Coixol

HCID 10772

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Basic information

CAS: 532-91-2
Standard SMILES: COc1ccc2[nH]c(=O)oc2c1
InChIKey: MKMCJLMBVKHUMS-UHFFFAOYSA-N
Molecular formula: C8H7NO3
Average molar mass: 165.15 g/mol
Monoisotopic mass: 165.04259308

Overview

6-methoxy-2-benzoxazolinone is a 2-benzoxazolinone that is substituted by a methoxy group at position 6. It has a role as an antibacterial agent, an anticonvulsant, an antifungal agent, a muscle relaxant and a plant metabolite. It is an aromatic ether and a benzoxazole. It is functionally related to a 2-benzoxazolinone.

Names & identifiers

Preferred name: Coixol
IUPAC: 6-methoxy-3H-1,3-benzoxazol-2-one
English name: 6-Methoxy-2-benzoxazolinone
Molecular formula: C8H7NO3
Molecular weight: 165.15

Names & synonyms

Coixol532-91-26-Methoxy-2-benzoxazolinone6-methoxy-3H-1,3-benzoxazol-2-one6-Methoxybenzoxazolinone6-MBOADTXSID30201260RefChem:918912DTXCID301237516-METHOXYBENZO[D]OXAZOL-2(3H)-ONEMBOA2(3H)-Benzoxazolone, 6-methoxy-

Show more names

Coixol, 10 mM in DMSO6-Methoxy-2-benzoxazolineChlorzoxazone Impurity 366-Methoxy benzoxazol-2-one6-methoxy-2-benzoxazolinon

6-Methoxy-2(3H)-benzoxazolone2-BENZOXAZOLINONE, 6-METHOXY-6-Methoxy-1,3-benzoxazol-2(3H)-oneMFCD000517266-methoxy-3H-benzooxazol-2-one6-methoxybenzoxazolin-2(3h)-one6-methoxy-benzoxazolin-2(3h)-one6-Methoxy-2-benzoxazolinone;6-MBOA

Database identifiers

CAS: 532-91-2
PubChem CID: 10772
DTXSID: DTXSID30201260
ChEMBL: CHEMBL454809
ChEBI: CHEBI:195240
Nikkaji: J11.724B

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 47.6 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 1
Heavy atoms: 12
Formal charge: 0
Complexity: 195

Experimental & physicochemical properties

Melting Point160 - 161 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 151 · 151-156 °C(lit.)
Boiling point: 292.97 °C · 292.97°C (rough estimate)
Density: 1.345 · 1.3450 (rough estimate)
refractive index: 1.5468 · 1.5468 (estimate)
storage temp.: Sealed in dry,Room Temperature
solubility: Acetone, Dichloromethane, Methanol, Tetrahydrofuran
form: Solid
pka: 8.73 · 8.73±0.70(Predicted)
color: light tan
BRN: 141041 · 141041
InChI: 1S/C8H7NO3/c1-11-5-2-3-6-7(4-5)12-8(10)9-6/h2-4H,1H3,(H,9,10)
InChIKey: MKMCJLMBVKHUMS-UHFFFAOYSA-N
SMILES: COc1ccc2NC(=O)Oc2c1
EWG's Food Scores: 1 · 1
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
RTECS: 5275200 · DM5275200
HS Code: 2934999090 · 2934999090
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
rtecs: DM5275200
hs_code: 2934999090
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 22-24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 2 items

Uses6-Methoxybenzoxazolinone is an intermdiate in the synthesis of DIMBOA-4-O-β-D-glucuronide which is a metabolite of DIMBOA which acts as an antifungal and antialgal agent in crops. The benzoxazinone group within the structure allows for these effects.

General Description6-Methoxy-2-benzoxazolinone (MBOA) is obtained by reacting 2-amino-5-methoxyphenol hydrochloride with urea. MOBA is a naturally occurring auxin-inhibiting substance present in maize shoots.