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Guanidine Hydrochloride

HCID 5742
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
50-01-1
Standard SMILES
Cl.N=C(N)N
InChIKey
PJJJBBJSCAKJQF-UHFFFAOYSA-N
Molecular formula
CH5N3.ClH
Average molar mass
95.53 g/mol
Monoisotopic mass
95.02502487

Overview

Guanidine Hydrochloride is the hydrochloride salt form of guanidine, a strong basic compound with parasympathomimetic activity. Guanidine hydrochloride enhances the release of acetylcholine following a nerve impulse and potentiates acetylcholine actions on muscarinic and nicotinic receptors. It also appears to slow the rates of depolarization and repolarization of muscle cell membranes. (NCI05)

Names & identifiers

Preferred name
Guanidine Hydrochloride
IUPAC
guanidine;hydrochloride
English name
Guanidine hydrochloride
Molecular formula
CH5N3.ClH
Molecular weight
95.53

Names & synonyms

Guanidine hydrochloride50-01-1Guanidinium chlorideguanidine HClAminoformamidine hydrochlorideGUANIDINE MONOHYDROCHLORIDECarbamidine hydrochlorideAminomethanamidine hydrochlorideIminourea hydrochloride3YQC9ZY4YBNSC-755884DTXSID7058757
Show more names
GAClGdmClAMINOFORMAMIDINE HCLguanidiniumhydrochlorideGUANIDINE HYDROCHLORIDE 99%guanidine,monohydrochlorideGuanidine, hydrochloride (1:1)
Chloride, GuanidiniumGuanidium chlorideCHEBI:32735Chloride, GuanidiumHydrochloride, GuanidineRefChem:58639Monohydrochloride, GuanidineDTXCID4040763

Database identifiers

CAS
50-01-1
PubChem CID
5742
DTXSID
DTXSID7058757
ChEMBL
CHEMBL1200728
UNII
3YQC9ZY4YB

Properties

Computed structural propertiesFilling in

Topological polar surface area
75.9 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
5
Formal charge
0
Complexity
26.3

Experimental & physicochemical properties

CosmeticsBuffering
LogP-1.7
Density1.3 g/cm³
SolubilitySolubility in water, g/100ml at 20 °C: 215
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point · 2 items

178-185 °C

183 °C

Physical Description · 2 items

Large Crystals; Dry Powder; Liquid

HYGROSCOPIC CRYSTALLINE POWDER.

Physicochemical properties

Melting point
180 · 180-185 °C(lit.)
Density
1.18 g/mL · 1.18 g/mL at 25 °C(lit.)
bulk density
550 · 550-620kg/m3

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 9.2% (37 of 404) of reports.

Warning

H302 (90.8%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 4 items

Chemical: Guanidine, monohydrochloride

Guanidine, hydrochloride (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Guanidine, hydrochloride (1:1) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 12-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13899

Guanidinium chloride: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsCombustible.
EC ClassificationSymbol: Xn; R: 22-36/38; S: (2)-22
Chemical DangersOn combustion, forms toxic and corrosive fumes including hydrogen chloride and nitrogen oxides. The solution in water is a weak acid.
Hazard Classes and Categories · 4 items

Acute Tox. 4 (90.8%)

Acute toxicity - category 4

Acute toxicity (Oral) - Category 4

Acute Tox. 4 *

Safety & protection

Chemistry & industry

Uses & manufacturing

U.S. Production2023: 100,000 - <250,000 lb
Consumer UsesLaboratory chemicals
Industry UsesLaboratory chemicals
Use ClassificationCosmetics -> Buffering
General Manufacturing Information · 2 items

Pharmaceutical and Medicine Manufacturing

Guanidine, hydrochloride (1:1): ACTIVE

Applications · 4 items

UsesGuanidine hydrochloride is used in RNA isolation to dissociate nucleoproteins and inhibit RNase. Strong chaotropic agent useful for the denaturation and subsequent refolding of proteins. This strong denaturant can solubilize insoluble or denatured proteins such as inclusion bodies. This can be used as the first step in refolding proteins or enzymes into their active form. Urea and dithiothreitol (DTT) may also be necessary.

UsesGuanidine has a good bacterial and fungicidal efficacy when used in low concentration and can also be used as disinfectant.

UsesGuanidine hydrochloride is used for purification of proteins and nucleic acids. It can be used as a medicine, organic synthesis intermediate and is used in dyes. It acts as an intermediate in the preparation of sulfadiazine, which is an important raw material for sulfamethyldiazine, sulfamethazine and folic acid. It is utilized in the synthesis of 2-amino-pyrimidine, 2- amino -6- methyl-pyrimidine and 2-amino -4,6 - dimethyl-pyrimidine. Also used in RNA isolation to dissociate nucleoproteins and inhibit RNase.

General DescriptionGuanidine hydrochloride (GdnHCl) is a well-known protein and enzyme denaturant. It is a small molecule and hydroscopic in nature. It is used to synthesis medicine, pesticide, dye and other organic compound, is the important material to make sulfanilamide medicine and folacin, and can be used as anti-static agent of compound fibre.

Related reactions

510 records
New reaction record
HRID 3905 reaction equation
HRID 3905As reactantuspto-grants-1988_02
HRID 3906 reaction equation
HRID 3906As reactantuspto-grants-1988_02
HRID 4448 reaction equation
HRID 4448As reactantuspto-grants-1988_02
HRID 28565 reaction equation
HRID 28565As reactantuspto-grants-2008_09
HRID 34462 reaction equation
HRID 34462As reactantuspto-grants-1988_08
HRID 34467 reaction equation
HRID 34467As reactantuspto-grants-1988_08
HRID 38429 reaction equation
HRID 38429As reactantuspto-grants-2013_09
HRID 38430 reaction equation
HRID 38430As reactantuspto-grants-2013_09
Page 1 of 64

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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EC Number
200-002-3
refractive index
20 · n20/D 1.465
storage temp.
room temp
solubility
2 O: · H2O: 6 M, clear, colorless
form
Crystals
pka
13.5 · 13.5(Temp: 27 °C; Solvent: Water)
color
White to slightly yellow
PH
4.5 · 4.5-5.5 (100g/l, H2O, 20℃)
Odor
Odorless
PH Range
4.5 · 4.5 - 6.0 at 573 g/l at 25 °C
biological source
synthetic (organic)
Water Solubility
2280 g/L · 2280 g/L (20 ºC)
Sensitive
Hygroscopic
λmax
260 nm · λ: 260 nm Amax: 0.040λ: 280 nm Amax: 0.025
Merck
14 · 14,4562
BRN
3591990 · 3591990
Stability
Stable. Hygroscopic. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions
BUFFERING
InChI
1S/CH5N3.ClH/c2-1(3)4;/h(H5,2,3,4);1H
InChIKey
PJJJBBJSCAKJQF-UHFFFAOYSA-N
SMILES
Cl[H].NC(N)=N
CAS DataBase Reference
50 · 50-01-1(CAS DataBase Reference)
EWG's Food Scores
1 · 1-2
FDA UNII
3 YQC9ZY4YB · 3YQC9ZY4YB
EPA Substance Registry System
Guanidine monohydrochloride (50-01-1)
Absorption
0.1 at · ≤0.10 at 260nm in H2O at 6M
UNSPSC Code
41116107 · 41116107
NACRES
55 · NA.55
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302+H332-H315-H319
Precautionary statements
261 · P261-P264-P301+P312-P302+P352-P304+P340+P312-P305+P351+P338
PPE
95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes
Xn,Xi
Risk Statements
22 · 22-36/38
Safety Statements
26 · 26-36-22
WGK Germany
1 · 1
RTECS
4300000 · MF4300000
F
3 · 3-10
TSCA
TSCA listed
HS Code
29252000 · 29252000
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 InhalationAcute · Acute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2
Toxicity
50 orally · LD50 orally in Rabbit: 655.3 - 907.1 mg/kg LD50 dermal Rabbit > 2000 mg/kg
REACH Registrations
Active
Fire FightingUse foam, powder.
First Aid Measures · 4 items

Fresh air, rest.

Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Induce vomiting (ONLY IN CONSCIOUS PERSONS!).

Safe StorageWell closed. Dry.
Spillage DisposalSweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water. Personal protection: P2 filter respirator for harmful particles.
Eye PreventionWear safety goggles or eye protection in combination with breathing protection.
Fire PreventionNO open flames.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionPREVENT DISPERSION OF DUST!
Ingestion PreventionDo not eat, drink, or smoke during work.
Inhalation PreventionUse local exhaust or breathing protection.
Effects of Short Term ExposureThe substance is irritating to the eyes and skin.

Toxicology

Exposure RoutesThe substance can be absorbed into the body by ingestion.
Signs and Symptoms · 4 items

Cough.

Redness.

Redness. Pain.

Diarrhoea.

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Guanidine hydrochloride

Ambiguous-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

RAIS Toxicity Values · 4 items

0.02

PPRTV Current

0.02

PPRTV Current

EPA Provisional Peer-Reviewed Toxicity Values · 6 items

Guanidine Chloride

2 x 10^-2 mg/kg-day

2 x 10^-2 mg/kg-day

PDF Document

Inadequate information to assess carcinogenic potential

2014

Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06 · 6 items

1.30e+03

1.60e+04

4.00e+02

7.00e+02

2.00e-02

Volatile

Hazard Quotient Level 3 or Cancer Risk Level 1E-04 · 6 items

3.80e+03

4.90e+04

1.20e+03

7.00e+02

2.00e-02

Volatile

Safety data

F
3-10
PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
MF4300000
hs_code
29252000
Toxicity
LD50 orally in Rabbit: 655.3 - 907.1 mg/kg LD50 dermal Rabbit > 2000 mg/kg
risk_code
22-36/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,Xi
safety_code
26-36-22
Storage Class
11 - Combustible Solids
Hazard statements
H302+H332-H315-H319
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2
Precautionary statements
P261-P264-P301+P312-P302+P352-P304+P340+P312-P305+P351+P338
Preparation methods · 2 items

PreparationIn Dicyanodiamide and ammonium (Ammonium chloride) as raw material, melt reaction at 170-230 ℃, guanidine hydrochloride obtained crude, refined products.

PreparationThe process for preparing guanidine hydrochloride is as follows:Step 1: Fritting - Combine dicyandiamide and ammonium chloride in a reactor with a 1:1.27 weight ratio and carry out a frit reaction at 170-230°C to obtain crude guanidine hydrochloride.Step 2: Dissolving - Dissolve the crude guanidine hydrochloride in water at a 1:1 ratio at normal temperature. Then, add ammonium salt alkaloid in an amount determined by the ammonium salt content in the crude guanidine hydrochloride.Step 3: Filtering - Remove raw materials and reaction by-products with filtration.Step 4: Dehydrating - Dehydrate the filtered ground mother liquor at a high temperature.Step 5: Crystallizing - Cool the supersaturated solution, concentrate, and crystallize to obtain high-purity guanidine hydrochloride.Step 6: Repeat steps 2-5 and add dicyandiamide in the reactor with the guanidine hydrochloride to carry out frit reaction at 170-230°C for 3-4 hours to obtain even higher purity guanidine hydrochloride. This step can be repeated several times if needed.Step 7: To obtain higher purity guanidine hydrochloride, subject the guanidine hydrochloride obtained in step 5 to steps 2-5 again, with the water ratio in step 2 adjusted to 1.5:1. This step can be repeated numerous times as required.

Upstream & downstream products

Upstream raw materials

Double cyanamideAmmonium chloride

Downstream products

2-Amino-5-nitropyrimidine2,5-Diamino-4,6-dichloropyrimidineGuanidine carbonate5-Amino-2-fluoropyrimidineshark soft bone preparation2-Amino-4-chloro-6-methylpyrimidine2-Amino-pyrimidine-5-carboxylic acid ethyl ester2-Amino-6-hydroxypyrimidin-4(3H)-one ,97%2,4-Diamino-1,3,5-triazine5-Amino-2-chloropyrimidine2-Amino-5-pyrimidinecarboxyaldehydeAmiloride hydrochloride9-Ethylguanine2-Aminopyrimidine7-(Trifluoromethyl)-3-iodoimidazo[1,2-a]pyrimidine6-Hydroxy-2,4,5-triaminopyrimidineFormamidine hydrochloride3-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine2-amino-6-chloropyrimidin-4(3H)-one2-Chloro-5-nitropyrimidine2-Amino-6-methyl-4-pyrimidinolGUANINE SULFATEGuanidine phosphate2-Amino-6-hydroxy-pyrimidine-4-carboxylic acid2,4-Diaminopyrimidine2-Aminopyrimidine-5-carboxylic acidISOXANTHOPTERIN
Additional notes · 1 item

DefinitionChEBI: Guanidine Hydrochloride is an aminocarboxamidine, the parent compound of the guanidines. It is a strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism.