563-41-7

Basic information

• Product Name: Semicarbazide hydrochloride
• Synonyms: amidoureahydrochloride;semicarbazide,monohydrochloride;semicarbazidechloride;N-AMINOUREA HYDROCHLORIDE;SEMICARBAZIDE HYDROCHLORIDE;SEMICARBAZIDE CHLORHYDRATE;SEMICARBAZIDE HCL;AMINOUREA HYDROCHLORIDE
• CAS NO: 563-41-7
• Molecular Formula: CH₆N₃O*Cl
• Molecular Weight: 111.53
• EINECS: 209-247-0
• Product Categories: Bases & Related Reagents;Inhibitors;Nucleotides;Amines;Metabolites & Impurities;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Ureas;API;Amines, Metabolites & Impurities
• Mol File: 563-41-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: 175-177 °C (dec.)(lit.)
• Boiling Point: 235.3 °C at 760 mmHg
• Flash Point: 96.1 °C
• Appearance: White/Crystalline Powder and/or Chunks
• Density: 1.2908 (rough estimate)
• Vapor Pressure: 0.0407mmHg at 25°C
• Refractive Index: 1.4480 (estimate)
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: H2O: 0.1 g/mL at 20 °C, clear, colorless
• Water Solubility: 100 g/L (15 ºC)
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
• Merck: 14,8444
• BRN: 3593642
• CAS DataBase Reference: Semicarbazide hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Semicarbazide hydrochloride(563-41-7)
• EPA Substance Registry System: Semicarbazide hydrochloride(563-41-7)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-40-36/38-25-45-23/24/25
• Safety Statements: 24/25-22-45-53
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: VT3500000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 563-41-7(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 563-41-7 differently. You can refer to the following data:
1. White Solid
2. Semicarbazide hydrochloride is a white crystalline solid.

Uses

Different sources of media describe the Uses of 563-41-7 differently. You can refer to the following data:
1. Inhibitor of enzyme. Hypotensive
2. A metabolite of Nitrofuran.
3. Semicarbazide hydrochloride is used as urease substrate and MAO inhibitor. Derivatizing agent for carbonyl compounds as their semicarbazones which produces crystalline compounds with characteristic melting points. Also used in heterocyclic synthesis. Semicarbazone formation has been used to separate carbonyl compounds from mixtures by adsorption onto silica gel from a hydrocarbon solution. Regeneration is by hydrolysis with oxalic acid.

Hazard

Toxic by ingestion. Questionable carcino- gen.

Health Hazard

Semicarbazide hydrochloride is a chemical reagent, and an indicator for its metabolic parent nitrofurazone, a veterinary drug that has been banned for use in livestock production in the European Union and the U.S. amongst other jurisdictions. After Semicarbazide hydrochloride ingestion, experimental animals have developed tremors, ataxia, equilibrium difficulties, and convulsions. Its proposed mechanism of action is by binding to cytosine residues in RNA, to deoxycytosine residues in DNA and to cytosine and deoxycytosine nucleosides. Semicarbazide hydrochloride has an oral LD50 of 225mg/kg in mice and 123 mg/kg in the rat. Some studies suggest that Semicarbazide hydrochloride is a mutagen, an animal carcinogen and a teratogen. Due to the lack of data in humans and overall limited evidence of carcinogenicity in animals, semicarbazide hydrochloride was classified as an IARC Group 3 agent: not classifiable as to its carcinogenicity to humans. Due to its equivocal carcinogenic and mutagenic properties, when handling Semicarbazide hydrochloride and animals treated with Semicarbazide hydrochloride, it is imperative to take caution and adhere to the following guidelines to minimize exposure and the effects of exposure during normal and emergency situations.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by ingestion and intraperitoneal routes. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic and teratogenic data. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl

Potential Exposure

This material is used as a reagent for ketones and aldehydes with which it affords crystalline compounds having characteristic freezing/melting points. Also used in isolation of hormones and certain fractions from essential oils.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Crystallise the salt from aqueous 75% EtOH and dry it under vacuum over CaSO4. Alternatively crystallise it from a mixture of 3.6 mole % MeOH and 6.4 mole % of water. [Kovach et al. J Am Chem Soc 107 7360 1985.] IR: 700, 3500 cm-1 [Ingersoll et al. Org Synth Coll Vol I 485 1941, Davison & Christie J Chem Soc 3389 1955, Thiele & Stange Chem Ber 27 33 1894, pK: Bartlett J Am Chem Soc 54 2853 1923]. The free base crystallises as prisms from absolute EtOH, m 96o. [Curtius & Heidenreich Chem Ber 27 55 1894, Beilstein 3 IV 177.] TOXIC ORALLY, possible CARCINOGEN and TERATOGEN.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. May ignite combustible materials (wood, oil, paper).

InChI:InChI=1/CH5N3O.ClH/c2-1(5)4-3;/h3H2,(H3,2,4,5);1H

Synthetic route

benzaldehyde semicarbazone (1574-10-3) → semicarbazide hydrochloride (563-41-7)

Conditions	Yield
With hydrogenchloride; water

hydrogenchloride (7647-01-0) + thiazolidine-2,4-dione-2-semicarbazone (39130-96-6) → 2,4-thiazolidinedion (2295-31-0) + semicarbazide hydrochloride (563-41-7)

hydrogenchloride (7647-01-0) + 2,6-dimethyl-6-semicarbazido-hept-2-en-4-one semicarbazone → phorone (504-20-1) + semicarbazide hydrochloride (563-41-7)

hydrogenchloride (7647-01-0) + 2-carbamothioyl-N-phenylhydrazine carboxamide (10153-17-0) → N,N-diphenylurea (603-54-3) + semicarbazide hydrochloride (563-41-7) + 2-imino-1.3.4-thiodiazolone-(5)

potassium cyanate (590-28-3) + hydrazine sulfate → semicarbazide hydrochloride (563-41-7)

Conditions	Yield
With water; sodium carbonate at 50 - 60℃; in mehreren Stufen;

C17H17N3O2S (745076-15-7) → 1,1'-(sulfonylbis(4,1-phenylene))bis(ethan-1-one) (10424-68-7) + semicarbazide hydrochloride (563-41-7)

Conditions	Yield
With dihydrogen peroxide; acetic acid at 20℃; for 168h;

C18H20N6O2S (745076-14-6) → 1,1'-(sulfonylbis(4,1-phenylene))bis(ethan-1-one) (10424-68-7) + semicarbazide hydrochloride (563-41-7)

Conditions	Yield
With dihydrogen peroxide; acetic acid at 20℃; for 168h;

C18H20N6OS2 (745076-16-8) → 1,1'-(sulfonylbis(4,1-phenylene))bis(ethan-1-one) (10424-68-7) + semicarbazide hydrochloride (563-41-7) + thiosemicarbazide (79-19-6)

Conditions	Yield
With dihydrogen peroxide; acetic acid at 20℃; for 168h;

methyl benzoylformate semicarbazone (38132-39-7) → methyl 2-oxo-2-phenylacetate (15206-55-0) + semicarbazide hydrochloride (563-41-7)

Conditions	Yield
In water at 30℃; pH=5.00; Equilibrium constant;

potassium cyanate (590-28-3) + hydrazinium sulfate (10034-93-2) → semicarbazide hydrochloride (563-41-7)

Conditions	Yield
With hydrogenchloride; sodium carbonate; acetone In water byproducts: hydrazodicarbonamide; addn. of aq. KOCN to warm (50-60°C) aq. soln. of hydrazine sulfate and Na2CO3; mixt. allowed to stand for 1 d; filtration of hydrazodicarbonamide; addn. of acetone; acetone semicarbazone extd. with ethanol and heated with concd. HCl;
With Na2CO3; benzaldehyde; HCl In water addn. of aq. KOCN to a warm (50-60°C) aq. soln. of hydrazine sulfate and Na2CO3; allow to stand for 1 d; addn. of benzaldehyde; benzaldehyde semicarbazone heated with concd. HCl; extn. of free benzaldehyde with benzene or toluene;
With Na2CO3; acetone; HCl In water
With Na2CO3; benzaldehyde; HCl In water

4-carbamimidoyl semicarbazide; dihydrochloride (28787-22-6) → semicarbazide hydrochloride (563-41-7)

Conditions	Yield
With hydrogenchloride; sodium ethanolate the intermediate 4-(4,6-dihydroxy-pyrimidyl-(2))-semicarbazide hydrochloride is decomposed with concd. HCl;

Mn(2+)*2CH6N3O(1+)*4Cl(1-)=Mn(CH6N3O)2Cl4 → semicarbazide hydrochloride (563-41-7) + manganese(ll) chloride

Conditions	Yield
decompn. at 135°C;
decompn. at 135°C;

nitrofurazone (59-87-0) → semicarbazide hydrochloride (563-41-7)

Conditions	Yield
With hydrogenchloride In water at 25℃; for 12h;

semicarbazide hydrochloride (563-41-7) + 3-phenyl-propenal (104-55-2) → cinnamaldehyde semicarbazone (3839-82-5)

Conditions	Yield
With acetic acid In water for 0.5h; Reflux;	100%
With aluminum oxide In water; tert-butyl alcohol for 0.0833333h;	90%
With ethanol
In ethanol

6,7-benzoisatin (5353-96-8) + semicarbazide hydrochloride (563-41-7) → syn-Benzisatin-3-semicarbazone (110536-39-5, 110536-40-8)

Conditions	Yield
With hydrogenchloride 1.) aq. EtOH, reflux, 25 min, 2.) EtOH, room temp.;	100%

1H-benzo[e]indole-1,2(3H)-dione (5588-87-4) + semicarbazide hydrochloride (563-41-7) → C13H10N4O2 (110536-33-9)

Conditions	Yield
In ethanol for 2h; Heating;	100%

semicarbazide hydrochloride (563-41-7) + (E)-2-formyl-3-(furan-2-yl)acrylonitrile (148840-19-1) → C9H8N4O2

Conditions	Yield
With pyridine for 0.25h; Ambient temperature;	100%

semicarbazide hydrochloride (563-41-7) + 4-methoxy-benzaldehyde (123-11-5) → 4-methoxybenzaldehyde semicarbazone (6292-71-3, 120445-53-6)

Conditions	Yield
With sodium acetate In ethanol; water at 20℃;	100%
Stage #1: semicarbazide hydrochloride With sodium acetate In ethanol at 20℃; for 0.25h; Stage #2: 4-methoxy-benzaldehyde In ethanol at 20℃;	93%
With hydroxylamine hydrochloride; potassium carbonate for 0.025h; microwave irradiation;	90%

semicarbazide hydrochloride (563-41-7) + 1-{4-[4-mono(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone (191398-65-9) → 1-{4-[4-mono(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone-N-aminocarbonylsemicarbazone

Conditions	Yield
With sodium acetate In ethanol Heating;	100%
Stage #1: semicarbazide hydrochloride With sodium acetate In ethanol for 0.25h; Heating; Stage #2: 1-{4-[4-mono(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone With hydrogenchloride Heating;	98%

semicarbazide hydrochloride (563-41-7) + 1-{4-[3,5-di(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone (199865-07-1) → 1-{4-[3,5-di(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone-N-aminocarbonylsemicarbazone

Conditions	Yield
With sodium acetate In ethanol Heating;	100%
Stage #1: semicarbazide hydrochloride With sodium acetate In ethanol for 0.25h; Heating; Stage #2: 1-{4-[3,5-di(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone With hydrogenchloride Heating;	96%

4-[(2,2-diethoxy)acetyl]methyl benzoate (1006876-04-5) + semicarbazide hydrochloride (563-41-7) → methyl 4-(3-oxo-2,3-dihydro-1,2,4-triazin-6-yl)benzoate (1006876-05-6)

Conditions	Yield
Stage #1: 4-[(2,2-diethoxy)acetyl]methyl benzoate; semicarbazide hydrochloride With N-ethyl-N,N-diisopropylamine In methanol; 1,2-dichloro-ethane at 95℃; for 5h; Stage #2: With acetic acid In water Heating / reflux;	100%
Stage #1: 4-[(2,2-diethoxy)acetyl]methyl benzoate; semicarbazide hydrochloride With N-ethyl-N,N-diisopropylamine In methanol; 1,2-dichloro-ethane at 95℃; for 5h; Stage #2: With acetic acid In water Heating / reflux;	100%

semicarbazide hydrochloride (563-41-7) → 2,4-dihydro-1,2,4-triazol-3-one (930-33-6)

Conditions	Yield
With trimethyl orthoformate In methanol; toluene	100%

semicarbazide hydrochloride (563-41-7) + ortho-bromobenzaldehyde (6630-33-7) → 1-(2-bromobenzylidene)semicarbazide (351980-45-5)

Conditions	Yield
With sodium acetate In ethanol; water at 20℃;	100%
With sodium acetate In water

semicarbazide hydrochloride (563-41-7) + 3-methoxy-benzaldehyde (591-31-1) → 2-[(3-methoxyphenyl)methylene]hydrazinecarboxamide

Conditions	Yield
With sodium acetate In ethanol; water at 20℃;	100%
With sodium acetate In ethanol; water Heating;
In 1,4-dioxane for 0.5h; Reflux;
With sodium acetate
With sodium acetate In methanol; water at 20℃; for 0.5h;

3-(3-Hydroxy-17-oxo-estra-1,3,5(10)-trien-15β-yl)-N-(5-methyl-thiazol-2-yl)-propionamide (852519-81-4) + semicarbazide hydrochloride (563-41-7) → 3-{(13S,15R)-3-hydroxy-17-[(E)-N-urea-imino]-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl}-N-(5-methylthiazol-2-yl)propanamide

Conditions	Yield
With sodium acetate In tetrahydrofuran; ethanol at 70℃; for 5h;	100%

semicarbazide hydrochloride (563-41-7) + 4-(Methylthio)benzaldehyde (3446-89-7) → 1-(4-(methylthio)benzylidene)semicarbazide

Conditions	Yield
With sodium acetate In ethanol; water at 20℃;	100%

semicarbazide hydrochloride (563-41-7) + 3-Chlorobenzaldehyde (587-04-2) → 2-[(3-fluorophenyl)methylene]hydrazinecarboxamide

Conditions	Yield
With sodium acetate In ethanol; water at 20℃;	99.2%
With sodium acetate In ethanol; water for 0.0194444h; Microwave irradiation;	89.1%
With acetic acid In ethanol Reflux;	77%

3-hydroxy-6,7-dimethoxy-3H-isobenzofuran-1-one (479-87-8) + semicarbazide hydrochloride (563-41-7) → 6-<(semicarbazono)methyl>-2,3-dimethoxybenzoic acid (26342-00-7)

Conditions	Yield
With pyridine at 42℃; for 6h;	99%

semicarbazide hydrochloride (563-41-7) + 6-Oxo-trans,trans-2,4-hexadienoic acid (88973-46-0) → Semicarbazone l'acide formyl-5 pentadiene-2,4 oique (88973-54-0)

Conditions	Yield
With sodium acetate In ethanol; water Ambient temperature;	99%

m-bromobenzoic aldehyde (3132-99-8) + semicarbazide hydrochloride (563-41-7) → 1-(3-bromobenzylidene)semicarbazide (38407-30-6)

Conditions	Yield
With sodium acetate In ethanol; water at 20℃;	99%
With sodium acetate In ethanol; water for 0.0166667h; Microwave irradiation;	94.2%
Stage #1: semicarbazide hydrochloride With sodium acetate In ethanol at 20℃; for 0.25h; Stage #2: m-bromobenzoic aldehyde In ethanol at 20℃;	85%

semicarbazide hydrochloride (563-41-7) + 1-(3-Bromophenyl)ethanone (2142-63-4) → 1-(1-(3-bromophenyl)ethylidene)semicarbazide (99847-76-4)

Conditions	Yield
With sodium acetate In ethanol; water at 20℃;	99%
Stage #1: semicarbazide hydrochloride With sodium acetate In ethanol at 20℃; for 0.25h; Stage #2: 1-(3-Bromophenyl)ethanone In ethanol at 20℃;	91%
Stage #1: semicarbazide hydrochloride With sodium acetate In ethanol for 0.75h; Heating; Stage #2: 1-(3-Bromophenyl)ethanone In ethanol for 1h; Heating;

semicarbazide hydrochloride (563-41-7) + 4-fluorobenzaldehyde (459-57-4) → 2-[(4-fluorophenyl)methylene]hydrazinecarboxamide (3862-85-9)

Conditions	Yield
With sodium acetate In ethanol; water at 20℃;	99%
With sodium acetate In ethanol; water for 0.0208333h; Microwave irradiation;	90.7%
With hydrogenchloride In ethanol at 20℃; for 3h;	84%

semicarbazide hydrochloride (563-41-7) + o-carboxybenzaldehyde (119-67-5) → 2-((2-carbamoylhydrazono)methyl)benzoic acid (347309-96-0)

Conditions	Yield
With sodium acetate In ethanol; water at 20℃;	99%
With sodium acetate In water

semicarbazide hydrochloride (563-41-7) + vanillin (121-33-5) → vanillin semicarbazone (16742-60-2, 120445-66-1)

Conditions	Yield
With acetic acid In ethanol for 1.5h; Reflux;	98%
With sodium acetate In ethanol; water at 20℃;	94%
With hydrogenchloride In ethanol; water at 20℃;	81%

3-acetylpentane-2,4-dione (815-68-9) + semicarbazide hydrochloride (563-41-7) → 3,5-dimethylpyrazole hydrochloride (31705-88-1)

Conditions	Yield
With hydrogenchloride In methanol for 48h; Ambient temperature;	98%

semicarbazide hydrochloride (563-41-7) + tris-dimorpholinomethyl s-triazine (112055-19-3) → C9H12N12O3 (112055-23-9)

Conditions	Yield
In water at 100℃; for 0.25h;	98%

semicarbazide hydrochloride (563-41-7) + 2-(phenylmethoxy)benzaldehyde (5896-17-3) → o-benzyloxybenzaldehyde semicarbazone

Conditions	Yield
With sodium acetate In ethanol	98%

semicarbazide hydrochloride (563-41-7) + 1-(4-fluorophenyl)ethanone (403-42-9) → 4-fluoroacetophenone semicarbazone (326-33-0)

Conditions	Yield
With sodium acetate In methanol; water	98%
With sodium acetate In methanol; water at 20℃;	98%
Stage #1: semicarbazide hydrochloride With potassium acetate In ethanol at 1℃; for 1h; Reflux; Stage #2: 1-(4-fluorophenyl)ethanone In ethanol Reflux;	87%

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (771-03-9) + semicarbazide hydrochloride (563-41-7) → 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one semicarbazone (54107-20-9)

Conditions	Yield
With sodium acetate In acetic acid 1.) r.t., 2 h, 2.) reflux;	98%

semicarbazide hydrochloride (563-41-7) + 3-methylthio-5,6,7,8-tetrahydro benzothiophene-4-one (168279-57-0) → 6,7-Dihydro-3-(methylthio)benzothiophen-4(5H)-one semicarbazone

Conditions	Yield
With sodium carbonate In ethanol for 15h; Heating;	98%

semicarbazide hydrochloride (563-41-7) + 2-chloro-1,1,1-trimethoxyethane (74974-54-2) → 3-(chloromethyl)-1H-1,2,4-triazol-5(4H)-one (252742-72-6)

Conditions	Yield
In methanol at 20℃; for 72h;	98%
In methanol at 20℃;	62%
In methanol at 20℃; for 72h;
In methanol at 20℃; for 144h;
In methanol at 20℃; for 3h;

2-Hydroxy-5-methylisophthalaldehyde (7310-95-4) + semicarbazide hydrochloride (563-41-7) → 2,2'-[(2-hydroxy-5-methyl-1,3-phenylene)bis(methanylidene)]bis(hydrazine-1-carboxamide) (300731-04-8)

Conditions	Yield
With sodium acetate In ethanol; water at 20℃; for 0.0833333h; Sonication; Green chemistry;	98%
With sodium carbonate In ethanol for 2h; Heating;	76.4%
Stage #1: semicarbazide hydrochloride In methanol for 1h; Stage #2: 2-Hydroxy-5-methylisophthalaldehyde In methanol for 6h; Reflux;	76%

semicarbazide hydrochloride (563-41-7) + 1-[(2R,6R,8R,10S,13R)-13-hydroxy-10-(2'-hydroxyethyl)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanone (389086-29-7) → 1-[(2R,6R,8R,10S,13R)-13-hydroxy-10-(2'-hydroxyethyl)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanone semicarbazone

Conditions	Yield
With sodium acetate In ethanol for 8h;	98%

Upstream product

• 10217-52-4 Hydrazinium hydroxide 
• 57-56-7 Semicarbazide 
• 7803-57-8 Hydrazine hydrate 

Downstream Products

• 58756-26-6 ETHYL 4-PHENYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE 
• 1572-10-7 3-Amino-5-phenylpyrazole 
• 88127-85-9 5-CHLORO-4-(CHLOROMETHYL)-1,2,3-THIADIAZOLE, 97%, 97 
• 57-56-7 Semicarbazide 
• 932-53-6 6-AZATHYMINE 
• 306936-57-2 3-(4-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBALDEHYDE 
• 932-22-9 4,5-Dichloro-3(2H)-pyridazinone 
• 26033-20-5 3-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE 

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