Product Name

Stability

    Stable. Incompatible with strong oxidizing agents.

Toxicology

    Harmful if swallowed; causes psychotropic effects.

    Toxicity data
    (The meaning

  • Melting Point 59-61 ºC
  • Formula C6H10 N4
  • Boiling Point 194 ºC (12 mmHg)
  • Molecular Weight 138.172
  • Flash Point 194°C/12mm
  • Transport Information UN 2811
  • Appearance white crystalline powder
  • Safety A human poison by ingestion and intravenous routes. Poison experimentally by ingestion, intravenous, intraperitoneal, subcutaneous, rectal, and parenteral routes. When heated to decomposition it emits toxic fumes of NOx.
  • Risk Codes R25;R36/37/38   
  • Molecular Structure Molecular Structure of 54-95-5 (Pentetrazol)
  • Hazard Symbols
  • Synonyms 1,2,3,3a-Tetrazacyclohepta-8a,2-cyclopentadiene;1,5-Pentamethylenetetrazole; 6,7,8,9-Tetrahydro-5H-tetrazoloazepine;7,8,9,10-Tetrazabicyclo[5.3.0]-8,10-decadiene; Angiazol; Cardiazol; Cardiazole;Cardiol; Cenalene M; Cenazol; Cerebro-nicin; Coranormal; Coranormol; Corasol;Corazol; Corazole; Corazole (analeptic); Corisan; Corsedrol; Cortis; Corvasol;Delzol W; Deumacard; Gewazol; Korazol; Korazole; Leptazol; Leptazole; Metrazol;Metrazole; NSC 5729; NSC 66489; PTZ; Pentamethylenetetrazole; Pentavet;Pentazol; Pentetrazol; Pentetrazole; Pentrazol; Pentrolone; Pentrozol;Pentylenetetrazol; Pentylenetetrazole; Phrenazol; Tetracor; Tetrazol;Tetrazole, (1,5-pentanediyl)-; Ventrazol; Yetrazol; a,b-Cyclopentamethylenetetrazole
  • PSA 43.60000
  • LogP 0.39950

Synthetic route

cyclohexanone
108-94-1

cyclohexanone

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
With sodium azide; tetrachlorosilane In acetonitrile for 20h; Ambient temperature;95%
With aluminium trichloride; sodium azide at 50℃; for 0.2h;95%
With tin(II) chloride dihdyrate; trimethylsilylazide In neat (no solvent) at 55℃; for 16h; Schmidt Reaction; Inert atmosphere; Sealed tube;87%
cyclohexanone oxime methanesulfonate
80053-69-6

cyclohexanone oxime methanesulfonate

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 24h; Heating;94%
cyclohexanone
108-94-1

cyclohexanone

A

pentetrazole
54-95-5

pentetrazole

B

4,5,6,7,8,9-hexahydrotetrazolo[1,5-a][1,3]diazocine

4,5,6,7,8,9-hexahydrotetrazolo[1,5-a][1,3]diazocine

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; trimethylsilylazide at 20℃; for 2h; Schmidt Reaction; Inert atmosphere; Sealed tube;A 91%
B 4%
1-azacycloheptane-2-thione
7203-96-5

1-azacycloheptane-2-thione

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
With sodium azide; tetrachlorosilane In acetonitrile at 20 - 82℃; for 8h;88%
With trimethylsilylazide; tin(IV) chloride In dichloromethane for 22h; Ambient temperature;72%
With tetrahydrofuran; aluminium trichloride; sodium azide
cyclohexanone oxime benzoyl ester
29456-22-2

cyclohexanone oxime benzoyl ester

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 24h; Heating;84%
Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene for 16h; Solvent; Beckmann Rearrangement; Reflux; stereospecific reaction;81%
With chlorosulfonic acid; sodium azide
With sodium azide; trichlorophosphate
6-aminohexanoic acid
60-32-2

6-aminohexanoic acid

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
With trimethylsilylazide; trichlorophosphate In acetonitrile at 180℃; for 0.133333h; Microwave irradiation;76%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

cycloheptanone
502-42-1

cycloheptanone

A

pentetrazole
54-95-5

pentetrazole

B

(E)-8-(2,4,6-trimethoxyphenyl)-2,3,4,5,6,7-hexahydroazocinium bromide

(E)-8-(2,4,6-trimethoxyphenyl)-2,3,4,5,6,7-hexahydroazocinium bromide

Conditions
ConditionsYield
With aluminum tri-bromide; trimethylsilylazide at 35℃; for 21h; Temperature; Schmidt Reaction; Inert atmosphere;A 18%
B 66%
...Expand
trimethylsilylazide
4648-54-8

trimethylsilylazide

cyclohexanone
108-94-1

cyclohexanone

A

pentetrazole
54-95-5

pentetrazole

B

1-azido-1-(trimethylsiloxy)cyclohexane
69664-68-2

1-azido-1-(trimethylsiloxy)cyclohexane

Conditions
ConditionsYield
With tin(ll) chloride 1.) 0 deg C 2.) rt., 20 h;A 2%
B 61%
...Expand
caprolactam
105-60-2

caprolactam

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
With chlorosulfonic acid; tris-(2-chloro-ethyl)-amine
With sodium azide; trichlorophosphate
O-methylcaprolactim
2525-16-8

O-methylcaprolactim

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
With tris-(2-chloro-ethyl)-amine
Multi-step reaction with 2 steps
1: chloroform
2: water; acetic acid; NaNO2
View Scheme
7-ethylsulfanyl-3,4,5,6-tetrahydro-2H-azepine
85028-07-5

7-ethylsulfanyl-3,4,5,6-tetrahydro-2H-azepine

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
With tris-(2-chloro-ethyl)-amine
hexahydro-azepin-2-one-hydrazone
31030-25-8

hexahydro-azepin-2-one-hydrazone

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
With water; acetic acid; sodium nitrite
7-ethoxy-3,4,5,6-tetrahydro-2H-azepine
13414-33-0

7-ethoxy-3,4,5,6-tetrahydro-2H-azepine

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrazine hydrate
2: water; acetic acid; NaNO2
View Scheme
5-(5-bromo-pentyl)-1H-tetrazole

5-(5-bromo-pentyl)-1H-tetrazole

pentetrazole
54-95-5

pentetrazole

Conditions
ConditionsYield
With phenol In N,N-dimethyl-formamide
perchloric acid
7601-90-3

perchloric acid

pentetrazole
54-95-5

pentetrazole

1-ferrocenylmethanol
1273-86-5

1-ferrocenylmethanol

3(4)-(ferrocenylmethylene)-1,5-pentamethylenetetrazolium perchlorate

3(4)-(ferrocenylmethylene)-1,5-pentamethylenetetrazolium perchlorate

Conditions
ConditionsYield
In dichloromethane; water aq. HClO4 was added to mixt. of corazol and Fe-complex in CH2Cl2, 12 min, Et2O was added; filtered, washed with ether, dried; elem. anal.;100%
...Expand
pentetrazole
54-95-5

pentetrazole

1-ferrocenylmethanol
1273-86-5

1-ferrocenylmethanol

antimony(III) chloride
10025-91-9

antimony(III) chloride

3(4)-(ferrocenylmethylene)-1,5-pentamethylenetetrazolium trichlorohydroxystibate

3(4)-(ferrocenylmethylene)-1,5-pentamethylenetetrazolium trichlorohydroxystibate

Conditions
ConditionsYield
In dichloromethane SbCl3 was added to mixt. of corazol and Fe-complex in CH2Cl2, stirred for 25 min, treated with Et2O, left to stand for 10 d at 4-5°C; filtered, washed with Et2O, dried at room temp.; elem. anal.;100%
...Expand
tetrafluoroboric acid

tetrafluoroboric acid

pentetrazole
54-95-5

pentetrazole

1-ferrocenylmethanol
1273-86-5

1-ferrocenylmethanol

3(4)-(ferrocenylmethylene)-1,5-pentamethylenetetrazolium tetrafluoroborate

3(4)-(ferrocenylmethylene)-1,5-pentamethylenetetrazolium tetrafluoroborate

Conditions
ConditionsYield
In dichloromethane; water aq. HBF4 was added to mixt. of corazol and Fe-complex in CH2Cl2, 15 min,Et2O was added; filtered, washed with ether, dried; elem. anal.;99%
...Expand
pentetrazole
54-95-5

pentetrazole

nickel(II) perchlorate hexahydrate

nickel(II) perchlorate hexahydrate

Ni(2+)*6C6H10N4*2ClO4(1-)={Ni(C6H10N4)6}(ClO4)2

Ni(2+)*6C6H10N4*2ClO4(1-)={Ni(C6H10N4)6}(ClO4)2

Conditions
ConditionsYield
In further solvent(s) stirring 0.01 mol Ni(ClO4)2*6H2O in 2.2-dimethoxy-propane for 5-10 min, addn. of small excess of C6H10N4 (0.08 mol);; pptn., washing with cooled ether (several times), drying at ambient temp.;;95%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

pentetrazole
54-95-5

pentetrazole

cis-Pt(pentamethylenetetrazole)2I2
76625-16-6

cis-Pt(pentamethylenetetrazole)2I2

Conditions
ConditionsYield
With KI In water addn. of excess KI to Pt-complex, then addn. of 2 equiv. ligand (pptn.); filtration, washing (H2O), drying (60°C, vac., over P2O5); elem.anal.;95%
pentetrazole
54-95-5

pentetrazole

potassium tetrachloropalladate(II)
10025-98-6

potassium tetrachloropalladate(II)

cis-Pd(pentamethylenetetrazole)2I2
76625-14-4

cis-Pd(pentamethylenetetrazole)2I2

Conditions
ConditionsYield
With KI In water addn. of excess KI to Pd-complex, then addn. of 2 equiv. ligand (pptn.); filtration, washing (H2O), drying (60°C, vac., over P2O5); elem.anal.;95%
pentetrazole
54-95-5

pentetrazole

1,5-pentamethylenetetrazole-3-oxide
1221230-55-2

1,5-pentamethylenetetrazole-3-oxide

Conditions
ConditionsYield
With acetonitrile complex of hypofluorous acid In dichloromethane at 0℃;95%
tetrafluoroboric acid

tetrafluoroboric acid

pentetrazole
54-95-5

pentetrazole

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

C5H5FeC5H4CHCH3N4C(CH2)5(1+)*BF4(1-)=C5H5FeC5H4CHCH3N4C(CH2)5BF4

C5H5FeC5H4CHCH3N4C(CH2)5(1+)*BF4(1-)=C5H5FeC5H4CHCH3N4C(CH2)5BF4

Conditions
ConditionsYield
In dichloromethane; water aq. HBF4 was added to mixt. of corazol and Fe-complex in CH2Cl2, 15 min,Et2O was added; filtered, washed with ether, dried; elem. anal.;94%
...Expand
perchloric acid
7601-90-3

perchloric acid

pentetrazole
54-95-5

pentetrazole

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

C5H5FeC5H4CHCH3N4C(CH2)5(1+)*ClO4(1-)=C5H5FeC5H4CHCH3N4C(CH2)5ClO4

C5H5FeC5H4CHCH3N4C(CH2)5(1+)*ClO4(1-)=C5H5FeC5H4CHCH3N4C(CH2)5ClO4

Conditions
ConditionsYield
In dichloromethane; water aq. HClO4 was added to mixt. of corazol and Fe-complex in CH2Cl2, 15 min, Et2O was added; filtered, washed with ether, dried; elem. anal.;92%
...Expand
pentetrazole
54-95-5

pentetrazole

nickel(II) perchlorate

nickel(II) perchlorate

Ni(2+)*6C6H10N4*2ClO4(1-)={Ni(C6H10N4)6}(ClO4)2

Ni(2+)*6C6H10N4*2ClO4(1-)={Ni(C6H10N4)6}(ClO4)2

Conditions
ConditionsYield
In water addn. of 20-fold excess of C6H10N4 to aq. soln. of Ni(ClO4)2, storing for 5-10 d;; crystn.;91%
pentetrazole
54-95-5

pentetrazole

(C5(CH3)5)2SmI(OC4H8)

(C5(CH3)5)2SmI(OC4H8)

(C5(CH3)5)2SmI(C6H10N4)

(C5(CH3)5)2SmI(C6H10N4)

Conditions
ConditionsYield
In toluene N2;; crystn. at -34°C within several h, recrystn., elem. anal.;;90%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

pentetrazole
54-95-5

pentetrazole

cis-Pt(pentamethylenetetrazole)2Cl2
76847-85-3

cis-Pt(pentamethylenetetrazole)2Cl2

Conditions
ConditionsYield
In water addn. of 2 equiv. ligand to Pt-complex, stirring (room temp., pptn.); filtration, washing (H2O), drying (60°C, vac., over P2O5); elem.anal.;90%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

pentetrazole
54-95-5

pentetrazole

cis-Pt(pentamethylenetetrazole)2Br2
76625-15-5

cis-Pt(pentamethylenetetrazole)2Br2

Conditions
ConditionsYield
With KBr In water addn. of excess KBr to Pt-complex, then addn. of 2 equiv. ligand (pptn.); filtration, washing (H2O), drying (60°C, vac., over P2O5); elem.anal.;90%
pentetrazole
54-95-5

pentetrazole

potassium tetrachloropalladate(II)
10025-98-6

potassium tetrachloropalladate(II)

cis-Pd(pentamethylenetetrazole)2Br2
76625-13-3

cis-Pd(pentamethylenetetrazole)2Br2

Conditions
ConditionsYield
In water addn. of 2 equiv. ligand to Pd-complex, stirring (room temp., pptn.); filtration, washing (H2O), drying (60°C, vac., over P2O5); elem.anal.;90%
With KBr In water addn. of excess KBr to Pd-complex, then addn. of 2 equiv. ligand (pptn.); filtration, washing (H2O), drying (60°C, vac., over P2O5); elem.anal.;90%
pentetrazole
54-95-5

pentetrazole

potassium tetrachloropalladate(II)
10025-98-6

potassium tetrachloropalladate(II)

cis-Pd(pentamethylenetetrazole)2Cl2
76625-12-2

cis-Pd(pentamethylenetetrazole)2Cl2

Conditions
ConditionsYield
In water addn. of 2 equiv. ligand to Pd-complex, stirring (room temp., pptn.); filtration, washing (H2O), drying (60°C, vac., over P2O5); elem.anal.;90%
pentetrazole
54-95-5

pentetrazole

benzaldehyde
100-52-7

benzaldehyde

acetyl chloride
75-36-5

acetyl chloride

phenyl(6,7,8,9-tetrahydro-5H-tetrazolo[1,5-a]azepin-9-yl)methyl acetate
926290-85-9

phenyl(6,7,8,9-tetrahydro-5H-tetrazolo[1,5-a]azepin-9-yl)methyl acetate

Conditions
ConditionsYield
Stage #1: pentetrazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78℃; for 0.333333h;
Stage #3: acetyl chloride In tetrahydrofuran; hexane at -78 - 20℃;		81%
...Expand
pentetrazole
54-95-5

pentetrazole

copper(II) perchlorate hexahydrate

copper(II) perchlorate hexahydrate

tetrakis(1,5-pentamethylenetetrazol)copper(II) perchlorate

tetrakis(1,5-pentamethylenetetrazol)copper(II) perchlorate

Conditions
ConditionsYield
In isopropyl alcohol tetrazole deriv. added to soln. of copper perchlorate in isopropanol under stirring; mixt. heated at 60°C for 1 h; cooling at 17°C; small amt. of ethyl acetate added; ppt. filteredoff, washed with ethyl acetate and recrystd. from isopropanol; elem. an al.;80%
In water tetrazole deriv. added to aq. soln. of copper perchlorate under stirring; mixt. heated at 60°C for 2 h; cooling at 17°C; ppt. filtered off, washed with ethyl acetate andrecrystd. from isopropanol; elem. anal.;60%
tetrafluoroboric acid

tetrafluoroboric acid

pentetrazole
54-95-5

pentetrazole

vinyl ferrocene
1271-51-8

vinyl ferrocene

C5H5FeC5H4CHCHCH2N4C(CH2)5(1+)*BF4(1-)=C5H5FeC5H4CHCHCH2N4C(CH2)5BF4

C5H5FeC5H4CHCHCH2N4C(CH2)5(1+)*BF4(1-)=C5H5FeC5H4CHCHCH2N4C(CH2)5BF4

Conditions
ConditionsYield
In dichloromethane; water aq. HBF4 was added to mixt. of corazol and Fe-complex in CH2Cl2, 40 min,Et2O was added; filtered, washed with ether, dried; elem. anal.;63%
...Expand
tetrafluoroboric acid

tetrafluoroboric acid

pentetrazole
54-95-5

pentetrazole

1-ferrocenylphenylmethanol

1-ferrocenylphenylmethanol

C5H5FeC5H4CHC6H5N4C(CH2)5(1+)*BF4(1-)=C5H5FeC5H4CHC6H5N4C(CH2)5BF4

C5H5FeC5H4CHC6H5N4C(CH2)5(1+)*BF4(1-)=C5H5FeC5H4CHC6H5N4C(CH2)5BF4

Conditions
ConditionsYield
In dichloromethane; water aq. HBF4 was added to mixt. of corazol and Fe-complex in CH2Cl2, 30 min,Et2O was added; filtered, washed with ether, dried; elem. anal.;62%
...Expand
pentetrazole
54-95-5

pentetrazole

copper(II) perchlorate

copper(II) perchlorate

copper(II) perchlorate bis(1,5-pentamethylentetrazole)

copper(II) perchlorate bis(1,5-pentamethylentetrazole)

Conditions
ConditionsYield
In water at 20 - 60℃;60%
pentetrazole
54-95-5

pentetrazole

cobalt(III) diaquatetrammine perchlorate

cobalt(III) diaquatetrammine perchlorate

A

tetraammine-bis(cyclopentamethylenetetrazole)cobalt(III) perchlorate

tetraammine-bis(cyclopentamethylenetetrazole)cobalt(III) perchlorate

B

tetraammine(aqua)(cyclopentamethylenetetrazole)cobalt(III) perchlorate

tetraammine(aqua)(cyclopentamethylenetetrazole)cobalt(III) perchlorate

Conditions
ConditionsYield
In hydrogenchloride complex Co(NH3)4(H2O)2(ClO4)3 reacted with cyclopentamethylenetetrazole in aq. soln. of HCl for 3 h at 100°C; complex (Co(NH3)4(C6H10N4))(ClO4)3 isolated; mother liquor concd.; ppt. formed upon cooling filtered off; elem. anal.;A 59%
B 38%
...Expand

Pentetrazol Chemical Properties

Chemical Name: Pentetrazol
IUPAC NAME: 6,7,8,9-Tetrahydro-5H-tetrazolo[1,5-a]azepine
CAS No.: 54-95-5
EINECS: 200-219-3
RTECS: XF8225000
RTECS Class: Drug; Human Data
Molecular Formula: C6H10N4
Molecular Weight: 138.17 g/mol
Melting Point: 59-61 °C(lit.)
Density: 1.42 g/cm3
Flash Point: 159 °C
Boiling Point: 339.3 °C at 760 mmHg
Sensitive: Hygroscopic
Following is the structure of 1,5-Pentamethylenetetrazole (CAS No.54-95-5):


The chemical synonymous of 1,5-Pentamethylenetetrazole (CAS No.54-95-5) are Cardiazole ; Metrazole ; 1,5-Pentamethylenetetrazole ; 1,5-Pentamethylene-1h-Tetrazole ; 6,7,8,9-Tetrahydro-5h-Tetrazolo-[1,5-A]Azepine ; 6,7,8,9-Tetrahydro-5h-Tetrazoloazepine ; Alpha,Beta-Cyclopentamethylenetetrazole ; Pentamethylenetetrazole

Pentetrazol Toxicity Data With Reference

1.    

orl-man LDLo:147 mg/kg

     85DCAI    Poisoning; Toxicology, Symptoms, Treatments. 2 (1970),73.
2.    

ivn-man LDLo:29 mg/kg

     85DCAI    Poisoning; Toxicology, Symptoms, Treatments. 2 (1970),73.
3.    

orl-rat LD50:140 mg/kg

     JPPMAB    Journal of Pharmacy and Pharmacology. 13 (1961),244.
4.    

ipr-rat LD50:62 mg/kg

     TXAPA9    Toxicology and Applied Pharmacology. 18 (1971),185.
5.    

scu-rat LD50:85 mg/kg

     TXAPA9    Toxicology and Applied Pharmacology. 18 (1971),185.
6.    

ivn-rat LD50:45 mg/kg

     AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 135 (1962),9.
7.    

rec-rat LD50:8 mg/kg AACRAT 46,395,67
8.    

orl-mus LD50:88 mg/kg

     JPETAB    Journal of Pharmacology and Experimental Therapeutics. 128 (1960),176.
9.    

ipr-mus LD50:71 mg/kg

     JPETAB    Journal of Pharmacology and Experimental Therapeutics. 128 (1960),176.
10.    

scu-mus LD50:80 mg/kg

     ARZNAD    Arzneimittel-Forschung. Drug Research. 8 (1958),190.
     

 

Pentetrazol Consensus Reports

Reported in EPA TSCA Inventory.

Pentetrazol Safety Profile

A human poison by ingestion and intravenous routes. Poison experimentally by ingestion, intravenous, intraperitoneal, subcutaneous, rectal, and parenteral routes. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: ToxicT
Risk Statements about 1,5-Pentamethylenetetrazole (CAS No.54-95-5):
R25 :Toxic if swallowed. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements about 1,5-Pentamethylenetetrazole (CAS No.54-95-5):
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
Attention:
1. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture.
2. Handling: Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Do not allow contact with water. Keep from contact with moist air and steam.

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