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Cas Database

622-37-7

622-37-7

Identification

  • Product Name:Benzene, azido-

  • CAS Number: 622-37-7

  • EINECS:210-730-3

  • Molecular Weight:119.126

  • Molecular Formula: C6H5 N3

  • HS Code:

  • Mol File:622-37-7.mol

Synonyms:Azidobenzene;Benzene, triazo-; NSC 512574; Phenyl azide

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Safety information and MSDS view more

  • Hazard Codes:F,Xn

  • Signal Word:Danger

  • Hazard Statement:H241 Heating may cause a fire or explosionH315 Causes skin irritation H319 Causes serious eye irritation H372 Causes damage to organs through prolonged or repeated exposure

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:Azidobenzene
  • Packaging:100mg
  • Price:$ 45
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:Azidobenzene
  • Packaging:1g
  • Price:$ 310
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Azidobenzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0%
  • Packaging:50ml
  • Price:$ 486
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Azidobenzene solution ~0.5 M in 2-methyltetrahydrofuran, ≥95.0% (HPLC)
  • Packaging:50ml
  • Price:$ 479
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Azidobenzene solution ~0.5 M in 2-methyltetrahydrofuran, ≥95.0% (HPLC)
  • Packaging:10ml
  • Price:$ 124
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Azidobenzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0%
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  • Price:$ 120
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Azidomethane solution - 0.5M solution in?tert-butyl methyl ether
  • Packaging:5 g
  • Price:$ 165
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Azidomethane solution - 0.5M solution in?tert-butyl methyl ether
  • Packaging:10 g
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Azidomethane solution - 0.5M solution in?tert-butyl methyl ether
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Azidomethane solution - 0.5M solution in?tert-butyl methyl ether
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Relevant articles and documentsAll total 197 Articles be found

Hybrid Pyrazolyl-1,2,3-Triazolyl Tripodal Tetraamine Ligands: Click Synthesis and Cobalt(III) Complexes

Cubanski, John R.,Reish, Matthew E.,Blackman, Allan G.,Steel, Peter J.,Gordon, Keith C.,McMorran, David A.,Crowley, James D.

, p. 1160 - 1170 (2015)

A family of tripodal tetraamine ligands incorporating two pyrazolyl and one 1,2,3-triazolyl donor arm have been synthesized in modest-to-excellent yields (42-90%) using the copper(i)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Mono-, bis-, and tris-tripodal ligand scaffolds were readily generated using this method. The coordination chemistry of the ligands with cobalt(iii) ions has been studied, and cobalt(iii) carbonato complexes of the ligands have been isolated and characterized spectroscopically and crystallographically. X-ray crystallography and NMR spectroscopy of the mono-metallic complexes showed that racemic mixtures of the cis-isomer are formed selectively. The di- and tri-metallic systems could not be crystallized, but NMR spectroscopy indicates that these compounds were isolated as mixtures of stereoisomers.

-

Vignon

, p. 233 (1905)

-

A simple copper-catalysed tandem cyclisation of ynamides leading to triazolo-1,2,4-benzothiadiazine-1,1-dioxides in PEG-400 medium

Reddy, Alla Siva,Reddy, M. Nagarjuna,Swamy, K. C. Kumara

, p. 28359 - 28367 (2014)

An efficient one-pot approach for the synthesis of fused triazolo 1,2,4-benzothiadiazine-1,1-dioxide derivatives from functionalised ynamides and sodium azide in the presence of CuI using PEG-400 as the medium is described. The cyclisation process involves intermolecular C-N bond formation and subsequent cycloaddition between ynamide and azide. Thus three new C-N bonds are formed in a single step. It is also demonstrated that the triazole ring in triazolo-1,2,4-benzothiadiazine-1,1-dioxide can be readily decyclised in the presence of glacial acetic acid with the elimination of molecular nitrogen.

Pyridyl-Functionalised 3H-1,2,3,4-Triazaphospholes: Synthesis, Coordination Chemistry and Photophysical Properties of Low-Coordinate Phosphorus Compounds

Sklorz, Julian A. W.,Hoof, Santina,Rades, Nadine,Derycke, Nicolas,K?ncz?l, Lászl?,Szieberth, Dénes,Weber, Manuela,Wiecko, Jelena,Nyulászi, Lászl?,Hissler, Muriel,Müller, Christian

, p. 11096 - 11109 (2015)

Novel conjugated, pyridyl-functionalised triazaphospholes with either tBu or SiMe3 substituents at the 5-position of the N3PC heterocycle have been prepared by a [3+2] cycloaddition reaction and compared with structurally related, triazole-based systems. Photoexcitation of the 2-pyridyl-substituted triazaphosphole gives rise to a significant fluorescence emission with a quantum yield of up to 12 %. In contrast, the all-nitrogen triazole analogue shows no emission at all. DFT calculations indicate that the 2-pyridyl substituted systems have a more rigid and planar structure than their 3- and 4-pyridyl isomers. Time-dependent (TD) DFT calculations show that only the 2-pyridyl-substituted triazaphosphole exhibits similar planar geometry, with matching conformational arrangements in the lowest energy excited state and the ground state; this helps to explain the enhanced emission intensity. The chelating P,N-hybrid ligand forms a ReI complex of the type [(N^N)Re(CO)3Br] through the coordination of nitrogen atom N2 to the metal centre rather than through the phosphorus donor. Both structural and spectroscopic data indicate substantial π-accepting character of the triazaphosphole, which is again in contrast to that of the all-nitrogen-containing triazoles. The synthesis and photophysical properties of a new class of phosphorus-containing extended π systems are described. Mix and match: Hitherto unknown pyridyl-functionalized triazaphospholes have been synthesized by a [3+2] cycloaddition reaction starting from phosphaalkynes and pyridyl-substituted azides (see figure). Both experiments and theoretical calculations established these compounds as novel π-conjugated organophosphorus derivatives for future optoelectronic applications.

-

Ito

, p. 635 (1966)

-

Homogeneous catalyst containing Pd in the reduction of aryl azides to primary amines

Aydinli, E.,Cantopcu, E.,Goksu, H.

, (2022/03/17)

Abstract: Commercially available dichloro[2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II) (BINAP.PdCl2) homogeneous catalyst was used for the reduction of aryl azides to primary amines. The reactions were carried out in water and yields above 95% were obtained in a short time. Sodium borohydride was used as the reducing reagent. A number of aryl azide derivatives have been converted into primary amines, thanks to the hydrogen gas released by sodium borohydride with the help of water and catalyst. Graphical Abstract: [Figure not available: see fulltext.] Synopsis Commercially available dichloro[2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II) (BINAP.PdCl2) homogeneous catalyst was used for the reduction of aryl azides to primary amines. The reactions were carried out in water and yields above 95% were obtained in a short time. Sodium borohydride was used as the reducing reagent. A number of aryl azide derivatives have been converted into primary amines, thanks to the hydrogen gas released by sodium borohydride with the help of water and catalyst.

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter

supporting information, p. 133 - 146 (2021/11/04)

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Immobilization of vitamin B1 on the magnetic dialdehyde starch as an efficient carbene-type support for the copper complexation and its catalytic activity examination

Abbaspour, M.,Mohammadi Ziarani, G.,Rafiee, F.

, (2021/11/16)

Since the starch biopolymer is an available and inexpensive matrix with modifiable functionality and stabilization capability for metal ions, in this report, we oxidized it to dialdehyde form for the further functionalization with vitamin B1 as a green σ-donor and π-acceptor carbene type ligand. Immobilization of vitamin B1 on this biopolymer was done through imine bond formation between NH2 groups of aminopyrimidine segment of vitamin B1 and aldehyde functional groups of starch oxide. Thiazolium heterocycle part in this biomolecule provided a carbene type precursor for the metal complexation. After the magnetization process by using of Fe3O4 nanoparticles that lead to quick and facile magnetic separation and metal catalyst recycling, copper ions immobilized on the magnetic support (5.9 wt% Cu, 0.93 mmol/g). The prepared copper N-heterocyclic carbene complex (Fe3O4@DAS@VB1@CuCl nanocomposite) was characterized by FT-IR, SEM, EDX, XRD, VSM, TGA and ICP-OES analysis and then its catalytic activity investigated in azidonation of arylboronic acids and also one-pot coupling reaction of the synthesized aryl azides with phenylacetylene. 1,4-Diaryl 1,2,3-triazoles were obtained in excellent yields (≥90%) at proper reaction times (30–200 min). The magnetic catalyst was recovered by a magnetic field and reused in azidation reaction up to 7 cycle.

Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions

Nannapaneni, Madhavi,Pendem, Venkata Bhavanarushi,Tamminana, Ramana

, (2022/01/12)

The iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology. All the reactions are rapid, facile, and accomplished at room temperature. A variety of substrates readily underwent the optimized reaction conditions to provide their respective target products in good to excellent yields. Furthermore, we have confirmed that no other by-products could be identified during our experimental reaction process. Graphical abstract: Iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology.[Figure not available: see fulltext.].

Structural and Activity Relationships of 6-Sulfonyl-8-Nitrobenzothiazinones as Antitubercular Agents

Chiarelli, Laurent R.,Fan, Dongguang,Han, Quanquan,Lu, Yu,Qiao, Chunhua,Shi, Rui,Stelitano, Giovanni,Wang, Bin,Huszár, Stanislav,Miku?ová, Katarína,Savková, Karin

supporting information, p. 14526 - 14539 (2021/10/26)

The benzothiazinone (BTZ) scaffold compound PBTZ169 kills Mycobacterium tuberculosis by inhibiting the essential flavoenzyme DprE1, consequently blocking the synthesis of the cell wall component arabinans. While extraordinarily potent against M. tuberculosis with a minimum inhibitory concentration (MIC) less than 0.2 ng/mL, its low aqueous solubility and bioavailability issues need to be addressed. Here, we designed and synthesized a series of 6-methanesulfonyl substituted BTZ analogues; further exploration introduced five-member aromatic heterocycles as linkers to attach an aryl group as the side chain. Our work led to the discovery of a number of BTZ derived compounds with potent antitubercular activity. The optimized compounds 6 and 38 exhibited MIC 47 and 30 nM, respectively. Compared to PBTZ169, both compounds displayed increased aqueous solubility and higher stability in human liver microsomes. This study suggested that an alternative side-chain modification strategy could be implemented to improve the druglike properties of the BTZ-based compounds.

Process route upstream and downstream products

Process route

diethyl ether
60-29-7,927820-24-4

diethyl ether

aniline
62-53-3

aniline

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

benzene diazonium chloride
100-34-5

benzene diazonium chloride

Phenyl azide
622-37-7

Phenyl azide

Conditions
Conditions Yield
diethyl ether
60-29-7,927820-24-4

diethyl ether

aniline
62-53-3

aniline

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

2-nitro-aniline
88-74-4

2-nitro-aniline

Phenyl azide
622-37-7

Phenyl azide

Conditions
Conditions Yield
unter Kuehlung;
cis-nitrous acid
7782-77-6

cis-nitrous acid

phenylhydrazine
100-63-0

phenylhydrazine

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

Phenyl azide
622-37-7

Phenyl azide

dinitrogen monoxide
10024-97-2

dinitrogen monoxide

Conditions
Conditions Yield
byproducts: benzene diazonium salt; react. with 2 mol HNO2;
byproducts: benzene diazonium salt; react. with 2 mol HNO2;
hydroxylamine
7803-49-8

hydroxylamine

N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine

aniline
62-53-3

aniline

Phenyl azide
622-37-7

Phenyl azide

azoxybenzene
495-48-7,55599-32-1

azoxybenzene

1-(phenyl)-3-phenyl-3-hydroxytriazene
5756-82-1

1-(phenyl)-3-phenyl-3-hydroxytriazene

Conditions
Conditions Yield
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

p-toluene sulfinic acid
536-57-2

p-toluene sulfinic acid

Phenyl azide
622-37-7

Phenyl azide

Conditions
Conditions Yield
With potassium hydroxide; benzene diazonium chloride;
3-[(4-methylphenyl)sulfonyl]-1-phenyltriaz-1-ene
65739-06-2

3-[(4-methylphenyl)sulfonyl]-1-phenyltriaz-1-ene

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

p-toluene sulfinic acid
536-57-2

p-toluene sulfinic acid

Phenyl azide
622-37-7

Phenyl azide

Conditions
Conditions Yield
benzene diazonium chloride
100-34-5

benzene diazonium chloride

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

p-toluene sulfinic acid
536-57-2

p-toluene sulfinic acid

Phenyl azide
622-37-7

Phenyl azide

phenylazo 4-methylphenyl sulfone
26788-89-6

phenylazo 4-methylphenyl sulfone

Conditions
Conditions Yield
in stark alkalischer Loesung;
1-methyl-4,5-diphenyl-4,5-dihydro-1<i>H</i>-tetrazole
51456-62-3

1-methyl-4,5-diphenyl-4,5-dihydro-1H-tetrazole

methyl azide
624-90-8

methyl azide

benzylidene phenylamine
538-51-2

benzylidene phenylamine

N-Benzylidenemethylamine
622-29-7

N-Benzylidenemethylamine

Phenyl azide
622-37-7

Phenyl azide

Conditions
Conditions Yield
In (2)H8-toluene; at 100 ℃; for 1h; Yield given. Yields of byproduct given;
1-Benzyl-4,5-diphenyl-4,5-dihydro-1H-tetrazole
97325-74-1

1-Benzyl-4,5-diphenyl-4,5-dihydro-1H-tetrazole

benzylidene phenylamine
538-51-2

benzylidene phenylamine

N-benzylidene benzylamine
780-25-6

N-benzylidene benzylamine

benzyl azide
622-79-7

benzyl azide

Phenyl azide
622-37-7

Phenyl azide

Conditions
Conditions Yield
In (2)H8-toluene; at 100 ℃; for 2h; Yield given. Yields of byproduct given;
1-Methyl-1-phenylhydrazine
618-40-6

1-Methyl-1-phenylhydrazine

diethylazodicarboxylate
1972-28-7,218603-74-8

diethylazodicarboxylate

diethyl hydrazodicarboxylate
4114-28-7

diethyl hydrazodicarboxylate

Phenyl azide
622-37-7

Phenyl azide

1,4-dimethyl-1,4-diphenyl-2-tetrazine
5579-27-1

1,4-dimethyl-1,4-diphenyl-2-tetrazine

Conditions
Conditions Yield

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