CAS 59-49-4 2(3H)-Benzoxazolone (HCID 6043)

Overview

2-benzoxazolinone is a member of the class of benzoxazoles that is 2,3-dihydro-1,3-benzoxazole carrying an oxo group at position 2. It has a role as a phytoalexin and an allelochemical.

Names & identifiers

Preferred name: 2(3H)-Benzoxazolone
IUPAC: 3H-1,3-benzoxazol-2-one
English name: 2-Benzoxazolinone
Molecular formula: C7H5NO2
Molecular weight: 135.12

Names & synonyms

2-BENZOXAZOLINONE59-49-4Benzoxazolone2(3H)-Benzoxazolonebenzoxazolin-2-onebenzoxazolin-2(3H)-onebenzoxalinoneDTXSID9049324CHEBI:145233NSC-38123X996Q809VDTXCID8029280

Show more names

benzo[d]oxazol-2-ol3H-BENZOOXAZOL-2-ONEusafek-5429USAF ek-5429AKOS B0297572-Benzoxaxolol2-BENZOXAZOLONE

benzoxazolone-2RefChem:85562200-430-0Benzoxazolinone1,3-Benzoxazol-2(3H)-one2-HydroxybenzoxazoleBenzo[D]Oxazol-2(3H)-One2-Benzoxazolol

Database identifiers

CAS: 59-49-4
PubChem CID: 6043
DTXSID: DTXSID9049324
ChEMBL: CHEMBL280323
ChEBI: CHEBI:145233
UNII: 3X996Q809V
EC Number: 200-430-0
Nikkaji: J36.095C

Properties

Computed structural properties

XLogP: 1.2
Topological polar surface area: 38.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 0
Heavy atoms: 10
Formal charge: 0
Complexity: 158

Experimental & physicochemical properties

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy

LogP · 2 items

1.16

Solubility>20.3 [ug/mL] (The mean of the results at pH 7.4)

Boiling Point335.00 °C. @ 760.00 mm Hg

Melting Point141 - 142 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 137 · 137-139 °C(lit.)
Boiling point: 248.79 °C · 248.79°C (rough estimate)
Density: 1.3124 · 1.3124 (rough estimate)
refractive index: 1.58 · 1.5800 (estimate)
Flash point: 160 °C · 160 °C
storage temp.: Sealed in dry,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly)
pka: 9.5 · 9.50±0.70(Predicted)
form: Powder
color: Light beige to brown-gray
Water Solubility: soluble in hot water
BRN: 119481 · 119481
InChI: 1S/C7H5NO2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)
InChIKey: ASSKVPFEZFQQNQ-UHFFFAOYSA-N
SMILES: O=C1Nc2ccccc2O1
LogP: 1.16 · 1.160
CAS DataBase Reference: 59 · 59-49-4(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 3 X996Q809V · 3X996Q809V
NIST Chemistry Reference: Benzoxazolone(59-49-4)
EPA Substance Registry System: 2 · 2-Benzoxazolinone (59-49-4)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302+H312+H332
Precautionary statements: 280 · P280-P301+P312+P330-P302+P352+P312-P304+P340+P312
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xn
Risk Statements: 20 · 20/21/22-22-24/25-36/37/38
Safety Statements: 36 · 36-24/25-26
RIDADR: 2811 · 2811
WGK Germany: 3 · 3
RTECS: 4905000 · DM4905000
Hazard Note: Harmful
TSCA: TSCA listed
HS Code: 29349990 · 29349990
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
Toxicity: 50 orl-rat: · LD50 orl-rat: 700 mg/kg MDCHAG 4(1),308,64

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302+H312+H332 (36.8%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 76 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
rtecs: DM4905000
ridadr: 2811
hs_code: 29349990
Toxicity: LD50 orl-rat: 700 mg/kg MDCHAG 4(1),308,64
risk_code: 20/21/22-22-24/25-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
hazard_note: Harmful
safety_code: 36-24/25-26
Storage Class: 11 - Combustible Solids
Hazard statements: H302+H312+H332
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
Precautionary statements: P280-P301+P312+P330-P302+P352+P312-P304+P340+P312

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

General Manufacturing Information2(3H)-Benzoxazolone: ACTIVE

Applications · 2 items

Uses2-Benzoxazolinone is used in the study of the antioxidant activity of heterocyclic chalcones, screening of hydrazines as inhibitors of immune suppressive enzyme indoleamine dioxygenase 1, design and the development of the inhibitors of nitric oxide synthases.

General Description2-Benzoxazolinone is a phytoanticipin and its biotransformation by endophytic fungi isolated from Aphelandra tetragona was studied. 2-Benzoxazolinone is a natural chemical produced by rye (Secale cereale) and has strong phytotoxic properties.

Preparation methods · 1 item

Preparation2-benzoxazolinone synthesis method: add o-aminophenol, urea and solvent chlorobenzene into the reaction kettle, protect with nitrogen, the reaction temperature is 50～132 ℃, the reaction time is 6h, after the reaction is completed, it is cooled with ice brine, crystallized, Filter the finished product. It is also possible to use o-aminophenol to react with phosgene in the solvent chlorobenzene, quickly pass phosgene within 20 ~ 40 ° C, then heat up to 100 ~ 130 ° C, and then pass phosgene at a lower speed, after the reaction is completed, pass nitrogen to catch up. Phosgene, after work-up, can also obtain 2-benzoxazolinone.

Upstream & downstream products

Upstream raw materials

2-Aminophenol S,S-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate 1-Phenyltetrazole-5-thiol 2,3-Dichloro-5-nitropyridine Salicylhydroxamic acid 3-Chloro-2-hydroxy-5-nitropyridine

Downstream products

2,6-Dichlorobenzoxazole (2-Oxo-1,3-benzoxazol-3(2H)-yl)acetaldehyde 2(3H)-Benzoxazolone, 3-(3-hydroxypropyl)-3-(2-Chloro-acetyl)-3H-benzooxazol-2-one [3-(3-Chloro-9-oxa-1,2,10-triaza-anthracen-10-yl)-propyl]-dimethyl-amine 2-Chloro-10-methyl-3,4-diazaphenoxazine 2(3H)-Benzoxazolone, 5-hydroxy-

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]

INTATRADE GmbH+49 3493/605464 · [email protected]

爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Additional notes

DefinitionChEBI: 2-benzoxazolinone is a member of the class of benzoxazoles that is 2,3-dihydro-1,3-benzoxazole carrying an oxo group at position 2. It has a role as an allelochemical and a phytoalexin.

Related reactions

87 records

New reaction record

HRID 33371As reactantuspto-grants-2008_09

HRID 33373As reactantuspto-grants-2008_09

HRID 158132As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)

HRID 192122As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)

HRID 206492As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)

HRID 216308As reactantuspto-grants-2012_06

HRID 243619As reactantuspto-grants-2014_02

HRID 288624As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)

Compound notes

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Basic information