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Chemical Product CAS:103-16-2Hydroquinone monobenzyl ether

CAS:103-16-2
Hydroquinone monobenzyl ether

  • CAS No:

    103-16-2
  • Name:

    Hydroquinone monobenzyl ether
  • Molecular Formula:

    C13H12O2
  • Molecular Weight:

    200.24
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Hydroquinone monobenzyl ether ( CASNO:103-16-2 )

Identification and Related Records
Name:
Hydroquinone monobenzyl ether
CAS Registry number:
103-16-2
Iupac name:
4-phenylmethoxyphenol
Synonyms:
p-(Benzyloxy)phenol
p-Hydroxyphenyl benzyl ether
4-(Phenylmethoxy)phenol
Agerite alba
Benoquin
Benzoquin
Benzyl hydroquinone
Depigman
Hydroquinone benzyl ether
Monobenzone
Monobenzyl hydroquinone
PBP
Pigmex
4-benzyloxy phenol (Monobenzone)
4-benzyloxy phenol
EINECS(EC#):
203-083-3
Molecular Formula:
C13H12O2
Molecular Weight:
200.24
Inchi:
InChI=1/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2
InChIKey:
VYQNWZOUAUKGHI-UHFFFAOYSA-N
Canonical SMILES:
C1=CC=C(C=C1)COC2=CC=C(C=C2)O
Chemical and Physical Properties
Appearance:
amber crystalline powder
Density:
1.26
Melting Point:
117-122℃
Boiling Point:
359.1°Cat760mmHg
Flash Point:
213.4°C
Water:
slightly soluble
Solubilities:
Insoluble
Color/Form:
LUSTROUS LEAFLETS FROM WATER
WHITE CRYSTALLINE POWDER
Stability:
Stable under normal temperatures and pressures.
HS Code:
29095090
Storage temp:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.
Spectral properties:
IR: 15254 (Sadtler Research Laboratories IR Grating Collection)
UV: 167 (Sadtler Research Laboratories Spectral Collection)
NMR: 6552 (Sadtler Research Laboratories Spectral Collection)
IR: 474 (Sadtler Research Laboratories Prism Collection)
UV: 167 (Sadtler Research Laboratories Spectral Collection)
Computed Properties:
Molecular Weight:200.23318 [g/mol]
Molecular Formula:C13H12O2
XLogP3:3.4
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:3
Tautomer Count:2
Exact Mass:200.08373
MonoIsotopic Mass:200.08373
Topological Polar Surface Area:29.5
Heavy Atom Count:15
Formal Charge:0
Complexity:167
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Ring Count:2
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:14
Safety and Handling
Hazard Codes:
Xi:Irritant
Risk Statements:
R36;R43
Safety Statements:
S24/25;S26;S37
HazardClass:
8
Hazard Note:
Irritant
Safety:
Hazard Codes:Xi
Risk Statements:36-43
36:Irritating to the eyes
43:May cause sensitization by skin contact
Safety Statements:24/25-26-37
24/25:Avoid contact with skin and eyes
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
37:Wear suitable gloves
WGK Germany:2
Hazard Note:Irritant
HS Code:29095090
Hazardous Substances Data:103-16-2(Hazardous Substances Data)
PackingGroup:
I; II; III
Transport:
25kgs
Formulations/Preparations:
IT IS MARKETED AS MONOBENZONE LOTION, NF, 5% SOLN IN ISOPROPYL ALCOHOL & PROPYLENE GLYCOL, & MONOBENZONE OINTMENT, NF, WHICH CONTAINS 20% OF ACTIVE INGREDIENT IN SUITABLE BASE.
Specification:

cream to beige-light brownish crystals or
Safety Statements:24/25-26-37
24/25:Avoid contact with skin and eyes
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
37:Wear suitable gloves
Disposal Methods:
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

REACTION OF SODIUM PHENOXIDE WITH BENZYL CHLORIDE; REACTION OF HYDROQUINONE AND BENZYL BROMIDE IN ALCOHOLIC POTASSIUM HYDROXIDE
PREPD IN VARIOUS WAYS. ONE METHOD INVOLVES CONDENSING SODIUM P-NITROPHENOLATE WITH BENZYL CHLORIDE TO PRODUCE BENZYL P-NITROPHENYL ETHER FOLLOWED BY 1) REDUCTION OF NITRO TO AMINO, 2) DIAZOTIZATION OF AMINO, & 3) HYDROLYTIC DECOMP OF DIAZONIUM CMPD TO CORRESPONDING PHENOL.
U.S. Production

(1974) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS
Usage:
Antioxidant for paraffins and polyvinyl chloride, polypropylene and polypropylene oxide, chemical intermediate in organic synthesis.
Biomedical Effects and Toxicity
Therapeutic Uses:
MONOBENZONE, MONOBENZYL ETHER OF HYDROQUINONE, IS AMELANOTIC AGENT USED IN SEVERE FRECKLING & OTHER CONDITIONS CHARACTERIZED BY HYPERPIGMENTATION OF SKIN.
IT IS APPLIED TO HYPERPIGMENTED AREAS 2 OR 3 TIMES DAILY FOR UP TO 4 MO, OR UNTIL DEPIGMENTATION HAS OCCURRED, & THEN TWICE WEEKLY TO MAINTAIN EFFECT. ... IF SATISFACTORY RESPONSE IS NOT OBSERVED WITHIN 4 MO, TREATMENT SHOULD BE DISCONTINUED.
...POSSIBLY EFFECTIVE FOR TREATMENT OF HYPERPIGMENTATION CAUSED BY EXCESSIVE FORMATION OF MELANIN, SUCH AS OCCURS IN GENERALIZED LENTIGO...MELASMA OF PREGNANCY, & HYPERPIGMENTATION FOLLOWING INFLAMMATION OF SKIN.
VITILIGO PATIENTS USED 20% MONOBENZONE 2 TIMES/DAY UNTIL DEPIGMENTATION; THOSE ACHIEVING COMPLETE DEPIGMENTATION WERE TREATED FOR 10 MO OR MORE. DEPIGMENTATION INDUCED BY MONOBENZONE IS GENERALLY IRREVERSIBLE.
EXPERIMENTAL USE: VET: BY TOPICAL APPLICATION TO HYPERPIGMENTED AREAS (5-20% CONCN).
... Cancer patients tolerated ingestion of up to 10 g/day of ... /hydroquinone monobenzyl ether/ without toxic symptoms. Nausea and vomiting occurred above this dose. Its use for depigmentation is therefore limited by its ability to cause contact dermatitis rather than its effect when absorbed internally.
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