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100-97-0

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Basic Information
CAS No.: 100-97-0
Name: Hexamethylenetetramine
Article Data: 93
Molecular Structure:
Molecular Structure of 100-97-0 (Hexamethylenetetramine)
Formula: C6H12N4
Molecular Weight: 140.188
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;
EINECS: 202-905-8
Density: 1.428 g/cm3
Melting Point: 280 °C (subl.)(lit.)
Boiling Point: 252.704 °C at 760 mmHg
Flash Point: 103.945 °C
Solubility: 895 g/L (20 °C)
Appearance: white crystalline powder
Hazard Symbols: FlammableF,HarmfulXn
Risk Codes: 11-42/43
Safety: 16-22-24-37
Transport Information: UN 1328 4.1/PG 3
PSA: 12.96000
LogP: -1.26820
Synthetic route
2691-41-0

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

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%
121-82-4

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

100-97-0

hexamethylenetetramine

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

C17H30B2O2

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%
50-00-0

formaldehyd

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
50-00-0

formaldehyd

999-97-3

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

A

107-46-0

Hexamethyldisiloxane

B

100-97-0

hexamethylenetetramine

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

formaldehyd

A

5962-66-3

1,3,5-dithiazinane

B

281-20-9

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

C

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%
2035-89-4

N-methyl-N-(methyleneamino)methanamine

107-13-1

acrylonitrile

A

34714-77-7

dimethylaminomethyleneacetonitrile

B

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

A

691-24-7

1,3-di-tert-butylcarbodiimide

B

100-97-0

hexamethylenetetramine

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

2-Aminomethylbenzimidazole

75-09-2

dichloromethane

A

100-97-0

hexamethylenetetramine

B

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%
34557-54-5

methane

100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With ammonia; oxygen; copper at 500 - 700℃;
With silver copper; ammonia; oxygen at 500 - 700℃;
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Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Standards and Recommendations

DOT Classification:  4.1; Label: Flammable Solid

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.