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CAS RN: 563-41-7 | Product Number: S0032

Semicarbazide Hydrochloride

Purity: >99.0%(T)
2   ≥20 
2   ≥20 

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Product Number S0032
Purity / Analysis Method >99.0%(T)
Molecular Formula / Molecular Weight CH__5N__3O·HCl = 111.53  
Physical State (20 deg.C) Solid
CAS RN 563-41-7
Reaxys Registry Number 3593642
PubChem Substance ID 87575661
Merck Index (14) 8444
MDL Number


Appearance White to Almost white powder to crystal
Purity(Bromination Method) min. 99.0 %
Properties (reference)
Solubility in water Completely soluble
Solubility (slightly sol. in) Alcohol
Solubility (insoluble in) Ether
Pictogram Pictogram Pictogram
Signal Word Danger
Hazard Statements H301 : Toxic if swallowed.
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
H361 : Suspected of damaging fertility or the unborn child.
H373 : May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements P260 : Do not breathe dust/ fume/ gas/ mist/ vapours/ spray.
P201 : Obtain special instructions before use.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P308 + P313 : IF exposed or concerned: Get medical advice/ attention.
P301 + P310 + P330 : IF SWALLOWED: Immediately call a POISON CENTER/doctor. Rinse mouth.
Related Laws:
EC Number 209-247-0
RTECS# VT3500000
Transport Information:
UN Number UN2811
Class 6.1
Packing Group III
HS Number 2928009090
Synthesis of Alkynyl Ketones using Eschenmoser-Tanabe Fragmentation(alternative method)

Typical Procedure:
To a stirred solution of semicarbazide hydrochloride (12.94 g, 116.0 mmol) and sodium acetate trihydrate (0.95 g, 12 mmol) in water (116 mL) is added 1 (2.63 g, 11.6 mmol) at room temperature. Sufficient 95% ethanol is added to bring about a homogenous solution. After stirring at room temperature for 7 h, the reaction mixture is extracted with ethyl acetate. The combined organic phases are washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product is purified by silica gel chromatography (ethyl acetate → ethyl acetate : methanol = 9 : 1) to give 2 (2.92 g, 89%) as a white solid.
Next, to a stirred solution of 2 (1.86 g, 6.57 mmol) in dichloromethane (65.7 mL) is added portionwise 95% lead tetraacetate (6.42 g, 13.8 mmol), maintaining the bath temperature at –10 °C After stirring for 1 h at –10 °C, ethyl acetate is added to the reaction mixture, which is allowed to warm to room temperature. Then the mixture is filtered through a Celite pad and concentrated under reduced pressure. The crude product is purified by silica gel column chromatography (hexane : ethyl acetate = 4 : 1) to give 3 (0.83 g, 60%) as a colorless oil.


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