p-Toluenesulfonyl azide

HCID 13661

Notes Reactions

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Basic information

CAS: 941-55-9
Standard SMILES: Cc1ccc(S(=O)(=O)N=[N+]=[N-])cc1
InChIKey: NDLIRBZKZSDGSO-UHFFFAOYSA-N
Molecular formula: C7H7N3O2S
Average molar mass: 197.22 g/mol
Monoisotopic mass: 197.02589765

Names & identifiers

Preferred name: p-Toluenesulfonyl azide
IUPAC: N-diazo-4-methylbenzenesulfonamide
English name: Tosyl azide
Molecular formula: C7H7N3O2S
Molecular weight: 197.21

Names & synonyms

p-Toluenesulfonyl azideTosyl azideBenzenesulfonyl azide, 4-methyl-p-Toluenesulfonazidep-Toluenesulfonic acid azide4-methylbenzenesulfonyl azideTosyl nitridep-Tolylsulfonyl azidep-Tosyl azidep-Methylphenylsulfonyl azideAzido-p-toluenesulfonic acid4-METHYLPHENYLSULFONYL AZIDE

Show more names

TsN3CB54978704-methylbenzene-1-sulfonyl azideTosyl azide (75% in ethyl acetate)p-Toluenesulfonyl azide, 99%, 25% in Ethyl acetateosyl azide

4-TOLUENESULFONYL AZIDEP-METHYLBENZENESULFONYL AZIDENSC-138649TOLUENESULFONAZIDE, P-97F7BLE97SDTXSID4061333UNII-97F7BLE97SEINECS 213-381-5

Database identifiers

CAS: 941-55-9
PubChem CID: 13661
UNII: 97F7BLE97S
EC Number: 213-381-5
Nikkaji: J145.099I

Properties

Computed structural properties

XLogP: 2.8
Topological polar surface area: 56.9 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 13
Formal charge: 0
Complexity: 305

Physicochemical properties

Melting point: 22 °C · 22 °C
Density: 0.9 g/mL · ~0.90 g/mL at 20 °C
refractive index: 20 · n20/D 1.548
Flash point: 4 ℃ · 4℃
storage temp.: 2 · 2-8°C
form: liquid
InChI: InChI=1S/C7H7N3O2S/c1-6-2-4-7(5-3-6)13(11,12)10-9-8/h2-5H,1H3
InChIKey: NDLIRBZKZSDGSO-UHFFFAOYSA-N
SMILES: C1(C=CC(C)=CC=1)S(=O)(=O)N=[N+]=[N-]
FDA UNII: 97 F7BLE97S · 97F7BLE97S
EPA Substance Registry System: 4 · Benzenesulfonyl azide, 4-methyl- (941-55-9)
UNSPSC Code: 12352125 · 12352125
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS06,GHS08
Signal word: Danger
Hazard statements: 225 · H225-H300-H304-H315-H336-H361d-H373-H412
Precautionary statements: 201 · P201-P210-P273-P301+P310-P303+P361+P353-P331
target organs: Central nervous system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: F,T+
Risk Statements: 5 · 5-67-65-48/20-38-28-11-63
Safety Statements: 16 · 16-35-45-36/37-28-9
RIDADR: UN REST
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 29299090 · 29299090
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 2 OralAquatic · Acute Tox. 2 OralAquatic Chronic 3Asp. Tox. 1Flam. Liq. 2Repr. 2Skin Irrit. 2STOT RE 2STOT SE 3

Safety & regulation

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
ridadr: UN REST
hs_code: 29299090
risk_code: 5-67-65-48/20-38-28-11-63
Signal word: Danger
Symbol(GHS): GHS02,GHS06,GHS08
hazard_code: F,T+
safety_code: 16-35-45-36/37-28-9
Storage Class: 3 - Flammable liquids
target organs: Central nervous system
Hazard statements: H225-H300-H304-H315-H336-H361d-H373-H412
Hazard Classifications: Acute Tox. 2 OralAquatic Chronic 3Asp. Tox. 1Flam. Liq. 2Repr. 2Skin Irrit. 2STOT RE 2STOT SE 3
Precautionary statements: P201-P210-P273-P301+P310-P303+P361+P353-P331

Chemistry & industry

Applications · 4 items

DescriptionTosyl azide is a reagent used in organic synthesis. It is prepared by the reaction of tosyl chloride with sodium azide in aqueous acetone.

UsesUsed for the introduction of azide and diazo functional groups. It is also used as a nitrene source and as a substrate for [3+2] cycloaddition reactions.

Uses4-Methylbenzenesulfonyl Azide can be used to target Bcl-2 family proteins to potentially treat cancer.

Usesp-Toluenesulfonyl azide solution can be employed as a reagent along with alkyne, and amine in the three-component coupling reaction for the synthesis of N-sulfonylamidines in presence of copper catalyst.It can also be used in the synthesis of N-sulfonyl-1,2,3-triazoles by azide-alkyne cycloaddition reaction in the presence of copper catalyst.