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Cas Database

100-97-0

100-97-0

Identification

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;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF,HarmfulXn

  • Hazard Codes:F,Xn,Xi

  • Signal Word:Warning

  • Hazard Statement:H228 Flammable solidH317 May cause an allergic skin reaction

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention . SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Exposure may cause skin rash and kidney irritation. Inhalation may cause coughing and shortness of breath. It may cause corrosion of the respiratory tract. Skin contact may cause redness, pain, rashes and burns of the skin. Eye contact may cause redness, pain and blurred vision. Ingestion of this compound may cause urinary tract irritation, digestive disturbances, and severe nephritis which may be fatal. If large amounts are ingested it can cause sore throat, abdominal pain, vomiting, diarrhea, painful and frequent urination, and blood in the urine. Large oral doses can also cause gastrointestinal irritation, albuminuria, hemorrhagic cystitis, mild azotemia, gross hematuria and dysuria, with inflammatory lesions in the renal tubules, renal pelvis, and urinary bladder. It can also cause irritation of the bladder, and nausea. Repeated use can lead to skin sensitization with urticaria or dermatitis. Prolonged contact can cause smarting and reddening of the skin. It can produce an asthma-like condition. Kidney damage has been reported. ACUTE/CHRONIC HAZARDS: This compound may be harmful by inhalation, ingestion or skin absorption. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide, nitrogen oxides, ammonia, and formaldehyde. Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aldehydes and Related Compounds/

  • Fire-fighting measures: Suitable extinguishing media Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special Hazards of Combustion Products: Formaldehyde gas and ammonia may be given off when hot. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water. Accidental Release Measures: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Avoid breathing dust; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains; Methods and materials for containment and cleaning up: Sweep up and shovel. Contain spillage, and then collect with an electrically protected vacuum cleaner or by wetbrushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong acids and strong oxidants. Dry.Keep container tightly closed in a dry and well-ventilated place. Hygroscopic. Storage class (TRGS 510): Flammable solid hazardous materials

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:Hexamethylenetetramine
  • Packaging:1g
  • Price:$ 135
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Hexamethylenetetramine 99%
  • Packaging:5 kg
  • Price:$ 195
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Hexamethylenetetramine 99%
  • Packaging:500 g
  • Price:$ 25
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Hexamethylenetetramine 99%
  • Packaging:1 kg
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Hexamethylenetetramine ACS reagent, ≥99.0%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Hexamethylenetetramine for synthesis. CAS 100-97-0, pH 7.0 - 9.0 (100 g/l, H O, 20 °C)., for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Hexamethylenetetramine for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Hexamethylenetetramine ACS reagent, ≥99.0%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Hexamethylenetetramine ReagentPlus , 99%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Hexamethylenetetramine puriss. p.a., reag. Ph. Eur., ≥99.5% (calc. to the dried substance)
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Relevant articles and documentsAll total 31 Articles be found

-

Bachmann et al.

, p. 2769,2772 (1951)

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Hexaazapolycycles by selective multimethylenations with dichloromethane and base or with hexamethylenetetramine

Kaupp, Gerd,Sailer, Klaus

, p. 47 - 50 (1996)

Multiple methylenations of 2-aminomethylbenzimidazole with dichloromethane and methylamine or ammonia or with hexamethylenetetramine lead to highly selective formations of 6 new single bonds to give only a polycyclic bis-spiro-1,5-diazocine 2 or only a polycyclic spiro-1,3,6-triazonine 4 or only a polycyclic 1,3,6,8-tetrazecine derivative 6. 4 and 6 may be equally well obtained starting with 2-chloromethyl-benzimidazole. All of these selectively formed products are concave cryptands with 6 amino nitrogen atoms. No template metals are used in their syntheses. The reasons for the unusual changes in selectivity are investigated using semi-empirical PM3 calculations and mechanistic considerations. Experimental and spectroscopic details are given. Johann Ambrosius Barth 1996.

N-denitration of nitramines by dihydronicotinamides

Chapman, Robert D.,O'Brien, Richard A.,Kondracki, Paul A.

, p. 9655 - 9664 (1996)

N-NO2 bond scission in organic nitramines occurs in high yields by reaction with 1,4-dihydronicotinamides. HMX (3) and tetryl (4) were used as model aliphatic and aromatic nitremines in reactions with 1-benzyl-1,4- dihydronicotinamide (BNAH, 1), resulting in hexamethylenetetramine and N- methylpicramide (5), respectively, as the predominant products. Radical initiation of the electron-transfer denitrohydrogenation mechanism is achieved either by photolysis or chemically by dithionite ion. A polymer- supported analogue of BNAH effects similar, though slower, N-denitration.

Elucidating the Reaction Mechanisms between Triazine and Hydrogen Sulfide with pH Variation Using Mass Spectrometry

Wang, Xiaoting,Zheng, Yajun,Shi, Jun,Gong, Xiaoyun,Ji, Yue,Han, Weiwei,Jiang, You,Austin, Daniel E.,Fang, Xiang,Zhang, Zhiping

, p. 11138 - 11145 (2018)

Triazine is one of the most economical and effective scavengers for hydrogen sulfide (H2S) removal, but the reaction mechanisms between triazine and H2S with pH variation in solution are still poorly understood. Herein, we show that the reaction process can be directly probed by means of paper spray mass spectrometry, in which an aprotic solvent (e.g., acetonitrile) is more favorable to the observation of reaction intermediates than a protic solvent (e.g., methanol), because of hydrogen bond interaction. Varying the pH of the reaction leads to completely different reaction pathways. With the pH in the range of 5.58 to 7.73, the major product was thiadiazine. With a pH of 3.02-3.69, thiadiazine is converted to 2-(5-(2-hydroxyethyl)-1,3,5-thiadiazinan-3-yl)acetaldehyde, which differs from the traditional pathway of analogous reactions. However, as ammonia was added into the reaction and the pH was adjusted to the range 8.45-9.43, triazine readily undergoes hydrolysis, and the formed intermediate reacts with ammonia and formaldehyde generated in situ from triazine to produce 1-(2-hydroxyethyl)-3,5,7-triaza-1-azoniatricyclo [3.3.1.13,7]decane (HTAD). Further increasing the pH up to 10.27-11.21 leads to the decomposition of HTAD. Based on the experimental observation and evidence from high-resolution and tandem mass spectrometry, we propose the plausible reaction mechanisms between triazine and H2S, as well as the derived reaction from triazine under different pH conditions.

Baur,Rueetschi

, p. 754,761,764 (1941)

The first controlled reduction of the high explosive RDX

McHugh, Callum J.,Smith, W. Ewen,Lacey, Richard,Graham, Duncan

, p. 2514 - 2515 (2002)

The first reduction chemistry of the high explosive RDX that allows subsequent functionalization into a SERRS active species.

-

Koehn

, p. 903 (1899)

-

-

Rombaut,Nieuwland

, p. 2061 ()

-

Hexamethylenetetramine carboxyborane: synthesis, structural characterization and CO releasing properties

Ayudhya,Raymond,Dingra

, p. 882 - 889 (2017)

Carbon monoxide, although widely known as a toxic gas, has received great attention in the past few decades due to its promising role as a medical gas. Several classes of carbon monoxide releasing molecules (CORMs) have been synthesised with many of them having pharmacological activities under physiological conditions. Herein, we report the synthesis and structural characterization of the first example of amine carboxyborane that releases CO under physiological conditions without the aid of inducers. A representative compound hexamethylenetetramine carboxyborane (HMTA-CB) described here has a half-life of 2.7 days and gradually releases CO with the rate constant of 3.0 × 10?6 s?1. Its ability to promote cell growth shows the beneficial effect of slow CO release to supplement CO in small amounts over time.

Synthesis of 14C-labeled octahydro-1,3,5,7-tetranitro-1,3,5,7- tetrazocine (HMX)

Huang, Chi-Yu,Mah, Robert A.,Que Hee, Shane S.

, p. 377 - 385 (1998)

The 14C-uniformly labeled (UL) explosive, octahydro-1,3,5,7- tetranitro-1,3,5,7-tetrazocine (HMX) was synthesized in 40% yield by nitrolysis of 14C-labeled hexamethylenetetramine (hexamine) in the presence of boron trifluoride diethyl etherate as catalyst. The labeled hexamine was synthesized in 77% yield from 14C-labeled formaldehyde and ammonium hydroxide. The specific activity of 14C-labeled HMX was 0.24 mCi/mmol, a total of 58 μCi was prepared. The radiochemical purity of the labeled substance was 95% by HPLC-Liquid scintillation counting and 98% by HPLC-UV at 232 nm.

Consistency of NMR and mass spectrometry determinations of natural- abundance site-specific carbon isotope ratios. The case of glycerol

Zhang,Trierweiler,Jouitteau,Martin

, p. 2301 - 2306 (1999)

Quantitative determinations of natural-abundance carbon isotope ratios by nuclear magnetic resonance (SNIF-NMR) have been optimized by appropriate selection of the experimental conditions and by signal analysis based on a dedicated algorithm. To check the consistency of the isotopic values obtained by NMR and mass spectrometry (IRMS) the same glycerol samples have been investigated by both techniques. To have access to site-specific isotope ratios by IRMS, the products have been degraded and transformed into two derivatives, one of which contains carbons 1 and 3 and the other carbon 2 of glycerol. The sensitivity of the isotopic parameters determined by IRMS to fractionation effects possibly occurring in the course of the chemical transformations has been investigated, and the repeatability and reproducibility of both analytical chains have been estimated. The good agreement observed between the two series of isotopic results supports the reliability of the two different approaches. SNIF-NMR is therefore a very attractive tool for routine determination, in a single nondestructive experiment, of the carbon isotope distribution in glycerol, and the method can be applied to other compounds. Using this method, the isotopic distributions have been compared for glycerol samples, obtained from plant or animal oils, extracted from fermented media, or prepared by chemical synthesis. Typical behaviors are characterized.

Naked fluoride ion sources: Synthesis, characterization, and coupling reaction of 1-methylhexamethylenetetramine fluoride

Gnann, Robert Z.,Wagner, Ross I.,Christe, Karl O.,Bau, Robert,Olah, George A.,Wilson, Wiliam W.

, p. 112 - 115 (1997)

Anhydrous 1-methylhexamethylenetetramine (also referred to as N-methylurotropinium or methylhexaminium) fluoride was prepared by either halogen exchange between the corresponding iodide and AgF or by a single-step, one-pot, self-assembling synthesis from aqueous CH3NH2, HF, formaldehyde, and NH3. It was characterized by NMR and vibrational spectroscopy. Its hydrate undergoes at 70 °C a Sommelet-type ring opening and coupling reaction to form a potential cryptand system consisting of two bicyclic triazine groups that are connected through a methylene bridge and contain eight ternary nitrogen atoms. The compound was characterized by multinuclear NMR and vibrational spectroscopy, and its structure was determined from single-crystal X-ray diffraction data.

-

Richmond,Myers,Wright

, p. 3659,3663 (1948)

-

METHODS FOR PREPARING FORMALDEHYDE FROM CARBON DIOXIDE

-

Paragraph 0017, (2020/11/27)

The present disclosure provides, inter alia, methods for preparing formaldehyde from carbon dioxide using bis(silyl)acetals, methods for incorporating carbon derived from carbon dioxide into a complex organic molecule derived from formaldehyde using bis(silyl)acetals, and methods for generating an isotopologue of a complex organic molecule derived from formaldehyde using bis(silyl)acetals.

Selective Conversion of Carbon Dioxide to Formaldehyde via a Bis(silyl)acetal: Incorporation of Isotopically Labeled C1 Moieties Derived from Carbon Dioxide into Organic Molecules

Rauch, Michael,Strater, Zack,Parkin, Gerard

supporting information, p. 17754 - 17762 (2019/11/05)

The conversion of carbon dioxide to formaldehyde is a transformation that is of considerable significance in view of the fact that formaldehyde is a widely used chemical, but this conversion is challenging because CO2 is resistant to chemical transformations. Therefore, we report here that formaldehyde can be readily obtained from CO2 at room temperature via the bis(silyl)acetal, H2C(OSiPh3)2. Specifically, formaldehyde is released from H2C(OSiPh3)2 upon treatment with CsF at room temperature. H2C(OSiPh3)2 thus serves as a formaldehyde surrogate and provides a means to incorporate CHx (x = 1 or 2) moieties into organic molecules. Isotopologues of H2C(OSiPh3)2 may also be synthesized, thereby providing a convenient means to use CO2 as a source of isotopic labels in organic molecules.

Iodopropynyl a, 1,4-butyne diol and hexamine three cogeneration method for continuous production of

-

Paragraph 0041-0052, (2017/06/19)

The invention discloses a trigeneration continuous production method for propiolic alcohol, 1,4-butinodiol and urotropine, and belongs to the technical field of chemical engineering. According to the method, a formaldehyde aqueous solution (10%-37% wt) and acetylene are taken as raw materials for synthesizing propiolic alcohol and co-producing 1,4-butinodiol and urotropine, the reaction temperature is 80-120 DEG C, the pressure is 1.0-2.5 MPa, and propiolic alcohol with the purity of 99.5% or more, a 1,4-butinodiol aqueous solution and a urotropine aqueous solution are obtained. The conversion rate of formaldehyde in the whole technology is 100%, and the method has the advantages of safety and environment friendliness.

Process route upstream and downstream products

Process route

ammonia
7664-41-7

ammonia

<i>N</i>,<i>N</i>'-methanediyl-di-anthranilic acid dimethyl ester
21038-62-0

N,N'-methanediyl-di-anthranilic acid dimethyl ester

hexamethylenetetramine
100-97-0

hexamethylenetetramine

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
Conditions Yield
at 140 ℃;
Hexahydro-1,3,5-trinitro-1,3,5-triazine
121-82-4,82030-42-0

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

MEDINA
14168-44-6

MEDINA

hexamethylenetetramine
100-97-0

hexamethylenetetramine

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

Conditions
Conditions Yield
With hydrogen; palladium on activated charcoal; for 2h;
1,3,6,8-tetraazatricyclo[4.4.1.1<sup>3,8</sup>]dodecane
51-46-7

1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane

tetrahydroimidazole
504-74-5

tetrahydroimidazole

1,3,5-triazabicyclo[3.2.1]-octane
280-29-5

1,3,5-triazabicyclo[3.2.1]-octane

hexamethylenetetramine
100-97-0

hexamethylenetetramine

1,3,6,8-tetraazatricyclo[4.3.1.1<sup>3,8</sup>]undecane
125251-91-4

1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecane

Conditions
Conditions Yield
With ammonium fluoride; In water-d2; at 23 ℃; for 8h; Title compound not separated from byproducts.;
hexamethylenetetramine
100-97-0

hexamethylenetetramine

barium formate
541-43-5

barium formate

Conditions
Conditions Yield
With barium dihydroxide; phosphoric acid; ammonia; periodic acid; Product distribution; multistep reaction;
5-methyl-4-oxo-1,3-dioxolane
13372-32-2

5-methyl-4-oxo-1,3-dioxolane

ammonia
7664-41-7

ammonia

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
Conditions Yield
ethanol
64-17-5

ethanol

bis(benzoyloxy)methane
5342-31-4

bis(benzoyloxy)methane

ammonia
7664-41-7

ammonia

water
7732-18-5

water

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
Conditions Yield
diethyl ether
60-29-7,927820-24-4

diethyl ether

sulfuric acid chloromethyl ester-methyl ester
73455-06-8

sulfuric acid chloromethyl ester-methyl ester

ammonia
7664-41-7

ammonia

hexamethylenetetramine
100-97-0

hexamethylenetetramine

methylamine hydrochloride
593-51-1

methylamine hydrochloride

Conditions
Conditions Yield
diacetoxymethane
628-51-3,25231-38-3

diacetoxymethane

ammonia
7664-41-7

ammonia

acetamide
60-35-5

acetamide

hexamethylenetetramine
100-97-0

hexamethylenetetramine

ammonium acetate
631-61-8,92206-38-7

ammonium acetate

Conditions
Conditions Yield
in der Kaelte;
bis-hydroxymethyl peroxide
17088-73-2

bis-hydroxymethyl peroxide

ammonium hydroxide

ammonium hydroxide

formic acid
64-18-6

formic acid

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
Conditions Yield
hexamethylenetetramine (H) tetrachloroaurate
121538-39-4

hexamethylenetetramine (H) tetrachloroaurate

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
Conditions Yield
In neat (no solvent); byproducts: HCl; thermal decompn. (205-530°C); X-ray diffraction, DTA, TGA, DTGA;

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