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DL-Mandelic acid

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DL-Mandelic acid

EINECS 210-277-1
CAS No. 611-72-3 Density 1.322 g/cm3
PSA 57.53000 LogP 0.80460
Solubility 150 g/L (20℃) Melting Point 119-121 °C(lit.)
Formula C8H8O3 Boiling Point 321.827 °C at 760 mmHg
Molecular Weight 152.15 Flash Point 162.649 °C
Transport Information N/A Appearance Wihte crystal or crystal powder
Safety 22-24/25 Risk Codes 21/22
Molecular Structure Molecular Structure of 611-72-3 (DL-Mandelic acid) Hazard Symbols R21/22:;
Synonyms

DL-2-Hydroxy-2-phenylacetic acid;(+/-)-alpha-Hydroxyphenylacetic acid;

Article Data 268

DL-Mandelic acid Consensus Reports

DL-mandelic acid is reported in EPA TSCA Inventory.

DL-Mandelic acid Specification

The DL-Mandelic acid, with the CAS registry number 611-72-3, is also known as (+/-)-alpha-Hydroxyphenylacetic acid. It belongs to the product category of Fine Chemical & Intermediates. Its EINECS registry number is 202-007-6. This chemical's molecular formula is C8H8O3 and molecular weight is 152.15. What's more, its IUPAC name is called 2-Hydroxy-2-phenylacetic acid. It should be stored in a cool, dry and well-ventilated place. When you are dealing with this chemical, you should be very careful. This chemical is harmful in contact with skin and if swallowed. Therefore, you should avoid contacting with skin and eyes. 

Physical properties about DL-Mandelic acid are: (1)ACD/LogP: 0.55; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.98; (4)ACD/LogD (pH 7.4): -3.12; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 57.53 Å2; (13)Index of Refraction: 1.591; (14)Molar Refractivity: 38.904 cm3; (15)Molar Volume: 115.131 cm3; (16)Polarizability: 15.423×10-24 cm3; (17)Surface Tension: 60.47 dyne/cm; (18)Density: 1.322 g/cm3; (19)Flash Point: 162.649 °C; (20)Enthalpy of Vaporization: 59.501 kJ/mol; (21)Boiling Point: 321.827 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of DL-Mandelic acid: this chemical can be prepared by 2,2-dichloro-1-phenyl-ethanone. This reaction needs reagent NaOH at temperature of 120-125 °C. The reaction time is 3 hours. The yield is 50 %.

DL-Mandelic acid can be prepared by 2,2-dichloro-1-phenyl-ethanone.

Uses of DL-Mandelic acid: it is used to produce other chemicals. For example, it can react with 4-methyl-aniline to get mandelic acid-p-toluidide. The reaction occurs with reagents N-(1-methanesulfonyl)benzotriazole, triethylamine and other condition of heating for 18 hours. The yield is 72 %.

DL-Mandelic acid can react with 4-methyl-aniline to get mandelic acid-p-toluidide.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)C(O)c1ccccc1
(2) InChI: InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)
(3) InChIKey: IWYDHOAUDWTVEP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LDLo oral 2gm/kg (2000mg/kg) GASTROINTESTINAL: GASTRITIS

LIVER: OTHER CHANGES

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 64, Pg. 79, 1940.
rat LD50 intramuscular > 300mg/kg (300mg/kg)   Experimental Medicine and Surgery. Vol. 4, Pg. 223, 1946.
rat LD50 intraperitoneal 4100mg/kg (4100mg/kg)   Bollettino Chimico Farmaceutico. Vol. 112, Pg. 53, 1973.
rat LDLo oral 3gm/kg (3000mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 64, Pg. 79, 1940.

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