Hexamethylenetetramine
- CAS No.
- 100-97-0
- Chemical Name:
- Hexamethylenetetramine
- Synonyms
- HMTA;HEXAMINE;METHENAMINE;UROTROPINE;1,3,5,7-TETRAAZAADAMANTANE;UROTROPIN;hexamethylentetramine;WLTP;Hexamethylenetetraamine;Hexamin
- CBNumber:
- CB8852597
- Molecular Formula:
- C6H12N4
- Molecular Weight:
- 140.19
- MOL File:
- 100-97-0.mol
- Modify Date:
- 2023/4/23 13:52:06
| Melting point | 280 °C (subl.) (lit.) |
|---|---|
| Boiling point | 246.7°C (rough estimate) |
| Density | 1.33 |
| vapor density | 4.9 (vs air) |
| vapor pressure | <0.01 mm Hg ( 20 °C) |
| refractive index | 1.4260 (estimate) |
| Flash point | 482 °F |
| storage temp. | Store below +30°C. |
| solubility | H2O: 1 M at 20 °C, clear, colorless |
| form | Solid |
| pka | 5.1(at 25℃) |
| color | white |
| Odor | Odorless |
| PH | 7-10 (100g/l, H2O, 20℃) |
| Water Solubility | 895 g/L (20 ºC) |
| Sensitive | Hygroscopic |
| Sublimation | 263-295 ºC |
| Merck | 14,5966 |
| BRN | 2018 |
| Stability | Stable. Incompatible with strong acids, strong oxidizing agents. |
| LogP | -2.18--2 at 20℃ |
| CAS DataBase Reference | 100-97-0(CAS DataBase Reference) |
| NIST Chemistry Reference | Hexamethylenetetramine(100-97-0) |
| EPA Substance Registry System | Hexamethylenetetramine (100-97-0) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS02,GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H228-H317 | |||||||||
| Precautionary statements | P210-P240-P241-P261-P280-P302+P352 | |||||||||
| Hazard Codes | F,Xn,Xi | |||||||||
| Risk Statements | 11-42/43-43 | |||||||||
| Safety Statements | 16-22-24-37 | |||||||||
| RIDADR | UN 1328 4.1/PG 3 | |||||||||
| WGK Germany | 1 | |||||||||
| RTECS | MN4725000 | |||||||||
| F | 9-23 | |||||||||
| Autoignition Temperature | 770 °F | |||||||||
| TSCA | Yes | |||||||||
| HS Code | 2933 69 40 | |||||||||
| HazardClass | 4.1 | |||||||||
| PackingGroup | III | |||||||||
| Toxicity | LD50 orally in Rabbit: 9200 mg/kg | |||||||||
| NFPA 704 |
|
Hexamethylenetetramine price More Price(42)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | H11300 | Hexamethylenetetramine ReagentPlus?, 99% | 100-97-0 | 500G | ₹3929.48 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | H11300 | Hexamethylenetetramine ReagentPlus?, 99% | 100-97-0 | 25G | ₹4005.25 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | H11300 | Hexamethylenetetramine ReagentPlus?, 99% | 100-97-0 | 4KG | ₹5423.33 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | H11300 | Hexamethylenetetramine ReagentPlus?, 99% | 100-97-0 | 1KG | ₹5455.8 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.18712 | Hexamethylenetetramine for synthesis | 100-97-0 | 100G | ₹6310 | 2022-06-14 | Buy |
Hexamethylenetetramine Chemical Properties,Uses,Production
Description
Hexamethylenetetramine is a hardener in epoxy resins of the bisphenol A type and can also be used as an anticorrosive agent. It is a sensitizing agent in ceramics workers.
Chemical Properties
White or almost white, crystalline powder or colourless crystals.
Uses
Hexamethylenetetramine is a versatile reagent in organic synthesis. It is used in the Duff reaction, the Sommelet reaction, and in the Delepine reaction.
Definition
ChEBI: A polycyclic cage that is adamantane in which the carbon atoms at positions 1, 3, 5 and 7 are replaced by nitrogen atoms.
Preparation
Hexamethylenetetramine (also known as hexamine, hexa or HMT) is prepared
from ammonia and formaldehyde:
Ammonia is passed into formalin at 20-30??C, with agitation. The resulting solution is evaporated under reduced pressure until most of the water is removed and the hexamethylenetetramine crystallizes. Yields of about 95% on both ammonia and formaldehyde can be achieved. Hexamethylenetetramine is a colourless crystalline solid which, on heating, sublimes with decomposition.
General Description
Odorless white crystalline powder or colorless lustrous crystals. Sublimes in a vacuum at about 505° F with some decomposition. Solutions are strong bases (pH of 0.2 molar aqueous solution is 8.4).
Air & Water Reactions
Highly flammable. Burns readily on contact with a flame with a smokeless flame. Finely powdered dust is significant dust explosion hazard. Water soluble.
Reactivity Profile
Hexamethylenetetramine is hygroscopic. Hexamethylenetetramine is sensitive to exposure to heat. Hexamethylenetetramine is incompatible with oxidizing agents. Hexamethylenetetramine is also incompatible with acids. Hexamethylenetetramine reacts violently with sodium peroxide. Hexamethylenetetramine reacts explosively with 1-bromopentaborane(9) at temperatures above 194° F. The complex with iodine deflagrates at 280° F. The 1:1 addition complex with iodoform has exploded at 352° F. Hexamethylenetetramine is corrosive to some metals, such as aluminum and zinc . Special Hazards of Combustion Products: Formaldehyde gas and ammonia may be given off when hot [USCG, 1999].
Hazard
Skin irritant. Flammable, dangerous fire risk.
Fire Hazard
Special Hazards of Combustion Products: Formaldehyde gas and ammonia may be given off when hot.
Contact allergens
Hexamethylenetetramine is used in the foundry, tire and rubber, and phenol formaldehyde resins industries and in other applications such as a hardener in epoxy resins Bisphenol A type and as an anticorrosive agent. It is an ammonia and formaldehyde releaser sometimes used in topical medicaments and cosmetics
Clinical Use
A venerable drug used for the disinfection of acidic urine, methenamine is a low-molecular-weight polymer of ammonia and formaldehyde that reverts to its components under mildly acidic conditions. Formaldehyde is the active antimicrobial component. Methenamine is used for recurrent urinary tract infections. The drug is available in various dosage forms as well as various salts, including the hippurate and mandelate.
Carcinogenicity
No significantly increased incidence
of tumors was observed in rats or mice given HMTA
for their lifetimes. Exposures in rats included 400 mg/day for
1 year, 10,000 ppm in drinking water for 2 years in each
of three generations, 10,000 ppm in water for a lifetime
(261), and up to 1000 ppm in the diet for 2 years.
In mice, testing conditions included up to 10,000 ppm in
drinking water for 60 weeks or 50,000 ppm for 30 weeks and
a lifetime holding period, and up to 10,000 ppm in
the diet for 2 years.
Injection of 25–30 g subcutaneously per mouse led to
an increase in subcutaneous sarcomas in two experiments
(418, 419) but not in two other studies. The
relevance of this methodology to the workplace condition is
questionable.
Purification Methods
It is soluble in H2O (67%), CHCl3 (10%), EtOH (8%) and Et2O (0.3%), and a 0.2M solution has a pH of 8.4. Dissolve it in hot absolute EtOH (reflux, Norit), filter using a heated funnel, cool at room temperature first, then in ice. Wash the crystals with cold Et2O, dry them in air or under a vacuum. A further crop can be obtained by adding Et2O to the filtrate. It sublimes above 260o without melting. The picrate has m 179o(dec). [pK2 0 4.85: Reilley & Schmid Anal Chem 30 947 1958, pK2 0 6.30: Pummerer & Hofmann Chem Ber 56 1255 1923.] [Beilstein 26 I 306, 26 II 200, 26 III/IV 1680.]
Hexamethylenetetramine Preparation Products And Raw materials
Raw materials
Preparation Products
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