| Identification | More | [Name]
Dimethyl 5-hydroxyisophthalate | [CAS]
13036-02-7 | [Synonyms]
5-HYDROXYISOPHTHALIC ACID DIMETHYL ESTER
DIMETHYL-5-HYDROXY-BENZENE-1,3-DICARBONATE
DIMETHYL 5-HYDROXYBENZENE-1,3-DICARBOXYLATE
DIMETHYL 5-HYDROXYISOPHTHALATE
TIMTEC-BB SBB000491
3-benzenedicarboxylicacid,5-hydroxy-dimethylester
Dimethyl 5-hydroxybenzene-1,3-dicarboxylate~5-Hydroxyisophthalic acid dimethyl ester
Dimethyl 5-hydroxyisophtalate
5-HYDROXYISOPHTHALIC ACID DIMETHYL
5-HYDROXY-DIMETHYLISOPHTHALATE | [EINECS(EC#)]
235-899-0 | [Molecular Formula]
C10H10O5 | [MDL Number]
MFCD00134367 | [Molecular Weight]
210.18 | [MOL File]
13036-02-7.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white crystal powder | [Melting point ]
162-164 °C (lit.) | [Boiling point ]
360.6±22.0 °C(Predicted) | [density ]
1.284±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Powder and/or Lumps | [pka]
8.33±0.10(Predicted) | [color ]
White to light beige | [Water Solubility ]
Soluble in water. | [BRN ]
2650120 | [InChI]
InChI=1S/C10H10O5/c1-14-9(12)6-3-7(10(13)15-2)5-8(11)4-6/h3-5,11H,1-2H3 | [InChIKey]
DOSDTCPDBPRFHQ-UHFFFAOYSA-N | [SMILES]
C1(C(OC)=O)=CC(O)=CC(C(OC)=O)=C1 | [LogP]
2.570 (est) | [CAS DataBase Reference]
13036-02-7(CAS DataBase Reference) | [EPA Substance Registry System]
13036-02-7(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29182900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white crystal powder | [Uses]
Dimethyl 5-Hydroxyisophthalate is a useful synthetic intermediate in the synthesis of N,N?-Bis(2,3-dihydroxypropyl)-5-[(N-(2-hydroxyethyl)carbamoyl)methoxy]-2,4,6-triiodoisophthalamide (B426310); a compound related to Ioversol( I737000) which is a nonionic, low osmolality, radiographic contrast agent. | [General Description]
Dimethyl 5-hydroxyisophthalate undergoes a base-catalyzed nucleophilic oxirane ring-opening addition reaction with allyl glycidyl ether, to afford 5-substituted derivatives of isophthalic acid. Influence of third component, i.e. a series of 1,ω-alkanediols on the copolymerization reaction of dimethyl 5-hydroxyisophthalate with poly(ethylene glycol) has been studied. Lipase-catalyzed condensation polymerization of dimethyl 5-hydroxyisophthalate with polyethylene glycol is reported. | [Synthesis]
To a 1 L round-bottomed flask equipped with a magnetic stirrer was added 187.8 g (1 mol) of 5-hydroxyisophthalic acid (~97% purity, available from Aldrich) and 500 mL (12.3 mol) of methanol. After slowly adding 28 mL of concentrated sulfuric acid, the reaction mixture was heated to reflux temperature and stirred under reflux conditions for 4 hours. Upon completion of the reaction, the hot reaction solution was carefully poured into 500mL of ice water. Subsequently, the white solid product was collected by filtration and washed several times with deionized water until the washings were neutral. The product was dried under vacuum at 60 °C overnight to give 206.8 g of dimethyl 5-hydroxyisophthalate. The product characterization data were as follows: melting point 164-166 °C; GC purity >99%; yield 98.2%; 1H NMR (CDCl3 + DMSO-d6, TMS as internal standard, ppm): 3.68 (s, 6H, OCH3), 7.45 (s, 2H, Ar-H), 7.89 (s, 1H, Ar-H), 9.35 (broad peak, 1H, OH ); 13C NMR (CDCl3 + DMSO-d6, TMS as internal standard, ppm): 51.92 (OCH3), 120.50 (C4, C6), 121.10 (C2), 131.15 (C1, C3), 157.36 (C5), 165.85 (COOR); 1H-13C NMR correlation spectrum (CDCl3 + DMSO-d6, TMS as internal standard, ppm): 51.92 (quadruple peaks, OCH3, 1JCH = 147 Hz), 120.50 (double peaks, C4, C6, 1JCH = 164.4 Hz), 121.10 (double peaks, C2, 1JCH = 168.3 Hz), 131.15 (single peaks, C1, C3), 157.36 (single peaks , C5), 165.85 (single peak, COOR); GC-MS (acetone as solvent): m/z 210 (M+). | [References]
[1] Tetrahedron Letters, 1996, vol. 37, # 20, p. 3475 - 3478
[2] Tetrahedron, 1997, vol. 53, # 30, p. 10239 - 10252
[3] Organic and Biomolecular Chemistry, 2007, vol. 5, # 2, p. 276 - 285
[4] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 6988 - 6993
[5] Angewandte Chemie, 1996, vol. 108, # 17, p. 2078 - 2081 |
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