6
MEDINA

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

Conditions

Conditions	Yield
With ammonium nitrate; acetic anhydride; acetic acid

: 50-00-0
formaldehyd

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

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

Conditions

Conditions	Yield
With acetic anhydride

: 50-00-0
formaldehyd

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

Conditions

Conditions	Yield
With ammonium nitrate; acetic anhydride

: 7020-51-1
2-thia-1,3,5,7-tetraaza-adamantane-2,2-dioxide

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

Conditions

Conditions	Yield
With nitric acid

: 13980-04-6
1,3,5-trinitroso-1,3,5-triazinane

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

Conditions

Conditions	Yield
With dihydrogen peroxide; nitric acid at -40℃;

: 100-97-0
hexamethylenetetramine

: 79-05-0
Propionamid

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

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

Conditions

Conditions	Yield
With ammonium nitrate; nitric acid; acetic anhydride; acetic acid

...Expand

: 5755-27-1
1-nitroso-3,5-dinitro-1,3,5-triazacyclohexane

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

Conditions

Conditions	Yield
With sulfuric acid; nitric acid
With dihydrogen peroxide; nitric acid at -40℃;

: 18423-20-6, 18423-21-7, 75853-48-4, 84376-11-4, 94388-82-6
hexamethylenetetramine; dinitrate

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

Conditions

Conditions	Yield
With ammonium nitrate; water; nitric acid; acetic anhydride

: 18423-20-6, 18423-21-7, 75853-48-4, 84376-11-4, 94388-82-6
hexamethylenetetramine; dinitrate

: 108-24-7
acetic anhydride

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

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

Conditions

Conditions	Yield
With nitric acid

...Expand

: 55-21-0
benzamide

A: 1575-94-6
N,N'-methylenebisbenzamide

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

Conditions

Conditions	Yield
With ammonium nitrate; hexamethylenetetramine; nitric acid at 65℃; weiteres Reagens: Acetanhydrid, Essigsaeure;

: 100-97-0
hexamethylenetetramine

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

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

Conditions

Conditions	Yield
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;

: 283-66-9
3,4,8,9,12,13-Hexaoxa-1,6-diaza-bicyclo[4.4.4]tetradecane

: 7697-37-2
nitric acid

NH4NO3: NH4NO3

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

...Expand

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

: 100-97-0
hexamethylenetetramine

Conditions

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

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

: N,N'-dinitromethylenediamine dipotassium salt

Conditions

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

CYCLONITE Chemical Properties

Cyclonite's Molecular formula: C₃H₆N₆O₆
Cyclonite's Molar mass: 222.12 g.mol^-1
Appearance: Colorless crystals
Density: 1.82 g/cm³
Melting point: 205.5 °C, 479 K, 402 °F
Boiling point: 234 °C, 507 K, 453 °F
Other names: RDX;1,3,5-Trinitro-1,3,5-triazacyclohexane

CYCLONITE History

The discovery of cyclonite dates from 1898 when Georg Friedrich Henning obtained a German patent (patent No. 104280) for its manufacture, by nitrating hexamethylenetetramine. In this patent, its properties as an explosive were at length described, as well as its possible use as a medical compound mentioned. Research and development were not published further until G. C. V. Herz obtained a British patent in 1921 and a U.S. patent in 1922, for its manufacture by nitrating hexamethylenetetramine. Later in the 1920s cyclonite was produced by the direct nitration of hexamine.

CYCLONITE Uses

Cyclonite is an explosive nitroamine widely used in military and industrial applications.
As an explosive, cyclonite is usually used in mixtures with other explosives and plasticizers, phlegmatizers or desensitizers.
Cyclonite is also used as a major component of many plastic bonded explosives used in nuclear weapons.

CYCLONITE Toxicity Data With Reference

1.	orl-cld TDLo: 85 mg/kg	JTCTDW Journal of Toxicology, Clinical Toxicology. 24 (1986),305.
2.	orl-rat LD50:100 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 39 (1977),531.
3.	ipr-rat LDLo:10 mg/kg	EATR** U.S. Army, Edgewood Arsenal Technical Report. (Aberdeen Proving Ground, MD 21010) EB-TR-73040 .
4.	ivn-rat LDLo:18 mg/kg	EATR** U.S. Army, Edgewood Arsenal Technical Report. (Aberdeen Proving Ground, MD 21010) EB-TR-73040 .
5.	orl-mus LD50:59 mg/kg	NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD-A092-531 .
6.	ivn-mus LD50:19 mg/kg	EATR** U.S. Army, Edgewood Arsenal Technical Report. (Aberdeen Proving Ground, MD 21010) EB-TR-73040 .
7.	orl-cat LDLo:100 mg/kg	FATOAO Farmakologiya i Toksikologiya (Moscow). 7 (1944),43.
8.	orl-rbt LDLo:500 mg/kg	FATOAO Farmakologiya i Toksikologiya (Moscow). 7 (1944),43.
9.	ivn-gpg LD50:25 mg/kg	EATR** U.S. Army, Edgewood Arsenal Technical Report. (Aberdeen Proving Ground, MD 21010) EB-TR-73040 .

CYCLONITE Consensus Reports

Reported in EPA TSCA Inventory.

CYCLONITE Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. An experimental teratogen. Other experimental reproductive effects. A corrosive irritant to skin, eyes, and mucous membranes. Cases of epileptiform convulsions have been reported from exposure. It is one of the most powerful high explosives in use today. Has more shattering power than TNT and is often mixed with TNT as a bursting charge for aerial bombs, mines, and torpedoes. It is easily initiated by mercury fulminate, which may be used as a booster. When heated to decomposition it emits toxic fumes of NO_x. See also AMINES, NITRATES, and EXPLOSIVES, HIGH.

CYCLONITE Standards and Recommendations

OSHA PEL: TWA 1.5 mg/m³ (skin)
ACGIH TLV: TWA 0.5 mg/m³ (skin); Not Classifiable as a Human Carcinogen
DOT Classification: EXPLOSIVE 1.1D; Label: EXPLOSIVE 1.1D

Product Name

HEXAHYDRO-1,3,5-TRINITRO-1,3,5-TRIAZINE

Synthetic route

CYCLONITE Chemical Properties

CYCLONITE History

CYCLONITE Uses

CYCLONITE Toxicity Data With Reference

CYCLONITE Consensus Reports

CYCLONITE Safety Profile

CYCLONITE Standards and Recommendations

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