4023-02-3

Basic information

• Product Name: 1H-Pyrazole-1-carboxamidine hydrochloride
• Synonyms: AMIDINOPYRAZOLE HCL;1H-PYRAZOLE-1-CARBOXAMIDINE HYDROCHLORIDE;1H-PYRAZOLE-1-CARBOXAMIDINE MONOHYDROCHLORIDE;1H-PYRAZOLE-1-CARBAMIDINE HCL;1-AMIDINOPYRAZOLE HYDROCHLORIDE;1-AMIDINOPYRAZOLE MONOHYDROCHLORIDE;PYRAZOLE CARBOXAMIDINE HCL;PYRAZOLE-1-CARBOXAMIDINE
• CAS NO: 4023-02-3
• Molecular Formula: C₄H₆N₄*ClH
• Molecular Weight: 146.58
• EINECS: 429-520-1
• Product Categories: Pyrazoles & Triazoles;Miscellaneous Reagents;Pyrazoles & Triazoles;Heterocycles;amine
• Mol File: 4023-02-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 167-170 °C(lit.)
• Boiling Point: 891.5oC at 760 mmHg。 产品描述 安全性：
• Flash Point: 493oC
• Appearance: White to light yellow/Crystals or Crystalline Powder
• Density: 2.2 g/cm3
• Vapor Pressure: 0.00111mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Soluble
• BRN: 5448758
• CAS DataBase Reference: 1H-Pyrazole-1-carboxamidine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-1-carboxamidine hydrochloride(4023-02-3)
• EPA Substance Registry System: 1H-Pyrazole-1-carboxamidine hydrochloride(4023-02-3)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-36/37-34
• Safety Statements: 26-37/39-45-36/37/39
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 4023-02-3(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystals or crystalline

Uses

Different sources of media describe the Uses of 4023-02-3 differently. You can refer to the following data:
1. 1H-Pyrazole-1-carboxamidine hydrochloride may be used in the following studies: ? Preparation of guanidylated hollow fiber membranes. ? Guanylation of amines and in peptide synthesis. ? Synthesis of bis-guanidinium-cholesterol derivatives.
2. 1H-Pyrazole-1-carboxamidine hydrochloride is a stable and versatile reagent for the efficient and chemically specific guanylation of sterically unhindered primary and secondary aliphatic amines under mild conditions. 1H-Pyrazole-1-carboxamidine hydrochloride is a useful reagent in peptide synthesis

General Description

1H-Pyrazole-1-carboxamidine hydrochloride, a pyrazole derivative, is a heterocyclic compound. It is widely used in drug syntheses studies. Pyrazole ring forms the main core of various nonsteroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs.

InChI:InChI=1/C4H5N3O.ClH/c5-4(8)7-3-1-2-6-7;/h1-3H,(H2,5,8);1H

Synthetic route

tert-butyl (1H-pyrazol-1-ylcarbonoimidoyl)carbamate (152120-61-1) → 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3)

Conditions	Yield
With sulfuric acid; sodium chloride In neat (no solvent) at 20℃; for 3h; Sealed tube;	99%

CYANAMID (420-04-2) + 1H-pyrazole hydrochloride (35877-22-6) → 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3)

Conditions	Yield
at 80℃; for 0.1h;	98%

NH-pyrazole (288-13-1) + CYANAMID (420-04-2) → 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 2h; Heating;	95%
With hydrogenchloride In 1,4-dioxane for 2h; Heating;	90%
With hydrogenchloride In 1,4-dioxane for 1h; Reflux;	43%
With hydrogenchloride In 1,4-dioxane
With hydrogenchloride In 1,4-dioxane

malonaldehydebis(dimethylacetal) (102-52-3) + aminoguanidine bicarbonate (2582-30-1) → 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3)

Conditions	Yield
With hydrogenchloride In water at 20 - 45℃;	70.3%

malonaldehydebis(dimethylacetal) (102-52-3) + 1-aminoguanidine hydrochloride (1937-19-5) → 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3)

Conditions	Yield
In water at 45℃; for 1h;

di-tert-butyl dicarbonate (24424-99-5) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → tert-butyl (1H-pyrazol-1-ylcarbonoimidoyl)carbamate (152120-61-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	100%
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 4 - 20℃; for 8h; Inert atmosphere;	91%
With potassium carbonate In water; acetone at 20℃;	88%

1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) + (1S,3R)-3-amino-cyclopentanecarboxylic acid methyl ester hydrochloride → methyl (1S,3R)-3-carbamimidamidocyclopentane-1-carboxylate (959680-24-1)

Conditions	Yield
With triethylamine In acetonitrile at 70℃; for 4h;	100%

1-[4-[[(2-pyridinylmethyl)amino]methyl]phenyl]methylamine (298681-03-5) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → C15H19N5

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h;	100%

1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) + benzyl-methyl-amine (103-67-3) → N-benzyl-N-methylguanidine hydrochloride (330-69-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	100%
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20℃;	100%

1-(2-aminoethyl)-5,5-dimethyl-imidazolidine-2,4-dione (893433-60-8) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → N-[2-(5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl)-ethyl]-guanidine hydrochloride (893433-72-2)

Conditions	Yield
In acetonitrile for 16h; Heating / reflux;	100%

N-BOC-1,2-diaminoethane (57260-73-8) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → guanidine N-[2-(amidinoamino)ethyl](tert-butoxy)carboxamide, hydrochloride

Conditions	Yield
In acetonitrile	100%

N1,N1'-(1,10-phenanthroline-4,7-diyl)dibutane-1,4-diamine (1204587-47-2) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → 1,1'-(4,4'-(1,10-phenanthroline-4,7-diyl)bis(azanediyl)bis(butane-4,1-diyl))diguanidine (1204587-52-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃;	100%

N1,N1'-(1,10-phenanthroline-4,7-diyl)diethane-1,2-diamine (1204587-46-1) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → 1,1'-(2,2'-(1,10-phenanthroline-4,7-diyl)bis(azanediyl)bis(ethane-2,1-diyl))diguanidine (1204587-50-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃;	100%

1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) + N1,N1'-(1,10-phenanthroline-4,7-diyl)dipropane-1,3-diamine (156492-35-2) → 1,1'-(3,3'-(1,10-phenanthroline-4,7-diyl)bis(azanediyl)bis(propane-3,1-diyl))diguanidine (1204587-51-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃;	100%

5-tert-butoxycarbonylamino-1-aminopentane (51644-96-3) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) + trifluoroacetic acid (76-05-1) → tert-butyl N-(5-guanidinopentyl)carbamate trifluoroacetate

Conditions	Yield
Stage #1: 5-tert-butoxycarbonylamino-1-aminopentane; 1H-pyrazole-1-carboximidamide hydrochloride With triethylamine In dichloromethane at 20℃; Inert atmosphere; Stage #2: trifluoroacetic acid	100%

1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) + 4-(2-methoxy-phenyl)-[1,4]diazepane-1-carboxylic acid tret-butyl ester (152943-97-0) → C13H20N4O

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;	100%

4-(3-aminopropoxy)-N-(2-phenoxyphenyl)benzamide + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) + trifluoroacetic acid (76-05-1) → N-(2-phenoxyphenyl)-4-(3-guanidinopropoxy)benzamide trifluoroacetate

Conditions	Yield
Stage #1: 4-(3-aminopropoxy)-N-(2-phenoxyphenyl)benzamide; 1H-pyrazole-1-carboximidamide hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 44h; Inert atmosphere; Stage #2: trifluoroacetic acid In water; acetonitrile	100%

(10H-phenoxazin-10-yl)(4-(3-aminopropoxy))phenylmethanone + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) + trifluoroacetic acid (76-05-1) → (10H-phenoxazin-10-yl)(4-(3-guanidinopropoxy))phenylmethanone trifluoroacetate

Conditions	Yield
Stage #1: (10H-phenoxazin-10-yl)(4-(3-aminopropoxy))phenylmethanone; 1H-pyrazole-1-carboximidamide hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 44h; Inert atmosphere; Stage #2: trifluoroacetic acid In water; acetonitrile	100%

1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) + (6S,11Z,13S)-6-amino-8-(1',3'-dioxan-2'-yl)-2-methyl-13-triisopropylsiloxypentadeca-2,11-diene (246266-26-2) → N-{(S)-5-Methyl-1-[2-((Z)-(S)-5-triisopropylsilanyloxy-hept-3-enyl)-[1,3]dioxan-2-ylmethyl]-hex-4-enyl}-guanidine; hydrochloride

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	99%

4-aminophenyl-cellulose + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → 4-[1-(1H-pyrazol-1-yl-iminomethyl)triazen-3-yl]phenyl-cellulose

Conditions	Yield
Stage #1: 4-aminophenyl-cellulose With hydrogenchloride; sodium nitrite In water at 0℃; for 3h; Stage #2: 1H-pyrazole-1-carboximidamide hydrochloride With sodium hydrogencarbonate In water at 0 - 20℃; for 15h;	99%

1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) + Allyl chloroformate (2937-50-0) → 1H-pyrazole-N-allyloxycarbonyl-1-carboxamidine (277334-62-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 4h;	99%

4-(4-chlorophenyl) piperazine (38212-33-8) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → 4-(4-chloro-phenyl)-piperazine-1-carboximidic acid amide (17238-60-7)

Conditions	Yield
Stage #1: 4-(4-chlorophenyl) piperazine; 1H-pyrazole-1-carboximidamide hydrochloride With N-ethyl-N,N-diisopropylamine In ethanol for 7h; Heating / reflux; Stage #2: With water In ethanol	99%

n-Octylamine (111-86-4) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → octylguanidinium chloride

Conditions	Yield
In neat (no solvent) at 25℃; for 0.17h; Sonication;	99%
In acetonitrile for 3h; Reflux;	59%
In ethanol at 35℃; for 48h;

4-methoxy-N-methylbenzylamine + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → N-[(4-methoxyphenyl)methyl]-N-methylguanidine hydrochloride (1344719-01-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	98%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	45%

4-azatetracyclo[5.4.2.02,6.08.11]tridecane hydrochloride + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → 4-amidino-4-azatetracyclo[5.4.2.02,6.08.11]tridecane hydrochloride

Conditions	Yield
With triethylamine In acetonitrile for 6h; Reflux;	98%

1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) + 1-(o-fluorophenyl)piperazine (1011-15-0) → 4-(4-fluorophenyl)piperazine-1-carboximidamide (77723-19-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;	97%

AmBisome (1397-89-3) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → guanidine-AmB (1033521-39-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	97%

2,5-dioxopyrrolidin-1-yl methylcarbamate (18342-66-0) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → N'-(N-methylcarbamoyl)-1H-pyrazole-1-carboxamidine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 9h; Inert atmosphere;	97%

C106H140N10S + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → C114H156N26S

Conditions	Yield
Stage #1: C106H140N10S With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; methanol at 20℃; for 1h; Stage #2: 1H-pyrazole-1-carboximidamide hydrochloride In tetrahydrofuran; methanol at 20℃; for 24h;	97%

3-[3-(5-chloro-2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxyamine (208642-83-5) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → 3-[3-(5-chloro-2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxyguanidine hydrochloride

Conditions	Yield
In N,N-dimethyl-formamide; acetonitrile	96%

5-(4-aminobutoxy)-2-(6-aminohexanamido)-N-(4-phenoxyphenyl)benzamide (1192471-20-7) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → 5-(4-guanidinobutoxy)-2-(6-guanidinohexanamido)-N-(4-phenoxyphenyl)benzamide dihydrochloride

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Inert atmosphere;	96%

3-azatetracyclo[5.2.1.15,8.01,5]undecane hydrochloride + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → 3-amidino-3-azatetracyclo[5.2.1.15,8.01,5]undecane hydrochloride

Conditions	Yield
With triethylamine In acetonitrile at 70℃; for 6h;	96%

1-(4-methylphenyl)-3,3,3-trifluoropropan-1-one (121194-34-1) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → 4-fluoro-2-(1H-pyrazol-1-yl)-6-(p-tolyl)pyrimidine

Conditions	Yield
With potassium hydrogencarbonate In 1,4-dioxane at 60℃;	96%

Upstream product

• 152120-61-1 tert-butyl (1H-pyrazol-1-ylcarbonoimidoyl)carbamate 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 2582-30-1 aminoguanidine bicarbonate 
• 1937-19-5 1-aminoguanidine hydrochloride 
• 420-04-2 CYANAMID 
• 35877-22-6 1H-pyrazole hydrochloride 
• 288-13-1 NH-pyrazole 

Downstream Products

• 63885-25-6 2-ethanolamine-N-carboxamidine hydrochloride 
• 911857-32-4 4-(3,3-dimethoxypropyl)-6-phenyl-2-pyrazol-1-yl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester 
• 911856-91-2 6-methyl-4-propyl-2-pyrazol-1-yl-1,4-dihydropyrimidine-5-carboxylic acid benzyl ester 
• 911856-90-1 4-isopropyl-6-methyl-2-pyrazol-1-yl-1,4-dihydropyrimidine-5-carboxylic acid benzyl ester 
• 1197-49-5 1-benzylguanidine hydrochloride 
• 262277-44-1 (S)-2-Benzenesulfonylamino-3-{3-[7-(3-guanidino-propoxy)-4-oxo-4H-quinolizin-3-yl]-ureido}-propionic Acid 
• 262277-88-3 3-{[8-(4-Carbamimidoyl-piperazin-1-yl)-4-oxo-4H-quinolizine-3-carbonyl]-amino}-3-phenyl-propionic acid trifluoroacetate 

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