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Carbobenzoxyhydrazide

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CAS:5331-43-1
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  • 2026-01-23
  • CAS:5331-43-1
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  • CAS:5331-43-1
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  • Purity: 99%
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Carbobenzoxyhydrazide Basic information
Product Name:Carbobenzoxyhydrazide
Synonyms:hydrazinecarboxylicacid,phenymethylester;phenymethylhydrazinecarboxylate;Phenylmethyl N-aminocarbamate;Carbobenzoxyhydrazide,98%;Carbobenzoxyhydrazid;Carbobenzyloxyhydrazine;Hydrazincarboxylic Acid Benzyl Ester;NSC 2287
CAS:5331-43-1
MF:C8H10N2O2
MW:166.18
EINECS:226-230-3
Product Categories:Phosgene Derivatives
Mol File:5331-43-1.mol
Carbobenzoxyhydrazide Structure
Carbobenzoxyhydrazide Chemical Properties
Melting point 65-68 °C (lit.)
Boiling point 294.38°C (rough estimate)
density 1.2265 (rough estimate)
refractive index 1.6180 (estimate)
Fp >230 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility DMSO, Methanol
pka10.56±0.20(Predicted)
form Solid
color Beige
Water Solubility Soluble in water (slightly), methanol and DMSO.
BRN 1952982
Major Applicationpeptide synthesis
InChI1S/C8H10N2O2/c9-10-8(11)12-6-7-4-2-1-3-5-7/h1-5H,6,9H2,(H,10,11)
InChIKeyRXUBZLMIGSAPEJ-UHFFFAOYSA-N
SMILESNNC(=O)OCc1ccccc1
CAS DataBase Reference5331-43-1(CAS DataBase Reference)
NIST Chemistry ReferenceHydrazinecarboxylic acid, phenylmethyl ester(5331-43-1)
EPA Substance Registry SystemHydrazinecarboxylic acid, phenylmethyl ester (5331-43-1)
Safety Information
Hazard Codes Xi
Risk Statements 41
Safety Statements 26-36
WGK Germany 3
RTECS MV1724950
TSCA TSCA listed
HS Code 29280000
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Dam. 1
MSDS Information
ProviderLanguage
Carbobenzoxyhydrazide English
SigmaAldrich English
ACROS English
ALFA English
Carbobenzoxyhydrazide Usage And Synthesis
Chemical PropertiesLIGHT BEIGE SHINY FLAKES
UsesBenzyl Carbazate has been shown to prevent the occurrence of oligonucleosome-sized DNA fragmentation in the cell-free system.
UsesBenzyl carbazate is used as a reagent for preparation of benzyloxycarbonyl (Z, Cbz) hydrazides of carboxylic acids, particularly N-protected amino acids. Subsequent hydrogenolysis gives the hydrazide which can be converted to the azide for coupling with a further amino acid residue by the azide method. It is also used in the preparation of simple acyl or sulfonyl hydrazides avoiding diacylation.
Synthesis
Benzyl chloroformate

501-53-1

Carbobenzoxyhydrazide

5331-43-1

1. General procedure for the synthesis of benzyl hydrazinecarboxylate: In a three-necked reaction flask equipped with temperature control, hydrazine hydrate (2.0 mol), potassium carbonate (2.0 mol), and 50 mL of tetrahydrofuran are added sequentially. After cooling the reaction system to -20°C, benzyl chloroformate (2.0 mol) was slowly added. After completion of the reaction, stirring was continued for 2 h. The potassium carbonate was subsequently removed by filtration and washed with water. The organic phase was concentrated to give the crude product of benzyl hydrazinecarboxylate (95.0% yield, 96.0% purity as determined by high performance gas chromatography (GC)). 2. Purification of the crude product of benzyl hydrazinecarboxylate: In another three-necked reaction flask, add the crude product of benzyl hydrazinecarboxylate (40.0 g, purity 96.0%, determined by high performance gas chromatography (GC)) and 400 mL of dichloromethane. 80 mL of 30% hydrochloric acid was added dropwise to the reaction system and solid precipitation was observed. 150 mL of water was added to dissolve some of the solids. The organic layer was separated and retained. Add 80 mL of ammonia dropwise to the aqueous layer and adjust the pH to alkaline. The aqueous layer was extracted three times with 250 mL of dichloromethane. The organic phases were combined and concentrated to give purified benzyl hydrazinecarboxylate (36.0 g, 99.5% purity, 90.0% yield as determined by high performance gas chromatography (GC)).

References[1] Patent: CN103819366, 2016, B. Location in patent: Paragraph 0024-0027
[2] Canadian Journal of Chemistry, 2000, vol. 78, # 7, p. 942 - 949
[3] Chemische Berichte, 1959, vol. 92, p. 1478
[4] Chemische Berichte, 1965, vol. 98, p. 797 - 802
Tag:Carbobenzoxyhydrazide(5331-43-1) Related Product Information
Benzyl chloroformate 4-Nitrobenzyl chloroformate Benzyl formate Benzyl alcohol Benzyl benzoate tert-Butyl carbazate Methyl carbazate Ethyl carbazate 4-METHOXYBENZYL CARBAZATE 1,2-DICARBOBENZYLOXYHYDRAZINE Benzyl PHENYL FORMATE Benzylhydrazine H-PHE-NHNH-Z TFA 1,3,4-OXADIAZOL-2(3H)-ONE, 5-PHENYL- BOC-ASP(OBZL)-TYR(BZL)-NHNH-Z N-ALPHA-CARBOBENZOXYHYDRAZIDE HYDROCHLORIDE (CBZ-HYDRAZIDO)GLYCINE TRIFLUOROACETATE SALT

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