Cyanogen bromide

Base Information

• Chemical Name: Cyanogen bromide
• CAS No.: 506-68-3
• Molecular Formula: CBrN
• Molecular Weight: 105.922
• Hs Code.: 28530090
• European Community (EC) Number: 208-051-2
• ICSC Number: 0136
• NSC Number: 89684
• UN Number: 1889
• UNII: OS382OHJ8P
• DSSTox Substance ID: DTXSID9021550
• Nikkaji Number: J2.608E
• Wikipedia: Cyanogen bromide,Cyanogen_bromide
• Wikidata: Q420258
• NCI Thesaurus Code: C402
• ChEMBL ID: CHEMBL3561885
• Mol file: 506-68-3.mol

Synonyms:Cyanogenbromide (8CI);Bromine cyanide;Bromine cyanide (BrCN);Bromine monocyanide;Bromocyan;Bromocyanide;Bromocyanide (BrCN);Bromocyanogen;Campilit;Cyanobromide;Cyanogen bromide (BrCN);Cyanogen monobromide;NSC 89684;

Chemical Property of Cyanogen bromide

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 100 mm Hg ( 22.6 °C)
• Melting Point: 50-53 °C(lit.)
• Refractive Index: 1.467
• Boiling Point: 61.5 °C at 760 mmHg
• Flash Point: 61.4°C
• PSA: 23.79000
• Density: 2.052 g/cm³
• LogP: 0.86238
• Storage Temp.: 0-6°C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: Soluble in chloroform, dichloromethane, ethanol, diethyl ether,
• Water Solubility.: decomposed slowly by cold H2O [HAW93]
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 104.92141
• Heavy Atom Count: 3
• Complexity: 31.3
• Transport DOT Label: Poison Corrosive

Purity/Quality:

99.9% ^*data from raw suppliers

Cyanogen Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N,F,C
• Hazard Codes: T+,N,F,C
• Statements: 26/27/28-34-50/53-40-11-36/37-32-51/53
• Safety Statements: 53-28-36/37/39-45-60-61-26-16-7/9-29-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Cyanides
• Canonical SMILES: C(#N)Br
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes, skin and respiratory tract. Inhalation of the vapour may cause lung oedema. The effects may be delayed. The substance may cause effects on the cellular respiration. This may result in convulsions, unconsciousness and respiratory failure. Medical observation is indicated. Exposure could cause death.
• General Description: Cyanogen bromide (BrCN) is utilized as a reagent in the synthesis of azadipeptide nitriles, serving as a key component in reacting with amino acid-derived hydrazides to form these protease inhibitors. Its role in the optimized N1,N2-dimethylation method highlights its importance in generating highly potent and stable inhibitors for papain-like cysteine proteases, though the study primarily focuses on the inhibitory properties and stability of the resulting compounds rather than the specific characteristics of cyanogen bromide itself.

Technology Process of Cyanogen bromide

There total 82 articles about Cyanogen bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

Thiocyanate (302-04-5,1111-68-8,37223-05-5,62476-95-3,69924-38-5,81210-01-7,60168-45-8) + hypobromite → bromocyane (506-68-3) + bromide (10097-32-2,16759-25-4,24959-67-9) + Sulfate (14808-79-8)

Guidance literature:

With sodium hydroxide; sodium perchlorate; In water; Rapid addn. of thermostated aq. NaOBr soln. to aq. NaClO4 soln. contg. SCN(1-) and NaOH, 293-313 K; Monitored by iodometric estimation of unreacted OBr(1-), react. mechanism discussed.; Kinetics;

Reference yield: 94.0%

sodium hypobromide + potassium thioacyanate (333-20-0) → bromocyane (506-68-3) + bromide (10097-32-2,16759-25-4,24959-67-9) + Sulfate (14808-79-8)

Guidance literature:

With sodium hydroxide; sodium perchlorate; In water; Rapid addn. of thermostated aq. NaOBr soln. to aq. NaClO4 soln. contg. SCN(1-) and NaOH, 293-313 K; Monitored by iodometric estimation of unreacted OBr(1-), react. mechanism discussed.; Kinetics;

Reference yield: 94.0%

N-Bromosuccinimide (128-08-5) + mercury(II) diacetate (1600-27-7) + potassium thioacyanate (333-20-0) → Succinimide (123-56-8,89963-74-6) + bromocyane (506-68-3) + bromide (10097-32-2,16759-25-4,24959-67-9) + Sulfate (14808-79-8) + hydrogen cation

Guidance literature:

With sodium hydroxide; In methanol; water; oxidation of SCN(1-) by NBS in aq. methanol in presence of mercuric acetate and NaOH at 303 K; gravimetric and iodometric methods; Kinetics;

upstream raw materials:

dibromo-dinitro-methane

potassium cyanide

1,1,2-tribromotrinitroethane

sodium cyanide

Downstream raw materials:

pyrrolidine-1-carbonitrile

4-bromo-2-methyl-2H-1,2,3-triazole

1-piperidinylcarbonnitrile

2-bromofuran

Refernces

Azadipeptide nitriles: Highly potent and proteolytically stable inhibitors of papain-like cysteine proteases

10.1002/anie.200705858

The study focuses on the development and evaluation of azadipeptide nitriles as potent and proteolytically stable inhibitors of papain-like cysteine proteases, which are medically significant due to their role in various diseases and as virulence factors in human pathogenic parasites. The researchers synthesized azadipeptide nitriles by reacting amino acid-derived hydrazides with cyanogen bromide, a method that initially faced challenges with cyclization but was optimized through N1,N2-dimethylation. These compounds, particularly the first representative 6, showed low nanomolar to picomolar inhibitory activity against papain and therapeutically important cathepsins L, S, and K. The study highlights the impact of CH/N exchange in the P1 position of dipeptide nitriles on enzyme-inhibitor interactions, leading to significantly increased inhibitory activities compared to their carba-analogues. The azadipeptide nitriles demonstrated time-dependent slow-binding inhibition and a high degree of stability against protease-catalyzed degradation, making them promising candidates for developing selective and stable inhibitors for this class of proteases.

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