Conditions | Yield |
---|---|
With 1-Benzyl-1,4-dihydronicotinamide In N,N-dimethyl-formamide for 24h; Kinetics; Ambient temperature; Irradiation; other nitramines, var. solvents, var. temperatures; | 100% |
Conditions | Yield |
---|---|
With borohydride exchange resin; nickel diacetate In methanol for 3h; | 100% |
hexamethylenetetramine
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With ammonium hydroxide In water Schlenk technique; Glovebox; Inert atmosphere; | 97% |
With ammonium hydroxide at 15 - 20℃; | 83% |
With ammonium sulfate |
formaldehyd
1,1,1,3,3,3-hexamethyl-disilazane
A
Hexamethyldisiloxane
B
hexamethylenetetramine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 1h; | A 93% B 77% |
formaldehyd
A
1,3,5-dithiazinane
B
1,5-dithia-3,7-diazabicyclo<3.3.1>nonane
C
hexamethylenetetramine
Conditions | Yield |
---|---|
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% |
N-methyl-N-(methyleneamino)methanamine
acrylonitrile
A
dimethylaminomethyleneacetonitrile
B
hexamethylenetetramine
Conditions | Yield |
---|---|
With hydroquinone In acetonitrile at 100℃; for 10h; Product distribution; | A 36% B 12% |
Conditions | Yield |
---|---|
With sodium hydride In cyclohexane at 180℃; for 0.583333h; | A n/a B 32% |
Conditions | Yield |
---|---|
With ammonia at 40℃; for 10h; | A 12% B 27% |
methane
hexamethylenetetramine
Conditions | Yield |
---|---|
With ammonia; oxygen; copper at 500 - 700℃; | |
With silver copper; ammonia; oxygen at 500 - 700℃; |
Conditions | Yield |
---|---|
With ammonium hydroxide at 100 - 120℃; | |
With sodium hydroxide; ammonia at 100 - 120℃; | |
With ammonium hydroxide at 100 - 120℃; |
hexamethylenetetramine; compound with phenol
benzene
A
hexamethylenetetramine
B
phenol
β-naphthol
A
hexamethylenetetramine
B
bis(2-hydroxy-1-naphthyl)methane
C
1,3-diformyl-2-naphthol
D
2-formyl-2,3-dihydro-1H-naphth<1,2-e><1,3>oxazine
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid 1) 2h, steambath, 2) 30 min.; Yield given. Multistep reaction. Yields of byproduct given; |
A
azobisisopropane
B
hexamethylenetetramine
Conditions | Yield |
---|---|
for 10h; Product distribution; thermolysis; |
Conditions | Yield |
---|---|
With ammonia at 40℃; for 10h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With hydrogen fluoride; ammonia In methanol |
Conditions | Yield |
---|---|
With barium dihydroxide; phosphoric acid; ammonia; periodic acid Product distribution; multistep reaction; |
hexamethylenetetramine
Conditions | Yield |
---|---|
With nickel kieselguhr; ammonia; hydrogen at 250 - 280℃; |
Conditions | Yield |
---|---|
With water bei der Beruehrung mit einem gluehenden Nickel-Draht; |
Conditions | Yield |
---|---|
With water |
Conditions | Yield |
---|---|
bei der Einwirkung dunkler elektrischer Entladungen; |
Conditions | Yield |
---|---|
With ethanol at 125℃; |
Conditions | Yield |
---|---|
With ethanol |
Conditions | Yield |
---|---|
With ethanol |
ammonia
epichlorohydrin
A
(E)-2-penten-4-yn-1-ol
B
hexamethylenetetramine
C
propargyl alcohol
5-methyl-4-oxo-1,3-dioxolane
ammonia
A
hexamethylenetetramine
B
(+/-)-lactamide
tris(chloromethyl)-s-triazinetrione
ammonia
A
hexamethylenetetramine
C
isocyanuric acid
Conditions | Yield |
---|---|
at 100℃; |
Z-1,4-dichlorobutene
hexamethylenetetramine
1-<(Z)-4-Chloro-2-butenyl>-1-azonia-3,5,7-triazatricyclo<3.3.1.1.3,7>decane chloride
Conditions | Yield |
---|---|
In dichloromethane for 5h; Reflux; Large scale reaction; | 100% |
In ethanol; chloroform for 4h; Heating; | 99% |
In chloroform at 60℃; for 4h; | 94% |
In chloroform for 4h; Heating; | 91% |
In chloroform for 4h; Reflux; | 91% |
1-(3-(benzyloxy)phenyl)-2-bromoethanone
hexamethylenetetramine
1-[2-(3-Benzyloxy-phenyl)-2-oxo-ethyl]-3,5,7-triaza-1-azonia-tricyclo[3.3.1.13,7]decane; bromide
Conditions | Yield |
---|---|
In diethyl ether; chloroform Ambient temperature; | 100% |
hexamethylenetetramine
1,4-bis(chloromethyl)-2,5-dimethoxybenzene
1,1'-(2,5-dimethoxy-p-xylylene)-bis-hexamethylenetetraminium; dichloride
Conditions | Yield |
---|---|
In dichloromethane for 16h; Heating; | 100% |
In chloroform 1.) reflux, 30 min, 2.) r.t., overnight; | |
In chloroform at 90℃; for 24h; |
hexamethylenetetramine
4-Nitrophenacyl bromide
(4-nitrophenacyl)hexaminium bromide
Conditions | Yield |
---|---|
In chloroform for 2h; | 100% |
In chloroform at 20℃; for 12h; Delepine reaction; |
hexamethylenetetramine
2-chloro-N-(4-chlorophenyl)acetamide
N,N'-methylenebis<3-(4-chlorophenyl)>-4-imidazolidinone
Conditions | Yield |
---|---|
In ethanol 60 deg C, 1 h, then reflux, 1.5 h; | 100% |
hexamethylenetetramine
methyl iodide
N-methylhexamethylenetetrammonium iodide
Conditions | Yield |
---|---|
In chloroform at 20℃; | 100% |
at 80℃; for 7h; Temperature; | 95.8% |
In ethanol | |
In chloroform |
hexamethylenetetramine
4-tert-butyl-2-(diphenyl-phosphinoyl)-phenol
Conditions | Yield |
---|---|
With trifluoroacetic acid for 20h; Heating; | 100% |
1-benzo[1,3]dioxol-5-yl-2-(2,5-dichloro-phenyl)-ethane-1,2-dione
hexamethylenetetramine
5-benzo[1,3]dioxol-5-yl-4-(2,5-dichloro-phenyl)-1H-imidazole
Conditions | Yield |
---|---|
With ammonium acetate In acetic acid at 95℃; for 2.5h; | 100% |
2-(2-Hydroxyphenyl)benzoxazole
hexamethylenetetramine
5-(1,3-benzoxazol-2-yl)-4-hydroxyisophthalic aldehyde
Conditions | Yield |
---|---|
With trifluoroacetic acid for 48h; Reflux; | 100% |
With acetic acid In toluene for 18h; Duff reaction; Reflux; | 91% |
With trifluoroacetic acid Reflux; | 91% |
hexamethylenetetramine
2-chloro-1,4-dimethoxybenzene
2,5-dimethoxy-4-chlorobenzaldehyde
Conditions | Yield |
---|---|
With trifluoroacetic acid at 95℃; for 5h; | 100% |
With trifluoroacetic acid at 95℃; | 72.7% |
Ethyl 4-hydroxybenzoate
hexamethylenetetramine
3,5-diformyl-4-hydroxybenzoic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: Ethyl 4-hydroxybenzoate; hexamethylenetetramine With trifluoroacetic acid Reflux; Stage #2: With water at 20 - 80℃; for 2h; | 100% |
With trifluoroacetic acid | |
With trifluoroacetic acid Duff Aldehyde Synthesis; Reflux; | |
With trifluoroacetic acid Duff Aldehyde Synthesis; |
hexamethylenetetramine
4-hydroxy-benzoic acid
3,5-diformyl-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: hexamethylenetetramine; 4-hydroxy-benzoic acid With trifluoroacetic acid for 72h; Reflux; Stage #2: With water at 20 - 80℃; for 4h; | 100% |
With trifluoroacetic acid at 110℃; for 48h; | 70% |
With trifluoroacetic acid at 110℃; for 48h; | 70% |
hexamethylenetetramine
C9H5MnO5*C6H12N4
Conditions | Yield |
---|---|
In methanol at 20 - 60℃; Darkness; | 100% |
α-chloro-2',5'-difluoroacetophenone
hexamethylenetetramine
Conditions | Yield |
---|---|
In chloroform Solvent; Temperature; Reflux; | 100% |
hexamethylenetetramine
2-bromo-1-cyclopropylethan-1-one
Conditions | Yield |
---|---|
In chloroform at 20℃; for 12h; | 100% |
In chloroform at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
In chloroform at 60℃; for 12h; | 99.9% |
Conditions | Yield |
---|---|
In toluene for 2h; Solvent; Reflux; Industrial scale; | 99.9% |
1,1,2,3-Tetrachloropropene
hexamethylenetetramine
Conditions | Yield |
---|---|
In chloroform at 60℃; for 12h; | 99.6% |
hexamethylenetetramine
tris-(chloromethyl)amine
Conditions | Yield |
---|---|
With phosphorus pentachloride at 100℃; for 5.5h; Neat (no solvent); | 99% |
With phosphorus pentachloride | |
With phosphorus pentachloride |
2-bromoacetyl-1-methyl-5-nitropyrrole
hexamethylenetetramine
Conditions | Yield |
---|---|
In chloroform Alkylation; | 99% |
In chloroform | 99% |
hexamethylenetetramine
2-bromo-1-[5-fluoro-2-(methylthio)phenyl]ethanone
Conditions | Yield |
---|---|
In chloroform at 20℃; | 99% |
hexamethylenetetramine
2-Bromo-1-(3,4-dimethoxyphenyl)ethanone
2-hexamethylenetetramino-1-(3,4-dimethoxyphenyl)ethanone-2-ium bromide
Conditions | Yield |
---|---|
In chloroform at 20℃; for 4h; | 99% |
In chloroform at 20℃; |
Conditions | Yield |
---|---|
Stage #1: hexamethylenetetramine; C76H120O4 With trifluoroacetic acid at 125℃; for 4h; Stage #2: With hydrogenchloride; water In dichloromethane at 20℃; for 3h; | 99% |
hexamethylenetetramine
4-Bromoacetyl-1-(t-butoxycarbonyl)piperidine
Conditions | Yield |
---|---|
In chloroform at 50℃; for 1h; | 99% |
hexamethylenetetramine
Conditions | Yield |
---|---|
In dichloromethane for 24h; Reflux; | 99% |
6-ethyl-1H-pyrrolo[2,3-b]pyridine
hexamethylenetetramine
Conditions | Yield |
---|---|
With acetic acid In water at 120℃; for 8h; | 99% |
hexamethylenetetramine
Conditions | Yield |
---|---|
In chloroform at 20℃; for 12h; | 99% |
7-Azaindole
hexamethylenetetramine
1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde
Conditions | Yield |
---|---|
With propionic acid In ethanol at 80℃; for 6h; Temperature; | 98.9% |
Stage #1: 7-Azaindole; hexamethylenetetramine With acetic acid for 6h; Duff reaction; Heating; Stage #2: With water at 20℃; Further stages.; | 77% |
With acetic acid In water for 12h; Heating / reflux; | 76% |
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. |
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