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Basic Information
CAS No.: 283-66-9
Name: HMTD
Molecular Structure:
Molecular Structure of 283-66-9 (HMTD)
Formula: C6H12 N2 O6
Molecular Weight: 208.171
Synonyms: HMTD;Hexamethylenetriperoxidediamine
Density: 1.46g/cm3
Melting Point: Decomposes at 75 °C, Ignites spontaneously at 133 °C
Boiling Point: 229.1°Cat760mmHg
Flash Point: 65.7°C
Appearance: White crystalline solid
Safety: The dry material is a powerful explosive that is heat- and shock-sensitive. Explodes on contact with bromine or sulfuric acid. When heated to decomposition it emits toxic fumes of NOx. See also PEROXIDES, INORGANIC; PEROXIDES, ORGANIC.
PSA: 61.86000
LogP: -0.91700
Synthetic route
100-97-0

hexamethylenetetramine

283-66-9

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

Conditions
ConditionsYield
With dihydrogen peroxide; citric acid for 3h; 1) 4 deg C, 3 h;57%
With dihydrogen peroxide; citric acid at 0℃; for 8h;55%
With dihydrogen peroxide; citric acid
50-00-0

formaldehyd

283-66-9

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

Conditions
ConditionsYield
With ammonium sulfate; dihydrogen peroxide at 55℃;
17088-73-2

bis-hydroxymethyl peroxide

283-66-9

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

Conditions
ConditionsYield
With ammonia
14002-32-5

tris-(hydroxymethyl)amine

283-66-9

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

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid at 20℃;

hexamethylenetetramine

283-66-9

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

Conditions
ConditionsYield
With dihydrogen peroxide In water at 0℃;
283-66-9

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

1,2,6,7,4,9-Tetraoxadiazaperhydroecine-4,9-dicarbaldehyde

Conditions
ConditionsYield
With oxygen In acetic acid butyl ester at 120℃; for 1h;10%
With oxygen In various solvent(s)
283-66-9

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

74-90-8

hydrogen cyanide

283-66-9

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

7782-77-6

cis-nitrous acid

74-90-8

hydrogen cyanide

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

283-66-9

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

diluted acid

diluted acid

A

17088-73-2

bis-hydroxymethyl peroxide

B

7664-41-7

ammonia

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Chemistry

IUPAC Name: 3,4,8,9,12,13-Hexaoxa-1,6-diazabicyclo[4.4.4]tetradecane
The molecular formula of Hexamethylenetriperoxidediamine (CAS NO.283-66-9) is C6H12N2O6.

                                             
The molecular weight of Hexamethylenetriperoxidediamine (CAS NO.283-66-9) is 208.17.
Synonyms of Hexamethylenetriperoxidediamine (CAS NO.283-66-9): 3,4,8,9,12,13-Hexaoxa-1,6-diazabicyclo[4.4.4]tetradecane ; Hexamethylene triperoxide diamine
Appearance: White crystalline solid
Enthalpy of Vaporization: 46.57 kJ/mol
Index of Refraction: 1.532 
Density: 1.46 g/ml 
Flash Point: 65.7 °C   
Boiling Point: 229.1 °C

Uses

Despite no longer being used in any official application,Hexamethylenetriperoxidediamine (CAS NO.283-66-9) remains a fairly popular home-made explosive and has been used in a large number of suicide bombings throughout the world, and was possibly used in the 7 July 2005 London bombings.The New York Times reported it as the planned explosive in the 2006 transatlantic aircraft plot.

Production

 HMTD may be prepared by the reaction of an aqueous solution of hydrogen peroxide and hexamine in the presence of citric acid or dilute sulfuric acid as a catalyst.Like other organic peroxides such as acetone peroxide, HMTD is an unstable compound that is sensitive to shock, friction, and heat. This makes the substance extremely dangerous to manufacture. It also reacts with most common metals, which can lead to detonation. HMTD is very stable when pure (acid free) and does not quickly sublime like its acetone counterparts.

Safety Profile

The dry material is a powerful explosive that is heat- and shock-sensitive. Explodes on contact with bromine or sulfuric acid. When heated to decomposition it emits toxic fumes of NOx. See also PEROXIDES, INORGANIC; PEROXIDES, ORGANIC.

Standards and Recommendations

DOT Classification:  Forbidden

Specification

It is a high explosive organic compound, first synthesised in 1885 by Legler. The theorised structure lent itself well to acting as an initiating, or primary explosive. While still quite sensitive to shock and friction, it was relatively stable compared to other initiating explosives of the time, such as mercury fulminate, and proved to be relatively inexpensive and easy to synthesise. As such, it was quickly taken up as a primary explosive in mining applications. However, it has since been superseded by even more stable compounds such as tetryl.